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连续流动合成源自苯甲酸的亲脂性阳离子作为人头颈部癌细胞系中的新型细胞毒性化学实体。

Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines.

作者信息

Catalán Mabel, Castro-Castillo Vicente, Gajardo-de la Fuente Javier, Aguilera Jocelyn, Ferreira Jorge, Ramires-Fernandez Ricardo, Olmedo Ivonne, Molina-Berríos Alfredo, Palominos Charlotte, Valencia Marcelo, Domínguez Marta, Souto José A, Jara José A

机构信息

Clinical and Molecular Pharmacology Program , Institute of Biomedical Sciences (ICBM) , Faculty of Medicine , Universidad de Chile , Santiago , 8380453 , Chile.

Department of Organic and Physical Chemistry , Faculty of Chemical and Pharmaceutical Sciences , Universidad de Chile , Santos Dumont 964 , Santiago 8380494 , Chile.

出版信息

RSC Med Chem. 2020 Aug 19;11(10):1210-1225. doi: 10.1039/d0md00153h. eCollection 2020 Oct 1.

DOI:10.1039/d0md00153h
PMID:33479625
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7652000/
Abstract

Continuous flow chemistry was used for the synthesis of a series of delocalized lipophilic triphenylphosphonium cations (DLCs) linked by means of an ester functional group to several hydroxylated benzoic acid derivatives and evaluated in terms of both reaction time and selectivity. The synthesized compounds showed cytotoxic activity and selectivity in head and neck tumor cell lines. The mechanism of action of the molecules involved a mitochondrial uncoupling effect and a decrease in both intracellular ATP production and apoptosis induction.

摘要

连续流动化学被用于合成一系列通过酯官能团与几种羟基化苯甲酸衍生物相连的离域亲脂性三苯基鏻阳离子（DLCs），并从反应时间和选择性方面进行了评估。合成的化合物在头颈肿瘤细胞系中显示出细胞毒性活性和选择性。这些分子的作用机制涉及线粒体解偶联效应以及细胞内ATP生成和凋亡诱导的减少。

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