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Position matters in ester thiolysis by cysteine-containing peptides in micelles and vesicles

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Autor(es):
Lacerda, C. D. ; Juliano, M. A. ; Liria, C. W. ; Machini, M. T. ; Park, P. ; Matsubara, D. K. ; Barzotto, D. R. ; Lima, F. S. ; Chaimovich, H. ; Cuccovia, I. M.
Número total de Autores: 10
Tipo de documento: Artigo Científico
Fonte: RESULTS IN CHEMISTRY; v. 6, p. 10-pg., 2023-12-01.
Resumo

Hypothesis: The interaction of peptides with nanoaggregates is an active research topic. Cysteine (Cys)-containing peptides open opportunities for developing low molecular weight compounds with interesting properties and potential applications. Knowledge of the relationship between the position of the Cys in the peptides and the aggregate interface is essential.Experiments: We synthesized a series of Cys-containing peptides having a variable number of glycines (Gly) as spacers between the N-palmitoyl chain at their N-terminal portion and Cys at their carboxy-terminal. The apparent pKa of the Cys-thiol group of each peptide was measured in micelles of CTAC (hexadecyltrimethylammonium chloride) and vesicles of DHDAC (dihexadecyldimethylammonium chloride). No clear correlation existed between the pKa's and the number of Gly in the peptides. However, the rate of p-nitro-phenyloctanoate (NPO) thiolysis by the peptides in micelles and vesicles decreased regularly with peptide length. Molecular Dynamics (MD) analysis of the peptides in CTAC micelles was carried out.Findings: pKa determinations and rate dependence of the peptides in a thiolysis reaction and MD analysis strongly suggested that the higher rates observed with shorter peptides can be attributed to an increased probability of Cys being located below the micellar surface, where the carbonyl reaction center of NPO resides. (AU)

Processo FAPESP: 19/03023-8 - Como adentram a membrana os peptídeos penetradores de células?
Beneficiário:Peter Park
Modalidade de apoio: Bolsas no Brasil - Doutorado Direto
Processo FAPESP: 14/50983-3 - INCT 2014: fluidos complexos
Beneficiário:Antonio Martins Figueiredo Neto
Modalidade de apoio: Auxílio à Pesquisa - Temático
Processo FAPESP: 15/10411-3 - EMU concedido no processo 2013/08166-5: stopped-flow
Beneficiário:Iolanda Midea Cuccovia
Modalidade de apoio: Auxílio à Pesquisa - Programa Equipamentos Multiusuários
Processo FAPESP: 22/01825-2 - Desenvolvimento e estudo de novos compostos peptídicos com potencial para atuar como agentes antimicrobianos, penetrantes em células e/ou quelantes de metais
Beneficiário:Maria Teresa Machini
Modalidade de apoio: Auxílio à Pesquisa - Regular
Processo FAPESP: 13/08166-5 - Química em interfaces: interações de fármacos, peptídios e enzimas com membranas modelos
Beneficiário:Iolanda Midea Cuccovia
Modalidade de apoio: Auxílio à Pesquisa - Temático