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1
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Ugwu DI, Conradie J. Anticancer properties of complexes derived from bidentate ligands. J Inorg Biochem 2023; 246:112268. [PMID: 37301166 DOI: 10.1016/j.jinorgbio.2023.112268] [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] [Received: 03/30/2023] [Revised: 05/09/2023] [Accepted: 05/27/2023] [Indexed: 06/12/2023]
Abstract
Cancer is the abnormal division and multiplication of cells in an organ or tissue. It is the second leading cause of death globally. There are various types of cancer such as prostate, breast, colon, lung, stomach, liver, skin, and many others depending on the tissue or organ where the abnormal growth originates. Despite the huge investment in the development of anticancer agents, the transition of research to medications that improve substantially the treatment of cancer is less than 10%. Cisplatin and its analogs are ubiquitous metal-based anticancer agents notable for the treatment of various cancerous cells and tumors but unfortunately accompanied by large toxicities due to low selectivity between cancerous and normal cells. The improved toxicity profile of cisplatin analogs bearing bidentate ligands has motivated the synthesis of vast metal complexes of bidentate ligands. Complexes derived from bidentate ligands such as β-diketones, diolefins, benzimidazoles and dithiocarbamates have been reported to possess 20 to 15,600-fold better anticancer activity, when tested on cell lines, than some known antitumor drugs currently on the market, e.g. cisplatin, oxaliplatin, carboplatin, doxorubicin, and 5-fluorouracil. This work discusses the anticancer properties of various metal complexes derived from bidentate ligands, for possible application in chemotherapy. The results discussed were evaluated by the IC50 values as obtained from cell line tests on various metal-bidentate complexes. The structure-activity relationship study of the complexes discussed, revealed that hydrophobicity is a key factor that influences anticancer properties of molecules.
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Affiliation(s)
- David Izuchukwu Ugwu
- Department of Chemistry, University of the Free State, South Africa; Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
| | - Jeanet Conradie
- Department of Chemistry, University of the Free State, South Africa.
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2
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Cebotari D, Buils J, Garbuz O, Balan G, Marrot J, Guérineau V, Touboul D, Haouas M, Segado-Centelles M, Bo C, Gulea A, Floquet S. A new series of bioactive Mo (V)2O 2S 2-based thiosemicarbazone complexes: Solution and DFT studies, and antifungal and antioxidant activities. J Inorg Biochem 2023; 245:112258. [PMID: 37244168 DOI: 10.1016/j.jinorgbio.2023.112258] [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] [Received: 02/26/2023] [Revised: 05/09/2023] [Accepted: 05/15/2023] [Indexed: 05/29/2023]
Abstract
This paper deals with the synthesis, characterization, and studies of biological properties of a series of 5 coordination compounds based on binuclear core [Mo(V)2O2S2]2+ with thiosemicarbazones ligands bearing different substituents on the R1 position of the ligand. The complexes are first studied using MALDI-TOF mass spectrometry and NMR spectroscopy to determine their structures in solution in relation to single-crystal X-Ray diffraction data. In a second part, the antifungal and antioxidative activities are explored and the high potential of these coordination compounds compared to the uncoordinated ligands is demonstrated for these properties. Finally, DFT calculation provides important support to the solution studies by identifying the most stable isomers in each [Mo2O2S2]2+/Ligand system, while the determination of HUMO and LUMO levels is performed to explain the antioxidative properties of these systems.
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Affiliation(s)
- Diana Cebotari
- Institute Lavoisier de Versailles, CNRS UMR 8180, Univ. Versailles Saint Quentin en Yvelines, Université Paris-Saclay, 45 av. des Etats-Unis, 78035 Versailles cedex, France; State University of Moldova, 60 Alexei Mateevici str., MD-2009, Chisinau, Republic of Moldova
| | - Jordi Buils
- Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain; Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Tarragona, Spain
| | - Olga Garbuz
- Institute of Zoology, 1 Academiei str., MD-2028, Chisinau, Republic of Moldova
| | - Greta Balan
- State University of Medicine and Pharmacy "Nicolae Testemiţanu", 165 Ştefan cel Mare and Sfânt Street, Chişinău MD-2004, Republic of Moldova
| | - Jérôme Marrot
- Institute Lavoisier de Versailles, CNRS UMR 8180, Univ. Versailles Saint Quentin en Yvelines, Université Paris-Saclay, 45 av. des Etats-Unis, 78035 Versailles cedex, France
| | - Vincent Guérineau
- Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France
| | - David Touboul
- Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France
| | - Mohamed Haouas
- Institute Lavoisier de Versailles, CNRS UMR 8180, Univ. Versailles Saint Quentin en Yvelines, Université Paris-Saclay, 45 av. des Etats-Unis, 78035 Versailles cedex, France
| | - Mireia Segado-Centelles
- Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
| | - Carles Bo
- Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain.
| | - Aurelian Gulea
- State University of Moldova, 60 Alexei Mateevici str., MD-2009, Chisinau, Republic of Moldova.
| | - Sébastien Floquet
- Institute Lavoisier de Versailles, CNRS UMR 8180, Univ. Versailles Saint Quentin en Yvelines, Université Paris-Saclay, 45 av. des Etats-Unis, 78035 Versailles cedex, France.
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3
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Gopal J, Muthu M, Sivanesan I. A Comprehensive Survey on the Expediated Anti-COVID-19 Options Enabled by Metal Complexes-Tasks and Trials. Molecules 2023; 28:molecules28083354. [PMID: 37110587 PMCID: PMC10143858 DOI: 10.3390/molecules28083354] [Citation(s) in RCA: 3] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/02/2023] [Revised: 03/31/2023] [Accepted: 04/07/2023] [Indexed: 04/29/2023] Open
Abstract
Contemporary pharmacology dating back to the late 19th/early 20th centuries has benefitted largely from the incorporation of metal complexes. Various biological attributes have been successfully realized using metal/metal complex-based drugs. Among anticancer, antimicrobial, and antiviral applications, anticancer applications have extracted the maximum benefit from the metal complex, Cisplatin. The following review has compiled the various antiviral benefits harnessed through inputs from metal complexes. As a result of exploiting the pharmacological aspects of metal complexes, the anti-COVID-19 deliverables have been summarized. The challenges ahead, the gaps in this research area, the need to improvise incorporating nanoaspects in metal complexes, and the need to test metal complex-based drugs in clinical trials have been discussed and deliberated. The pandemic shook the entire world and claimed quite a percentage of the global population. Metal complex-based drugs are already established for their antiviral property with respect to enveloped viruses and extrapolating them for COVID-19 can be an effective way to manipulate drug resistance and mutant issues that the current anti-COVID-19 drugs are facing.
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Affiliation(s)
- Judy Gopal
- Department of Research and Innovation, Saveetha School of Engineering, Saveetha Institute of Medical and Technical Sciences (SIMATS), Chennai 602105, Tamil Nadu, India
| | - Manikandan Muthu
- Department of Research and Innovation, Saveetha School of Engineering, Saveetha Institute of Medical and Technical Sciences (SIMATS), Chennai 602105, Tamil Nadu, India
| | - Iyyakkannu Sivanesan
- Department of Bioresources and Food Science, Institute of Natural Science and Agriculture, Konkuk University, Gwangjin-gu, Seoul 05029, Republic of Korea
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4
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Fernández-Fariña S, Velo-Heleno I, Carballido R, Martínez-Calvo M, Barcia R, Palacios Ò, Capdevila M, González-Noya AM, Pedrido R. Exploring the Biological Properties of Zn(II) Bisthiosemicarbazone Helicates. Int J Mol Sci 2023; 24:ijms24032246. [PMID: 36768568 PMCID: PMC9916454 DOI: 10.3390/ijms24032246] [Citation(s) in RCA: 2] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 12/22/2022] [Revised: 01/10/2023] [Accepted: 01/20/2023] [Indexed: 01/24/2023] Open
Abstract
The design of artificial helicoidal molecules derived from metal ions with biological properties is one of the objectives within metallosupramolecular chemistry. Herein, we report three zinc helicates derived from a family of bisthiosemicarbazone ligands with different terminal groups, Zn2(LMe)2∙2H2O 1, Zn2(LPh)2∙2H2O 2 and Zn2(LPhNO2)23, obtained by an electrochemical methodology. These helicates have been fully characterized by different techniques, including X-ray diffraction. Biological studies of the zinc(II) helicates such as toxicity assays with erythrocytes and interaction studies with proteins and oligonucleotides were performed, demonstrating in all cases low toxicity and an absence of covalent interaction with the proteins and oligonucleotides. The in vitro cytotoxicity of the helicates was tested against MCF-7 (human breast carcinoma), A2780 (human ovarian carcinoma cells), NCI-H460 (human lung carcinoma cells) and MRC-5 (normal human lung fibroblasts), comparing the IC50 values with cisplatin. We will try to demonstrate if the terminal substituent of the ligand precursor exerts any effect in toxicity or in the antitumor activity of the zinc helicates.
