Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies

Detalhes bibliográficos
Autor(a) principal: Bairros, André Valle de
Data de Publicação: 2018
Outros Autores: Pereira, Danillo Baptista, Cordeiro, Everson Willian Fialho, Paim, Clésio Soldateli, Silva, Fabiana Ernestina Barcellos da, Malesuik, Marcelo Donadel, Paula, Fávero Reisdorfer
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Brazilian Journal of Pharmaceutical Sciences
Texto Completo: https://www.revistas.usp.br/bjps/article/view/146820
Resumo: Fluoroquinolones are a known antibacterial class commonly used around the world. These compounds present relative stability and they may show some adverse effects according their distinct chemical structures. The chemical hydrolysis of five fluoroquinolones was studied using alkaline and photolytic degradation aiming to observe the differences in molecular reactivity. DFT/B3LYP-6.31G* was used to assist with understanding the chemical structure degradation. Gemifloxacin underwent degradation in alkaline medium. Gemifloxacin and danofloxacin showed more degradation perceptual indices in comparison with ciprofloxacin, enrofloxacin and norfloxacin in photolytic conditions. Some structural features were observed which may influence degradation, such as the presence of five member rings attached to the quinolone ring and the electrostatic positive charges, showed in maps of potential electrostatic charges. These measurements may be used in the design of effective and more stable fluoroquinolones as well as the investigation of degradation products from stress stability assays.
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spelling Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studiesFluoroquinolones/evaluationForced degradation studiesMolecular modeling Fluoroquinolones are a known antibacterial class commonly used around the world. These compounds present relative stability and they may show some adverse effects according their distinct chemical structures. The chemical hydrolysis of five fluoroquinolones was studied using alkaline and photolytic degradation aiming to observe the differences in molecular reactivity. DFT/B3LYP-6.31G* was used to assist with understanding the chemical structure degradation. Gemifloxacin underwent degradation in alkaline medium. Gemifloxacin and danofloxacin showed more degradation perceptual indices in comparison with ciprofloxacin, enrofloxacin and norfloxacin in photolytic conditions. Some structural features were observed which may influence degradation, such as the presence of five member rings attached to the quinolone ring and the electrostatic positive charges, showed in maps of potential electrostatic charges. These measurements may be used in the design of effective and more stable fluoroquinolones as well as the investigation of degradation products from stress stability assays.Universidade de São Paulo. Faculdade de Ciências Farmacêuticas2018-06-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://www.revistas.usp.br/bjps/article/view/14682010.1590/s2175-97902018000100188Brazilian Journal of Pharmaceutical Sciences; Vol. 54 Núm. 1 (2018); e00188Brazilian Journal of Pharmaceutical Sciences; v. 54 n. 1 (2018); e00188Brazilian Journal of Pharmaceutical Sciences; Vol. 54 No. 1 (2018); e001882175-97901984-8250reponame:Brazilian Journal of Pharmaceutical Sciencesinstname:Universidade de São Paulo (USP)instacron:USPenghttps://www.revistas.usp.br/bjps/article/view/146820/140349Copyright (c) 2018 Brazilian Journal of Pharmaceutical Sciences (Impresso)info:eu-repo/semantics/openAccessBairros, André Valle dePereira, Danillo BaptistaCordeiro, Everson Willian FialhoPaim, Clésio SoldateliSilva, Fabiana Ernestina Barcellos daMalesuik, Marcelo DonadelPaula, Fávero Reisdorfer2018-06-07T16:31:56Zoai:revistas.usp.br:article/146820Revistahttps://www.revistas.usp.br/bjps/indexPUBhttps://old.scielo.br/oai/scielo-oai.phpbjps@usp.br||elizabeth.igne@gmail.com2175-97901984-8250opendoar:2018-06-07T16:31:56Brazilian Journal of Pharmaceutical Sciences - Universidade de São Paulo (USP)false
dc.title.none.fl_str_mv Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies
title Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies
spellingShingle Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies
Bairros, André Valle de
Fluoroquinolones/evaluation
Forced degradation studies
Molecular modeling
title_short Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies
title_full Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies
title_fullStr Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies
title_full_unstemmed Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies
title_sort Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies
author Bairros, André Valle de
author_facet Bairros, André Valle de
Pereira, Danillo Baptista
Cordeiro, Everson Willian Fialho
Paim, Clésio Soldateli
Silva, Fabiana Ernestina Barcellos da
Malesuik, Marcelo Donadel
Paula, Fávero Reisdorfer
author_role author
author2 Pereira, Danillo Baptista
Cordeiro, Everson Willian Fialho
Paim, Clésio Soldateli
Silva, Fabiana Ernestina Barcellos da
Malesuik, Marcelo Donadel
Paula, Fávero Reisdorfer
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Bairros, André Valle de
Pereira, Danillo Baptista
Cordeiro, Everson Willian Fialho
Paim, Clésio Soldateli
Silva, Fabiana Ernestina Barcellos da
Malesuik, Marcelo Donadel
Paula, Fávero Reisdorfer
dc.subject.por.fl_str_mv Fluoroquinolones/evaluation
Forced degradation studies
Molecular modeling
topic Fluoroquinolones/evaluation
Forced degradation studies
Molecular modeling
description Fluoroquinolones are a known antibacterial class commonly used around the world. These compounds present relative stability and they may show some adverse effects according their distinct chemical structures. The chemical hydrolysis of five fluoroquinolones was studied using alkaline and photolytic degradation aiming to observe the differences in molecular reactivity. DFT/B3LYP-6.31G* was used to assist with understanding the chemical structure degradation. Gemifloxacin underwent degradation in alkaline medium. Gemifloxacin and danofloxacin showed more degradation perceptual indices in comparison with ciprofloxacin, enrofloxacin and norfloxacin in photolytic conditions. Some structural features were observed which may influence degradation, such as the presence of five member rings attached to the quinolone ring and the electrostatic positive charges, showed in maps of potential electrostatic charges. These measurements may be used in the design of effective and more stable fluoroquinolones as well as the investigation of degradation products from stress stability assays.
publishDate 2018
dc.date.none.fl_str_mv 2018-06-07
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://www.revistas.usp.br/bjps/article/view/146820
10.1590/s2175-97902018000100188
url https://www.revistas.usp.br/bjps/article/view/146820
identifier_str_mv 10.1590/s2175-97902018000100188
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv https://www.revistas.usp.br/bjps/article/view/146820/140349
dc.rights.driver.fl_str_mv Copyright (c) 2018 Brazilian Journal of Pharmaceutical Sciences (Impresso)
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Copyright (c) 2018 Brazilian Journal of Pharmaceutical Sciences (Impresso)
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Universidade de São Paulo. Faculdade de Ciências Farmacêuticas
publisher.none.fl_str_mv Universidade de São Paulo. Faculdade de Ciências Farmacêuticas
dc.source.none.fl_str_mv Brazilian Journal of Pharmaceutical Sciences; Vol. 54 Núm. 1 (2018); e00188
Brazilian Journal of Pharmaceutical Sciences; v. 54 n. 1 (2018); e00188
Brazilian Journal of Pharmaceutical Sciences; Vol. 54 No. 1 (2018); e00188
2175-9790
1984-8250
reponame:Brazilian Journal of Pharmaceutical Sciences
instname:Universidade de São Paulo (USP)
instacron:USP
instname_str Universidade de São Paulo (USP)
instacron_str USP
institution USP
reponame_str Brazilian Journal of Pharmaceutical Sciences
collection Brazilian Journal of Pharmaceutical Sciences
repository.name.fl_str_mv Brazilian Journal of Pharmaceutical Sciences - Universidade de São Paulo (USP)
repository.mail.fl_str_mv bjps@usp.br||elizabeth.igne@gmail.com
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