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

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Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines
RSC Medicinal Chemistry ( IF 4.1 ) Pub Date : 2020-08-19 , DOI: 10.1039/d0md00153h
Mabel Catalán ₁ , Vicente Castro-Castillo ₂ , Javier Gajardo-de la Fuente ₂ , Jocelyn Aguilera ₃ , Jorge Ferreira ₁ , Ricardo Ramires-Fernandez ₄ , Ivonne Olmedo ₅ , Alfredo Molina-Berríos ₃ , Charlotte Palominos ₁ , Marcelo Valencia ₁ , Marta Domínguez ₆ , José A Souto ₆ , José A Jara ₃

Affiliation

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.

中文翻译：

从苯甲酸衍生的亲脂性阳离子的连续流动合成作为人头颈癌细胞系中的新细胞毒性化学实体

连续流动化学用于合成一系列离域亲脂性三苯基鏻阳离子 (DLC)，这些阳离子通过酯官能团与几种羟基化苯甲酸衍生物相连，并在反应时间和选择性方面进行评估。合成的化合物在头颈部肿瘤细胞系中显示出细胞毒活性和选择性。分子的作用机制涉及线粒体解偶联效应和细胞内 ATP 产生和细胞凋亡诱导的减少。

更新日期：2020-08-19

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