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Affiliation(s)
- Sandra Fernández-Fariña
- Departamento de Química Inorgánica, Facultade de Química, Campus Vida, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
- Correspondence: (S.F.-F.); (A.M.G.-N.)
| | - Isabel Velo-Heleno
- Departamento de Química Inorgánica, Facultade de Química, Campus Vida, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
| | - Rocío Carballido
- Departamento de Química Inorgánica, Facultade de Química, Campus Vida, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
| | - Miguel Martínez-Calvo
- Departamento de Química Inorgánica, Facultade de Química, Campus Vida, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
| | - Ramiro Barcia
- Departamento de Bioquímica y Biología Molecular, Facultade de Veterinaria, Campus Terra, Universidade de Santiago de Compostela, 27002 Lugo, Spain
| | - Òscar Palacios
- Departament de Química, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Spain
| | - Mercè Capdevila
- Departament de Química, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Spain
| | - Ana M. González-Noya
- Departamento de Química Inorgánica, Facultade de Química, Campus Vida, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
- Correspondence: (S.F.-F.); (A.M.G.-N.)
| | - Rosa Pedrido
- Departamento de Química Inorgánica, Facultade de Química, Campus Vida, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
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5
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Mamta P, Chaudhary A. Synthesis, Spectroscopic elucidation, In vitro Antimicrobial, Cytotoxic and CT-DNA binding Evaluation of Heterobimetallic Complexes of Ni(II) with Main Group/Transition Metal dichlorides. J Mol Struct 2023. [DOI: 10.1016/j.molstruc.2023.134936] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/15/2023]
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6
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Synthesis and crystal structures of zinc complexes derived from N,N'-bis(4-bromosalicylidene)-1,3-propanediamine with antimicrobial activity. Polyhedron 2022. [DOI: 10.1016/j.poly.2022.116090] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/18/2023]
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7
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Dong X, Wang H, Zhang H, Li M, Huang Z, Wang Q, Li X. Copper-thiosemicarbazone complexes conjugated-cellulose fibers: Biodegradable materials with antibacterial capacity. Carbohydr Polym 2022; 294:119839. [PMID: 35868782 DOI: 10.1016/j.carbpol.2022.119839] [Citation(s) in RCA: 5] [Impact Index Per Article: 1.7] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/09/2022] [Revised: 06/09/2022] [Accepted: 07/04/2022] [Indexed: 11/24/2022]
Abstract
Personal protective equipment (PPE) is vital in battling bacteria crisis, but conventional PPE materials lack antimicrobial activities and environmental friendliness. Our work focused on developing biodegradable and antibacterial fibers as promising bioprotective materials. Here, we grafted highly effective antibacterial copper-thiosemicarbazone complexes (CT1-4) on cellulose fibers via covalent linkages. Multiple methods were used to characterize the chemical composition or morphology of CT1-4 conjugated-fibers. Conjugation of CT1-4 maintains the mechanical properties (Breaking strength: 2.35-2.45 cN/dtex, Breaking elongation: 7.19 %-7.42 %) and thermal stability of fibers. CT1 can endow cellulose fibers with the excellent growth inhibition towards Escherichia coli (E. coli) (GIR: 61.5 % ± 1.28 %), Staphylococcus aureus (S. aureus) (GIR: 85.7 % ± 1.93 %), and Bacillus subtilis (B. subtilis) (GIR: 87.6 % ± 1.44 %). We believe that the application of CT1 conjugated-cellulose fibers is not limited to the high-performance PPE, and also can be extended to various types of protective equipment for food and medicine safety.
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Affiliation(s)
- Xiongwei Dong
- National Local Joint Engineering Laboratory for Advanced Textile Processing and Clean Production, Wuhan Textile University, Wuhan 430073, Hubei, PR China
| | - Huipeng Wang
- National Local Joint Engineering Laboratory for Advanced Textile Processing and Clean Production, Wuhan Textile University, Wuhan 430073, Hubei, PR China
| | - Hui Zhang
- School of Fashion of Wuhan Textile University, Wuhan Textile University, Wuhan 430073, Hubei, PR China
| | - Man Li
- School of Chemistry, Central China Normal University, Wuhan 430079, Hubei, PR China
| | - Zheng Huang
- Best Textile Co., Ltd. Yichang, 443200, Hubei, PR China
| | - Qian Wang
- National Local Joint Engineering Laboratory for Advanced Textile Processing and Clean Production, Wuhan Textile University, Wuhan 430073, Hubei, PR China.
| | - Xiang Li
- National Local Joint Engineering Laboratory for Advanced Textile Processing and Clean Production, Wuhan Textile University, Wuhan 430073, Hubei, PR China; College of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062, Hubei, PR China; College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, PR China.
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8
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A New Hybrid ligand and its metal complexes From a Natural Plant (
Styrax officinalis
) bearing Egonol, Thiosemicarbazone and Oxime Units, and Their Anti‐cancer Activities. Appl Organomet Chem 2022. [DOI: 10.1002/aoc.6784] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/07/2022]
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9
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Parsekar S, Paliwal K, Haldar P, Antharjanam PKS, Kumar M. Synthesis, Characterization, Crystal Structure, DNA and HSA Interactions, and Anticancer Activity of a Mononuclear Cu(II) Complex with a Schiff Base Ligand Containing a Thiadiazoline Moiety. ACS OMEGA 2022; 7:2881-2896. [PMID: 35097283 PMCID: PMC8792924 DOI: 10.1021/acsomega.1c05750] [Citation(s) in RCA: 35] [Impact Index Per Article: 11.7] [Reference Citation Analysis] [Abstract] [Grants] [Track Full Text] [Download PDF] [Figures] [Subscribe] [Scholar Register] [Received: 10/14/2021] [Accepted: 12/30/2021] [Indexed: 05/07/2023]
Abstract
A mononuclear Cu(II) complex [Cu(HL)(o-phen)]·H2O (1) [H3L =, o-phen = 1,10-phenanthroline] was isolated from methanol, and its X-ray single-crystal structure was determined. Frozen glass X-band EPR of 1 in dimethylformamide (DMF) at LNT showed a spectrum that is characteristic of a monomeric tetragonal character with g ∥ = 2.164, g ⊥ = 2.087, A ∥ = 19.08 mT, and A ⊥ ≤ 4 mT. Electronic spectroscopic studies using calf thymus DNA (CT-DNA) showed strong binding affinity of 1 as reflected from its intrinsic binding constant (K b) value of 2.85 × 105 M-1. Competitive behavior of 1 with ethidium bromide (EB) displayed intercalative binding of DNA (K app = 1.3 × 106 M-1). The compound displayed significant oxidative cleavage of pUC19 DNA. The interaction between HSA and complex 1 was examined by employing fluorescence and electronic absorption spectroscopic experiments. The secondary and tertiary structures of HSA were found to be altered as suggested by three-dimensional (3D) fluorescence experiments. The affinity of 1 to bind to HSA was found to be strong as indicated from its value of the binding constant (K a = 2.89 × 105 M-1). Intrinsic fluorescence of the protein was found to be reduced through a mechanism of static quenching as suggested from the k q (2.01 × 1013 M-1 s-1) value, the bimolecular quenching constant. The Förster resonance energy transfer (FRET) process may also be accounted for such a high k q value. The r value (2.85 nm) calculated from FRET theory suggested that the distance between complex 1 (acceptor) and HSA (donor) is quite close. Complex 1 primarily bound to HSA in subdomain IIA as suggested by molecular docking studies. IC50 values (0.80 and 0.43 μM, respectively) obtained from the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay with HeLa and MCF7 cells suggested remarkable in vitro anticancer activity of 1. Nuclear dual staining assays revealed that cell death occurred via apoptosis in HeLa cells and reactive oxygen species (ROS) accumulation caused apoptosis induction. On treatment with a 5 μM dose of 1 in HeLa cells, the cell population significantly increased in the G2/M phase, while it was decreased in G0/G1 and S phases as compared to the control, clearly indicating G2/M phase arrest.
