Controlling Antibacterial Activity Exclusively with Visible Light: Introducing a Tetra‐ ortho ‐Chloro‐Azobenzene Amino Acid

作者：Xavier Just‐Baringo, Alejandro Yeste‐Vázquez, Javier Moreno, Clara Ballesté‐Delpierre, Jordi Vilà, Ernest Giralt · 发表于：Chemistry - A European Journal · 年份：2021 · DOI：10.1002/chem.202102370 · 被引用次数：19 · 研究领域：Photochromic and Fluorescence Chemistry、Photoreceptor and optogenetics research、Synthesis of Indole Derivatives

The introduction of a novel tetra-ortho-chloroazobenzene amino acid (CEBA) has enabled photoswitching of the antimicrobial activity of tyrocidine A analogues by using exclusively visible light, granting spatiotemporal control under benign conditions. Compounds bearing this photoswitchable amino acid become active upon irradiation with red light, but quickly turn-off upon exposure to other visible light wavelengths. Critically, sunlight quickly triggers isomerisation of the red light-activated compounds into their original trans form, offering an ideal platform for self-deactivation upon release into the environment. Linear analogues of tyrocidine A were found to provide the best photocontrol of their antimicrobial activity, leading to compounds active against Acinetobacter baumannii upon isomerisation. Exploration of their N- and C-termini has provided insights into key elements of their structure and has allowed obtaining new antimicrobials displaying excellent strain selectivity and photocontrol.