Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Outros Autores: | , , , , , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.jinorgbio.2017.04.024 http://hdl.handle.net/11449/178814 |
Resumo: | 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. |
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Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studiesAntitumoral activityApoptosisCopper(II) complexesDNA bindingHydrazideMycobacterium tuberculosisFive 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.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)Instituto de Química Universidade Federal de UberlândiaDepartamento de Química Universidade Federal de Minas GeraisFaculdade de Ciências Farmacêuticas UNESP - Universidade Estadual Paulista, Campus AraraquaraInstituto de Química de São Carlos Universidade de São PauloInstituto de Ciências Naturais Exatas e Educação Universidade Federal do Triângulo MineiroInstituto de Química Universidade de São PauloInstituto de Ciências Biomédicas Universidade Federal de UberlândiaInstituto de Genética e Bioquímica Universidade Federal de UberlândiaFaculdade de Ciências Farmacêuticas UNESP - Universidade Estadual Paulista, Campus AraraquaraCNPq: 442328/2014-1FAPEMIG: APQ-00330-14FAPEMIG: APQ-00668-15FAPEMIG: CEX - RED-00010-14Universidade Federal de Uberlândia (UFU)Universidade Federal de Minas Gerais (UFMG)Universidade Estadual Paulista (Unesp)Universidade de São Paulo (USP)Universidade Federal do Triângulo MineiroPaixão, Drielly A.Marzano, Ivana M.Jaimes, Edgar H.L.Pivatto, MarcosCampos, Débora L. [UNESP]Pavan, Fernando R. [UNESP]Deflon, Victor M.Maia, Pedro Ivo da S.Da Costa Ferreira, Ana M.Uehara, Isadora A.Silva, Marcelo J.B.Botelho, Françoise V.Pereira-Maia, Elene C.Guilardi, SilvanaGuerra, Wendell2018-12-11T17:32:13Z2018-12-11T17:32:13Z2017-07-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article138-146application/pdfhttp://dx.doi.org/10.1016/j.jinorgbio.2017.04.024Journal of Inorganic Biochemistry, v. 172, p. 138-146.1873-33440162-0134http://hdl.handle.net/11449/17881410.1016/j.jinorgbio.2017.04.0242-s2.0-850182470142-s2.0-85018247014.pdfScopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Inorganic Biochemistry0,743info:eu-repo/semantics/openAccess2023-11-09T06:09:29Zoai:repositorio.unesp.br:11449/178814Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462023-11-09T06:09:29Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies |
title |
Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies |
spellingShingle |
Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies Paixão, Drielly A. Antitumoral activity Apoptosis Copper(II) complexes DNA binding Hydrazide Mycobacterium tuberculosis |
title_short |
Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies |
title_full |
Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies |
title_fullStr |
Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies |
title_full_unstemmed |
Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies |
title_sort |
Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies |
author |
Paixão, Drielly A. |
author_facet |
Paixão, Drielly A. Marzano, Ivana M. Jaimes, Edgar H.L. Pivatto, Marcos Campos, Débora L. [UNESP] Pavan, Fernando R. [UNESP] Deflon, Victor M. Maia, Pedro Ivo da S. Da Costa Ferreira, Ana M. Uehara, Isadora A. Silva, Marcelo J.B. Botelho, Françoise V. Pereira-Maia, Elene C. Guilardi, Silvana Guerra, Wendell |
author_role |
author |
author2 |
Marzano, Ivana M. Jaimes, Edgar H.L. Pivatto, Marcos Campos, Débora L. [UNESP] Pavan, Fernando R. [UNESP] Deflon, Victor M. Maia, Pedro Ivo da S. Da Costa Ferreira, Ana M. Uehara, Isadora A. Silva, Marcelo J.B. Botelho, Françoise V. Pereira-Maia, Elene C. Guilardi, Silvana Guerra, Wendell |
author2_role |
author author author author author author author author author author author author author author |
dc.contributor.none.fl_str_mv |
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 |
dc.contributor.author.fl_str_mv |
Paixão, Drielly A. Marzano, Ivana M. Jaimes, Edgar H.L. Pivatto, Marcos Campos, Débora L. [UNESP] Pavan, Fernando R. [UNESP] Deflon, Victor M. Maia, Pedro Ivo da S. Da Costa Ferreira, Ana M. Uehara, Isadora A. Silva, Marcelo J.B. Botelho, Françoise V. Pereira-Maia, Elene C. Guilardi, Silvana Guerra, Wendell |
dc.subject.por.fl_str_mv |
Antitumoral activity Apoptosis Copper(II) complexes DNA binding Hydrazide Mycobacterium tuberculosis |
topic |
Antitumoral activity Apoptosis Copper(II) complexes DNA binding Hydrazide Mycobacterium tuberculosis |
description |
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. |
publishDate |
2017 |
dc.date.none.fl_str_mv |
2017-07-01 2018-12-11T17:32:13Z 2018-12-11T17:32:13Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1016/j.jinorgbio.2017.04.024 Journal of Inorganic Biochemistry, v. 172, p. 138-146. 1873-3344 0162-0134 http://hdl.handle.net/11449/178814 10.1016/j.jinorgbio.2017.04.024 2-s2.0-85018247014 2-s2.0-85018247014.pdf |
url |
http://dx.doi.org/10.1016/j.jinorgbio.2017.04.024 http://hdl.handle.net/11449/178814 |
identifier_str_mv |
Journal of Inorganic Biochemistry, v. 172, p. 138-146. 1873-3344 0162-0134 10.1016/j.jinorgbio.2017.04.024 2-s2.0-85018247014 2-s2.0-85018247014.pdf |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Inorganic Biochemistry 0,743 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
138-146 application/pdf |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1799964869765627904 |