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Affiliation(s)
- Sidhali
U. Parsekar
- Department
of Chemical Engineering, Birla Institute
of Technology and Science-Pilani, K.K. Birla Goa Campus, Zuarinagar 403726, Goa, India
| | - Kumudini Paliwal
- Department
of Chemical Engineering, Birla Institute
of Technology and Science-Pilani, K.K. Birla Goa Campus, Zuarinagar 403726, Goa, India
| | - Paramita Haldar
- Department
of Chemical Engineering, Birla Institute
of Technology and Science-Pilani, K.K. Birla Goa Campus, Zuarinagar 403726, Goa, India
| | | | - Manjuri Kumar
- Department
of Chemical Engineering, Birla Institute
of Technology and Science-Pilani, K.K. Birla Goa Campus, Zuarinagar 403726, Goa, India
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Lin Y, Betts H, Keller S, Cariou K, Gasser G. Recent developments of metal-based compounds against fungal pathogens. Chem Soc Rev 2021; 50:10346-10402. [PMID: 34313264 DOI: 10.1039/d0cs00945h] [Citation(s) in RCA: 56] [Impact Index Per Article: 14.0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/29/2022]
Abstract
This review provides insight into the rapidly expanding field of metal-based antifungal agents. In recent decades, the antibacterial resistance crisis has caused reflection on many aspects of public health where weaknesses in our medicinal arsenal may potentially be present - including in the treatment of fungal infections, particularly in the immunocompromised and those with underlying health conditions where mortality rates can exceed 50%. Combination of organic moieties with known antifungal properties and metal ions can lead to increased bioavailability, uptake and efficacy. Development of such organometallic drugs may alleviate pressure on existing antifungal medications. Prodigious antimicrobial moieties such as azoles, Schiff bases, thiosemicarbazones and others reported herein lend themselves easily to the coordination of a host of metal ions, which can vastly improve the biocidal activity of the parent ligand, thereby extending the library of antifungal drugs available to medical professionals for treatment of an increasing incidence of fungal infections. Overall, this review shows the impressive but somewhat unexploited potential of metal-based compounds to treat fungal infections.
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Affiliation(s)
- Yan Lin
- Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences, Laboratory for Inorganic Chemical Biology, 75005 Paris, France.
| | - Harley Betts
- Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences, Laboratory for Inorganic Chemical Biology, 75005 Paris, France.
| | - Sarah Keller
- Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences, Laboratory for Inorganic Chemical Biology, 75005 Paris, France.
| | - Kevin Cariou
- Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences, Laboratory for Inorganic Chemical Biology, 75005 Paris, France.
| | - Gilles Gasser
- Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences, Laboratory for Inorganic Chemical Biology, 75005 Paris, France.
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11
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Lobana TS, Indoria S, Sood H, Arora DS, Hundal G, Jasinski JP. Synthesis and structures of 3-nitro-salicylaldehyde-N-substituted thiosem-icarbazonates of copper(II): Novel bio-active materials against E. faecalis, E. coli, and K. pneumoniae. Inorganica Chim Acta 2021. [DOI: 10.1016/j.ica.2021.120334] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/17/2022]
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12
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Parsekar SU, Haldar P, Antharjanam PS, Kumar M, Koley AP. Synthesis, characterization, crystal structure, DNA and human serum albumin interactions, as well as antiproliferative activity of a Cu(II) complex containing a Schiff base ligand formed in situ from the Cu(II)‐induced cyclization of 1,5‐bis(salicylidene)thiocarbohydrazide. Appl Organomet Chem 2021. [DOI: 10.1002/aoc.6152] [Citation(s) in RCA: 6] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/24/2022]
Affiliation(s)
- Sidhali U. Parsekar
- Department of Chemical Engineering Birla Institute of Technology and Science‐Pilani, K.K. Birla Goa Campus Zuarinagar India
| | - Paramita Haldar
- Department of Chemical Engineering Birla Institute of Technology and Science‐Pilani, K.K. Birla Goa Campus Zuarinagar India
| | | | - Manjuri Kumar
- Department of Chemical Engineering Birla Institute of Technology and Science‐Pilani, K.K. Birla Goa Campus Zuarinagar India
| | - Aditya P. Koley
- Department of Chemistry Birla Institute of Technology and Science‐Pilani, K.K. Birla Goa Campus Zuarinagar India
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13
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Singh NK, Kumbhar AA, Pokharel YR, Yadav PN. Anticancer potency of copper(II) complexes of thiosemicarbazones. J Inorg Biochem 2020; 210:111134. [DOI: 10.1016/j.jinorgbio.2020.111134] [Citation(s) in RCA: 29] [Impact Index Per Article: 5.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/23/2020] [Revised: 05/31/2020] [Accepted: 06/06/2020] [Indexed: 12/20/2022]
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14
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Rajendran N, Kamatchi N, Periyasamy A, Solomon V. DNA-interaction, antibacterial and in vitro cytotoxic properties of copper(II) complexes bearing (E)-2-(2-(benzo[d]thiazol-2-ylthio)-1-phenylethylidene)thiosemicarbazone and diimine co-ligands. J COORD CHEM 2020. [DOI: 10.1080/00958972.2020.1751830] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/24/2022]
Affiliation(s)
- Neelaveni Rajendran
- PG and Research Department of Chemistry, Lady Doak College, Madurai, Tamil Nadu, India
| | - Nithya Kamatchi
- PG and Research Department of Zoology, Lady Doak College, Madurai, Tamil Nadu, India
| | - Abirami Periyasamy
- Department of Biotechnology, Lady Doak College, Madurai, Tamil Nadu, India
| | - Vasantha Solomon
- PG and Research Department of Chemistry, Lady Doak College, Madurai, Tamil Nadu, India
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15
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Ramachandran E, Gandin V, Bertani R, Sgarbossa P, Natarajan K, Bhuvanesh NSP, Venzo A, Zoleo A, Mozzon M, Dolmella A, Albinati A, Castellano C, Reis Conceição N, C. Guedes da Silva MF, Marzano C. Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones. Molecules 2020; 25:E1868. [PMID: 32316698 PMCID: PMC7221752 DOI: 10.3390/molecules25081868] [Citation(s) in RCA: 11] [Impact Index Per Article: 2.2] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/04/2020] [Revised: 04/11/2020] [Accepted: 04/13/2020] [Indexed: 02/06/2023] Open
Abstract
Three new 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde-thiosemicarbazones-N-4-substituted pro-ligands and their Cu(II) complexes (1, -NH2; 2, -NHMe; 3, -NHEt) have been prepared and characterized. In both the X-ray structures of 1 and 3, two crystallographically independent complex molecules were found that differ either in the nature of weakly metal-binding species (water in 1a and nitrate in 1b) or in the co-ligand (water in 3a and methanol in 3b). Electron Paramagnetic Resonance (EPR) measurements carried out on complexes 1 and 3 confirmed the presence of such different species in the solution. The electrochemical behavior of the pro-ligands and of the complexes was investigated, as well as their biological activity. Complexes 2 and 3 exhibited a high cytotoxicity against human tumor cells and 3D spheroids derived from solid tumors, related to the high cellular uptake. Complexes 2 and 3 also showed a high selectivity towards cancerous cell lines with respect to non-cancerous cell lines and were able to circumvent cisplatin resistance. Via the Transmission Electron Microscopy (TEM) imaging technique, preliminary insights into the biological activity of copper complexes were obtained.
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Affiliation(s)
- Eswaran Ramachandran
- Department of Industrial Engineering, University of Padova, 35131 Padova, Italy; (E.R.); (R.B.); (M.M.)
- Chemistry Research Center, National Engineering College, K. R. Nagar, Kovilpatti, Tamilnadu 628503, India
| | - Valentina Gandin
- Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, Italy; (V.G.); (A.D.); (C.M.)
| | - Roberta Bertani
- Department of Industrial Engineering, University of Padova, 35131 Padova, Italy; (E.R.); (R.B.); (M.M.)
| | - Paolo Sgarbossa
- Department of Industrial Engineering, University of Padova, 35131 Padova, Italy; (E.R.); (R.B.); (M.M.)
| | - Karuppannan Natarajan
- Department of Chemistry, Sri Ramakrishna Mission Vidyalaya College of Arts and Science, Coimbatore, Tamil Nadu 641020, India
| | | | - Alfonso Venzo
- Department of Chemical Sciences, University of Padova, 35131 Padova, Italy; (A.V.); (A.Z.)
| | - Alfonso Zoleo
- Department of Chemical Sciences, University of Padova, 35131 Padova, Italy; (A.V.); (A.Z.)
| | - Mirto Mozzon
- Department of Industrial Engineering, University of Padova, 35131 Padova, Italy; (E.R.); (R.B.); (M.M.)
| | - Alessandro Dolmella
- Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, Italy; (V.G.); (A.D.); (C.M.)
| | - Alberto Albinati
- Department of Chemistry, University of Milan, 20133 Milan, Italy; (A.A.); (C.C.)
| | - Carlo Castellano
- Department of Chemistry, University of Milan, 20133 Milan, Italy; (A.A.); (C.C.)
| | - Nuno Reis Conceição
- Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal; (N.R.C.); (M.F.C.G.d.S.)
| | - M. Fátima C. Guedes da Silva
- Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal; (N.R.C.); (M.F.C.G.d.S.)
| | - Cristina Marzano
- Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, Italy; (V.G.); (A.D.); (C.M.)
