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Redox-active and DNA-binding coordination complexes of clotrimazole
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Betanzos-Lara, Soledad, Chmel, Nikola Paul, Zimmerman, Matthew T., Barrón-Sosa, Lidia R., Garino, Claudio, Salassa, Luca, Rodger, Alison, Brumaghim, Julia L., Gracia-Mora, Isabel and Barba-Behrens, Norah (2015) Redox-active and DNA-binding coordination complexes of clotrimazole. Dalton Transactions, 44 (8). pp. 3673-3685. doi:10.1039/c4dt02883j
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Official URL: http://dx.doi.org/10.1039/C4DT02883J
Abstract
DNA interactions of anticancer mononuclear Cu2+, Co2+, Zn2+, and Ni2+ complexes with the biologically active ligand clotrimazole (clotri) are reported. To fully characterize DNA binding modes for these complexes of the formulae [M(clotri)2Cl2]·nH2O (1–4), [M(clotri)2Br2]·nH2O (5,6), [M(clotri)3NO3]NO3·nH2O (9), and [M(clotri)3(NO3)2] (10), circular dichroism (CD) and linear dichroism (LD) spectroscopy, UV melting experiments, atomic force microscopy (AFM) and ethidium bromide (EtBr) displacement methods were used. Results indicate mixed electrostatic interactions, possibly through groove binding, that result in accretion and coiling of DNA. Electrochemical studies indicate that the Cu2+ complex 9 readily reduces to the reactive-oxygen-species-generating Cu+, which oxidatively damages DNA. There is a subtle correlation between log P values, calculated electrostatic potentials, and cytotoxicity of the complexes. The extent of cell-nucleus DNA-metal adduct formation in the HeLa cervix-uterine carcinoma cell line does not necessarily correlate with cytotoxicity, indicating that the nature of DNA lesions may be crucial to activity.
| Item Type: | Journal Article | ||||||||||
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| Subjects: | R Medicine > RC Internal medicine > RC0254 Neoplasms. Tumors. Oncology (including Cancer) | ||||||||||
| Divisions: | Faculty of Science > Chemistry | ||||||||||
| Library of Congress Subject Headings (LCSH): | Cancer -- Chemotherapy, Cancer -- Treatment, Cisplatin, Antineoplastic agents, Transition metal complexes., Chemistry, Inorganic, Platinum compounds -- Therapeutic use, Coordination compounds -- Therapeutic use, Complex compounds -- Therapeutic use | ||||||||||
| Journal or Publication Title: | Dalton Transactions | ||||||||||
| Publisher: | Royal Society of Chemistry | ||||||||||
| ISSN: | 1477-9226 | ||||||||||
| Official Date: | 28 February 2015 | ||||||||||
| Dates: |
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| Volume: | 44 | ||||||||||
| Number: | 8 | ||||||||||
| Page Range: | pp. 3673-3685 | ||||||||||
| DOI: | 10.1039/c4dt02883j | ||||||||||
| Status: | Peer Reviewed | ||||||||||
| Publication Status: | Published | ||||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||||
| Funder: | Dirección General de Asuntos del Personal Académico (DGAPA-UNAM), Consejo Nacional de Ciencia y Tecnología (Mexico) [Mexican Council for Science and Technology] (CONACYT), National Science Foundation (U.S.) (NSF), Ministerio de Ciencia e Innovacion (MICINN) | ||||||||||
| Grant number: | DGAPA-222713 , CB2012-178851, RYC-2011-07787 | ||||||||||
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