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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

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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.

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

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Supplementary files

Article information


Submitted
13 May 2020
Accepted
30 Jul 2020
First published
19 Aug 2020

RSC Med. Chem., 2020, Advance Article
Article type
Research Article

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

M. Catalán, V. Castro-Castillo, J. Gajardo-de la Fuente, J. Aguilera, J. Ferreira, R. Ramires-Fernandez, I. Olmedo, A. Molina-Berríos, C. Palominos, M. Valencia, M. Domínguez, J. A. Souto and J. A. Jara, RSC Med. Chem., 2020, Advance Article , DOI: 10.1039/D0MD00153H

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