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Tavassoli M, Montazerozohori M, Naghiha R, Sadeghi H, Masoudiasl A, Joohari S, Lopez EV, Mahmoudi G. Some new nanostructure zinc complex: Synthesis, spectral analyses, crystal structure, Hirshfeld surface analyses, antimicrobial/anticancer, thermal behavior and usage as precursor for ZnO nanostructure. MATERIALS SCIENCE & ENGINEERING. C, MATERIALS FOR BIOLOGICAL APPLICATIONS 2020; 110:110642. [PMID: 32204075 DOI: 10.1016/j.msec.2020.110642] [Citation(s) in RCA: 14] [Impact Index Per Article: 2.8] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Subscribe] [Scholar Register] [Received: 02/13/2019] [Revised: 10/04/2019] [Accepted: 01/03/2020] [Indexed: 01/04/2023]
Abstract
In this work, a new tridentate ligand, its some novel zinc halide/pseudohalide complexes and their antimicrobial and cytotoxic effects of them are described. Characterization data of these compounds have been achieved via several physical and micro analytical techniques. As typical one, X-ray crystal structure analysis of zinc azide complex was run showing zinc center is penta-coordinated by three nitrogen atoms from Schiff base ligand and two terminal azide nitrogen atoms as a distorted square pyramidal geometry. Hirshfeld surfaces analysis clears the important role of interactions related to azide groups (NH⋯N and CH⋯N hydrogen bonds) in the stabilization of its supramolecular structure. According to data obtained from thermal analysis (TG/DTG/DTA), all complexes are decomposed at four or more thermal stages below 1000 °C. Moreover antimicrobial activities of the compounds were screened against some gram positive and gram negative bacteria. Furthermore anticancer activities of the complexes were studied against MDA-MB468 and k562 as two cancer cell lines. In final, three zinc complexes were also synthesized in nano scale by sonochemical method and one of them was utilized as the precursor for preparation of nanostructure ZnO confirmed by XRD pattern and SEM image.
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Affiliation(s)
| | | | - Reza Naghiha
- Department of Animal Sciences, Faculty of Agriculture, Yasouj University, Yasouj, Iran
| | - Hossein Sadeghi
- Medicinal Plants Research Center, Yasuj University of Medical Sciences, Yasuj, Iran
| | - Ardavan Masoudiasl
- Department of Chemistry, Faculty of Science, University of Maragheh, P.O. Box 55181-83111, Maragheh, Iran
| | - Shiva Joohari
- Department of Basic Sciences, Yasooj Branch, Islamic Azad University, Yasooj, Iran
| | | | - Ghodrat Mahmoudi
- Department of Chemistry, Faculty of Science, University of Maragheh, P.O. Box 55181-83111, Maragheh, Iran
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Syed Ali Fathima S, Mohamed Sahul Meeran M, Nagarajan E. Design and synthesis of novel pyrazolone based coordination compounds: DNA synergy, biological screening, apoptosis, molecular docking and in-silico ADMET profile. J Mol Struct 2019. [DOI: 10.1016/j.molstruc.2019.07.059] [Citation(s) in RCA: 6] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/29/2023]
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18
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Montazerozohori M, Musavi S, Masoudi-asl A, Mohammadi H, Naghiha R, Assoud A. Synthesis, spectral, crystal structural, antimicrobial, DNA interaction and thermal behavior of some new zinc halide complexes: 3D supramolecular structure of zinc bromide complex. ARAB J CHEM 2019. [DOI: 10.1016/j.arabjc.2014.11.005] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/24/2022] Open
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19
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Fathima SSA, Meeran MMS, Nagarajan ER. Synthesis, characterization and biological evaluation of novel 2,2′-((1,2-diphenylethane-1,2-diylidene)bis(azanylylidene))bis(pyridin-3-ol)and metal complexes: molecular docking and in silico ADMET profile. Struct Chem 2019. [DOI: 10.1007/s11224-019-01425-7] [Citation(s) in RCA: 13] [Impact Index Per Article: 2.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
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20
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The Use of Copper as an Antimicrobial Agent in Health Care, Including Obstetrics and Gynecology. Clin Microbiol Rev 2019; 32:32/4/e00125-18. [PMID: 31413046 DOI: 10.1128/cmr.00125-18] [Citation(s) in RCA: 83] [Impact Index Per Article: 13.8] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/20/2022] Open
Abstract
Health care-associated infections (HAIs) are a global problem associated with significant morbidity and mortality. Controlling the spread of antimicrobial-resistant bacteria is a major public health challenge, and antimicrobial resistance has become one of the most important global problems in current times. The antimicrobial effect of copper has been known for centuries, and ongoing research is being conducted on the use of copper-coated hard and soft surfaces for reduction of microbial contamination and, subsequently, reduction of HAIs. This review provides an overview of the historical and current evidence of the antimicrobial and wound-healing properties of copper and explores its possible utility in obstetrics and gynecology.
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21
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Rajendran N, Periyasamy A, Kamatchi N, Solomon V. Biological evaluation of copper(II) complexes on N(4)−substituted thiosemicarbazide derivatives and diimine co-ligands using DNA interaction, antibacterial and in vitro cytotoxicity. J COORD CHEM 2019. [DOI: 10.1080/00958972.2019.1634806] [Citation(s) in RCA: 6] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 02/08/2023]
Affiliation(s)
| | - Abirami Periyasamy
- Department of Biotechnology, Lady Doak College, Madurai, Tamil Nadu, India
| | - Nithya Kamatchi
- Department of Zoology, Lady Doak College, Madurai, Tamil Nadu, India
| | - Vasantha Solomon
- Department of Chemistry, Lady Doak College, Madurai, Tamil Nadu, India
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22
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Synthesis of novel (E)-2-((anthracen-9-ylmethylene)amino)pyridin-3-ol and its transition metal complexes: Multispectral characterization, biological evaluation and computational studies. J Mol Liq 2019. [DOI: 10.1016/j.molliq.2019.01.101] [Citation(s) in RCA: 11] [Impact Index Per Article: 1.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
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23
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Expatiating biological excellence of aminoantipyrine derived novel metal complexes: Combined DNA interaction, antimicrobial, free radical scavenging studies and molecular docking simulations. J Mol Struct 2019. [DOI: 10.1016/j.molstruc.2018.10.021] [Citation(s) in RCA: 19] [Impact Index Per Article: 3.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/31/2022]
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Alotaibi SH, Radwan AS, Abdel-Monem YK, Makhlouf MM. Synthesis, thermal behavior and optical characterizations of thin films of a novel thiazole azo dye and its copper complexes. SPECTROCHIMICA ACTA. PART A, MOLECULAR AND BIOMOLECULAR SPECTROSCOPY 2018; 205:364-375. [PMID: 30036804 DOI: 10.1016/j.saa.2018.07.043] [Citation(s) in RCA: 8] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Subscribe] [Scholar Register] [Received: 04/05/2018] [Revised: 07/11/2018] [Accepted: 07/13/2018] [Indexed: 06/08/2023]
Abstract
In the present paper, a novel dye of 4-methyl-5-(4-acetylphenyldiazenyl)thiazol-2-amine (L) and its corresponding copper complexes are synthesized and characterized using different techniques including elemental analysis, thermal analysis, 1H NMR, Mass, and FT-IR spectra. The thermal behavior of L and its complexes is carried out and discussed using thermogravimetric analysis, and it observed that the type of copper substituent affects the thermal decomposition of complexes. Homogenous thin films of L and its complexes are successfully grown onto quartz substrates using spin coating technique. Optical features and spectral phenomena of the thin films are studied using spectrophotometric measurements of absorbance, transmittance and reflectance. The optical constants such as refractive index, extinction coefficient, optical conductivity and energy loss functions of the thin films of L and its complexes are calculated. The refractive index curves for all films show a normal dispersion behavior in the non-absorbing region of spectra, from which the dispersion parameters can be calculated using Wemple-DiDomenico model. The type of optical transition bands shows indirect allowed. The values of the optical energy gap are calculated in the range from 2.13 to 2.33 eV, depending on the nature of Cu(II) substituent. Indeed, the present results show that the complexes as organic semiconductors acquired good characterizations better than metal free ligand (L) such as more thermal stability, reducing in the optical band gap and increasing in the absorption coefficient that refers to light harvesting capacity.
