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Sellin M, Koger H, Engesser TA, Grunenberg J, Krossing I. Isolation and Characterization of [MnFe(CO) 10] +: The Missing Link in the 3 d Dimetal Decacarbonyl Series. Chemistry 2025; 31:e202500489. [PMID: 39992077 DOI: 10.1002/chem.202500489] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/07/2025] [Revised: 02/21/2025] [Accepted: 02/24/2025] [Indexed: 02/25/2025]
Abstract
The heterodinuclear dimetal decacarbonyl cation [MnFe(CO)10]+ has been synthesized by combining the metalloradical [Fe(CO)5]+⋅ with half an equivalent of Mn2(CO)10. The complex was subsequently isolated and characterized using single-crystal X-Ray Diffraction (scXRD), as well as IR, Raman, NMR and Mössbauer spectroscopy. Experimental results, complemented by DFT calculations of the relaxed force constants and an analysis of the electron density, reveal that the interaction between the two {M(CO)5} fragments in [MnFe(CO)10]+ is in between a covalent and a dative bond, representing a borderline case between the 2x17 VE and the 16+18 VE electron counting. Additionally, the known isoelectronic anion [CrMn(CO)10]- was prepared as its [PPN]+ salt and characterized for the first time by scXRD. These finding complete the series of structurally characterized isoelectronic dimetal decacarbonyls, spanning from [Cr2(CO)10]2- to [Fe2(CO)10]2+, the characteristics of all of which are compared based on experiment and theory.
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Affiliation(s)
- Malte Sellin
- Institut für Anorganische und Analytische Chemie und Freiburger Materialforschungszentrum (FMF), Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104, Freiburg, Germany
| | - Hendrik Koger
- Institut für Anorganische und Analytische Chemie und Freiburger Materialforschungszentrum (FMF), Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104, Freiburg, Germany
| | - Tobias A Engesser
- Institut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth-Straße 2, 24118, Kiel, Germany
| | - Jörg Grunenberg
- Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany
| | - Ingo Krossing
- Institut für Anorganische und Analytische Chemie und Freiburger Materialforschungszentrum (FMF), Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104, Freiburg, Germany
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2
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Monteiro RP, Calhau IB, Gomes AC, Lopes AD, Da Silva JP, Gonçalves IS, Pillinger M. β-Cyclodextrin and cucurbit[7]uril as protective encapsulation agents of the CO-releasing molecule [CpMo(CO) 3Me]. Dalton Trans 2024; 54:166-180. [PMID: 39526807 DOI: 10.1039/d4dt01863j] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/16/2024]
Abstract
The CO releasing ability of the complex [CpMo(CO)3Me] (1) (Cp = η5-C5H5) has been assessed using a deoxymyoglobin-carbonmonoxymyoglobin assay. In the dark, CO release was shown to be promoted by the reducing agent sodium dithionite in a concentration-dependent manner. At lower dithionite concentrations, where dithionite-induced CO release was minimised, irradiation at 365 nm with a low-power UV lamp resulted in a strongly enhanced release of CO (half-life (t1/2) = 6.3 min), thus establishing complex 1 as a photochemically activated CO-releasing molecule. To modify the CO release behaviour of the tricarbonyl complex, the possibility of obtaining inclusion complexes between 1 and β-cyclodextrin (βCD) or cucurbit[7]uril (CB7) by liquid-liquid interfacial precipitation (1@βCD(IP)), liquid antisolvent precipitation (1@CB7), and mechanochemical ball-milling (1@βCD(BM)) was evaluated. All these methods led to the isolation of a true inclusion compound (albeit mixed with nonincluded 1 for 1@βCD(BM)), as evidenced by powder X-ray diffraction (PXRD), thermogravimetric analysis (TGA), FT-IR and FT-Raman spectroscopies, and 13C{1H} magic angle spinning (MAS) NMR. PXRD showed that 1@βCD(IP) was microcrystalline with a channel-type crystal packing structure. High resolution mass spectrometry studies revealed the formation of aqueous phase 1 : 1 complexes between 1 and CB7. For 1@βCD(IP) and 1@CB7, the protective effects of the hosts led to a decrease in the CO release rates with respect to nonincluded 1. βCD had the strongest effect, with a ca. 10-fold increase in t1/4 for dithionite-induced CO release, and a ca. 2-fold increase in t1/2 for photoinduced CO release.
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Affiliation(s)
- Rodrigo P Monteiro
- CICECO - Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal.
| | - Isabel B Calhau
- CICECO - Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal.
| | - Ana C Gomes
- CICECO - Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal.
| | - André D Lopes
- Centre of Marine Sciences (CCMAR/CIMAR LA), and Department of Chemistry and Pharmacy, FCT, University of the Algarve, 8005-039 Faro, Portugal
| | - José P Da Silva
- Centre of Marine Sciences (CCMAR/CIMAR LA), and Department of Chemistry and Pharmacy, FCT, University of the Algarve, 8005-039 Faro, Portugal
| | - Isabel S Gonçalves
- CICECO - Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal.
| | - Martyn Pillinger
- CICECO - Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal.
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Chang K, Sun X, Fu M, Han B, Jiang X, Qi Q, Zhang Y, Ni T, Ge C, Yang Z. H 2O 2-triggered controllable carbon monoxide delivery for photothermally augmented gas therapy. J Mater Chem B 2024; 12:2737-2745. [PMID: 38379390 DOI: 10.1039/d3tb02399k] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 02/22/2024]
Abstract
Carbon monoxide (CO) gas therapy has shown great potential as a very promising approach in the ongoing fight against tumors. However, delivering unstable CO to the tumor site and safely releasing it for maximum efficacy still have unsatisfactory outcomes. In this study, we've developed nanotheranostics (IN-DPPCO NPs) based on conjugated polymer IN-DPP and carbon monoxide (CO) carrier polymer mPEG(CO) for photothermal augmented gas therapy. The IN-DPPCO NPs can release CO with the hydrogen peroxide (H2O2) overexpressed in the tumor microenvironment. Meanwhile, IN-DPPCO NPs exhibit strong absorption in the near-infrared window, showing a high photothermal conversion efficiency of up to 41.5% under 808 nm laser irradiation. In vitro and in vivo experiments demonstrate that these nanotheranostics exhibit good biocompatibility. Furthermore, the synergistic CO/photothermal therapy shows enhanced therapeutic efficacy compared to gas therapy alone. This work highlights the great promise of conjugated polymer nanoparticles as versatile nanocarriers for spatiotemporally controlled and on-demand delivery of gaseous messengers to achieve precision cancer theranostics.
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Affiliation(s)
- Kaiwen Chang
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
| | - Xiaolin Sun
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
- Department of Scientific Research, The First Affiliated Hospital of Xinxiang Medical University, Xinxiang Medical University, Xinxiang 453003, P. R. China
| | - Mingying Fu
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
| | - Bing Han
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
| | - Xiaopeng Jiang
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
| | - Qiaofang Qi
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
| | - Yang Zhang
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
| | - Tianjun Ni
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
| | - Chunpo Ge
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
| | - Zhijun Yang
- Key Laboratory of Medical Molecular Probes, Department of Medical Chemistry, School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003, P. R. China.
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Radzhabov MR, Mankad NP. Activation of robust bonds by carbonyl complexes of Mn, Fe and Co. Chem Commun (Camb) 2023; 59:11932-11946. [PMID: 37727948 DOI: 10.1039/d3cc03078d] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 09/21/2023]
Abstract
Metal carbonyl complexes possess among the most storied histories of any compound class in organometallic chemistry. Nonetheless, these old dogs continue to be taught new tricks. In this Feature, we review the historic discoveries and recent advances in cleaving robust bonds (e.g., C-H, C-O, C-F) using carbonyl complexes of three metals: Mn, Fe, and Co. The use of Mn, Fe, and Co carbonyl catalysts in controlling selectivity during hydrofunctionalization reactions is also discussed. The chemistry of these earth-abundant metals in the field of robust bond functionalization is particularly relevant in the context of sustainability. We expect that an up-to-date perspective on these seemingly simple organometallic species will emphasize the wellspring of reactivity that continues to be available for discovery.
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Affiliation(s)
- Maxim R Radzhabov
- Department of Chemistry, University of Illinois Chicago, Chicago, Illinois 60607, USA.
| | - Neal P Mankad
- Department of Chemistry, University of Illinois Chicago, Chicago, Illinois 60607, USA.
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Ha TJ, Im DK, Kim SM, Lee JD. 1,2-Diphenyl- o-carborane and Its Chromium Derivatives: Synthesis, Characterization, X-ray Structural Studies, and Biological Evaluations. Molecules 2023; 28:4942. [PMID: 37446604 DOI: 10.3390/molecules28134942] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/31/2023] [Revised: 06/16/2023] [Accepted: 06/21/2023] [Indexed: 07/15/2023] Open
Abstract
The objective of this study is to design and synthesize substituted η6-chromium(0) tricarbonyl metal complexes carrying o-carborane units as potential boron neutron capture therapy (BNCT) agents. In this study, 1,2-diphenyl-o-carborane (1) units were used as starting materials to generate biologically active species. We investigated how the structural changes of 1 substituted with chromium(0) tricarbonyl affect the biological properties, and 1-(Phenyl-η6-chromium(0) tricarbonyl)-2-phenyl-o-carborane (2) and 1,2-bis(phenyl-η6-chromium(0) tricarbonyl)-o-carborane (3) species were produced in moderate yields. The molecular structures of compounds 1-3 were identified and established by infrared (IR); 1H, 11B, and 13C nuclear magnetic resonance (NMR) and X-ray crystallography analyses. Crystal structures of 1,2-diphenyl-o-carborane and the corresponding chromium complexes 1, 2, and 3 were obtained. In an in vitro study using B16 and CT26 cancer cells containing the triphenyl-o-carboranyl chromium(0) complexes Ph3C2BCr2 and Ph3C2BCr3, which we reported previously, compounds 2 and 3 accumulated at higher levels than compounds Ph3C2BCr2 and Ph3C2BCr3. However, the phenylated o-carboranyl chromium complexes have been found to be more cytotoxic than p-boronophenylalanine (BPA).
