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Push-pull fluorophores based on NHS esters of bithiophene for labelling of biomolecules containing primary amines

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Resumo:Fluorescent labelling is a versatile tool to visualize biomolecules containing primary amines in their cellular environment, allowing the study of their function or interactions. Here, three organic fluorophores that can irreversibly bind to the primary amine group on the target biomolecule are reported. They consist of push-pull heterocyclic dyes based on bithiophene and incorporating a terminal N-hydroxysuccinimidyl ester as a reactive group for labelling primary amine groups from biomolecules as (poly)amines, peptides or proteins. Their potential as chemosensors for primary amines, using N α -Boc protected amino acid l-lysine as a model, was assessed through UV-Visible, fluorescence and 1 H NMR titrations.
Autores principais:Barros, Mariana
Outros Autores:Arroyo, Pau; Sáez, Jose A.; Gil, Salvador; Parra, Margarita; Costa, Susana P. G.; Raposo, M. Manuela M.; Gaviña, Pablo
Assunto:bithiophene Boc-lysine fluorescent labelling primary amine chemosensor push-pull heterocyclic fluorophores
Ano:2025
País:Portugal
Tipo de documento:artigo
Tipo de acesso:acesso aberto
Instituição associada:Universidade do Minho
Idioma:inglês
Origem:RepositóriUM - Universidade do Minho
Descrição
Resumo:Fluorescent labelling is a versatile tool to visualize biomolecules containing primary amines in their cellular environment, allowing the study of their function or interactions. Here, three organic fluorophores that can irreversibly bind to the primary amine group on the target biomolecule are reported. They consist of push-pull heterocyclic dyes based on bithiophene and incorporating a terminal N-hydroxysuccinimidyl ester as a reactive group for labelling primary amine groups from biomolecules as (poly)amines, peptides or proteins. Their potential as chemosensors for primary amines, using N α -Boc protected amino acid l-lysine as a model, was assessed through UV-Visible, fluorescence and 1 H NMR titrations.