Biocatalytic Synthesis of Coumarin S-Glycosides: Towards Non-Cytotoxic Probes for Biomedical Imaging and Sensing

Molecules. 2024 Mar 16;29(6):1322. doi: 10.3390/molecules29061322.

Abstract

This study unveils an innovative method for synthesizing coumarin S-glycosides, employing original biocatalysts able to graft diverse carbohydrate structures onto 7-mercapto-4-methyl-coumarin in one-pot reactions. The fluorescence properties of the generated thio-derivatives were assessed, providing valuable insights into their potential applications in biological imaging or sensing. In addition, the synthesized compounds exhibited no cytotoxicity across various human cell lines. This research presents a promising avenue for the development of coumarin S-glycosides, paving the way for their application in diverse biomedical research areas.

Keywords: S-glycoside; biocatalyst; fluorescence; mercapto-coumarin.

MeSH terms

  • Coumarins* / chemistry
  • Glycosides* / chemistry
  • Humans

Substances

  • Glycosides
  • Coumarins

Grants and funding

N.B., A.P. and P.L. acknowledge financial support from the projects CHemBio (FEDER-FSE 2014-2020-EX003677); Valbiocosm (FEDER-FSE 2014-2020-EX003202); Techsab (FEDER-FSE 2014-2020-EX011313); QUALICHIM (APR-IA-PF 2021-00149467); the RTR Motivhealth (2019-00131403); and the Labex programs SYNORG (ANR-11-LABX-0029) and IRON (ANR-11-LABX-0018-01) for their financial support of ICOA, UMR 7311, University of Orléans, CNRS. N.B., A.P. and P.L. also thank the SALSA platform for analyses (NMR, HRMS). G.C. and R.D. gratefully acknowledge support from Orléans Métropole.