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

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

doi:10.1039/D0MD00153H

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

Mabel Catalán,‡^a Vicente Castro-Castillo,‡§^b Javier Gajardo-de la Fuente,^b Jocelyn Aguilera,^c Jorge Ferreira,^a Ricardo Ramires-Fernandez,^d Ivonne Olmedo,^e Alfredo Molina-Berríos,^c Charlotte Palominos,^a Marcelo Valencia,^a Marta Domínguez,^f José A. Souto*^f and José A. Jara

*^c

Author affiliations

* Corresponding authors

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

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

^c Institute for Research in Dental Sciences (ICOD), Faculty of Dentistry, Universidad de Chile, Santiago, Chile
E-mail: jsandovalj@u.uchile.cl
Tel: +56 2 29781730

^d Dentistry School, Universidad Mayor, Santiago 8340585, Chile

^e Physiopathology Program, Institute of Biomedical Sciences (ICBM), Faculty of Medicine, Universidad de Chile, Santiago 8380453, Chile

^f Departamento de Química Orgánica, Facultad de Química, CINBIO and IIS Galicia Sur, Universidade de Vigo, Vigo, Spain
E-mail: souto@uvigo.es

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.

This article is part of the themed collection: Celebrating Latin American Talent in Chemistry

RSC Medicinal Chemistry

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements