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

Org Biomol Chem. 2023 Nov 29;21(46):9242-9254. doi: 10.1039/d3ob01388j.

Abstract

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 Cu2+ 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Copper* / chemistry
  • Glycoconjugates
  • Serum Albumin, Bovine* / chemistry
  • Triazoles

Substances

  • Serum Albumin, Bovine
  • Copper
  • Glycoconjugates
  • Triazoles