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Affiliation(s)
- Tae-Jin Ha
- Department of Chemistry, College of Natural Sciences, Chosun University, 309 Pilmundaero, Gwangju 61452, Republic of Korea
| | - Dong-Kyung Im
- Department of Chemistry, College of Natural Sciences, Chosun University, 309 Pilmundaero, Gwangju 61452, Republic of Korea
| | - Seung-Min Kim
- Department of Chemistry, College of Natural Sciences, Chosun University, 309 Pilmundaero, Gwangju 61452, Republic of Korea
| | - Jong-Dae Lee
- Department of Chemistry, College of Natural Sciences, Chosun University, 309 Pilmundaero, Gwangju 61452, Republic of Korea
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S Mendes S, Sorg M, Luís CM, Fontinha D, Francisco D, Moita D, C Romão C, G Pinho M, Pimentel C, Prudêncio M, M Saraiva L. Conjugated carbon monoxide-releasing molecules have broad-spectrum antimicrobial activity. Future Med Chem 2023; 15:1037-1048. [PMID: 37458074 DOI: 10.4155/fmc-2023-0103] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 07/18/2023] Open
Abstract
Aim: To test the antimicrobial effect of carbon monoxide-releasing molecules (CORMs) conjugated with azoles on different microorganisms. Methods & results: We used broth microdilution, checkerboard and cytotoxicity assays, as well as imaging, fluorescence and bioluminescence experiments to study [Re(CO)3(2,2'-bipyridyl)(Ctz)]+ (also known as ReBpyCtz). ReBpyCtz exhibits a low minimum inhibitory concentration value, increases the intracellular formation of reactive oxygen species and causes significant alterations on Staphylococcus aureus's membrane. ReBpyCtz is active against fungi, having a more prolonged fungicidal effect on Candida glabrata than clotrimazole and is selectively active on blood-stage malaria parasites, at a concentration that is not toxic to kidney epithelial cells. Conclusion: Conjugated CORMs have the potential to be active against different types of pathogens, thus constituting a promising class of broad-spectrum antimicrobials.
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Affiliation(s)
- Sofia S Mendes
- Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Avenida da República (EAN), 2780-157, Oeiras, Portugal
| | - Moritz Sorg
- Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Avenida da República (EAN), 2780-157, Oeiras, Portugal
| | - Cláudia Malta Luís
- Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Avenida da República (EAN), 2780-157, Oeiras, Portugal
| | - Diana Fontinha
- Instituto de Medicina Molecular João Lobo Antunes, Universidade de Lisboa, Av. Prof. Egas Moniz, 1649-028, Lisboa, Portugal
| | - Denise Francisco
- Instituto de Medicina Molecular João Lobo Antunes, Universidade de Lisboa, Av. Prof. Egas Moniz, 1649-028, Lisboa, Portugal
| | - Diana Moita
- Instituto de Medicina Molecular João Lobo Antunes, Universidade de Lisboa, Av. Prof. Egas Moniz, 1649-028, Lisboa, Portugal
| | - Carlos C Romão
- Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Avenida da República (EAN), 2780-157, Oeiras, Portugal
| | - Mariana G Pinho
- Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Avenida da República (EAN), 2780-157, Oeiras, Portugal
| | - Catarina Pimentel
- Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Avenida da República (EAN), 2780-157, Oeiras, Portugal
| | - Miguel Prudêncio
- Instituto de Medicina Molecular João Lobo Antunes, Universidade de Lisboa, Av. Prof. Egas Moniz, 1649-028, Lisboa, Portugal
| | - Lígia M Saraiva
- Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Avenida da República (EAN), 2780-157, Oeiras, Portugal
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Hu M, Zhou H, Wang Z, Du Y, Wang Y, Eerdun C, Zhu B. Synthesis, structure, CO releasing, and biological activities of new 1-D chain Mn(I)/Mn(II) visible light activated CO-releasing molecules (CORMs). J COORD CHEM 2023. [DOI: 10.1080/00958972.2023.2165070] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/13/2023]
Affiliation(s)
- Mixia Hu
- College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, China
- College of Pharmacy, Inner Mongolia Medical University, Hohhot, China
- Inner Mongolia Key Laboratory of Fine Organic Synthesis, Hohhot, China
| | - Haofei Zhou
- College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, China
- College of Pharmacy, Inner Mongolia Medical University, Hohhot, China
- Inner Mongolia Key Laboratory of Fine Organic Synthesis, Hohhot, China
| | - Zhexu Wang
- College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, China
- Inner Mongolia Key Laboratory of Fine Organic Synthesis, Hohhot, China
| | - Yanqing Du
- College of Pharmacy, Inner Mongolia Medical University, Hohhot, China
| | - Yuewu Wang
- College of Pharmacy, Inner Mongolia Medical University, Hohhot, China
| | - Chaolu Eerdun
- College of Pharmacy, Inner Mongolia Medical University, Hohhot, China
| | - Baohua Zhu
- College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, China
- Inner Mongolia Key Laboratory of Fine Organic Synthesis, Hohhot, China
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Fandzloch M, Jędrzejewski T, Wiśniewska J, Sitkowski J, Dobrzańska L, Brożyna AA, Wrotek S. Sawhorse-type ruthenium complexes with triazolopyrimidine ligands - what do they represent in terms of cytotoxic and CORM compounds? Dalton Trans 2022; 51:8804-8820. [PMID: 35616922 DOI: 10.1039/d1dt04294g] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
Abstract
Three sawhorse-type ruthenium(I) complexes containing purine analogs such as triazolopyrimidines of the general formula [Ru2(CO)4(μ-OOCCH3)2(L)2], where L is 1,2,4-triazolo[1,5-a]pyrimidine (tp for 1), 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine (dbtp for 2) and 5,7-diphenyl-1,2,4-triazolo[1,5-a]pyrimidine (dptp for 3), have been synthesized and characterized by elemental analysis, infrared analysis, multinuclear magnetic resonance spectroscopic techniques (1H, 13C, 15N), and single-crystal X-ray diffraction (for 1 and 2). By assay with myoglobin, the photo-activated CO-releasing molecule (PhotoCORM) character of (1-3) has been confirmed, thus indicating the possibility of use in CO-based therapies. The importance of UV-induced modification has been investigated in the context of anticancer properties. Complexes (1) and (2) have been thoroughly screened for their in vitro cytotoxicity against various cancer cell lines: MCF-7 (breast cancer), HeLa (cervical cancer) and C32 (melanoma), as well as L929 normal fibroblasts in the dark and presence of UV-A light (365 nm). The results were compared with those for cisplatin and two reference ruthenium complexes, namely NAMI-A and KP1019. The most hydrophilic [Ru2(CO)4(μ-OOCCH3)2(tp)2] (1) (log P = -1.12) was found to be more cytotoxic than (2), despite the lower cellular uptake measured by ICP-MS toward HeLa cells. Importantly, photo-induced stimulation of cells with (1) resulted in a lower decrease in the viability of L929 normal cells (IC50 = 154.7 ± 6.5 μM) in comparison with HeLa cancer cells (IC50 = 66.7 ± 3.4 μM). The photo-induced stimulation of (1) and (2) increases ROS generation, and their anticancer activity may be a partially ROS-dependent phenomenon.
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Affiliation(s)
- Marzena Fandzloch
- Institute of Low Temperature and Structure Research, Polish Academy of Sciences, Okólna 2, 50-422 Wrocław, Poland.
| | - Tomasz Jędrzejewski
- Department of Immunology, Faculty of Biological and Veterinary Sciences, Nicolaus Copernicus University in Toruń, Lwowska 1, 87-100 Toruń, Poland
| | - Joanna Wiśniewska
- Faculty of Chemistry, Nicolaus Copernicus University in Toruń, Gagarina 7, 87-100 Toruń, Poland
| | - Jerzy Sitkowski
- National Institutes of Medicines, Chełmska 30/34, 00-725 Warszawa, Poland.,Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland
| | - Liliana Dobrzańska
- Faculty of Chemistry, Nicolaus Copernicus University in Toruń, Gagarina 7, 87-100 Toruń, Poland
| | - Anna A Brożyna
- Department of Human Biology, Faculty of Biological and Veterinary Sciences, Nicolaus Copernicus University in Toruń, Lwowska 1, 87-100 Toruń, Poland
| | - Sylwia Wrotek
- Department of Immunology, Faculty of Biological and Veterinary Sciences, Nicolaus Copernicus University in Toruń, Lwowska 1, 87-100 Toruń, Poland
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Fernández I, Noonikara‐Poyil A, Dias HVR. Bonding situation in isolable silver(I) carbonyl complexes of the Scorpionates. J Comput Chem 2022; 43:796-803. [DOI: 10.1002/jcc.26835] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/30/2021] [Revised: 01/26/2022] [Accepted: 02/22/2022] [Indexed: 01/08/2023]
Affiliation(s)
- Israel Fernández
- Departamento de Química Orgánica I and Centro de Innovación en Química Avanzada (ORFEO‐CINQA), Facultad de Ciencias Químicas Universidad Complutense de Madrid Madrid Spain
| | - Anurag Noonikara‐Poyil
- Department of Chemistry and Biochemistry The University of Texas at Arlington Arlington Texas USA
| | - H. V. Rasika Dias
- Department of Chemistry and Biochemistry The University of Texas at Arlington Arlington Texas USA
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A simple theoretical approach to converging of Myoglobin-Assay with different pH values. ACTA CHIMICA SLOVACA 2021. [DOI: 10.2478/acs-2021-0012] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 11/20/2022]
Abstract
Abstract
Many metal carbonyl complexes have been synthesized and analyzed as CO-releasing agents. As in many bioactivity assays, differences between in-vitro and in-vivo studies in Myoglobin Assay have been observed. Adjustment of in-vitro conditions to in-vivo conditions is one way to overcoming this problem. Changing the conditions of each in-vivo assay is not possible considering the available grant, material, and labor facilities. In-silico methods are suitable as they provide better in-vitro conditions before experimental procedures. A method which is easy to employ on a basic computer could be more suitable to observe the assay convergence. In this study, global reactivity descriptors were used as an approach to investigate pH differences in myoglobin assay. Global reactivity descriptors of the molecules were compared with myoglobin assay results at different pH values and molecular docking results performed with optimized molecules in different solvents. The following complexes were studied: [Mn(CO)3(bpy)(L)]PF6 (bpy: 2,2-bipyridyl, L: benzylbenzimidazole, 4-chlorobenzylbenzimidazole).