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Affiliation(s)
- S H Alotaibi
- Department of Chemistry, Turabah University College, Taif University, 21995, Saudi Arabia
| | - A S Radwan
- Department of Chemistry, Turabah University College, Taif University, 21995, Saudi Arabia
| | - Y K Abdel-Monem
- Department of Chemistry, Faculty of Science, Menoufia University, Egypt
| | - M M Makhlouf
- Department of Physics, Turabah University College, Taif University, 21995, Saudi Arabia; Department of Physics, Damietta Cancer Institute, Damietta, Egypt.
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25
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Saswati, Adão P, Majumder S, Dash SP, Roy S, Kuznetsov ML, Costa Pessoa J, Gomes CSB, Hardikar MR, Tiekink ERT, Dinda R. Synthesis, structure, solution behavior, reactivity and biological evaluation of oxidovanadium(iv/v) thiosemicarbazone complexes. Dalton Trans 2018; 47:11358-11374. [PMID: 30059099 DOI: 10.1039/c8dt01668b] [Citation(s) in RCA: 37] [Impact Index Per Article: 5.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/12/2022]
Abstract
The synthesis and characterization of an oxidovanadium(iv) [VIVO(L)(acac)] (1) and of two dioxidovanadium(v) [VVO2(L')] (2) and [VVO2(L)] (2a) complexes of the Schiff base formed from the reaction of 4-(p-fluorophenyl) thiosemicarbazone with pyridine-2-aldehyde (HL) are described. The oxidovanadium(iv) species [VIVO(L)(acac)] (1) was synthesized by the reaction of VIVO(acac)2 with the thiosemicarbazone HL in refluxing ethanol. The recrystallization of [VIVO(L)(acac)] (1) in DMF, CH3CN or EtOH gave the same product i.e. the dioxidovanadium(v) complex [VVO2(L)] (2a); however, upon recrystallization of 1 in DMSO a distinct compound [VVO2(L')] (2) was formed, wherein the original ligand L- is transformed to a rearranged one, L'-. In the presence of DMSO the ligand in complex 1 is found to undergo methylation at the carbon centre attached to imine nitrogen (aldimine) and transformed to the corresponding VVO2-species through in situ reaction. The synthesized HL and the metal complexes were characterized by elemental analysis, IR, UV-Vis, NMR and EPR spectroscopy. The molecular structure of [VVO2(L')] (2) was determined by single crystal X-ray crystallography. The methylation of various other ligands and complexes prepared from different vanadium precursors under similar reaction conditions was also attempted and it was confirmed that the imine methylation observed is both ligand and metal precursor specific. Complexes 1 and 2 show in vitro insulin-like activity against insulin responsive L6 myoblast cells, higher than VIVO(acac)2, with complex 1 being more potent. In addition, the in vitro cytotoxicity studies of HL, and of complexes 1 and 2 against the MCF-7 and Vero cell lines were also done. The ligand is not cytotoxic and complex 2 is significantly more cytotoxic than 1. DAPI staining experiments indicate that an increase in the time of incubation and an increase of concentration of the complexes lead to the increase in cell death.
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Affiliation(s)
- Saswati
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India.
| | - Pedro Adão
- Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal.
| | - Sudarshana Majumder
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India. and Darmstadt University of Technology, Clemens-Schöpf Institute of Organic Chemistry and Biochemistry, Alarich-Weiss Str. 4, 64287 Darmstadt, Germany
| | - Subhashree P Dash
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India. and Department of Basic Sciences, Parala Maharaja Engineering College, Sitalapalli, Brahmapur, Odisha 761003, India
| | - Satabdi Roy
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India. and Department of Chemistry, Indian Institute of Technology, Kanpur 208016, Uttar Pradesh, India
| | - Maxim L Kuznetsov
- Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal.
| | - João Costa Pessoa
- Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal.
| | - Clara S B Gomes
- Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal.
| | - Manasi R Hardikar
- Biometry and Nutrition Group, Agharkar Research Institute, G.G. Agrakar Road, Pune 411004, India
| | - Edward R T Tiekink
- Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
| | - Rupam Dinda
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India.
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26
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Copper-based metal coordination complexes with Voriconazole ligand: Syntheses, structures and antimicrobial properties. J SOLID STATE CHEM 2018. [DOI: 10.1016/j.jssc.2017.12.029] [Citation(s) in RCA: 18] [Impact Index Per Article: 2.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/13/2022]
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27
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Kumaravel G, Ponya Utthra P, Raman N. Exploiting the biological efficacy of benzimidazole based Schiff base complexes with l-Histidine as a co-ligand: Combined molecular docking, DNA interaction, antimicrobial and cytotoxic studies. Bioorg Chem 2018; 77:269-279. [PMID: 29421702 DOI: 10.1016/j.bioorg.2018.01.024] [Citation(s) in RCA: 30] [Impact Index Per Article: 4.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/01/2017] [Revised: 01/03/2018] [Accepted: 01/14/2018] [Indexed: 10/18/2022]
Abstract
Four new metal complexes were synthesized and screened for their cytotoxic activity after sufficient assertion from the preliminary DNA binding studies. The metal complexes could bind to CT-DNA through intercalation binding mode. This has also been confirmed by the molecular docking studies. The DNA cleavage efficiencies of these complexes with pBR322 DNA were investigated by gel electrophoresis. The complexes were found to promote the cleavage of pBR322 DNA from the supercoiled form I to the open circular form II in the presence of an oxidizing agent (H2O2). The in vitro chemosensitivity of the studied complexes exhibits significant cytotoxic effects, compared to those reported for cisplatin. These findings represent a prompting to search for the probable interaction of these complexes with other cellular elements of fundamental consequence in cell proliferation. The in vitro anticancer activities indicate that the Cu(II) complex is active against the selected human tumor cell lines, and the order of in vitro anticancer activities is consistent with the DNA-binding affinities. Towards noncancerous cell line, Cu(II) complex exhibits very low toxicity. On the other hand all the complexes have been found to exhibit cytotoxic effects against cancerous cell lines with potency more than that of the widely used drug cisplatin and hence they have the potential to act as promising anticancer agents. Captivatingly, they are non-toxic to normal cell lymphocytes revealing that they are selective in killing only the cancer cells.
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Affiliation(s)
- Ganesan Kumaravel
- Research Department of Chemistry, VHNSN College, Virudhunagar 626 001, India
| | | | - Natarajan Raman
- Research Department of Chemistry, VHNSN College, Virudhunagar 626 001, India.
