Photoactive glycoconjugates with a very large Stokes shift: synthesis, photophysics, and copper() and BSA sensing

This study presents the synthesis of novel glycoconjugates by connecting benzazole and carbohydrate units with a 1,2,3-triazole linker. A simple synthetic route employing a copper( i ) catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) was utilized. The synthesized compounds exhibit excited-st...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-11, Vol.21 (46), p.9242-9254
Main Authors: da Silva, Cláudia Brito, Silva, Luana, Debia, Natalí Pires, Chaves, Otávio Augusto, Lüdtke, Diogo Seibert, Rodembusch, Fabiano Severo
Format: Article
Language:English
Subjects:
Alkynes
Bovine serum albumin
Carbohydrates
Chemical sensors
Copper
Cycloaddition
Emission
Fluorescence
Glycoconjugates
Proteins
Serum albumin
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Summary:This study presents the synthesis of novel glycoconjugates by connecting benzazole and carbohydrate units with a 1,2,3-triazole linker. A simple synthetic route employing a copper( i ) catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) was utilized. The synthesized compounds exhibit excited-state intramolecular proton transfer (ESIPT), resulting in longer wavelength emission with a significantly large Stokes shift (∼10 000 cm −1 ). These compounds show potential as chemical sensors due to their ability to detect Cu 2+ ions, causing a decrease in fluorescence emission (turn-off effect). Additionally, they demonstrate strong interaction with proteins, exemplified by their interaction with bovine serum albumin (BSA) as a model protein. Photoactive glycoconjugates obtained via copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition, showing ESIPT properties with a very large Stokes shift, with notable sensing capabilities for both copper ions and bovine serum albumin in solution.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01388j