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11
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Synthesis of phenanthroline-based ligand and its UV activable tetracarbonyl photoCORMs based on chromium, molybdenum, and tungsten as cytotoxic and antimicrobial agents. J Organomet Chem 2021. [DOI: 10.1016/j.jorganchem.2021.122103] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/23/2022]
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12
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Varma RR, Vaidya FU, Pathak C, Dhaduk MP, Dabhi RA, Bhatt BS, Patel MN. Synthesis, spectroscopic characterization, computational and biological evaluation of organometallic Re(I) complexes with 5-(2-butyl-5-chloro-1H-imidazol-4-yl)-1,3-diaryl- 4,5-dihydro-1H-pyrazole. INORG CHEM COMMUN 2021. [DOI: 10.1016/j.inoche.2021.109005] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/20/2022]
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13
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Carbon Monoxide Modulation of Microglia-Neuron Communication: Anti-Neuroinflammatory and Neurotrophic Role. Mol Neurobiol 2021; 59:872-889. [PMID: 34796462 DOI: 10.1007/s12035-021-02643-z] [Citation(s) in RCA: 6] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/16/2021] [Accepted: 11/09/2021] [Indexed: 10/19/2022]
Abstract
Microglia, the 'resident immunocompetent cells' of the central nervous system (CNS), are key players in innate immunity, synaptic refinement and homeostasis. Dysfunctional microglia contribute heavily to creating a toxic inflammatory milieu, a driving factor in the pathophysiology of several CNS disorders. Therefore, strategies to modulate the microglial function are required to tackle exacerbated tissue inflammation. Carbon monoxide (CO), an endogenous gaseous molecule produced by the degradation of haem, has anti-inflammatory, anti-apoptotic, and pro-homeostatic and cytoprotective roles, among others. ALF-826A, a novel molybdenum-based CO-releasing molecule, was used for the assessment of neuron-microglia remote communication. Primary cultures of rat microglia and neurons, or the BV-2 microglial and CAD neuronal murine cell lines, were used to study the microglia-neuron interaction. An approach based on microglial-derived conditioned media in neuronal culture was applied. Medium derived from CO-treated microglia provided indirect neuroprotection against inflammation by limiting the lipopolysaccharide (LPS)-induced expression of reactivity markers (CD11b), the production of reactive oxygen species (ROS) and the secretion of inflammatory factors (TNF-α, nitrites). This consequently prevented neuronal cell death and maintained neuronal morphology. In contrast, in the absence of inflammatory stimulus, conditioned media from CO-treated microglia improved neuronal morphological complexity, which is an indirect manner of assessing neuronal function. Likewise, the microglial medium also prevented neuronal cell death induced by pro-oxidant tert-Butyl hydroperoxide (t-BHP). ALF-826 treatment reinforced microglia secretion of Interleukin-10 (IL-10) and adenosine, mediators that may protect against t-BHP stress in this remote communication model. Chemical inhibition of the adenosine receptors A2A and A1 reverted the CO-derived neuroprotective effect, further highlighting a role for CO in regulating neuron-microglia communication via purinergic signalling. Our findings indicate that CO has a modulatory role on microglia-to-neuron communication, promoting neuroprotection in a non-cell autonomous manner. CO enhances the microglial release of neurotrophic factors and blocks exacerbated microglial inflammation. CO improvement of microglial neurotrophism under non-inflammatory conditions is here described for the first time.
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Wittwer Y, Eichler R, Zingg R, Herrmann D, Türler A. The influence of gas purification and addition of macro amounts of metal-carbonyl complexes on the formation of single-atom metal-carbonyl-complexes. RADIOCHIM ACTA 2021. [DOI: 10.1515/ract-2020-0036] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/15/2022]
Abstract
Abstract
Using the Fast On-line Reaction Apparatus (FORA), the influence of various gas-purification columns onto the formation of metal carbonyl complexes (MCCs) under single-atom chemistry conditions was investigated. MCCs were synthesized from single atoms of Mo, Tc, Ru and Rh being produced by the spontaneous fission of 252Cf and recoiling into a CO-gas containing carrier gas atmosphere. The in-situ synthesized MCCs were volatile enough to be transported by the carrier gas to a charcoal trap where they were adsorbed and their subsequent decay was registered by γ-spectrometry. It was found that the type and combination of purification columns used to clean the applied CO-gas strongly influences the obtained formation and transport yields for all MCCs. With the exception of Rh-carbonyl, intense gas-purification strategies resulted in reduced formation and transport yields for MCCs in comparison with less efficient or even completely missing purification setups. It was postulated that the observed reduction in yield might depend on the content of Fe(CO)5 and Ni(CO)4, as well as potentially other MCCs, in the CO-gas, being formed by the interaction between CO and the steel-surfaces of FORA as well as from impurities in the used charcoal traps. Subsequently, it was shown that macro amounts of Fe(CO)5, Ni(CO)4, Mo(CO)6 and Re2(CO)10 added to the used process gas indeed increase significantly the overall yields for MCCs produced by 252Cf fission products. Ni(CO)4 appeared the most potent to increase the yield. Therefore, it was used in more detailed investigations. Using isothermal chromatography, it was shown that Ni(CO)4 does not affect the speciation of carbonyl species produced by the 252Cf fission product 104Mo. For 107Tc, 110Ru and 111Rh a speciation change cannot be excluded. For 111Rh a speciation change cannot be excluded. An inter-carbonyl transfer mechanism is suggested boosting the formation of MCCs. The current discovery might allow for new opportunities in various research fields, which are currently restricted by the low overall yields for MCCs produced under single-atom chemistry conditions. Examples are the chemical investigation of transactinides or the generation of radioactive ion beams from refractory metals at accelerators.
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Affiliation(s)
- Yves Wittwer
- Paul Scherrer Institute , Villigen , Switzerland
- University of Bern , Bern , Switzerland
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15
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Mir JM, Maurya RC, Khan MW. NO, CO and H2S based pharmaceuticals in the mission of vision (eye health): a comprehensive review. REV INORG CHEM 2021. [DOI: 10.1515/revic-2021-0009] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/05/2023]
Abstract
Abstract
A set of well defined signaling molecules responsible for normal functioning of human physiology including nitric oxide along with carbon monoxide and hydrogen sulphide are referred as “gasotransmitters”. Due to their involvement in almost every system of a human body, the care of highly sensitive organs using these molecules as drugs represents highly fascinating area of research. In connection with these interesting aspects, the applied aspects of these gaseous molecules in maintaining healthy eye and vision have been targeted in this review. Several examples of eye-droppers including NORMs like latanoprost and nipradiol, CORMs like CORM-3 and CORM-A1, and Hydrogen sulfide releasing system like GYY4137 have been discussed in this context. Therefore the relation of these trio-gasotransmitters with the ophthalmic homeostasis on one hand, and de-infecting role on the other hand has been mainly highlighted. Some molecular systems capable of mimicking gasotransmitter action have also been introduced in connection with the titled theme.
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Affiliation(s)
- Jan Mohammad Mir
- Coordination, Bioinorganic and Computational Chemistry Laboratory, Department of P.G. Studies and Research in Chemistry and Pharmacy , Rani Durgavati University , Jabalpur , M.P. , India
- Department of Chemistry , Islamic University of Science and Technology , Awantipora , J&K 192122 , India
| | - Ram Charitra Maurya
- Coordination, Bioinorganic and Computational Chemistry Laboratory, Department of P.G. Studies and Research in Chemistry and Pharmacy , Rani Durgavati University , Jabalpur , M.P. , India
| | - Mohd Washid Khan
- Coordination, Bioinorganic and Computational Chemistry Laboratory, Department of P.G. Studies and Research in Chemistry and Pharmacy , Rani Durgavati University , Jabalpur , M.P. , India
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16
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Wittwer Y, Eichler R, Herrmann D, Türler A. The influence of physical parameters on the in-situ metal carbonyl complex formation studied with the Fast On-line Reaction Apparatus (FORA). RADIOCHIM ACTA 2021. [DOI: 10.1515/ract-2020-0035] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/15/2022]
Abstract
Abstract
The Fast On-line Reaction Apparatus (FORA) was used to investigate the influence of various reaction parameters onto the formation and transport of metal carbonyl complexes (MCCs) under single-atom chemistry conditions. FORA is based on a 252Cf-source producing short-lived Mo, Tc, Ru and Rh isotopes. Those are recoiling from the spontaneous fission source into a reaction chamber flushed with a gas-mixture containing CO. Upon contact with CO, fission products form volatile MCCs which are further transported by the gas stream to the detection setup, consisting of a charcoal trap mounted in front of a HPGe γ-detector. Depending on the reaction conditions, MCCs are formed and transported with different efficiencies. Using this setup, the impact of varying physical parameters like gas flow, gas pressure, kinetic energy of fission products upon entering the reaction chamber and temperature of the reaction chamber on the formation and transport yields of MCCs was investigated. Using a setup similar to FORA called Miss Piggy, various gas mixtures of CO with a selection of noble gases, as well as N2 and H2, were investigated with respect to their effect onto MCC formation and transport. Based on this measurements, optimized reaction conditions to maximize the synthesis and transport of MCCs are suggested. Explanations for the observed results supported by simulations are suggested as well.
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Affiliation(s)
- Yves Wittwer
- Paul Scherrer Institute , Villigen , Switzerland
- University of Bern , Bern , Switzerland
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17
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Zhou Y, Chen Y, He C. Solid-phase synthesis of peptide Mn(i)-carbonyl bioconjugates and their CO release upon visible light activation. Dalton Trans 2021; 50:4231-4236. [PMID: 33687425 DOI: 10.1039/d1dt00395j] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/07/2023]
Abstract
A one-pot synthetic route has been developed for the assembly of peptide Mn(i)-carbonyl bioconjugates. It allows the installation of a variety of chelating agents at the late stage, and after just one purification step the TAT-MnCO complexes can be obtained. The resulting bioconjugates showed different and tunable CO releasing kinetics upon visible light activation.
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Affiliation(s)
- Yi Zhou
- School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China.
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18
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The influence of chemical parameters on the in-situ metal carbonyl complex formation studied with the fast on-line reaction apparatus (FORA). RADIOCHIM ACTA 2021. [DOI: 10.1515/ract-2020-0031] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/15/2022]
Abstract
Abstract
A new setup named Fast On-line Reaction Apparatus (FORA) is presented which allows for the efficient investigation and optimization of metal carbonyl complex (MCC) formation reactions under various reaction conditions. The setup contains a 252Cf-source producing short-lived Mo, Tc, Ru and Rh isotopes at a rate of a few atoms per second by its 3% spontaneous fission decay branch. Those atoms are transformed within FORA in-situ into volatile metal carbonyl complexes (MCCs) by using CO-containing carrier gases. Here, the design, operation and performance of FORA is discussed, revealing it as a suitable setup for performing single-atom chemistry studies. The influence of various gas-additives, such as CO2, CH4, H2, Ar, O2, H2O and ambient air, on the formation and transport of MCCs was investigated. O2, H2O and air were found to harm the formation and transport of MCCs in FORA, with H2O being the most severe. An exception is Tc, for which about 130 ppmv of H2O caused an increased production and transport of volatile compounds. The other gas-additives were not influencing the formation and transport efficiency of MCCs. Using an older setup called Miss Piggy based on a similar working principle as FORA, it was additionally investigated if gas-additives are mostly affecting the formation or only the transport stability of MCCs. It was found that mostly formation is impacted, as MCCs appear to be much less sensitive to reacting with gas-additives in comparison to the bare Mo, Tc, Ru and Rh atoms.
