Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosis
Autor(a) principal: | |
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Data de Publicação: | 2018 |
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.2018.03.010 http://hdl.handle.net/11449/166132 |
Resumo: | This work describes the synthesis, characterization and biological evaluation of three platinum complexes of the type [Pt(DMSO)(L)Cl]Cl, in which L represents a fluoroquinolone, namely, ciprofloxacin (cpl), ofloxacin (ofl), or sparfloxacin (spf). The new complexes were characterized by elemental analysis, high-resolution mass spectrometry (HRESIMS) and H-1, C-13 and Pt-195 NMR (nuclear magnetic resonance). The spectral data suggest that the fluoroquinolones act as bidentate ligands coordinated to Pt(II) through the nitrogen atoms of the piperazine ring. Microbiological assays against wild type Mycobacterium tuberculosis (ATCC 27294) showed that all complexes have been very potent, exhibiting antitubercular potency at concentrations < 2 mu M, although none of the complexes presented higher potency than established anti-TB drugs. As to the resistant strains, the complex with sparfloxacin, [Pt(DMSO)(spf)Cl]Cl exhibited the best potential against most Mycobacterium tuberculosis clinical isolates. The cytotoxicity of these compounds was also evaluated in three breast cell lines: MCF-10 (a healthy cell), MCF-7 (a hormone responsive cancer cell) and MDA-MB-231 (triple negative breast cancer cell). In both tumor cell lines, [Pt(DMSO)(spf)Cl]Cl was more active and more selective than cisplatin. Flow cytometry analysis revealed that [Pt(DMSO)(spf)Cl]Cl induced late apoptotic cell death in MDA-MB-231 cells. |
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Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosisPlatinum complexesFluoroquinoloneMycobacterium tuberculosisResistant strainsCytotoxicityApoptosisThis work describes the synthesis, characterization and biological evaluation of three platinum complexes of the type [Pt(DMSO)(L)Cl]Cl, in which L represents a fluoroquinolone, namely, ciprofloxacin (cpl), ofloxacin (ofl), or sparfloxacin (spf). The new complexes were characterized by elemental analysis, high-resolution mass spectrometry (HRESIMS) and H-1, C-13 and Pt-195 NMR (nuclear magnetic resonance). The spectral data suggest that the fluoroquinolones act as bidentate ligands coordinated to Pt(II) through the nitrogen atoms of the piperazine ring. Microbiological assays against wild type Mycobacterium tuberculosis (ATCC 27294) showed that all complexes have been very potent, exhibiting antitubercular potency at concentrations < 2 mu M, although none of the complexes presented higher potency than established anti-TB drugs. As to the resistant strains, the complex with sparfloxacin, [Pt(DMSO)(spf)Cl]Cl exhibited the best potential against most Mycobacterium tuberculosis clinical isolates. The cytotoxicity of these compounds was also evaluated in three breast cell lines: MCF-10 (a healthy cell), MCF-7 (a hormone responsive cancer cell) and MDA-MB-231 (triple negative breast cancer cell). In both tumor cell lines, [Pt(DMSO)(spf)Cl]Cl was more active and more selective than cisplatin. Flow cytometry analysis revealed that [Pt(DMSO)(spf)Cl]Cl induced late apoptotic cell death in MDA-MB-231 cells.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Univ Fed Uberlandia, Inst Quim, Av Joao Naves de Avila,2121,Campus Santa Monica, BR-38400902 Uberlandia, MG, BrazilUniv Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Anal Clin Toxicol & Bromatol, Ribeirao Preto, SP, BrazilUniv Estadual Paulista, Lab Pesquisa Tuberculose, Fac Ciencias Farmaceut, Campus Araraquara, Araraquara, SP, BrazilFundacao Oswaldo Cruz, Inst Tecnol Farmacos FarManguinhos, Rio De Janeiro, RJ, BrazilUniv Fed Minas Gerais, Dept Quim, Belo Horizonte, MG, BrazilUniv Estadual Paulista, Lab Pesquisa Tuberculose, Fac Ciencias Farmaceut, Campus Araraquara, Araraquara, SP, BrazilCNPq: 442328/2014-1FAPEMIG: APQ-00330-14Elsevier B.V.Universidade Federal de Uberlândia (UFU)Universidade de São Paulo (USP)Universidade Estadual Paulista (Unesp)Fundacao Oswaldo CruzUniversidade Federal de Minas Gerais (UFMG)Oliveira, Leticia P. deCarneiro, Zumira A.Ribeiro, Camila M. [UNESP]Lima, Mauricio F.Paixao, Drielly A.Pivatto, MarcosSouza, Marcus V. N. deTeixeira, Leticia R.Lopes, Carla D.Albuquerque, Sergio dePavan, Fernando R. [UNESP]Guerra, Wendell2018-11-29T14:59:46Z2018-11-29T14:59:46Z2018-06-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article77-83application/pdfhttp://dx.doi.org/10.1016/j.jinorgbio.2018.03.010Journal Of Inorganic Biochemistry. New York: Elsevier Science Inc, v. 183, p. 77-83, 2018.0162-0134http://hdl.handle.net/11449/16613210.1016/j.jinorgbio.2018.03.010WOS:000432233100008WOS000432233100008.pdfWeb of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal Of Inorganic Biochemistry0,743info:eu-repo/semantics/openAccess2023-10-21T06:03:58Zoai:repositorio.unesp.br:11449/166132Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462023-10-21T06:03:58Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosis |
