Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress
Autor(a) principal: | |
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Data de Publicação: | 2022 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNIFESP |
dARK ID: | ark:/48912/001300000q7m9 |
DOI: | 10.1002/slct.202203032 |
Texto Completo: | https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/slct.202203032 https://repositorio.unifesp.br/handle/11600/67461 |
Resumo: | Cephalexin is a beta-lactam antibiotic of the first generation of cephalosporins which is very effective against various bacterial infections. In this work, we investigate the structure and antibacterial activity of cephalexin solutions submitted to forced degradation under heat stress and photolytic irradiation. A combination of analytical techniques gathering LC/ESI-MS and NMR spectroscopy allowed us to identify different chemical species amongst the byproducts, revealing that photolysis via UV light leads to significant amounts of oxidized species that conserve the dihydrothiazine ring adjacent to the beta-lactam ring. In contrast, thermodegradation induces the rupture of the bioactive moiety possibly with the production of cephalosporinic acid and deaminated species, which are inactive to bacteria. Microbiological analyses using E. coli as a model organism indicated that the antimicrobial capacity of samples submitted to thermolysis is suppressed while solutions submitted to irradiation with UVA light preserve their bactericidal power. Atomic force microscopy showed that cells incubated with photodegraded cephalexin are much longer than those incubated with the undegraded antibiotic, indicating that byproducts from photolysis inhibit septum formation and likely affect the action of penicillin-binding protein 3 in the divisome of E. coli cells. |
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Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stressAntibioticsDegradationCephalosporinsPhotolysisCephalexin is a beta-lactam antibiotic of the first generation of cephalosporins which is very effective against various bacterial infections. In this work, we investigate the structure and antibacterial activity of cephalexin solutions submitted to forced degradation under heat stress and photolytic irradiation. A combination of analytical techniques gathering LC/ESI-MS and NMR spectroscopy allowed us to identify different chemical species amongst the byproducts, revealing that photolysis via UV light leads to significant amounts of oxidized species that conserve the dihydrothiazine ring adjacent to the beta-lactam ring. In contrast, thermodegradation induces the rupture of the bioactive moiety possibly with the production of cephalosporinic acid and deaminated species, which are inactive to bacteria. Microbiological analyses using E. coli as a model organism indicated that the antimicrobial capacity of samples submitted to thermolysis is suppressed while solutions submitted to irradiation with UVA light preserve their bactericidal power. Atomic force microscopy showed that cells incubated with photodegraded cephalexin are much longer than those incubated with the undegraded antibiotic, indicating that byproducts from photolysis inhibit septum formation and likely affect the action of penicillin-binding protein 3 in the divisome of E. coli cells.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)19/20907-7Willeyhttp://lattes.cnpq.br/7800589206457326http://lattes.cnpq.br/0596334947896054http://lattes.cnpq.br/9703373400186586http://lattes.cnpq.br/1357848049935882Lourenço, CecíliaSouza, Louise E. A.da Silva, Emerson Rodrigo [UNIFESP]Valêncio, André [UNIFESP]Machado, Marcelo Ferreira Marcondes [UNIFESP]Miranda, Antonio [UNIFESP]2023-05-08T17:22:54Z2023-05-08T17:22:54Z2022-11-21info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersione202203032application/pdfhttps://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/slct.202203032https://repositorio.unifesp.br/handle/11600/67461ark:/48912/001300000q7m9engChemistrySelectinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESP2024-08-12T16:23:54Zoai:repositorio.unifesp.br/:11600/67461Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestbiblioteca.csp@unifesp.bropendoar:34652024-12-11T20:30:48.474138Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false |
dc.title.none.fl_str_mv |
Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress |
