Synthesis and antibacterial activity of 6″-decanesulfonylacetamide-functionalised amphiphilic derivatives of amikacin and kanamycin

Dylan C. Farr; Lendl Tan; Juanelle Furness; I. Darren Grice; Nicholas P. West; Todd A. Houston

doi:10.1071/CH23154

COMMENT AND RESPONSE (Open Access)

Previous Contents Vol 76(11)

Synthesis and antibacterial activity of 6″-decanesulfonylacetamide-functionalised amphiphilic derivatives of amikacin and kanamycin

Dylan C. Farr ^A , Lendl Tan ^B , Juanelle Furness ^B , I. Darren Grice

^A ^C , Nicholas P. West

^B and Todd A. Houston

^A ^*

+ Author Affiliations

- Author Affiliations

^A Institute for Glycomics, Gold Coast campus, Griffith University, Qld 4222, Australia.

^B School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

^C School of Pharmacy and Medical Sciences, Gold Coast campus, Griffith University, Qld 4222, Australia.

^* Correspondence to: t.houston@griffith.edu.au

Handling Editor: Pall Thordarson

Australian Journal of Chemistry 76(11) 812-820 https://doi.org/10.1071/CH23154

Submitted: 16 August 2023 Accepted: 25 October 2023 Published online: 13 November 2023

© 2023 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)

Abstract

Aminoglycoside antibiotics represent the first class of successful drugs in the treatment of tuberculosis; however, mycobacteria and other bacterial species possess several drug resistance mechanisms to inactivate these natural products. In the past 15 years, a variety of amphiphilic aminoglycosides have been shown to have improved activity against infectious microorganisms and to subvert resistance mechanisms. Here, we report on four novel synthetic compounds derived from two existing potent antitubercular compounds and describe their activity against both Mycobacterium tuberculosis and Staphylococcus aureus. It was found that a decanesulfonylacetamide-based conjugate of amikacin displayed promising preliminary antitubercular activities, warranting further investigation to assess the therapeutic potential of these unique antimicrobials.

Keywords: amide–triazole conjugates, amikacin, amphiphilic aminoglycosides, antibiotics, antimicrobial agents, kanamycin, Mycobacterium tuberculosis, n-decanesulfonylacetamide.

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