Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2024 Mar 16;29(6):1322.
doi: 10.3390/molecules29061322.

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

Nastassja Burrini  1 , Arnaud Pâris  1 , Guillaume Collet  2 , Pierre Lafite  1 , Richard Daniellou  2   3
Affiliations

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

Nastassja Burrini et al. Molecules. .

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.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Structures of 7-MC and 4-MUB.
Scheme 1
Scheme 1
General scheme of thioglycosylation reaction.
Figure 2
Figure 2
Representative normalized emission spectra of 4-MUB, 7-MC, and S-3 in PBS (left) and DMF (right). All spectra are available in the Supplementary Materials.
See this image and copyright information in PMC

Similar articles

See all similar articles

References

    1. Wang J., Zhang Y., Lu Q., Xing D., Zhang R. Exploring Carbohydrates for Therapeutics: A Review on Future Directions. Front. Pharmacol. 2021;12:756724. doi: 10.3389/fphar.2021.756724. - DOI - PMC - PubMed
    1. Jiang H., Qin X., Wang Q., Xu Q., Wang J., Wu Y., Chen W., Wang C., Zhang T., Xing D., et al. Application of Carbohydrates in Approved Small Molecule Drugs: A Review. Eur. J. Med. Chem. 2021;223:113633. doi: 10.1016/j.ejmech.2021.113633. - DOI - PubMed
    1. Fernández-Tejada A., Cañada F.J., Jiménez-Barbero J. Recent Developments in Synthetic Carbohydrate-Based Diagnostics, Vaccines, and Therapeutics. Chem. Eur. J. 2015;21:10616–10628. doi: 10.1002/chem.201500831. - DOI - PubMed
    1. Guillotin L., Assaf Z., Pistorio S.G., Lafite P., Demchenko A.V., Daniellou R. Hydrolysis of Glycosyl Thioimidates by Glycoside Hydrolase Requires Remote Activation for Efficient Activity. Catalysts. 2019;9:826. doi: 10.3390/catal9100826. - DOI
    1. Driguez H. Thiooligosaccharides as Tools for Structural Biology. ChemBioChem. 2001;2:311–318. doi: 10.1002/1439-7633(20010504)2:5<311::AID-CBIC311>3.0.CO;2-L. - DOI - PubMed

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.

LinkOut - more resources