Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies
| Autor: | Drielly A. Paixão, Elene C. Pereira-Maia, Marcelo José Barbosa Silva, Marcos Pivatto, Isadora Akemi Uehara, Victor M. Deflon, Silvana Guilardi, Débora L. Campos, Pedro I. S. Maia, Françoise Vasconcelos Botelho, Wendell Guerra, Ivana M. Marzano, Fernando Rogério Pavan, Edgar H.L. Jaimes, Ana Maria da Costa Ferreira |
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| Přispěvatelé: | Universidade Federal de Uberlândia (UFU), Universidade Federal de Minas Gerais (UFMG), Universidade Estadual Paulista (Unesp), Universidade de São Paulo (USP), Universidade Federal do Triângulo Mineiro |
| Rok vydání: | 2017 |
| Předmět: |
Coordination sphere
Stereochemistry medicine.drug_class Antitumoral activity Antitubercular Agents chemistry.chemical_element Antineoplastic Agents Apoptosis Breast Neoplasms Microbial Sensitivity Tests APOPTOSE 010402 general chemistry Hydrazide Antimycobacterial Crystallography X-Ray 01 natural sciences Biochemistry Mycobacterium Inorganic Chemistry chemistry.chemical_compound Perchlorate Inhibitory Concentration 50 Coordination Complexes Heterocyclic Compounds Cell Line Tumor medicine Humans DNA binding Cytotoxicity Molecular Structure 010405 organic chemistry Mycobacterium tuberculosis Copper 0104 chemical sciences Hydrazines chemistry Octahedron Copper(II) complexes Female K562 Cells DNA |
| Zdroj: | Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP Scopus Repositório Institucional da UNESP Universidade Estadual Paulista (UNESP) instacron:UNESP |
| Popis: | Made available in DSpace on 2018-12-11T17:32:13Z (GMT). No. of bitstreams: 0 Previous issue date: 2017-07-01 Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG) Five new copper(II) complexes of the type [Cu(N[sbnd]O)(N[sbnd]N)(ClO4)2], in which N[sbnd]O = 4-fluorophenoxyacetic acid hydrazide (4-FH) or 4-nitrobenzoic hydrazide (4-NH) and N[sbnd]N = 1,10-phenanthroline (phen), 4–4′-dimethoxy-2-2′-bipyridine (dmb) or 2,2-bipyridine (bipy) were synthesized and characterized using various spectroscopic methods. The X-ray structural analysis of one representative compound indicates that the geometry around the copper ion is distorted octahedron, in which the ion is coordinated to hydrazide via the terminal nitrogen and the carbonyl oxygen, and to heterocyclic bases via their two nitrogen atoms. Two perchlorate anions occupy the apical positions, completing the coordination sphere. The cytotoxic activity of compounds was investigated in three tumor cell lines (K562, MDA-MB-231 and MCF-7). Concerning K562 cell line, the complexes with 1,10-phenanthroline exhibit high cytotoxic activity and are more active than carboplatin, free ligands and [Cu(phen)2]2 +. Considering the cytotoxicity results, further investigations for the compounds [Cu(4-FH)(phen)(ClO4)2] I and [Cu(4-NH)(phen)(ClO4)2]∙H2O III were performed. Flow cytometric analysis revealed that these complexes induce apoptotic cell death in MDA-MB-231 cell line and bind to DNA with K values of 4.38 × 104 and 2.62 × 104, respectively. These compounds were also evaluated against wild type Mycobacterium tuberculosis (ATCC 27294) and exhibited antimycobacterial activity, displayed MIC values lower than those of the corresponding free ligands. Instituto de Química Universidade Federal de Uberlândia Departamento de Química Universidade Federal de Minas Gerais Faculdade de Ciências Farmacêuticas UNESP - Universidade Estadual Paulista, Campus Araraquara Instituto de Química de São Carlos Universidade de São Paulo Instituto de Ciências Naturais Exatas e Educação Universidade Federal do Triângulo Mineiro Instituto de Química Universidade de São Paulo Instituto de Ciências Biomédicas Universidade Federal de Uberlândia Instituto de Genética e Bioquímica Universidade Federal de Uberlândia Faculdade de Ciências Farmacêuticas UNESP - Universidade Estadual Paulista, Campus Araraquara CNPq: 442328/2014-1 FAPEMIG: APQ-00330-14 FAPEMIG: APQ-00668-15 FAPEMIG: CEX - RED-00010-14 |
| Databáze: | OpenAIRE |
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