Synthesis and characterization of two novel red-shifted isothiocyanate BODIPYs and their application in protein conjugation

Autor(es):Mostrar menos -

Amorim, Vanessa G. ^[1] ; Melo, Shaiani M. G. ^[2] ; Leite, Ruan F. ^[3] ; Coutinho, Paulo Arthur ^[1] ; da Silva, Sarah M. P. ^{[1, 4]} ; da Silva, Andre R. ^{[1, 5]} ; Amorim, Fernanda G. ^[6] ; Pires, Rita G. W. ^{[1, 4]} ; Coitinho, Juliana B. ^[1] ; Emery, Flavio S. ^[2] ; Rezende, Lucas C. D. ^{[1, 3]}

Afiliação do(s) autor(es)

^[1] Univ Fed Espirito Santo, Grad Program Biochem, Vitoria, ES - Brazil

^[2] Univ Sao Paulo FCFRP USP, Sch Pharmaceut Sci Ribeirao Preto, Dept Pharmaceut Sci, Ribeirao Preto, SP - Brazil

^[3] Univ Fed Espirito Santo, Dept Nat Sci, Sao Mateus, ES - Brazil

^[4] Univ Fed Minas Gerais, Grad Program Biochem & Immunol, Belo Horizonte, MG - Brazil

^[5] Fed Inst Espirito Santo, Campus Aracruz, Aracruz, ES - Brazil

^[6] Vila Velha Univ, Vila Velha, ES - Brazil

• Tipo de documento: Artigo Científico
• Fonte: DYES AND PIGMENTS; v. 182, NOV 2020.
• Citações Web of Science: 0

Resumo

Fluorescent organic small molecules are very important tools for researchers in the fields of biochemistry and biotechnology, and boron-dipyrromethene (BODIPY) class of organic fluorophores gained much attention in recent years due to their remarkable photophysical properties and chemical versatility. Their application often involves conjugation with biomolecules, which can be accomplished by inserting a reactive functionality to the fluorescent dye. In this paper we present the preparation and characterization of two unpublished BODIPYs bearing the electrophilic isothiocyanate group, widely used for conjugation with proteins and biological amines. These dyes were prepared by inserting a nitrobenzene group to the BODIPY core via direct arylation, which was later converted to the isothiocyanate functionality. The arylated BODIPYs retained their fluorescence and showed red-shifted absorption and fluorescence spectra, when compared to previously published isothiocyanateBODIPYs. Their application in bioconjugation was tested with bovine serum albumin (BSA) and was confirmed from spectroscopic and electrophoretic analysis. (AU)

• Processo FAPESP: 14/18973-8 - Aplicação da química de sais de diazônio na modificação estrutural de fluoróforos do tipo BODIPY
• Beneficiário: Shaiani Maria Gil de Melo
• Modalidade de apoio: Bolsas no Brasil - Mestrado
• Processo FAPESP: 13/24408-9 - Modificação química de fluoróforos do tipo BODPY visando diversificação estrutural e fotofísica para obtenção de novas sondas fluorescentes
• Beneficiário: Lucas Cunha Dias de Rezende
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Doutorado
• Processo FAPESP: 11/23342-9 - Síntese,caracterização e aplicações de fluoróforos derivados do BODIPY.
• Beneficiário: Lucas Cunha Dias de Rezende
• Modalidade de apoio: Bolsas no Brasil - Doutorado