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19
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Varma RR, Pandya JG, Vaidya FU, Pathak C, Bhatt BS, Patel MN. Biological activities of pyrazoline-indole based Re(I) carbonyls: DNA interaction, antibacterial, anticancer, ROS production, lipid peroxidation, in vivo and in vitro cytotoxicity studies. Chem Biol Interact 2020; 330:109231. [DOI: 10.1016/j.cbi.2020.109231] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/01/2020] [Revised: 08/07/2020] [Accepted: 08/20/2020] [Indexed: 01/28/2023]
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20
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Unkrig W, Kloiber K, Butschke B, Kratzert D, Krossing I. Altering Charges on Heterobimetallic Transition-Metal Carbonyl Clusters. Chemistry 2020; 26:12373-12381. [PMID: 32613683 PMCID: PMC7589396 DOI: 10.1002/chem.202002339] [Citation(s) in RCA: 6] [Impact Index Per Article: 1.2] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/12/2020] [Revised: 06/16/2020] [Indexed: 12/29/2022]
Abstract
The homoleptic group 5 carbonylates [M(CO)6 ]- (M=Nb, Ta) serve as ligands in carbonyl-terminated heterobimetallic Agm Mn clusters containing 3 to 11 metal atoms. Based on our serendipitous [Ag6 {Nb(CO)6 }4 ]2+ (4 a2+ ) precedent, we established access to such Agm Mn clusters of the composition [Agm {M(CO)6 }n ]x (M=Nb, Ta; m=1, 2, 6; n=2, 3, 4, 5; x=1-, 1+, 2+). Salts of those molecular cluster ions were synthesized by the reaction of [NEt4 ][M(CO)6 ] and Ag[Al(ORF )4 ] (RF =C(CF3 )3 ) in the correct stoichiometry in 1,2,3,4-tetrafluorobenzene at -35 °C. The solid-state structures were determined by single-crystal X-ray diffraction methods and, owing to the thermal instability of the clusters, a limited scope of spectroscopic methods. In addition, DFT-based AIM calculations were performed to provide an understanding of the bonding within these clusters. Apparently, the clusters 3+ (m=6, n=5) and 42+ (m=6, n=4) are superatom complexes with trigonal-prismatic or octahedral Ag6 superatom cores. The [M(CO)6 ]- ions then bind through three CO units as tridentate chelate ligands to the superatom core, giving overall structures related to tetrahedral AX4 (42+ ) or trigonal bipyramidal AX5 molecules (3+ ).
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Affiliation(s)
- Wiebke Unkrig
- Institut für Anorganische und Analytische ChemieAlbert-Ludwigs-Universität FreiburgAlbertstrasse 2179104FreiburgGermany
| | - Konstantin Kloiber
- Institut für Anorganische und Analytische ChemieAlbert-Ludwigs-Universität FreiburgAlbertstrasse 2179104FreiburgGermany
| | - Burkhard Butschke
- Institut für Anorganische und Analytische ChemieAlbert-Ludwigs-Universität FreiburgAlbertstrasse 2179104FreiburgGermany
| | - Daniel Kratzert
- Institut für Anorganische und Analytische ChemieAlbert-Ludwigs-Universität FreiburgAlbertstrasse 2179104FreiburgGermany
| | - Ingo Krossing
- Institut für Anorganische und Analytische ChemieAlbert-Ludwigs-Universität FreiburgAlbertstrasse 2179104FreiburgGermany
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21
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Water-soluble UV/visible light activated Mn-CO-releasing molecules: Synthesis, structure, CO releasing and biological activities evaluation. INORG CHEM COMMUN 2020. [DOI: 10.1016/j.inoche.2020.108093] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/29/2022]
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22
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Morstein J, Höfler D, Ueno K, Jurss JW, Walvoord RR, Bruemmer KJ, Rezgui SP, Brewer TF, Saitoe M, Michel BW, Chang CJ. Ligand-Directed Approach to Activity-Based Sensing: Developing Palladacycle Fluorescent Probes That Enable Endogenous Carbon Monoxide Detection. J Am Chem Soc 2020; 142:15917-15930. [DOI: 10.1021/jacs.0c06405] [Citation(s) in RCA: 34] [Impact Index Per Article: 6.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/27/2022]
Affiliation(s)
| | | | - Kohei Ueno
- Tokyo Metropolitan Institute of Medical Science, Tokyo 1568506, Japan
| | | | | | | | - Samir P. Rezgui
- Department of Chemistry and Biochemistry, University of Denver, Denver, Colorado 80210, United States
| | | | - Minoru Saitoe
- Tokyo Metropolitan Institute of Medical Science, Tokyo 1568506, Japan
| | - Brian W. Michel
- Department of Chemistry and Biochemistry, University of Denver, Denver, Colorado 80210, United States
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23
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Geri S, Krunclova T, Janouskova O, Panek J, Hruby M, Hernández‐Valdés D, Probst B, Alberto RA, Mamat C, Kubeil M, Stephan H. Light-Activated Carbon Monoxide Prodrugs Based on Bipyridyl Dicarbonyl Ruthenium(II) Complexes. Chemistry 2020; 26:10992-11006. [PMID: 32700815 PMCID: PMC7496190 DOI: 10.1002/chem.202002139] [Citation(s) in RCA: 13] [Impact Index Per Article: 2.6] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/30/2020] [Indexed: 12/13/2022]
Abstract
Two photoactivatable dicarbonyl ruthenium(II) complexes based on an amide-functionalised bipyridine scaffold (4-position) equipped with an alkyne functionality or a green-fluorescent BODIPY (boron-dipyrromethene) dye have been prepared and used to investigate their light-induced decarbonylation. UV/Vis, FTIR and 13 C NMR spectroscopies as well as gas chromatography and multivariate curve resolution alternating least-squares analysis (MCR-ALS) were used to elucidate the mechanism of the decarbonylation process. Release of the first CO molecule occurs very quickly, while release of the second CO molecule proceeds more slowly. In vitro studies using two cell lines A431 (human squamous carcinoma) and HEK293 (human embryonic kidney cells) have been carried out in order to characterise the anti-proliferative and anti-apoptotic activities. The BODIPY-labelled compound allows for monitoring the cellular uptake, showing fast internalisation kinetics and accumulation at the endoplasmic reticulum and mitochondria.
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Affiliation(s)
- Stepan Geri
- Institute of Radiopharmaceutical Cancer ResearchHelmholtz-Zentrum Dresden-RossendorfBautzner Landstrasse 40001328DresdenGermany
| | - Tereza Krunclova
- Department of Biological ModelsInstitute of Macromolecular ChemistryHeyrovsky Square 216206PragueCzech Republic
| | - Olga Janouskova
- Department of Biological ModelsInstitute of Macromolecular ChemistryHeyrovsky Square 216206PragueCzech Republic
| | - Jiri Panek
- Supramolecular Polymer SystemsInstitute of Macromolecular ChemistryHeyrovsky Square 216206PragueCzech Republic
| | - Martin Hruby
- Supramolecular Polymer SystemsInstitute of Macromolecular ChemistryHeyrovsky Square 216206PragueCzech Republic
| | | | - Benjamin Probst
- Department of ChemistryUniversity of ZurichWinterthurerstr. 1908057ZurichSwitzerland
| | - Roger A. Alberto
- Department of ChemistryUniversity of ZurichWinterthurerstr. 1908057ZurichSwitzerland
| | - Constantin Mamat
- Institute of Radiopharmaceutical Cancer ResearchHelmholtz-Zentrum Dresden-RossendorfBautzner Landstrasse 40001328DresdenGermany
| | - Manja Kubeil
- Institute of Radiopharmaceutical Cancer ResearchHelmholtz-Zentrum Dresden-RossendorfBautzner Landstrasse 40001328DresdenGermany
| | - Holger Stephan
- Institute of Radiopharmaceutical Cancer ResearchHelmholtz-Zentrum Dresden-RossendorfBautzner Landstrasse 40001328DresdenGermany
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24
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Battistin F, Vidal A, Balducci G, Alessio E. Investigating the reactivity of neutral water-soluble Ru(ii)-PTA carbonyls towards the model imine ligands pyridine and 2,2'-bipyridine. RSC Adv 2020; 10:26717-26727. [PMID: 35515784 PMCID: PMC9055427 DOI: 10.1039/d0ra05898j] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Abstract] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 06/04/2020] [Accepted: 07/07/2020] [Indexed: 01/09/2023] Open
Abstract
As a continuation of our strategy for preparing new Ru(ii) precursors to be exploited as building blocks in the construction of metal-mediated supramolecular assemblies with improved solubility in water, here we describe the reactivity of selected neutral Ru(ii)-PTA carbonyls (PTA = 1,3,5-triaza-7-phosphaadamantane) towards the model imine ligands pyridine (py) and 2,2'-bipyridine (bpy) and the preparation and characterization of several neutral and cationic water-soluble derivatives: trans,trans,trans-[RuCl2(CO)(py)(PTA)2] (7), cis,cis,trans-[RuCl2(CO)2(py)(PTA)] (9), cis,trans-[Ru(bpy)Cl(CO)(PTA)2]Cl (10), mer-[Ru(bpy)(CO)(PTA)3](Cl)2 (12), cis,trans-[Ru(bpy)(CO)2Cl(PTA)]Cl (13), cis,trans-[Ru(bpy)(CO)2(PTA)2](NO3)2 (14NO3). In addition, we found that light-induced isomerization in some bpy compounds could be induced. The following species, either side-products isolated in low yield or compounds obtained exclusively in solution, were also unambiguously identified: cis,cis,trans-[RuCl2(CO)(py)(PTA)2] (8), trans-[RuCl2(bpy)(CO)(PTA)] (11), cis,cis-[Ru(bpy)Cl(CO)(PTA)2]Cl (15) and cis,cis-[Ru(bpy)(CO)2Cl(PTA)]Cl (16). The X-ray structures of 7, 11·H2O, and 12·7H2O are also reported. All compounds are new and - with few exceptions - show a good solubility in water.
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Affiliation(s)
- Federica Battistin
- Department of Chemical and Pharmaceutical Sciences, University of Trieste Via L. Giorgieri 1 34127 Trieste Italy
| | - Alessio Vidal
- Department of Chemical and Pharmaceutical Sciences, University of Trieste Via L. Giorgieri 1 34127 Trieste Italy
| | - Gabriele Balducci
- Department of Chemical and Pharmaceutical Sciences, University of Trieste Via L. Giorgieri 1 34127 Trieste Italy
| | - Enzo Alessio
- Department of Chemical and Pharmaceutical Sciences, University of Trieste Via L. Giorgieri 1 34127 Trieste Italy
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25
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Zhang M, Qiao R, Hu J. Engineering Metal-Organic Frameworks (MOFs) for Controlled Delivery of Physiological Gaseous Transmitters. NANOMATERIALS (BASEL, SWITZERLAND) 2020; 10:E1134. [PMID: 32521709 PMCID: PMC7353332 DOI: 10.3390/nano10061134] [Citation(s) in RCA: 15] [Impact Index Per Article: 3.0] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Download PDF] [Figures] [Subscribe] [Scholar Register] [Received: 04/30/2020] [Revised: 05/26/2020] [Accepted: 05/26/2020] [Indexed: 12/11/2022]
Abstract
Metal-organic frameworks (MOFs) comprising metal ions or clusters coordinated to organic ligands have become a class of emerging materials in the field of biomedical research due to their bespoke compositions, highly porous nanostructures, large surface areas, good biocompatibility, etc. So far, many MOFs have been developed for imaging and therapy purposes. The unique porous nanostructures render it possible to adsorb and store various substances, especially for gaseous molecules, which is rather challenging for other types of delivery vectors. In this review, we mainly focus on the recent development of MOFs for controlled release of three gaseous transmitters, namely, nitric oxide (NO), carbon monoxide (CO), and hydrogen sulfide (H2S). Although these gaseous molecules have been known as air pollutants for a long time, much evidence has been uncovered regarding their important physiological functions as signaling molecules. These signaling molecules could be either physically absorbed onto or covalently linked to MOFs, allowing for the release of loaded signaling molecules in a spontaneous or controlled manner. We highlight the designing concept by selective examples and display their potential applications in many fields such as cancer therapy, wound healing, and anti-inflammation. We hope more effort could be devoted to this emerging fields to develop signaling molecule-releasing MOFs with practical applications.
