Design and Synthesis of Novel Amino and Acetamidoaurones with Antimicrobial Activities

Attilio Di Maio; Hamza Olleik; Elise Courvoisier-Dezord; Sophie Guillier; Fabienne Neulat-Ripoll; Romain Haudecoeur; Jean-Michel Bolla; Magali Casanova; Jean-François Cavalier; Stéphane Canaan; Valérie Pique; Yolande Charmasson; Elias Baydoun; Akram Hijazi; Josette Perrier; Marc Maresca; Maxime Robin

doi:10.20944/preprints202402.1486.v1

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preprints.org > biology and life sciences > biology and biotechnology > doi: 10.20944/preprints202402.1486.v1

Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Design and Synthesis of Novel Amino and Acetamidoaurones with Antimicrobial Activities

Attilio Di Maio

Hamza Olleik

Elise Courvoisier-Dezord

Sophie Guillier

Fabienne Neulat-Ripoll

Romain Haudecoeur

Jean-Michel Bolla

Magali Casanova

Jean-François Cavalier

^* ,

Version 1 : Received: 26 February 2024 / Approved: 26 February 2024 / Online: 26 February 2024 (15:49:03 CET)

A peer-reviewed article of this Preprint also exists.

Di Maio, A.; Olleik, H.; Courvoisier-Dezord, E.; Guillier, S.; Neulat-Ripoll, F.; Haudecoeur, R.; Bolla, J.-M.; Casanova, M.; Cavalier, J.-F.; Canaan, S.; Pique, V.; Charmasson, Y.; Baydoun, E.; Hijazi, A.; Perrier, J.; Maresca, M.; Robin, M. Design and Synthesis of Novel Amino and Acetamidoaurones with Antimicrobial Activities. Antibiotics 2024, 13, 300. Di Maio, A.; Olleik, H.; Courvoisier-Dezord, E.; Guillier, S.; Neulat-Ripoll, F.; Haudecoeur, R.; Bolla, J.-M.; Casanova, M.; Cavalier, J.-F.; Canaan, S.; Pique, V.; Charmasson, Y.; Baydoun, E.; Hijazi, A.; Perrier, J.; Maresca, M.; Robin, M. Design and Synthesis of Novel Amino and Acetamidoaurones with Antimicrobial Activities. Antibiotics 2024, 13, 300.

Abstract

The development of new and effective antimicrobial compounds is an urgent need with the emergence of resistant bacteria. Natural plant flavonoids are known to be effective molecules but their activity and selectivity have to be increased. Based on previous aurone potency, we designed new aurone derivatives bearing acetamido and amino groups at the position 5 of the A ring and managing various monosubstitutions at the B ring. A series of 31 new aurone derivatives were first evaluated for their antimicrobial activity with five derivatives being the most active (compounds 10, 12, 15, 16, and 20). The evaluation of their cytotoxicity on human cells and of their therapeutic index (TI) showed that compounds 10 and 20 have the highest TI. Finally, screening against a large panel of pathogens confirmed that compounds 10 and 20 possess a large spectrum antimicrobial activity, including on bioweapon BSL3 strains, with MIC values as low as 0.78 µM. These results demonstrate that 5-acetamidoaurones are far more active and safest compared with 5-aminoaurones, and that benzyloxy and isopropyl substitutions at the B ring are the most promising strategy in the exploration of new antimicrobial aurones.

Keywords

Aurone; anti-bacterial agents, cytotoxicity tests; structure-activity relationship

Subject

Biology and Life Sciences, Biology and Biotechnology

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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