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28
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Kumar S, Hansda A, Chandra A, Kumar A, Kumar M, Sithambaresan M, Faizi MSH, Kumar V, John RP. Co(II), Ni(II), Cu(II) and Zn(II) complexes of acenaphthoquinone 3-(4-benzylpiperidyl)thiosemicarbazone: Synthesis, structural, electrochemical and antibacterial studies. Polyhedron 2017. [DOI: 10.1016/j.poly.2017.05.055] [Citation(s) in RCA: 20] [Impact Index Per Article: 2.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/12/2022]
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Majumder S, Pasayat S, Panda AK, Dash SP, Roy S, Biswas A, Varma ME, Joshi BN, Garribba E, Kausar C, Patra SK, Kaminsky W, Crochet A, Dinda R. Monomeric and Dimeric Oxidomolybdenum(V and VI) Complexes, Cytotoxicity, and DNA Interaction Studies: Molybdenum Assisted C═N Bond Cleavage of Salophen Ligands. Inorg Chem 2017; 56:11190-11210. [DOI: 10.1021/acs.inorgchem.7b01578] [Citation(s) in RCA: 39] [Impact Index Per Article: 4.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/15/2022]
Affiliation(s)
- Sudarshana Majumder
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Sagarika Pasayat
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Alok K. Panda
- School of Basic
Sciences, Indian Institute of Technology Bhubaneswar, Bhubaneswar 751013, Odisha, India
| | - Subhashree P. Dash
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India
- Department of Basic Sciences, Paralamaharaja Engineering College, Sitalapalli, Brahmapur, Odisha 761003, India
| | - Satabdi Roy
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Ashis Biswas
- School of Basic
Sciences, Indian Institute of Technology Bhubaneswar, Bhubaneswar 751013, Odisha, India
| | - Mokshada E. Varma
- Bioprospecting
Group, Agharkar Research Institute, G.G. Agharkar Road, Pune 411004, India
| | - Bimba N. Joshi
- Bioprospecting
Group, Agharkar Research Institute, G.G. Agharkar Road, Pune 411004, India
| | - Eugenio Garribba
- Dipartimento di Chimica e Farmacia, Università di Sassari, Via Vienna
2, I-07100 Sassari, Italy
| | - Chahat Kausar
- Department of Life Science, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Samir Kumar Patra
- Department of Life Science, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Werner Kaminsky
- Department of Chemistry, University of Washington, Box 351700, Seattle, Washington 98195, United States
| | - Aurélien Crochet
- Department of Chemistry, Fribourg Center
for Nanomaterials, University of Fribourg, CH-1700 Fribourg, Switzerland
| | - Rupam Dinda
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India
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Atlam FM, El-Nahass MN, Bakr EA, Fayed TA. Metal complexes of chalcone analogue: Synthesis, characterization, DNA binding, molecular docking and antimicrobial evaluation. Appl Organomet Chem 2017. [DOI: 10.1002/aoc.3951] [Citation(s) in RCA: 23] [Impact Index Per Article: 2.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/12/2022]
Affiliation(s)
- Faten M. Atlam
- Department of Chemistry, Faculty of Science; Tanta University; 31527 Tanta Egypt
| | - Marwa N. El-Nahass
- Department of Chemistry, Faculty of Science; Tanta University; 31527 Tanta Egypt
| | - Eman A. Bakr
- Department of Chemistry, Faculty of Science; Tanta University; 31527 Tanta Egypt
| | - Tarek A. Fayed
- Department of Chemistry, Faculty of Science; Tanta University; 31527 Tanta Egypt
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Kalinowska-Lis U, Szabłowska-Gadomska I, Lisowska K, Ochocki J, Małecki M, Felczak A. Cytotoxic and Antimicrobial Properties of Copper(II) Complexes of Pyridine and Benzimidazole Derivatives. Z Anorg Allg Chem 2017. [DOI: 10.1002/zaac.201700115] [Citation(s) in RCA: 6] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/11/2022]
Affiliation(s)
- Urszula Kalinowska-Lis
- Department of Cosmetic Raw Materials Chemistry; Medical University of Lodz; Muszyńskiego 1 90-151 Łódź Poland
| | - Ilona Szabłowska-Gadomska
- Department of Applied Pharmacy and Bioengineering; Medical University of Warsaw; Banacha 1 02-097 Warsaw Poland
| | - Katarzyna Lisowska
- Department of Industrial Microbiology and Biotechnology; Faculty of Biology and Environmental Protection; University of Lodz; 12/16 Banacha Street 90-237 Łódź Poland
| | - Justyn Ochocki
- Department of Bioinorganic Chemistry; Medical University of Lodz; Muszyńskiego 1 90-151 Łódź Poland
| | - Maciej Małecki
- Department of Applied Pharmacy and Bioengineering; Medical University of Warsaw; Banacha 1 02-097 Warsaw Poland
| | - Aleksandra Felczak
- Department of Industrial Microbiology and Biotechnology; Faculty of Biology and Environmental Protection; University of Lodz; 12/16 Banacha Street 90-237 Łódź Poland
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Pahonţu E, Julea F, Chumakov Y, Petrenco P, Roşu T, Gulea A. Synthesis, characterization, crystal structure and antiproliferative activity studies of Cu(II), Ni(II) and Co(II) complexes with 4-benzoyl-5-pyrazolones derived compounds. J Organomet Chem 2017. [DOI: 10.1016/j.jorganchem.2017.01.018] [Citation(s) in RCA: 12] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/20/2022]
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Lobana TS, Indoria S, Sood H, Arora DS, Randhawa BS, Garcia-Santos I, Smolinski VA, Jasinski JP. Synthesis of 5-nitro-salicylaldehyde-N-substituted thiosemicarbazonates of copper(II): Molecular structures, spectroscopy, ESI-mass studies and antimicrobial activity. Inorganica Chim Acta 2017. [DOI: 10.1016/j.ica.2017.02.032] [Citation(s) in RCA: 9] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/12/2023]
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Anticancer, antimicrobial, spectral, voltammetric and DFT studies with Cu(II) complexes of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its N(4)- substituted derivatives. J Organomet Chem 2017. [DOI: 10.1016/j.jorganchem.2016.12.020] [Citation(s) in RCA: 13] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/20/2022]
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[Cytotoxic effect of palladium (II) inclusion compounds in beta-cyclodextrin]. BIOMEDICA 2016; 36:603-611. [PMID: 27992987 DOI: 10.7705/biomedica.v36i4.2880] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Subscribe] [Scholar Register] [Received: 06/07/2015] [Revised: 05/02/2016] [Indexed: 11/21/2022]
Abstract
INTRODUCTION Thiosemicarbazones and palladium (II) complexes have antineoplastic activities with mild side effects, for which they are considered new alternative antineoplastic drugs. However, the IC50 ranges of these complexes vary due to differences in their structure and solubility and their sensitivities for various cellular targets. Beta-cyclodextrin is an additive used to improve the solubility and stability of various drugs for therapeutic use, but the combination of beta-cyclodextrin with palladium (II) complexes and thiosemicarbazones has not been tested yet. OBJECTIVE To study the cytotoxic effect of palladium (II) inclusion complexes in beta-cyclodextrin. MATERIALS AND METHODS We tested the cytotoxic activity of palladium complexes combined with beta-cyclodextrin in the breast cancer cell line MCF-7 using a sulforhodamine B assay. RESULTS We tested the antiproliferative activity of palladium (II) complexes with and without the ligands MePhPzTSC and Ph2PzTSC and with and without beta-cyclodextrin in MCF-7 cells and compared them to that of cisplatin. All combinations showed antiproliferative activity; however, the activity was greater for the combinations that included beta-cyclodextrin: ([Pd (MePhPzTSC) 2] • ß-CD and [Pd (Ph2PzTSC) 2] • ß-CD), at concentrations of 0.14 and 0.49 μM, respectively. The IC50 for this complex was 5-fold lower than that of the ligand-free combinations (1.4 and 2.9 μM, respectively). The IC50 for free palladium (II) complex was 0.571.24 μM and that for cisplatin was 6.87 μM. CONCLUSIONS Beta-cyclodextrin significantly enhanced the cytotoxic activities of palladium (II) complexes and thiosemicarbazones probably by improving their solubility and bioavailability. The addition of beta-cyclodextrin is a possible strategy for designing new anticancer drugs.
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Elshaarawy RF, Janiak C. Antibacterial susceptibility of new copper(II) N-pyruvoyl anthranilate complexes against marine bacterial strains – In search of new antibiofouling candidate. ARAB J CHEM 2016. [DOI: 10.1016/j.arabjc.2015.04.010] [Citation(s) in RCA: 22] [Impact Index Per Article: 2.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/22/2022] Open
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Pahonțu E, Paraschivescu C, Ilieș DC, Poirier D, Oprean C, Păunescu V, Gulea A, Roșu T, Bratu O. Synthesis and Characterization of Novel Cu(II), Pd(II) and Pt(II) Complexes with 8-Ethyl-2-hydroxytricyclo(7.3.1.0(2,7))tridecan-13-one-thiosemicarbazone: Antimicrobial and in Vitro Antiproliferative Activity. Molecules 2016; 21:molecules21050674. [PMID: 27213326 PMCID: PMC6273217 DOI: 10.3390/molecules21050674] [Citation(s) in RCA: 28] [Impact Index Per Article: 3.1] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/21/2016] [Revised: 04/30/2016] [Accepted: 05/16/2016] [Indexed: 11/16/2022] Open
Abstract
New Cu(II), Pd(II) and Pt(II) complexes, (Cu(L)(H2O)2(OAc)) (1), (Cu(HL)(H2O)2(SO4)) (2), (Cu(L)(H2O)2(NO3)) (3), (Cu(L)(H2O)2(ClO4)) (4), (Cu(L)2(H2O)2) (5), (Pd(L)(OAc))H2O (6), and (Pt(L)2) (7) were synthesized from 8-ethyl-2-hydroxytricyclo(7.3.1.02,7)tridecan-13-one thiosemicarbazone (HL). The ligand and its metal complexes were characterized by IR, 1H-NMR, 13C-NMR, UV-Vis, FAB, EPR, mass spectroscopy, elemental and thermal analysis, magnetic susceptibility measurements and molar electric conductivity. The free ligand and the metal complexes have been tested for their antimicrobial activity against E. coli, S. enteritidis, S. aureus, E. faecalis, C. albicans and cytotoxicity against the NCI-H1573 lung adenocarcinoma, SKBR-3 human breast, MCF-7 human breast, A375 human melanoma and HL-60 human promyelocytic leukemia cell lines. Copper complex 2 exhibited the best antiproliferative activities against MCF-7 human breast cancer cells. A significant inhibition of malignant HL-60 cell growth was observed for copper complex 2, palladium complex 6 and platinum complex 7, with IC50 values of 1.6 µM, 6.5 µM and 6.4 µM, respectively.