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Affiliation(s)
- Mengdan Zhang
- CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical Science at the Microscale, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China;
| | - Ruirui Qiao
- ARC Centre of Excellence in Convergent Bio-Nano Science and Technology, Australian Institute for Bioengineering and Nanotechnology, The University of Queensland, Brisbane, QLD 4072, Australia
| | - Jinming Hu
- CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical Science at the Microscale, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China;
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26
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Zhou W, Šmidlehner T, Jerala R. Synthetic biology principles for the design of protein with novel structures and functions. FEBS Lett 2020; 594:2199-2212. [PMID: 32324903 DOI: 10.1002/1873-3468.13796] [Citation(s) in RCA: 13] [Impact Index Per Article: 2.6] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/18/2020] [Revised: 03/29/2020] [Accepted: 04/03/2020] [Indexed: 12/14/2022]
Abstract
Nature provides a large number of functional proteins that evolved during billions of years of evolution. The diversity of natural proteins encompasses versatile functions and more than a thousand different folds, which, however, represents only a tiny fraction of all possible folds and polypeptide sequences. Recent advances in the rational design of proteins demonstrate that it is possible to design de novo protein folds unseen in nature. Novel protein topologies have been designed based on similar principles as natural proteins using advanced computational modelling or modular construction principles, such as oligomerization domains. Designed proteins exhibit several interesting features such as extreme stability, designability of 3D topologies and folding pathways. Moreover, designed protein assemblies can implement symmetry similar to the viral capsids, while, on the other hand, single-chain pseudosymmetric designs can address each position independently. Recently, the design is expanding towards the introduction of new functions into designed proteins, and we may soon be able to design molecular machines.
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Affiliation(s)
- Weijun Zhou
- Department of Synthetic Biology and Immunology, National Institute of Chemistry, Ljubljana, Slovenia
| | - Tamara Šmidlehner
- Department of Synthetic Biology and Immunology, National Institute of Chemistry, Ljubljana, Slovenia
| | - Roman Jerala
- Department of Synthetic Biology and Immunology, National Institute of Chemistry, Ljubljana, Slovenia
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27
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Stout MJ, Stefan A, Skelton BW, Sobolev AN, Massi M, Hochkoeppler A, Stagni S, Simpson PV. Synthesis and Photochemical Properties of Manganese(I) Tricarbonyl Diimine Complexes Bound to Tetrazolato Ligands. Eur J Inorg Chem 2020. [DOI: 10.1002/ejic.201900987] [Citation(s) in RCA: 8] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/07/2023]
Affiliation(s)
- Matthew J. Stout
- Curtin Institute for Functional Molecules and Interfaces School of Molecular and Life Sciences Curtin University Kent Street, Bentley 6102 Perth Australia
| | - Alessandra Stefan
- CSGI, Department of Chemistry School of Molecular and Life Sciences University of Florence 50019 Sesto Fiorentino (FI) Italy
- Department of Pharmacy and Biotechnology School of Molecular and Life Sciences University of Bologna Viale Risorgimento 4 40136 Bologna Italy
| | - Brian W. Skelton
- School of Molecular Sciences and CMCA School of Molecular and Life Sciences The University of Western Australia 35 Stirling Highway 6009 Perth Western Australia
| | - Alexandre N. Sobolev
- School of Molecular Sciences and CMCA School of Molecular and Life Sciences The University of Western Australia 35 Stirling Highway 6009 Perth Western Australia
| | - Massimiliano Massi
- Curtin Institute for Functional Molecules and Interfaces School of Molecular and Life Sciences Curtin University Kent Street, Bentley 6102 Perth Australia
| | - Alejandro Hochkoeppler
- CSGI, Department of Chemistry School of Molecular and Life Sciences University of Florence 50019 Sesto Fiorentino (FI) Italy
- Department of Pharmacy and Biotechnology School of Molecular and Life Sciences University of Bologna Viale Risorgimento 4 40136 Bologna Italy
| | - Stefano Stagni
- Department of Industrial Chemistry “Toso Montanari” School of Molecular and Life Sciences University of Bologna Viale Risorgimento 4 40136 Bologna Italy
| | - Peter V. Simpson
- Curtin Institute for Functional Molecules and Interfaces School of Molecular and Life Sciences Curtin University Kent Street, Bentley 6102 Perth Australia
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28
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Yang X, Jin J, Guo Z, Xiao Z, Chen N, Jiang X, He Y, Liu X. The monoiron anionfac-[Fe(CO)3I3]−and its organic aminium salts: their preparation, CO-release, and cytotoxicity. NEW J CHEM 2020. [DOI: 10.1039/d0nj01182g] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
Abstract
The anionfac-[Fe(CO)3I3]−undergoes rapid decomposition to release CO and involve iodine radical. The CO-release can be tuned by its cations. The radical causes severe cytotoxicity which may endow the anion a great potential as an anticancer drug.
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Affiliation(s)
- Xiuqin Yang
- College of Biological
- Chemical Sciences and Engineering
- Jiaxing University
- Jiaxing 314001
- China
| | - Jing Jin
- Department of Urology
- The Affiliated Hospital of Jiaxing University
- Jiaxing 314001
- China
| | - Zhuming Guo
- College of Chemistry and Bioengineering
- Guilin University of Technology
- Guilin 514006
- China
| | - Zhiyin Xiao
- College of Biological
- Chemical Sciences and Engineering
- Jiaxing University
- Jiaxing 314001
- China
| | - Naiwen Chen
- Department of Urology
- The Affiliated Hospital of Jiaxing University
- Jiaxing 314001
- China
| | - Xiujuan Jiang
- College of Biological
- Chemical Sciences and Engineering
- Jiaxing University
- Jiaxing 314001
- China
| | - Yi He
- Department of Urology
- The Affiliated Hospital of Jiaxing University
- Jiaxing 314001
- China
| | - Xiaoming Liu
- College of Biological
- Chemical Sciences and Engineering
- Jiaxing University
- Jiaxing 314001
- China
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29
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Suchland B, Malassa A, Görls H, Krieck S, Westerhausen M. Iron(I)‐Based Carbonyl Complexes with Bridging Thiolate Ligands as Light‐Triggered CO Releasing Molecules (photoCORMs). Z Anorg Allg Chem 2019. [DOI: 10.1002/zaac.201900162] [Citation(s) in RCA: 6] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/21/2023]
Affiliation(s)
- Benedikt Suchland
- Chair of Inorganic Chemistry 1 Friedrich Schiller University Jena Humboldtstraße 8 07743 Jena Germany
| | - Astrid Malassa
- Chair of Inorganic Chemistry 1 Friedrich Schiller University Jena Humboldtstraße 8 07743 Jena Germany
| | - Helmar Görls
- Chair of Inorganic Chemistry 1 Friedrich Schiller University Jena Humboldtstraße 8 07743 Jena Germany
| | - Sven Krieck
- Chair of Inorganic Chemistry 1 Friedrich Schiller University Jena Humboldtstraße 8 07743 Jena Germany
| | - Matthias Westerhausen
- Chair of Inorganic Chemistry 1 Friedrich Schiller University Jena Humboldtstraße 8 07743 Jena Germany
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Kourti M, Cai J, Jiang W, Westwell AD. Structural Modifications on CORM-3 Lead to Enhanced Anti-angiogenic Properties Against Triple-negative Breast Cancer Cells. Med Chem 2019; 17:40-59. [PMID: 31808392 DOI: 10.2174/1573406415666191206102452] [Citation(s) in RCA: 6] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/04/2019] [Revised: 09/21/2019] [Accepted: 11/04/2019] [Indexed: 01/08/2023]
Abstract
PURPOSE Carbon monoxide-releasing molecules (CORMs) are a special class of organometallic complexes that have been reported to offer beneficial effects against different conditions including several subtypes of cancer. Especially for the aggressive and poorly treated triplenegative breast cancer (TNBC), early CORMs have been shown to diminish malignant angiogenesis and may be considered as an alternative approach. So, this study aimed at testing novel CORM molecules against angiogenesis in TNBC seeking potent drug candidates for new therapies. METHODS Based on previous studies, CORM-3 was chosen as the lead compound and a group of 15 new ruthenium-based CORMs was synthesized and subsequently evaluated in vitro for potential anti-angiogenic properties. RESULTS A similar anti-angiogenic behaviour to the lead complex was observed and a new CORM, complex 4, emerged as a promising agent from this study. Specifically, this complex offered better inhibition of the activation of VEGFR2 and other downstream proteins of vascular endothelial cells. Complex 4 also retained the ability of the parent molecule to reduce the upregulated VEGF expression from TNBC cells and inhibit endothelial cell migration and new vessel formation. The lack of significant cytotoxicity and the downregulating activity over the cytoprotective enzyme haem oxygenase-1 (HO-1) in cancer cells may also favour CORMs against this poorly treated subtype of breast cancer. CONCLUSION Since the anti-angiogenic approach is one of the few available targeted strategies against TNBC, both CORM-3 and the new complex 4 should be considered for further research as combination agents with existing anti-angiogenic drugs for more effective treatment of malignant angiogenesis in TNBC.
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Affiliation(s)
- Malamati Kourti
- Cardiff China Medical Research Collaborative, School of Medicine, Cardiff University, Heath Park, Cardiff, CF14 4XN, United Kingdom
| | - Jun Cai
- Cardiff China Medical Research Collaborative, School of Medicine, Cardiff University, Heath Park, Cardiff, CF14 4XN, United Kingdom
| | - Wen Jiang
- Cardiff China Medical Research Collaborative, School of Medicine, Cardiff University, Heath Park, Cardiff, CF14 4XN, United Kingdom
| | - Andrew D Westwell
- School of Pharmacy and Pharmaceutical Sciences, Cardiff University, Cardiff, CF10 3NB, United Kingdom
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Ollivier A, Foresti R, El Ali Z, Martens T, Kitagishi H, Motterlini R, Rivard M. Design and Biological Evaluation of Manganese- and Ruthenium-Based Hybrid CO-RMs (HYCOs). ChemMedChem 2019; 14:1684-1691. [PMID: 31319021 DOI: 10.1002/cmdc.201900426] [Citation(s) in RCA: 14] [Impact Index Per Article: 2.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/16/2019] [Indexed: 01/07/2023]
Abstract
Interest in the therapeutic effects of carbon monoxide (CO), a product of heme degradation catalyzed by the enzyme heme oxygenase-1 (HO-1), has led to the development of CO-releasing molecules (CO-RMs) for the controlled delivery of this gas in vivo. We recently proposed conjugating a cobalt-based CO-RM with various activators of nuclear factor erythroid 2-related factor 2 (Nrf2), the transcription factor that regulates HO-1 expression, in order to exploit the beneficial effects of exogenous and endogenous CO. In this study, we describe the preparation of hybrid molecules (termed HYCOs) conjugating a fumaric acid derivative as an Nrf2 activator to a Mn- or a Ru-based CO-RM known to be pharmacologically active. With the exception of an acyl-manganese complex, these hybrids were obtained by associating the two bioactive entities by means of a linker of variable structure. X-ray diffraction analyses and preliminary biological investigations are also presented.
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Affiliation(s)
- Anthony Ollivier
- Université Paris Est, ICMPE (UMR 7182), CNRS, UPEC, 94320, Thiais, France
| | - Roberta Foresti
- INSERM U955, Equipe 12, 94000, Créteil, France.,Université Paris Est, Faculté de Médecine, 94000, Créteil, France
| | - Zeina El Ali
- INSERM U955, Equipe 12, 94000, Créteil, France.,Université Paris Est, Faculté de Médecine, 94000, Créteil, France
| | - Thierry Martens
- Université Paris Est, ICMPE (UMR 7182), CNRS, UPEC, 94320, Thiais, France
| | - Hiroaki Kitagishi
- Department of Molecular Chemistry and Biochemistry, Faculty of Science and Engineering, Doshisha University, Kyotanabe, Kyoto, 610-0321, Japan
| | - Roberto Motterlini
- INSERM U955, Equipe 12, 94000, Créteil, France.,Université Paris Est, Faculté de Médecine, 94000, Créteil, France
| | - Michael Rivard
- Université Paris Est, ICMPE (UMR 7182), CNRS, UPEC, 94320, Thiais, France
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Wang SB, Zhang C, Chen ZX, Ye JJ, Peng SY, Rong L, Liu CJ, Zhang XZ. A Versatile Carbon Monoxide Nanogenerator for Enhanced Tumor Therapy and Anti-Inflammation. ACS NANO 2019; 13:5523-5532. [PMID: 31046229 DOI: 10.1021/acsnano.9b00345] [Citation(s) in RCA: 89] [Impact Index Per Article: 14.8] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/22/2023]
Abstract
Carbon monoxide (CO) is regarded as a potential therapeutic agent with multiple beneficial functions for biomedical applications. In this study, a versatile CO nanogenerator (designated as PPOSD) was fabricated and developed for tumor therapy and anti-inflammation. Partially oxidized tin disulfide (SnS2) nanosheets (POS NSs) were decorated with a tumor-targeting polymer (polyethylene glycol-cyclo(Asp-d-Phe-Lys-Arg-Gly), PEG-cRGD), followed by the loading of chemotherapeutic drug doxorubicin (DOX) to prepare polymer@POS@DOX, or PPOSD. After injected intravenously, PPOSD could selectively accumulate in tumor tissue via the cRGD-mediated tumor recognition. Upon 561 nm laser irradiation, the POS moiety in PPOSD can photoreduce CO2 to CO, which significantly sensitized the chemotherapeutic effect of DOX. The POS in PPOSD can also act as a photothermal agent for effective photothermal therapy (PTT) of the tumor upon 808 nm laser irradiation. Furthermore, the generated CO can simultaneously decrease the inflammatory reaction caused by PTT. Blood analysis and hematoxylin-eosin staining of major organs showed that no obvious systemic toxicity was induced after the treatment, suggesting good biosafety of PPOSD. This versatile CO nanogenerator will find great potential for both enhanced tumor inhibition and anti-inflammation.
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Affiliation(s)
- Shi-Bo Wang
- Key Laboratory of Biomedical Polymers of Ministry of Education and Department of Chemistry , Wuhan University , Wuhan 430072 , P.R. China
- Institute for Advanced Studies (IAS) , Wuhan University , Wuhan 430072 , P.R. China
| | - Cheng Zhang
- Key Laboratory of Biomedical Polymers of Ministry of Education and Department of Chemistry , Wuhan University , Wuhan 430072 , P.R. China
| | - Zhao-Xia Chen
- Key Laboratory of Biomedical Polymers of Ministry of Education and Department of Chemistry , Wuhan University , Wuhan 430072 , P.R. China
| | - Jing-Jie Ye
- Key Laboratory of Biomedical Polymers of Ministry of Education and Department of Chemistry , Wuhan University , Wuhan 430072 , P.R. China
| | - Si-Yuan Peng
- Key Laboratory of Biomedical Polymers of Ministry of Education and Department of Chemistry , Wuhan University , Wuhan 430072 , P.R. China
| | - Lei Rong
- Key Laboratory of Biomedical Polymers of Ministry of Education and Department of Chemistry , Wuhan University , Wuhan 430072 , P.R. China
| | - Chuan-Jun Liu
- Key Laboratory of Biomedical Polymers of Ministry of Education and Department of Chemistry , Wuhan University , Wuhan 430072 , P.R. China
| | - Xian-Zheng Zhang
- Key Laboratory of Biomedical Polymers of Ministry of Education and Department of Chemistry , Wuhan University , Wuhan 430072 , P.R. China
- Institute for Advanced Studies (IAS) , Wuhan University , Wuhan 430072 , P.R. China
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DFT investigation and molecular docking studies on dinuclear metal carbonyls containing pyridyl ligands with alkyne unit. CHEMICAL PAPERS 2019. [DOI: 10.1007/s11696-019-00784-z] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 10/27/2022]
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Liu Y, Wang X, Xu X, Qin W, Sun B. Protective effects of carbon monoxide releasing molecule‑2 on pancreatic function in septic mice. Mol Med Rep 2019; 19:3449-3458. [PMID: 30896839 PMCID: PMC6470989 DOI: 10.3892/mmr.2019.10049] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Abstract] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/05/2018] [Accepted: 12/31/2018] [Indexed: 01/04/2023] Open
Abstract
The present study aimed to investigate the effect of carbon monoxide (CO)‑releasing molecule‑2 (CORM‑2) on pancreatic function in sepsis‑model mice. To perform the present investigation, mice were rendered septic by cecal ligation and puncture (CLP). Then, mice were either treated with or without CORM‑2 (8 mg/kg, intravenous) for different durations (6, 12 and 24 h) immediately following CLP. The levels of serum amylase and lipase, tumor necrosis factor α, interleukin‑1β and interleukin‑6 in addition to myeloperoxidase (MPO) activity in pancreatic tissues were determined at 6, 12 and 24 h post‑CLP. Histological scores and the expression of intercellular adhesion molecule 1 (ICAM‑1), vascular cell adhesion molecule 1 (VCAM‑1), nuclear factor‑κB (NF‑κB) and phosphorylated inhibitor of κB (p‑IκB‑α) in the pancreas were also evaluated at 24 h post‑CLP. The results of the present study revealed that compared with CLP‑alone group, CORM‑2 treatment significantly (P<0.05) reduced the levels of serum amylase, lipase and pro‑inflammatory cytokines. In parallel, the severity of pancreatic histology, MPO activity and the expression levels of ICAM‑1 and VCAM‑1 in the pancreas of CORM‑2 treated CLP mice were substantially decreased compared with the untreated group. Furthermore, CORM‑2 treatment inhibited the expression levels of NF‑κB and P‑IκB‑α in the pancreas of mice following CLP compared with the untreated group. CORM‑2‑liberated CO exerted protective effects on the pancreatic function of septic mice, and the beneficial effects may be due to the suppression of NF‑κB activation and subsequent regulation of NF‑κB‑dependent expression of cytokines.
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Affiliation(s)
- Yishu Liu
- Department of General Surgery, Affiliated Hospital of Jiangsu University, Zhenjiang, Jiangsu 212001, P.R. China
| | - Xu Wang
- Department of Oncology, Affiliated Hospital of Jiangsu University, Zhenjiang, Jiangsu 212001, P.R. China
| | - Xiaohan Xu
- Department of Burns and Plastic Surgery, Affiliated Hospital of Jiangsu University, Zhenjiang, Jiangsu 212001, P.R. China
| | - Weiting Qin
- Department of Burns and Plastic Surgery, Affiliated Hospital of Jiangsu University, Zhenjiang, Jiangsu 212001, P.R. China
| | - Bingwei Sun
- Department of Burns and Plastic Surgery, Affiliated Hospital of Jiangsu University, Zhenjiang, Jiangsu 212001, P.R. China
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Xiao Z, Jiang R, Jin J, Yang X, Xu B, Liu X, He Y, He Y. Diiron(ii) pentacarbonyl complexes as CO-releasing molecules: their synthesis, characterization, CO-releasing behaviour and biocompatibility. Dalton Trans 2019; 48:468-477. [PMID: 30488059 DOI: 10.1039/c8dt03982h] [Citation(s) in RCA: 11] [Impact Index Per Article: 1.8] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/15/2022]
Abstract
Four diiron(ii) carbonyl complexes, [Fe2(μ-SR)3(CO)5X] (X- = Br-, I-; R = CH2CH3, CH2CH2CH3) were facilely synthesized by reacting [Fe(CO)4X2] with monothiolates. Their potential as carbon monoxide-releasing molecules (CORMs) was systematically investigated, revealing that their CO-releasing behaviour is highly solvent-dependent. Specifically, in dimethyl sulfoxide (DMSO), the CO-releasing kinetics were fast. Intermediates with a lower oxidation state might be involved in the reaction. By contrast, in less polar solvents such as methanol, acetonitrile and dichloromethane, intermediates featuring the triiron carbonyl cation, [Fe3(μ-SCH2CH3)6(CO)6]+, were isolated. The triiron intermediate underwent further decomposition to liberate CO. One of the iodo complexes was also examined for its CO-release in PBS solution when solubilised with DMSO in the presence of deoxy-Mb and the CO-release was found to be quantitative. Furthermore, kinetic analyses were performed and the CO-release in general obeyed a first-order kinetic model. Plausible CO-releasing pathways are proposed for the parent complexes and the triiron intermediate. Assessments in cytotoxicity indicated that the cytoxicity of the diiron(ii) complexes varied with both the halide and thiolate and those bearing bromide and the thiolate with longer chains were more biocompatible.
