Evaluation of the influence of fluoroquinolone chemical structure on stability: forced degradation and in silico studies
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , , , |
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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Brazilian Journal of Pharmaceutical Sciences |
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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 |
_version_ |
1800222913352171520 |