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Affiliation(s)
- Elena Pahonțu
- Inorganic Chemistry Department, Faculty of Pharmacy, University of Medicine and Pharmacy "Carol Davila", 6 Traian Vuia Street, Bucharest 020956, Romania.
| | - Codruța Paraschivescu
- Organic Chemistry Department, Faculty of Chemistry, University of Bucharest, 90-92 Panduri Street, Bucharest 050663, Romania.
| | - Diana-Carolina Ilieș
- Organic Chemistry Department, Faculty of Pharmacy, University of Medicine and Pharmacy "Carol Davila", 6 Traian Vuia Street, Bucharest 020956, Romania.
| | - Donald Poirier
- Oncology and Molecular Endocrinology Research Center CHUL, Research Center and Universite Laval, CHUQ-CHUL, 2705 Boulevard Laurier, Quebec City, QC G1V 4G2, Canada.
| | - Camelia Oprean
- Pharmaceutical Chemistry Department, Faculty of Pharmacy, University of Medicine and Pharmacy "Victor Babeş", Timişoara 300041, Romania.
| | - Virgil Păunescu
- Functional Sciences Department, Faculty of Medicine, University of Medicine and Pharmacy "Victor Babeş", 2 Eftimie Murgu Square, Timişoara 300041, Romania.
| | - Aurelian Gulea
- Coordination Chemistry Department, Moldova State University, 60 Mateevici Street, Chisinau 2009, Moldova.
| | - Tudor Roșu
- Inorganic Chemistry Department, Faculty of Chemistry, University of Bucharest, 23 Dumbrava Rosie Street, Bucharest 020462, Romania.
| | - Ovidiu Bratu
- Clinic of Urology, Universitary Emergency Central Military Hospital, Clinical Departament 3, University of Medicine and Pharmacy "Carol Davila", 6 Traian Vuia Street, Bucharest 020956, Romania.
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Popov LD, Levchinkov SI, Shcherbakov IN, Alexandrov GG, Tupolova YP, Lukov VV, Etmetchenko LN, Kogan VA. Copper(II) complexes with N-(phenyl)alkylthiosemicarbazones of 3,5-dichloro- and 3,5-diiodosalicylic aldehydes. RUSS J GEN CHEM+ 2016. [DOI: 10.1134/s1070363216020249] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/23/2022]
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Liu HY. Synthesis, Structural Characterization, and Antibacterial Activity of Cu(II) and Zn(II) Complexes With Tetradentate Schiff Bases. ACTA ACUST UNITED AC 2015. [DOI: 10.1080/15533174.2014.963243] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/24/2022]
Affiliation(s)
- Huan-Yu Liu
- School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan, P. R. China
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Pahontu E, Julea F, Rosu T, Purcarea V, Chumakov Y, Petrenco P, Gulea A. Antibacterial, antifungal and in vitro antileukaemia activity of metal complexes with thiosemicarbazones. J Cell Mol Med 2015; 19:865-78. [PMID: 25708540 PMCID: PMC4395200 DOI: 10.1111/jcmm.12508] [Citation(s) in RCA: 78] [Impact Index Per Article: 7.8] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/17/2014] [Accepted: 11/01/2014] [Indexed: 11/28/2022] Open
Abstract
1-phenyl-3-methyl-4-benzoyl-5-pyrazolone 4-ethyl-thiosemicarbazone (HL) and its copper(II), vanadium(V) and nickel(II) complexes: [Cu(L)(Cl)]·C2H5OH·(1), [Cu(L)2]·H2O (2), [Cu(L)(Br)]·H2O·CH3OH (3), [Cu(L)(NO3)]·2C2H5OH (4), [VO2(L)]·2H2O (5), [Ni(L)2]·H2O (6), were synthesized and characterized. The ligand has been characterized by elemental analyses, IR, 1H NMR and 13C NMR spectroscopy. The tridentate nature of the ligand is evident from the IR spectra. The copper(II), vanadium(V) and nickel(II) complexes have been characterized by different physico-chemical techniques such as molar conductivity, magnetic susceptibility measurements and electronic, infrared and electron paramagnetic resonance spectral studies. The structures of the ligand and its copper(II) (2, 4), and vanadium(V) (5) complexes have been determined by single-crystal X-ray diffraction. The composition of the coordination polyhedron of the central atom in 2, 4 and 5 is different. The tetrahedral coordination geometry of Cu was found in complex 2 while in complex 4, it is square planar, in complex 5 the coordination polyhedron of the central ion is distorted square pyramid. The in vitro antibacterial activity of the complexes against Escherichia coli, Salmonella abony, Staphylococcus aureus, Bacillus cereus and the antifungal activity against Candida albicans strains was higher for the metal complexes than for free ligand. The effect of the free ligand and its metal complexes on the proliferation of HL-60 cells was tested.
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Affiliation(s)
- Elena Pahontu
- Inorganic Chemistry Department, Faculty of Pharmacy, University of Medicine and Pharmacy "Carol Davila", Bucharest, Romania
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41
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Popov LD, Gazieva GA, Kravchenko AN, Tkachenko YN, Askalepova OI, Levchenkov SI, Karpova TB, Tupolova YP, Kogan VA. Protolytic and complexation properties of the cyclic thiosemicarbazone ligand. RUSS J GEN CHEM+ 2015. [DOI: 10.1134/s1070363215010168] [Citation(s) in RCA: 5] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/23/2022]
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42
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Saswati S, Chakraborty A, Dash SP, Panda AK, Acharyya R, Biswas A, Mukhopadhyay S, Bhutia SK, Crochet A, Patil YP, Nethaji M, Dinda R. Synthesis, X-ray structure and in vitro cytotoxicity studies of Cu(i/ii) complexes of thiosemicarbazone: special emphasis on their interactions with DNA. Dalton Trans 2015; 44:6140-57. [DOI: 10.1039/c4dt03764b] [Citation(s) in RCA: 82] [Impact Index Per Article: 8.2] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/23/2022]
Abstract
The interactions of four Cu-TSC complexes with DNA & their cytotoxicity studies against the HeLa cell have been reported.
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43
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Ingle SA, Kate AN, Kumbhar AA, Khan AA, Rao SS, Gejji SP. Synthesis and biological evaluation of copper(ii) pyrenethiosemicarbazone. RSC Adv 2015. [DOI: 10.1039/c5ra00020c] [Citation(s) in RCA: 17] [Impact Index Per Article: 1.7] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022] Open
Abstract
A fluorescent Cu(ii) pyrenethiosemicarbazone complex exhibits enhanced DNA-cleavage and cytotoxicity on photoexcitation.
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Affiliation(s)
- Suwarna A. Ingle
- Department of Chemistry
- Savitribai Phule Pune University
- Pune-411007
- India
| | - Anup N. Kate
- Department of Chemistry
- Savitribai Phule Pune University
- Pune-411007
- India
| | - Anupa A. Kumbhar
- Department of Chemistry
- Savitribai Phule Pune University
- Pune-411007
- India
| | - Ayesha A. Khan
- Department of Chemistry
- Savitribai Phule Pune University
- Pune-411007
- India
| | - Soniya S. Rao
- Department of Chemistry
- Savitribai Phule Pune University
- Pune-411007
- India
| | - Shridhar P. Gejji
- Department of Chemistry
- Savitribai Phule Pune University
- Pune-411007
- India
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Dash SP, Panda AK, Pasayat S, Dinda R, Biswas A, Tiekink ERT, Mukhopadhyay S, Bhutia SK, Kaminsky W, Sinn E. Oxidovanadium(v) complexes of aroylhydrazones incorporating heterocycles: synthesis, characterization and study of DNA binding, photo-induced DNA cleavage and cytotoxic activities. RSC Adv 2015. [DOI: 10.1039/c4ra14369h] [Citation(s) in RCA: 34] [Impact Index Per Article: 3.4] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/07/2023] Open
Abstract
The interaction of four neutral oxidovanadium(v) complexes with DNA and their cytotoxic activities have been reported.