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Affiliation(s)
- Zhiyin Xiao
- College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China.
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Hu M, Yan Y, Zhu B, Chang F, Yu S, Alatan G. A series of Mn(i) photo-activated carbon monoxide-releasing molecules with benzimidazole coligands: synthesis, structural characterization, CO releasing properties and biological activity evaluation. RSC Adv 2019; 9:20505-20512. [PMID: 35515566 PMCID: PMC9065806 DOI: 10.1039/c9ra01370a] [Citation(s) in RCA: 9] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Abstract] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/23/2019] [Accepted: 06/17/2019] [Indexed: 11/21/2022] Open
Abstract
Five Mn(i) photo-activated carbon monoxide-releasing molecules were synthesized by reactions of MnBr(CO)5 with L1–L4, and characterized via single crystal X-ray diffraction, 1H-NMR, 13C-NMR, IR, UV-vis and fluorescence spectroscopy.
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Affiliation(s)
- Mixia Hu
- College of Chemistry and Chemical Engineering
- Inner Mongolia University
- Hohhot 010021
- China
- Key Lab of Fine Organic Synthesis Inner Mongolia Autonomous Region
| | - YaLi Yan
- School of Life Sciences
- Inner Mongolia University
- Hohhot 010021
- China
| | - Baohua Zhu
- College of Chemistry and Chemical Engineering
- Inner Mongolia University
- Hohhot 010021
- China
- Key Lab of Fine Organic Synthesis Inner Mongolia Autonomous Region
| | - Fei Chang
- College of Chemistry and Chemical Engineering
- Inner Mongolia University
- Hohhot 010021
- China
| | - Shiyong Yu
- College of Chemistry and Chemical Engineering
- Inner Mongolia University
- Hohhot 010021
- China
| | - Gaole Alatan
- School of Life Sciences
- Inner Mongolia University
- Hohhot 010021
- China
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Aucott BJ, Eastwood JB, Anders Hammarback L, Clark IP, Sazanovich IV, Towrie M, Fairlamb IJS, Lynam JM. Insight into the mechanism of CO-release from trypto-CORM using ultra-fast spectroscopy and computational chemistry. Dalton Trans 2019; 48:16426-16436. [DOI: 10.1039/c9dt03343b] [Citation(s) in RCA: 10] [Impact Index Per Article: 1.7] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/31/2022]
Abstract
Photolysis of trypto-CORM results in ultra-fast CO-dissociation and formation of a 16-e triplet followed by solvation.
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Affiliation(s)
| | | | | | - Ian P. Clark
- Central Laser Facility
- STFC Rutherford Appleton Laboratory
- Didcot
- UK
| | | | - Michael Towrie
- Central Laser Facility
- STFC Rutherford Appleton Laboratory
- Didcot
- UK
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39
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A gentle introduction to gasotransmitters with special reference to nitric oxide: biological and chemical implications. REV INORG CHEM 2018. [DOI: 10.1515/revic-2018-0011] [Citation(s) in RCA: 17] [Impact Index Per Article: 2.4] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/15/2022]
Abstract
AbstractNitric oxide (NO), carbon monoxide (CO) and hydrogen sulfide (H2S) are gaseous molecules of major impact in biology. Despite their toxicity, these molecules have profound effects on mammalian physiology and major implications in therapeutics. At tiny concentrations in human biology, they play key signaling and regulatory functions and hence are now labeled as “gasotransmitters.” In this literature survey, an introduction to gasotransmitters in relevance with NO, CO and H2S has been primarily focused. A special attention has been given to the conjoint physiological, pathophysiological and therapeutic aspects of NO in this work. In addition to the aforementioned elements of the investigation being reported, this report gives a detailed account of some of the recent advancements covering the NO release from both the nitro as well as nitroso compounds. The importance of the metallic center on the eve of producing the reduction center on NO and to develop photolabile properties have been elaborated within the effect of a few examples of metallic centers. Also, theoretical investigations that have been reported in the recent past and some other current theories pertaining to NO chemistry have been enlightened in this review. From the overall study, it is eminent that a number of facts are yet to be explored in context with NO for deeper mechanistic insights, model design for these molecules, other key roles and the search to find the best fit formalism in theoretical chemistry.
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Lin D, Lin YC, Yang SW, Zhou L, Leong WK, Feng SY, Kong KV. Organometallic-Constructed Tip-Based Dual Chemical Sensing by Tip-Enhanced Raman Spectroscopy for Diabetes Detection. ACS APPLIED MATERIALS & INTERFACES 2018; 10:41902-41908. [PMID: 30387600 DOI: 10.1021/acsami.8b11950] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/08/2023]
Abstract
Tip-enhanced Raman spectroscopy (TERS) is capable of probing specific molecular information with high sensitivity, but dual chemical sensing remains a challenge. Another major hindrance to TERS chemical detection in biosamples such as blood is the interference from the strong absorptions of biomolecules. Herein, we report the preparation of an organometallic-conjugated TERS tip. We demonstrate that organometallic chemistry can be perfectly coupled with TERS for dual-molecule sensing. The unique Raman signals generated by the organometallic compound circumvent signal interference from the biomolecules in blood, allowing the rapid analysis of two important molecules (glucose and thiol) in ultralow volume (50 nL) samples. This enabled a correlation between the thiol and glucose levels in the blood of nondiabetic and diabetic patients to be drawn.
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Affiliation(s)
- Duo Lin
- Key Laboratory of OptoElectronic Science and Technology for Medicine, Ministry of Education, Fujian Provincial Key Laboratory for Photonics Technology , Fujian Normal University , Fuzhou 350007 , China
- College of Integrated Traditional Chinese and Western Medicine , Fujian University of Traditional Chinese Medicine , Fuzhou 350122 , China
| | - Yi-Cheng Lin
- Department of Chemistry , National Taiwan University , Taipei 10617 , Taiwan
| | - Shang-Wei Yang
- Department of Chemistry , National Taiwan University , Taipei 10617 , Taiwan
| | - Lan Zhou
- Department of Urology, Shanghai East Hospital , Tongji University School of Medicine , Shanghai 200000 , China
| | - Weng Kee Leong
- Division of Chemistry & Biological Chemistry , Nanyang Technological University , 639798 , Singapore
| | - Shang-Yuan Feng
- Key Laboratory of OptoElectronic Science and Technology for Medicine, Ministry of Education, Fujian Provincial Key Laboratory for Photonics Technology , Fujian Normal University , Fuzhou 350007 , China
| | - Kien Voon Kong
- Department of Chemistry , National Taiwan University , Taipei 10617 , Taiwan
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Li J, Zhang J, Zhang Q, Bai Z, Zhao Q, He D, Wang Z, Chen Y, Liu B. Syntheses and anti-cancer activity of CO-releasing molecules with targeting galactose receptors. Org Biomol Chem 2018; 16:8115-8129. [PMID: 30334056 DOI: 10.1039/c8ob01921e] [Citation(s) in RCA: 8] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
Abstract
CO-releasing molecules (CORMs) containing cobalt have many bioactivities, but most of them do not dissolve in water and have no selectivity to tissue and organs. On the basis of the specific recognition of galactose or sialic acid by a receptor, a series of CORMs based on carbohydrates were synthesized and evaluated. The test results show that all the complexes displayed anticancer activity. Among them, the effects of the complexes of galactose (1), GalNAc (8) and sialic acid (10) were very distinct. Complex 1 displayed higher activity against HeLa, HePG2, MCF-7 and HT-29 cell proliferation than cis-platin (DDP), and its selectivity was far much better than DDP compared with normal cell W138. Furthermore, the uptakes of complexes 1, 8 and 10 by HePG2, HT-29, A549 and RAW264.7 cell lines were studied. The uptake ratio of each cell line for complex 1 was different, and the order of uptake ratio in the four cell lines was HePG2 > HT-29 > RAW264.7 > A549. The HePG2 cells absorbed complex 1 beyond 60% after incubation for 8 h, while A549 absorbed only 27.8%. For complex 8, the uptake trend was similar to that of complex 1 with it being absorbed by all the four cancer cells, but the uptake rate was lower. However, differently, complex 10 was absorbed heavily by macrophage RAW264.7, followed by HePG2; after 8 h incubation, the uptake ratio of RAW264.7 was over 50%. In addition, the mechanism of action was explored, and the results showed that the complexes inhibited cell cycle arrest at the G2/M phase; complex 1 up-regulated the expression levels of caspase-3 and Bax, and down-regulated the Bcl-2 expression, giving rise to HePG2 cell apoptosis.
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Affiliation(s)
- Jili Li
- Institute of Medicinal Chemistry, School of Pharmacy of Lanzhou University, Lanzhou 730000, China.
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Synthesis and biological activities of carbonyl cobalt CORMs with selectively inhibiting cyclooxygenase-2. J Organomet Chem 2018. [DOI: 10.1016/j.jorganchem.2018.08.013] [Citation(s) in RCA: 8] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/24/2022]
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Musikhina AA, Utepova IA, Chupakhin ON, Charushin VN, Slepukhin PA. Transition metal-free regioselective cross-coupling of azine N-oxides with cymantrenyl lithium. J Organomet Chem 2018. [DOI: 10.1016/j.jorganchem.2018.06.008] [Citation(s) in RCA: 7] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/19/2023]
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Jin Z, Zhao P, Zhang J, Yang T, Zhou G, Zhang D, Wang T, He Q. Intelligent Metal Carbonyl Metal-Organic Framework Nanocomplex for Fluorescent Traceable H 2 O 2 -Triggered CO Delivery. Chemistry 2018; 24:11667-11674. [PMID: 29851158 DOI: 10.1002/chem.201801407] [Citation(s) in RCA: 43] [Impact Index Per Article: 6.1] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/19/2018] [Revised: 05/29/2018] [Indexed: 01/14/2023]
Abstract
The recognized therapeutic benefits from carbon monoxide (CO) have caused booming attention to develop a CO therapy for various major diseases, such as cancer. However, the controlled release of CO gas and the monitoring of the CO release are vitally important to the on-demand CO administration for a safe and efficient therapy, but greatly challenging. In this work, a new CO-releasing nanocomplex was constructed by the adsorption and coordination of manganese carbonyl ([MnBr(CO)5 ], abbreviated as MnCO) with a Ti-based metal-organic framework (Ti-MOF) to realize an intratumoral H2 O2 -triggered CO release and real-time CO release monitoring by fluorescence imaging. A high CO prodrug loading capacity (0.532 g MnCO per gram Ti-MOF) is achieved due to the high surface area of Ti-MOF, and the intracellular H2 O2 -triggered CO release from the MnCO@Ti-MOF is realized to enable the nanocomplex selectively release CO in tumor cells and kill tumor cells rather than normal cells. Particularly significant is that the real-time fluorescence imaging monitoring of the CO release is realized based on an annihilation effect of the fluorescence after MnCO loading into Ti-MOF and an activation effect of the fluorescence after CO release from Ti-MOF. The quantitative relationship between the fluorescence intensity and the released CO amount is established in great favor of guiding on-demand CO administration. The results demonstrate the advantage of versatile MOFs for high efficient CO delivery and monitoring, which is critical for the improvement of the effectiveness of future therapeutic application.
