Multivariate analysis of protolytic and tautomeric equilibria of Erythrosine B and its ester derivatives in ionic and non-ionic micelles

Página do item simplificado
dc.citation.issue-pt_BR
dc.citation.volume313pt_BR
dc.contributor.authorFreitas, Camila Fabiano de
dc.contributor.authorVanzin, Douglas
dc.contributor.authorBraga, Thais Lazzarotto
dc.contributor.authorPellosi, Diogo Silva [UNIFESP]
dc.contributor.authorBatistela, Vagner Roberto
dc.contributor.authorWilker, Caetano
dc.contributor.authorNoboru, Hioka
dc.contributor.authorLatteshttp://lattes.cnpq.br/4319283598735971pt_BR
dc.coverage.spatialAmsterdãpt_BR
dc.date.accessioned2021-03-10T17:59:10Z
dc.date.available2021-03-10T17:59:10Z
dc.date.issued2020-09-01
dc.description.abstractErythrosine B (ERY) is a xanthene dye that has been widely used in recent years as a photoactive drug for Photodynamic Therapy. However, application of ERY and its derivatives as photosensitizer drugs depend not only on their singlet oxygen quantum yield, but also on their hydrophobicity, and photoactive protolytic and tautomeric species. In this work, the objective was to evaluate the acid-base equilibria of ERY and its derivatives: erythrosine methyl ester (ERYMET); erythrosine butyl ester (ERYBUT) and erythrosine decyl ester (ERYDEC), in biomimetic media (micelles of SDS and CTAB) as well as in some drug delivery systems of triblock copolymer Poloxamer (P-123 and F-127). All protolytic chemical equilibria were studied by employing chemometric multivariate analysis based on the Imbrie's Q-Mode Factor Analysis and k-Matrix methods. Tautomeric equilibria were evaluated taking into account of possible chemical structures and electronic spectroscopic approximations. Results from ester derivatives presenting only one protolytic equilibrium (at the phenolate group) and two possible tautomers, allow us to determine that protolytic equilibria follow the sequence pKaCOOH < pKaOH in SDS media for ERY by structure comparison. On the other hand, CTAB and polaxamers inverted the acidity of ERY protolytic groups (pKaOH < pKaCOOH) due to changes in the tautomeric equilibrium due to a lactone formation for the dyes neutral protolytic species inside the micelles. Chemometric approaches provided detailed analyses of protolytic/tautomeric equilibria of ERY. Through this, we achieved a deeper understanding of how ERY and its derivatives are affected by microenvironments in biomimetic and drug delivery systems.pt_BR
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorshipIDFAPESP: 2019/01604-3pt_BR
dc.format.extent113320pt_BR
dc.identifierhttps://www.sciencedirect.com/science/article/abs/pii/S016773222030266Xpt_BR
dc.identifier.citationFREITAS, C. F. de; VANZIN, D.; BRAGA, T. L.; PELLOSI, D. S.; BATISTELA, V. R.; CAETANO, W.; HIOKA, N. Multivariate analysis of protolytic and tautomeric equilibria of Erythrosine B and its ester derivatives in ionic and non-ionic micelles. Journal of Molecular Liquids, v. 313, p. 113320, 2020.pt_BR
dc.identifier.doihttps://doi.org/10.1016/j.molliq.2020.113320pt_BR
dc.identifier.issn0167-7322pt_BR
dc.identifier.urihttps://repositorio.unifesp.br/handle/11600/60324
dc.languageengpt_BR
dc.publisherW. Schröerpt_BR
dc.relation.ispartofJournal of Molecular Liquidspt_BR
dc.rightsinfo:eu-repo/semantics/restrictedAccesspt_BR
dc.subjectErythrosinept_BR
dc.subjectXanthenept_BR
dc.subjectProtolytic equilibriumpt_BR
dc.subjectTautomeric equilibriumpt_BR
dc.subjectMultivariate analysispt_BR
dc.titleMultivariate analysis of protolytic and tautomeric equilibria of Erythrosine B and its ester derivatives in ionic and non-ionic micellespt_BR
dc.typeinfo:eu-repo/semantics/articlept_BR
unifesp.assessoresproreitoriasNão se aplicapt_BR
unifesp.campusInstituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF)pt_BR
unifesp.departamentoQuímicapt_BR
Arquivos
Pacote Original
Agora exibindo 1 - 1 de 1
Imagem de Miniatura
Nome:
Multivariate analysis of protolytic and tautomeric equilibria of Erythrosine B and its ester derivatives in ionic and non-ionic micelles.pdf
Tamanho:
2.75 MB
Formato:
Adobe Portable Document Format
Descrição:
Manuscrito
Baixar
Licença do Pacote
Agora exibindo 1 - 1 de 1
Imagem de Miniatura
Nome:
license.txt
Tamanho:
5.38 KB
Formato:
Item-specific license agreed upon to submission
Descrição:
Baixar
Coleções
ICAQF - Artigos