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Aza-Michael promoted glycoconjugation of PETIM dendrimers and selectivity in mycobacterial growth inhibitions

Sarkar, B and Mahapa, A and Dey, K and Manhas, R and Chatterji, D and Jayaraman, N (2023) Aza-Michael promoted glycoconjugation of PETIM dendrimers and selectivity in mycobacterial growth inhibitions. In: RSC Advances, 13 (7). pp. 4669-4677.

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Official URL: https://doi.org/10.1039/d2ra08196b


The benign nature of aza-Michael addition reaction in aqueous solutions is demonstrated herein to conduct a direct glycoconjugation of amine-terminated poly(ether imine) (PETIM) dendrimers. Zero to three generations of dendrimers, possessing up to 16 amine functionalities at their peripheries, undergo aza-Michael reaction with unsaturated sugar vinyl sulfoxide in aq. MeOH solutions and afford the corresponding dendrimers modified with multiple glycosyl moieties at the periphery. First order kinetics of the glycoconjugation is monitored at varying temperatures and the rate constants are observed to be 60-508 s−1, for zero and first generation dendrimers. The antibacterial effects of amine-terminated dendrimers and the corresponding glycoconjugates are studied across Gram-positive, Gram-negative and acid-fast bacteria. Among the species, M. smegmatis and M. tuberculosis showed the greatest growth inhibition effect at micromolar concentrations, for the native amine-terminated and the corresponding glycoconjugated dendrimers. Quantitative assays are performed to adjudge the inhibition efficacies of dendrimers and the glycoconjugates. Selectivity to inhibit M. smegmatis and M. tuberculosis growth, and minimal effects on other bacterial species by dendrimers and glycoconjugates are emphasized.

Item Type: Journal Article
Publication: RSC Advances
Publisher: Royal Society of Chemistry
Additional Information: The copyright for this article belongs to the Authors.
Keywords: Addition reactions; Bacteria; Carbohydrates; Rate constants, Amine functionality; Aza-Michael addition; Aza-Michael reaction; Glycoconjugates; Growth inhibition; M. tuberculosis; Michael addition reactions; Mycobacterial; Three generations; Vinyl sulfoxide, Dendrimers
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Division of Chemical Sciences > Organic Chemistry
Date Deposited: 25 Feb 2023 07:46
Last Modified: 25 Feb 2023 07:46
URI: https://eprints.iisc.ac.in/id/eprint/80676

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