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Affiliation(s)
- Zhaokui Jin
- Guangdong Provincial Key Laboratory of Biomedical, Measurements and Ultrasound Imaging, National-Regional Key Technology Engineering, Laboratory for Medical Ultrasound, School of Biomedical Engineering, Health Science Center, Shenzhen University, No. 3688 Nanhai Road, Nanshan District, Shenzhen, 518060, Guangdong, China
| | - Penghe Zhao
- Guangdong Provincial Key Laboratory of Biomedical, Measurements and Ultrasound Imaging, National-Regional Key Technology Engineering, Laboratory for Medical Ultrasound, School of Biomedical Engineering, Health Science Center, Shenzhen University, No. 3688 Nanhai Road, Nanshan District, Shenzhen, 518060, Guangdong, China
| | - Junheng Zhang
- Key Laboratory of Catalysis and Materials Science of the, State Ethnic Affairs Commission and Ministry of Education, South-Central University for Nationalities, Wuhan, 430074, Hubei Province, China
| | - Tian Yang
- Guangdong Provincial Key Laboratory of Biomedical, Measurements and Ultrasound Imaging, National-Regional Key Technology Engineering, Laboratory for Medical Ultrasound, School of Biomedical Engineering, Health Science Center, Shenzhen University, No. 3688 Nanhai Road, Nanshan District, Shenzhen, 518060, Guangdong, China
| | - Gaoxin Zhou
- Guangdong Provincial Key Laboratory of Biomedical, Measurements and Ultrasound Imaging, National-Regional Key Technology Engineering, Laboratory for Medical Ultrasound, School of Biomedical Engineering, Health Science Center, Shenzhen University, No. 3688 Nanhai Road, Nanshan District, Shenzhen, 518060, Guangdong, China
| | - Daohong Zhang
- Key Laboratory of Catalysis and Materials Science of the, State Ethnic Affairs Commission and Ministry of Education, South-Central University for Nationalities, Wuhan, 430074, Hubei Province, China
| | - Tianfu Wang
- Guangdong Provincial Key Laboratory of Biomedical, Measurements and Ultrasound Imaging, National-Regional Key Technology Engineering, Laboratory for Medical Ultrasound, School of Biomedical Engineering, Health Science Center, Shenzhen University, No. 3688 Nanhai Road, Nanshan District, Shenzhen, 518060, Guangdong, China
| | - Qianjun He
- Guangdong Provincial Key Laboratory of Biomedical, Measurements and Ultrasound Imaging, National-Regional Key Technology Engineering, Laboratory for Medical Ultrasound, School of Biomedical Engineering, Health Science Center, Shenzhen University, No. 3688 Nanhai Road, Nanshan District, Shenzhen, 518060, Guangdong, China
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Lin D, Gong T, Hong ZY, Qiu S, Pan J, Tseng CY, Feng S, Chen R, Kong KV. Metal Carbonyls for the Biointerference-Free Ratiometric Surface-Enhanced Raman Spectroscopy-Based Assay for Cell-Free Circulating DNA of Epstein-Barr Virus in Blood. Anal Chem 2018; 90:7139-7147. [PMID: 29808995 DOI: 10.1021/acs.analchem.8b01931] [Citation(s) in RCA: 26] [Impact Index Per Article: 3.7] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/03/2023]
Abstract
By taking advantage of the spectral properties of metal carbonyls, we have designed a surface-enhanced Raman spectroscopy (SERS) ratiometric assay for measuring cell-free circulating DNA (cfDNA) from Epstein-Barr virus in blood for nasopharyngeal carcinoma (NPC). This assay consists of a rhenium carbonyl (Re-CO) to serve as a DNA probe, an osmium carbonyl (Os-CO) embedded within the SERS-active substrate as an internal reference, and a streptavidin layer on the surface of the substrate. Hybridization of cfDNA with biotinylated-capture sequence leads to immobilization of cfDNA on the substrate. The binding of Re-CO via daunorubicin (DNR) to cfDNA is accompanied by an appearance of a strong symmetry stretching vibrations peak at 2113 cm-1, which has spectral overlap with Os-CO (2025 cm-1). This results in an increase in the I2113/ I2025 ratio and quantitatively correlates with cfDNA. This SERS assay can be readily used to detect cfDNA in blood samples from patients due to the intensity ratio of I2113/ I2025 lying in a silent region (1780-2200 cm-1) in the SERS spectrum of the biomolecules.
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Affiliation(s)
- Duo Lin
- Key Laboratory of OptoElectronic Science and Technology for Medicine, Ministry of Education , Fujian Normal University , Fuzhou , Fujian 350007 , China.,College of Integrated Traditional Chinese & Western Medicine , Fujian University of Traditional Chinese Medicine , Fuzhou , Fujian 350122 , China
| | - Tianxun Gong
- State Key Laboratory of Electronic Thin Films and Integrated Devices , University of Electronic Science and Technology of China , Chengdu , Sichuan 610054 China
| | - Zi-Yao Hong
- Department of Chemistry , National Taiwan University , Taipei 10617 , Taiwan
| | - Sufang Qiu
- Department of Radiation Oncology , Fujian Provincial Cancer Hospital and Fujian Medical University Cancer Hospital , Fuzhou , Fujian 350014 , China
| | - Jianji Pan
- Department of Radiation Oncology , Fujian Provincial Cancer Hospital and Fujian Medical University Cancer Hospital , Fuzhou , Fujian 350014 , China
| | - Chinh-Yu Tseng
- Department of Chemistry , National Taiwan University , Taipei 10617 , Taiwan
| | - Shangyuan Feng
- Key Laboratory of OptoElectronic Science and Technology for Medicine, Ministry of Education , Fujian Normal University , Fuzhou , Fujian 350007 , China
| | - Rong Chen
- Key Laboratory of OptoElectronic Science and Technology for Medicine, Ministry of Education , Fujian Normal University , Fuzhou , Fujian 350007 , China
| | - Kien Voon Kong
- Department of Chemistry , National Taiwan University , Taipei 10617 , Taiwan
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Kim SY, Ma SY, Kang SO, Lee JD. B-phenylated o-carboranes and its chromium derivatives: Synthesis, electrochemical properties, and X-ray structural studies. J Organomet Chem 2018. [DOI: 10.1016/j.jorganchem.2018.02.048] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
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Battistin F, Balducci G, Milani B, Alessio E. Water-Soluble Ruthenium(II) Carbonyls with 1,3,5-Triaza-7-phosphoadamantane. Inorg Chem 2018; 57:6991-7005. [DOI: 10.1021/acs.inorgchem.8b00698] [Citation(s) in RCA: 11] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/30/2022]
Affiliation(s)
- Federica Battistin
- Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy
| | - Gabriele Balducci
- Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy
| | - Barbara Milani
- Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy
| | - Enzo Alessio
- Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy
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Kaczmarek R, Korczyński D, Królewska‐Golińska K, Wheeler KA, Chavez FA, Mikus A, Dembinski R. Organometallic Nucleosides: Synthesis and Biological Evaluation of Substituted Dicobalt Hexacarbonyl 2'-Deoxy-5-oxopropynyluridines. ChemistryOpen 2018; 7:237-247. [PMID: 29531887 PMCID: PMC5838391 DOI: 10.1002/open.201700168] [Citation(s) in RCA: 6] [Impact Index Per Article: 0.9] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/27/2017] [Indexed: 01/16/2023] Open
Abstract
Reactions of dicobalt octacarbonyl [Co2(CO)8] with 2'-deoxy-5-oxopropynyluridines and related compounds gave dicobalt hexacarbonyl nucleoside complexes (83-31 %). The synthetic outcomes were confirmed by X-ray structure determination of dicobalt hexacarbonyl 2'-deoxy-5-(4-hydroxybut-1-yn-1-yl)uridine, which exhibits intermolecular hydrogen bonding between a modified base and ribose. The electronic structure of this compound was characterized by the DFT calculations. The growth inhibition of HeLa and K562 cancer cell lines by organometallic nucleosides was examined and compared to that by alkynyl nucleoside precursors. Coordination of the dicobalt carbonyl moiety to the 2'-deoxy-5-alkynyluridines led to a significant increase in the cytotoxic potency. The cobalt compounds displayed antiproliferative activities with median inhibitory values (IC50) in the range of 20 to 80 μm for the HeLa cell line and 18 to 30 μm for the K562 cell line. Coordination of an acetyl-substituted cobalt nucleoside was expanded by using the 1,1-bis(diphenylphosphino)methane (dppm) ligand, which exhibited cytotoxicity at comparable levels. The formation of reactive oxygen species in the presence of cobalt compounds was determined in K562 cells. The results indicate that the mechanism of action for most antiproliferative cobalt compounds may be related to the induction of oxidative stress.
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Affiliation(s)
- Renata Kaczmarek
- Department of Bioorganic ChemistryCentre of Molecular and Macromolecular StudiesPolish Academy of SciencesSienkiewicza 11290–363ŁódźPoland
| | - Dariusz Korczyński
- Department of Bioorganic ChemistryCentre of Molecular and Macromolecular StudiesPolish Academy of SciencesSienkiewicza 11290–363ŁódźPoland
| | - Karolina Królewska‐Golińska
- Department of Bioorganic ChemistryCentre of Molecular and Macromolecular StudiesPolish Academy of SciencesSienkiewicza 11290–363ŁódźPoland
| | - Kraig A. Wheeler
- Department of ChemistryWhitworth University300 W. Hawthorne Rd.SpokaneWA99251USA
| | - Ferman A. Chavez
- Department of ChemistryOakland University146 Library DriveRochesterMI48309-4479USA
| | - Agnieszka Mikus
- Department of ChemistryOakland University146 Library DriveRochesterMI48309-4479USA
| | - Roman Dembinski
- Department of Bioorganic ChemistryCentre of Molecular and Macromolecular StudiesPolish Academy of SciencesSienkiewicza 11290–363ŁódźPoland
- Department of ChemistryOakland University146 Library DriveRochesterMI48309-4479USA
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50
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Metallocarbonyl complexes: (η5-C5H5)M(CO)n(η1-N-imidato) (M = Fe, Ru, Mo, W; n = 2, 3) as new photoactive CO-releasing molecules (CORMs). J Photochem Photobiol A Chem 2018. [DOI: 10.1016/j.jphotochem.2017.10.012] [Citation(s) in RCA: 9] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/23/2022]
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