title |
Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosis |
spellingShingle |
Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosis Oliveira, Leticia P. de Platinum complexes Fluoroquinolone Mycobacterium tuberculosis Resistant strains Cytotoxicity Apoptosis |
title_short |
Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosis |
title_full |
Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosis |
title_fullStr |
Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosis |
title_full_unstemmed |
Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosis |
title_sort |
Three new platinum complexes containing fluoroquinolones and DMSO: Cytotoxicity and evaluation against drug-resistant tuberculosis |
author |
Oliveira, Leticia P. de |
author_facet |
Oliveira, Leticia P. de Carneiro, Zumira A. Ribeiro, Camila M. [UNESP] Lima, Mauricio F. Paixao, Drielly A. Pivatto, Marcos Souza, Marcus V. N. de Teixeira, Leticia R. Lopes, Carla D. Albuquerque, Sergio de Pavan, Fernando R. [UNESP] Guerra, Wendell |
author_role |
author |
author2 |
Carneiro, Zumira A. Ribeiro, Camila M. [UNESP] Lima, Mauricio F. Paixao, Drielly A. Pivatto, Marcos Souza, Marcus V. N. de Teixeira, Leticia R. Lopes, Carla D. Albuquerque, Sergio de Pavan, Fernando R. [UNESP] Guerra, Wendell |
author2_role |
author author author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Federal de Uberlândia (UFU) Universidade de São Paulo (USP) Universidade Estadual Paulista (Unesp) Fundacao Oswaldo Cruz Universidade Federal de Minas Gerais (UFMG) |
dc.contributor.author.fl_str_mv |
Oliveira, Leticia P. de Carneiro, Zumira A. Ribeiro, Camila M. [UNESP] Lima, Mauricio F. Paixao, Drielly A. Pivatto, Marcos Souza, Marcus V. N. de Teixeira, Leticia R. Lopes, Carla D. Albuquerque, Sergio de Pavan, Fernando R. [UNESP] Guerra, Wendell |
dc.subject.por.fl_str_mv |
Platinum complexes Fluoroquinolone Mycobacterium tuberculosis Resistant strains Cytotoxicity Apoptosis |
topic |
Platinum complexes Fluoroquinolone Mycobacterium tuberculosis Resistant strains Cytotoxicity Apoptosis |
description |
This work describes the synthesis, characterization and biological evaluation of three platinum complexes of the type [Pt(DMSO)(L)Cl]Cl, in which L represents a fluoroquinolone, namely, ciprofloxacin (cpl), ofloxacin (ofl), or sparfloxacin (spf). The new complexes were characterized by elemental analysis, high-resolution mass spectrometry (HRESIMS) and H-1, C-13 and Pt-195 NMR (nuclear magnetic resonance). The spectral data suggest that the fluoroquinolones act as bidentate ligands coordinated to Pt(II) through the nitrogen atoms of the piperazine ring. Microbiological assays against wild type Mycobacterium tuberculosis (ATCC 27294) showed that all complexes have been very potent, exhibiting antitubercular potency at concentrations < 2 mu M, although none of the complexes presented higher potency than established anti-TB drugs. As to the resistant strains, the complex with sparfloxacin, [Pt(DMSO)(spf)Cl]Cl exhibited the best potential against most Mycobacterium tuberculosis clinical isolates. The cytotoxicity of these compounds was also evaluated in three breast cell lines: MCF-10 (a healthy cell), MCF-7 (a hormone responsive cancer cell) and MDA-MB-231 (triple negative breast cancer cell). In both tumor cell lines, [Pt(DMSO)(spf)Cl]Cl was more active and more selective than cisplatin. Flow cytometry analysis revealed that [Pt(DMSO)(spf)Cl]Cl induced late apoptotic cell death in MDA-MB-231 cells. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-11-29T14:59:46Z 2018-11-29T14:59:46Z 2018-06-01 |
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.2018.03.010 Journal Of Inorganic Biochemistry. New York: Elsevier Science Inc, v. 183, p. 77-83, 2018. 0162-0134 http://hdl.handle.net/11449/166132 10.1016/j.jinorgbio.2018.03.010 WOS:000432233100008 WOS000432233100008.pdf |
url |
http://dx.doi.org/10.1016/j.jinorgbio.2018.03.010 http://hdl.handle.net/11449/166132 |
identifier_str_mv |
Journal Of Inorganic Biochemistry. New York: Elsevier Science Inc, v. 183, p. 77-83, 2018. 0162-0134 10.1016/j.jinorgbio.2018.03.010 WOS:000432233100008 WOS000432233100008.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 |
77-83 application/pdf |
dc.publisher.none.fl_str_mv |
Elsevier B.V. |
publisher.none.fl_str_mv |
Elsevier B.V. |
dc.source.none.fl_str_mv |
Web of Science 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 |
|
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1792961605974097920 |