N-2 Alkylated analogues of aza-galactofagomine as potential inhibitors of β-glucosidase: Scientific paper

Filip  Đurković; Mario Zlatović; Dušan  Sladić; Irena Novaković; Filip  Bihelović; Zorana Ferjančić

doi:10.2298/JSC240315062D

PDF (3.08 MB) Supplementary Material (5.68 MB)

Published: Nov 9, 2024

Updated: 09.11.2024

DOI: https://doi.org/10.2298/JSC240315062D

Keywords:

iminosugars glycosidase inhibitor Gaucher’s disease

Filip Đurković

University of Belgrade - Faculty of Chemistry, Studenstki trg 12-16, Belgrade, Serbia

https://orcid.org/0000-0003-1507-1277

Mario Zlatović

University of Belgrade - Faculty of Chemistry, Studenstki trg 12-16, Belgrade, Serbia

https://orcid.org/0000-0003-4311-1731

Dušan Sladić

University of Belgrade - Faculty of Chemistry, Studenstki trg 12-16, Belgrade, Serbia

https://orcid.org/0000-0002-1000-9813

Irena Novaković

University of Belgrade – Institute of Chemistry, Technology and Metallurgy, Njegoševa 12, Belgrade, Serbia

https://orcid.org/0000-0001-9881-1204

Filip Bihelović

University of Belgrade - Faculty of Chemistry, Studenstki trg 12-16, Belgrade, Serbia

https://orcid.org/0000-0002-7654-3189

Zorana Ferjančić

Faculty of Chemistry, Departmet of Organic Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrad, Serbia

https://orcid.org/0000-0001-5932-629X

Abstract

The synthesis of four N-2-alkylated aza-galactofagomine (AGF) analogues was achieved by intermolecular reductive hydrazination or alkylation of suitably protected AGF. The synthesized compounds were evaluated as potential β-glucosidase inhibitors. The preliminary screening of inhibitor activity, conducted with sweet almond β-glucosidase immobilized in agar, as well as the standard inhibition assay with the same enzyme, showed the inhibitory potency of the synthesized analogues. In addition, these results are in a good agreement with the docking analysis of the human acid β-glucosidase, the enzyme implicated in Gaucher’s disease.

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How to Cite

[1]

F. . Đurković, M. Zlatović, D. . Sladić, I. Novaković, F. . Bihelović, and Z. Ferjančić, “N-2 Alkylated analogues of aza-galactofagomine as potential inhibitors of β-glucosidase: Scientific paper”, J. Serb. Chem. Soc., vol. 89, no. 10, pp. 1255–1267, Nov. 2024.

Issue

Vol. 89 No. 10 (2024)

Section

Organic Chemistry

This work is licensed under a Creative Commons Attribution 4.0 International License.

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

Funding data

Ministarstvo Prosvete, Nauke i Tehnološkog Razvoja
Grant numbers 451-03-65/2024-03/200168;451-03-66/2024-03/200026

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N-2 Alkylated analogues of aza-galactofagomine as potential inhibitors of β-glucosidase Scientific paper