Amphiphilic azobenzenes: Antibacterial activities and biophysical investigation of their interaction with bacterial membrane lipids

Abstract

With the emergence of multi-drug resistant bacteria and hospital-acquired infections, there is an urgent need to develop new antibiotics. Here, we report the synthesis, physico-chemical characterizations, and antimicrobial activity assays of four Azo compounds that differ in their alkyl chain length. The molecular mechanism of their antibacterial activity was investigated by complementary in vitro and in silico biophysical studies. The compounds with alkyl chain lengths of four or six carbons showed a low MIC 50 against Escherichia coli and Bacillus subtilis. Our investigations into the mechanism of their action revealed that phosphatidylethanolamine in the bacterial plasma membrane plays an important role in their antibacterial activity.

Linolenic fatty acid hydroperoxide acts as biocide on plant pathogenic bacteria: Biophysical investigation of the mode of action

“…Hypermatrix is a simple docking method described in [49,55]. Like it was recently done for saponins [56] and amphiphilic azobenzenes [34], it was used to dock 13-HPOT to different lipid molecules. 13-HPOT is fixed at a central position of the system and oriented at the hydrophobic/hydrophilic interface and the lipid molecule, also oriented at the lipid/water interface, is positioned around the HPOT molecule by rotations and translations (more than 10 7 positions tested).…”

“…But in recent years, numerous studies have focused on the complexity of the membranes and, in particular, the essential role of lipids in their organization and intrinsic properties. New perspectives have appeared on the effect of amphiphilic drugs on lipid-protein interactions, with direct consequences on membrane lipid domains [23,34,35]. In turn, these modifications influence the localization/activity of proteins, particularly highly sensitive to changes in the IM [28].…”

“…In turn, these modifications influence the localization/activity of proteins, particularly highly sensitive to changes in the IM [28]. Many amphiphilic molecules have shown their capacity to interact specifically with the lipids constituting the plasma membrane and, in certain cases, to influence its properties [23,34,[36][37][38]. Especially, some molecules extracted from plants or of plant origin would derive their multiple effects via their ability to interact with the lipid part of the membranes [39,40].…”

Antimicrobial Ionic Liquid‐Based Materials for Biomedical Applications

“…[137] The light-responsive feature of azo-based materials has been founded as a strategy to efficiently expose higher antibacterial activity under visible light exposure (λ > 400 nm trans-state) than UV light exposure (λ = 300-400 nm cis-state); one can speak of on-off antibacterial materials (Figure 15E). Although in most cases, the antibacterial efficacy of molecules with trans-state increases due to the more availability of their antibacterial agents, [138][139][140] in some cases, the molecules with cis-state perform better than their transstates; particularly the azobenzene groups carry carbohydrate or steroid moieties. [140][141][142] As well, in this study the intercalated azobenzene groups bearing antibacterial agents (i.e., imidazolium agents) inside the exfoliated montmorillonite nanosheets can act as antibacterial surfaces in cis-state (increased montmorillonite basal distance) due to the more availability of agents [129] Copyright 2019, Elsevier.…”

Sesamol‐based terpenoids as promising bio‐sourced crop protection compounds against the wheat pathogen Zymoseptoria tritici

“…Thanks to their numerous biological activities and their ability to permeate the skin, monoterpenes and monophenols constitute a significant part of the whole group of the aforementioned secondary metabolites 9–12 . As a consequence, and following our continuous interest in developing new antimicrobial agents, 13–23 a selection of 20 natural terpenoid candidates have been selected as potential crop protection compounds against Z. tritici for in vitro evaluation. Among them, three subgroups can be defined: (i) terpenes, (ii) terpenoic alcohols and ethers, and (iii) phenolic derivatives (Table 1).…”