title |
Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress |
spellingShingle |
Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress da Silva, Emerson Rodrigo [UNIFESP] Antibiotics Degradation Cephalosporins Photolysis da Silva, Emerson Rodrigo [UNIFESP] Antibiotics Degradation Cephalosporins Photolysis |
title_short |
Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress |
title_full |
Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress |
title_fullStr |
Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress |
title_full_unstemmed |
Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress |
title_sort |
Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress |
author |
da Silva, Emerson Rodrigo [UNIFESP] |
author_facet |
da Silva, Emerson Rodrigo [UNIFESP] da Silva, Emerson Rodrigo [UNIFESP] Valêncio, André [UNIFESP] Machado, Marcelo Ferreira Marcondes [UNIFESP] Miranda, Antonio [UNIFESP] Valêncio, André [UNIFESP] Machado, Marcelo Ferreira Marcondes [UNIFESP] Miranda, Antonio [UNIFESP] |
author_role |
author |
author2 |
Valêncio, André [UNIFESP] Machado, Marcelo Ferreira Marcondes [UNIFESP] Miranda, Antonio [UNIFESP] |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
http://lattes.cnpq.br/7800589206457326 http://lattes.cnpq.br/0596334947896054 http://lattes.cnpq.br/9703373400186586 http://lattes.cnpq.br/1357848049935882 Lourenço, Cecília Souza, Louise E. A. |
dc.contributor.author.fl_str_mv |
da Silva, Emerson Rodrigo [UNIFESP] Valêncio, André [UNIFESP] Machado, Marcelo Ferreira Marcondes [UNIFESP] Miranda, Antonio [UNIFESP] |
dc.subject.por.fl_str_mv |
Antibiotics Degradation Cephalosporins Photolysis |
topic |
Antibiotics Degradation Cephalosporins Photolysis |
description |
Cephalexin is a beta-lactam antibiotic of the first generation of cephalosporins which is very effective against various bacterial infections. In this work, we investigate the structure and antibacterial activity of cephalexin solutions submitted to forced degradation under heat stress and photolytic irradiation. A combination of analytical techniques gathering LC/ESI-MS and NMR spectroscopy allowed us to identify different chemical species amongst the byproducts, revealing that photolysis via UV light leads to significant amounts of oxidized species that conserve the dihydrothiazine ring adjacent to the beta-lactam ring. In contrast, thermodegradation induces the rupture of the bioactive moiety possibly with the production of cephalosporinic acid and deaminated species, which are inactive to bacteria. Microbiological analyses using E. coli as a model organism indicated that the antimicrobial capacity of samples submitted to thermolysis is suppressed while solutions submitted to irradiation with UVA light preserve their bactericidal power. Atomic force microscopy showed that cells incubated with photodegraded cephalexin are much longer than those incubated with the undegraded antibiotic, indicating that byproducts from photolysis inhibit septum formation and likely affect the action of penicillin-binding protein 3 in the divisome of E. coli cells. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-11-21 2023-05-08T17:22:54Z 2023-05-08T17:22:54Z |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/slct.202203032 https://repositorio.unifesp.br/handle/11600/67461 |
dc.identifier.dark.fl_str_mv |
ark:/48912/001300000q7m9 |
url |
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/slct.202203032 https://repositorio.unifesp.br/handle/11600/67461 |
identifier_str_mv |
ark:/48912/001300000q7m9 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
ChemistrySelect |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
e202203032 application/pdf |
dc.publisher.none.fl_str_mv |
Willey |
publisher.none.fl_str_mv |
Willey |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da UNIFESP instname:Universidade Federal de São Paulo (UNIFESP) instacron:UNIFESP |
instname_str |
Universidade Federal de São Paulo (UNIFESP) |
instacron_str |
UNIFESP |
institution |
UNIFESP |
reponame_str |
Repositório Institucional da UNIFESP |
collection |
Repositório Institucional da UNIFESP |
repository.name.fl_str_mv |
Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP) |
repository.mail.fl_str_mv |
biblioteca.csp@unifesp.br |
_version_ |
1822183930925678592 |
dc.identifier.doi.none.fl_str_mv |
10.1002/slct.202203032 |