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Affiliation(s)
- Subhashree P. Dash
- Department of Chemistry
- National Institute of Technology
- Rourkela 769008
- India
| | - Alok K. Panda
- School of Basic Sciences
- Indian Institute of Technology Bhubaneswar
- Bhubaneswar 751 013
- India
| | - Sagarika Pasayat
- Department of Chemistry
- National Institute of Technology
- Rourkela 769008
- India
| | - Rupam Dinda
- Department of Chemistry
- National Institute of Technology
- Rourkela 769008
- India
| | - Ashis Biswas
- School of Basic Sciences
- Indian Institute of Technology Bhubaneswar
- Bhubaneswar 751 013
- India
| | | | | | - Sujit K. Bhutia
- Department of Life Science
- National Institute of Technology
- Rourkela 769008
- India
| | | | - Ekkehard Sinn
- Department of Chemistry
- Western Michigan University
- Kalamazoo
- USA
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45
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Lobana TS, Indoria S, Kaur H, Arora DS, Jassal AK, Jasinski JP. Synthesis and structures of 5-nitro-salicylaldehyde thiosemicarb-azonates of copper(ii): molecular spectroscopy, ESI-mass studies, antimicrobial activity and cytotoxicity. RSC Adv 2015. [DOI: 10.1039/c4ra15006f] [Citation(s) in RCA: 24] [Impact Index Per Article: 2.4] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022] Open
Abstract
Salicylaldehyde thiosemicarbazonates of copper(ii) have shown significant growth inhibitory activity againstS. aureus, MRSA,K. pneumonia,S. flexneri,P. aeruginosaandC. albicansand are bactericidal in nature with low cytotoxicity.
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Affiliation(s)
- Tarlok S. Lobana
- Department of Chemistry
- Guru Nanak Dev University
- Amritsar-143 005
- India
| | - Shikha Indoria
- Department of Chemistry
- Guru Nanak Dev University
- Amritsar-143 005
- India
| | - Harpreet Kaur
- Department of Microbiology
- Guru Nanak Dev University
- Amritsar-143 005
- India
| | - Daljit S. Arora
- Department of Microbiology
- Guru Nanak Dev University
- Amritsar-143 005
- India
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46
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Lobana TS. Activation of C–H bonds of thiosemicarbazones by transition metals: synthesis, structures and importance of cyclometallated compounds. RSC Adv 2015. [DOI: 10.1039/c5ra03333k] [Citation(s) in RCA: 24] [Impact Index Per Article: 2.4] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022] Open
Abstract
Transition metals (PdII, PtII, RuII, RhIIIand IrIII) have induced activation of C–H bonds of thiosemicarbazones and yielded mono-, di-, tri- and tetra-nuclear complexes.
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Affiliation(s)
- Tarlok S. Lobana
- Department of Chemistry
- Center of Advanced Studies
- Guru Nanak Dev University
- Amritsar 143005
- India
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Dash SP, Panda AK, Pasayat S, Majumder S, Biswas A, Kaminsky W, Mukhopadhyay S, Bhutia SK, Dinda R. Evaluation of the cell cytotoxicity and DNA/BSA binding and cleavage activity of some dioxidovanadium(V) complexes containing aroylhydrazones. J Inorg Biochem 2014; 144:1-12. [PMID: 25575303 DOI: 10.1016/j.jinorgbio.2014.12.018] [Citation(s) in RCA: 38] [Impact Index Per Article: 3.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/25/2014] [Revised: 12/17/2014] [Accepted: 12/17/2014] [Indexed: 01/07/2023]
Abstract
Three dioxidovanadium(V) complexes [VO2L(1-3)] (1-3) [HL(1)=1-napthoyl hydrazone of 2-acetyl pyridine, HL(2)=2-furoyl hydrazone of 2-acetyl pyridine and H2L(3)=isonicotinoyl hydrazone of 2-hydroxy benzaldehyde] have been reported. All the complexes were characterized by various spectroscopy (IR, UV-visible and NMR) and the molecular structures of 1 and 2 were characterized by single crystal X-ray diffraction technique. Structural report established five-coordinate geometries, distorted toward square pyramidal for each of 1 and 2, based on a tridentate -O,N,N coordinating anion and two oxido-O atoms. The experimental results show that the complexes interact with calf-thymus DNA (CT-DNA) possibly by a groove binding mode, with binding constants of ~10(5)M(-1). All complexes show good photo-induced cleavage of pUC19 supercoiled plasmid DNA with complex 1 showing the highest photo-induced DNA cleavage activity of ~68%. 1-3 also exhibit moderate binding affinity in the range of 10(3)-10(4)M(-1) towards bovine serum albumin (BSA), while all the complexes show good photo-induced BSA cleavage activity. Moreover the antiproliferative activity of all these complexes was studied, which reveal all compounds are significantly cytotoxic towards the HeLa cell line.
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Affiliation(s)
- Subhashree P Dash
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Alok K Panda
- School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Bhubaneswar 751 013, Odisha, India
| | - Sagarika Pasayat
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Sudarshana Majumder
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Ashis Biswas
- School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Bhubaneswar 751 013, Odisha, India.
| | - Werner Kaminsky
- Department of Chemistry, University of Washington, Box 351700, Seattle, WA 98195, USA
| | - Subhadip Mukhopadhyay
- Department of Life Science, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Sujit K Bhutia
- Department of Life Science, National Institute of Technology, Rourkela 769008, Odisha, India
| | - Rupam Dinda
- Department of Chemistry, National Institute of Technology, Rourkela 769008, Odisha, India.
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Synthesis, characterization, crystal structure and antimicrobial activity of copper(II) complexes with a thiosemicarbazone derived from 3-formyl-6-methylchromone. Polyhedron 2014. [DOI: 10.1016/j.poly.2014.05.074] [Citation(s) in RCA: 31] [Impact Index Per Article: 2.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/14/2023]
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49
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Filho JCC, Sarria ALF, Becceneri AB, Fuzer AM, Batalhão JR, da Silva CMP, Carlos RM, Vieira PC, Fernandes JB, Cominetti MR. Copper (II) and 2,2'-bipyridine complexation improves chemopreventive effects of naringenin against breast tumor cells. PLoS One 2014; 9:e107058. [PMID: 25192075 PMCID: PMC4156406 DOI: 10.1371/journal.pone.0107058] [Citation(s) in RCA: 30] [Impact Index Per Article: 2.7] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/28/2014] [Accepted: 08/05/2014] [Indexed: 12/17/2022] Open
Abstract
Cancer is the second leading cause of death worldwide and there is epidemiological evidence that demonstrates this tendency is emerging. Naringenin (NGEN) is a trihydroxyflavanone that shows various biological effects such as antioxidant, anticancer, anti-inflammatory, and antiviral activities. It belongs to flavanone class, which represents flavonoids with a C6-C3-C6 skeleton. Flavonoids do not exhibit sufficient activity to be used for chemotherapy, however they can be chemically modified by complexation with metals such as copper (Cu) (II) for instance, in order to be applied for adjuvant therapy. This study investigated the effects of Cu(II) and 2,2′-bipyridine complexation with naringenin on MDA-MB-231 cells. We demonstrated that naringenin complexed with Cu(II) and 2,2′-bipyridine (NGENCuB) was more efficient inhibiting colony formation, proliferation and migration of MDA-MB-231 tumor cells, than naringenin (NGEN) itself. Furthermore, we verified that NGENCuB was more effective than NGEN inhibiting pro-MMP9 activity by zymography assays. Finally, through flow cytometry, we showed that NGENCuB is more efficient than NGEN inducing apoptosis in MDA-MB-231 cells. These results were confirmed by gene expression analysis in real time PCR. We observed that NGENCuB upregulated the expression of pro-apoptotic gene caspase-9, but did not change the expression of caspase-8 or anti-apoptotic gene Bcl-2. There are only few works investigating the effects of Cu(II) complexation with naringenin on tumor cells. To the best of our knowledge, this is the first work describing the effects of Cu(II) complexation of a flavonoid on MDA-MB-231 breast tumor cells.
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Affiliation(s)
| | | | | | - Angelina Maria Fuzer
- Departamento de Gerontologia, Universidade Federal de São Carlos, São Carlos, SP, Brazil
| | | | | | - Rose Maria Carlos
- Departamento de Química, Universidade Federal de São Carlos, São Carlos, SP, Brazil
| | - Paulo Cezar Vieira
- Departamento de Química, Universidade Federal de São Carlos, São Carlos, SP, Brazil
| | | | - Márcia Regina Cominetti
- Departamento de Gerontologia, Universidade Federal de São Carlos, São Carlos, SP, Brazil
- * E-mail:
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50
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Synthesis, structure, characterization and study of antiproliferative activity of dimeric and tetrameric oxidomolybdenum(VI) complexes of N,N′-disalicyloylhydrazine. Polyhedron 2014. [DOI: 10.1016/j.poly.2014.04.007] [Citation(s) in RCA: 17] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
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