Molecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stress

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dc.citation.issue44pt_BR
dc.citation.volume7pt_BR
dc.contributor.authorda Silva, Emerson Rodrigo [UNIFESP]
dc.contributor.authorValĂȘncio, AndrĂ© [UNIFESP]
dc.contributor.authorMachado, Marcelo Ferreira Marcondes [UNIFESP]
dc.contributor.authorMiranda, Antonio [UNIFESP]
dc.contributor.authorLatteshttp://lattes.cnpq.br/7800589206457326pt_BR
dc.contributor.authorLatteshttp://lattes.cnpq.br/0596334947896054
dc.contributor.authorLatteshttp://lattes.cnpq.br/9703373400186586
dc.contributor.authorLatteshttp://lattes.cnpq.br/1357848049935882
dc.contributor.otherLourenço, Cecília
dc.contributor.otherSouza, Louise E. A.
dc.date.accessioned2023-05-08T17:22:54Z
dc.date.available2023-05-08T17:22:54Z
dc.date.issued2022-11-21
dc.description.abstractCephalexin 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.en
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorshipID19/20907-7pt_BR
dc.format.extente202203032pt_BR
dc.identifierhttps://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/slct.202203032pt_BR
dc.identifier.urihttps://repositorio.unifesp.br/handle/11600/67461
dc.languageengpt_BR
dc.publisherWilleypt_BR
dc.relation.ispartofChemistrySelecten
dc.rightsinfo:eu-repo/semantics/openAccesspt_BR
dc.subjectAntibioticsen
dc.subjectDegradationen
dc.subjectCephalosporinsen
dc.subjectPhotolysisen
dc.titleMolecular structure and antibacterialactivity of degradation products from cephalexin solutions submitted to thermal and photolytic stressen
dc.typeinfo:eu-repo/semantics/articlept_BR
unifesp.campusEscola Paulista de Medicina (EPM)pt_BR
unifesp.departamentoBiofĂ­sicapt_BR
unifesp.knowledgeAreaBiofĂ­sicapt_BR
unifesp.researchAreaBiofĂ­sica molecularpt_BR
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