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基于硝咪唑的钌(II)配合物:通过结构参数设计设计稳定的光响应型抗菌剂。

Nitroimidazole-Based Ruthenium(II) Complexes: Playing with Structural Parameters to Design Photostable and Light-Responsive Antibacterial Agents.

机构信息

Department of Chemistry "Ugo Schiff", University of Florence, Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy.

Department of Biology, University of Florence, Via Madonna del Piano 6, 50019 Sesto Fiorentino, Florence, Italy.

出版信息

Inorg Chem. 2022 May 9;61(18):6689-6694. doi: 10.1021/acs.inorgchem.1c03032. Epub 2021 Nov 18.

Abstract

5-Nitroimidazole (5NIMH), chosen as a molecular model of nitroimidazole derivatives, which represent a broad-spectrum class of antimicrobials, was incorporated into the ruthenium complexes [Ru(tpy)(phen)(5NIM)]PF () and [Ru(tpy)(dmp)(5NIM)]PF () (tpy = terpyridine, phen = phenanthroline, dmp = 2,9-dimethyl-1,10-phenanthroline). Besides the uncommon metal coordination of 5-nitroimidazole in its imidazolate form (5NIM), the different architectures of the spectator ligands (phen and dmp) were exploited to tune the "mode of action" of the resulting complexes, passing from a photostable compound where the redox properties of 5NIMH are preserved () to one suitable for the nitroimidazole phototriggered release () and whose antibacterial activity against , chosen as cellular model, is effectively improved upon light exposure. This study may provide a fundamental knowledge on the use of Ru(II)-polypyridyl complexes to incorporate and/or photorelease biologically relevant nitroimidazole derivatives in the design of a novel class of antimicrobials.

摘要

5-硝基咪唑(5NIMH)被选为硝基咪唑衍生物的分子模型,此类衍生物是一类广谱抗菌药物。5-硝基咪唑(5NIMH)以其脒基形式(5NIM)参与到钌配合物[Ru(tpy)(phen)(5NIM)]PF 6 () 和 [Ru(tpy)(dmp)(5NIM)]PF 6 ()(tpy = 三吡啶,phen = 邻菲罗啉,dmp = 2,9-二甲基-1,10-菲罗啉)的配位中。除了 5-硝基咪唑罕见的金属配位以其脒基形式(5NIM)外,还利用了不同的辅助配体(邻菲罗啉和 2,9-二甲基-1,10-菲罗啉)的结构来调节所得配合物的“作用模式”,使其从一种光稳定的化合物()转变为适合于硝基咪唑光触发释放的化合物(),并且其对 的抗菌活性在光照下得到有效提高,所选细胞模型为 。该研究可能为利用 Ru(II)-多吡啶配合物在设计新型抗菌药物时掺入和/或光释放生物相关的硝基咪唑衍生物提供了基础知识。

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