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

Catalan, Mabel; Castro-Castillo, Vicente; Gajardo-de la Fuente, Javier; Aguilera, Jocelyn; Ferreira, Jorge; Ramires-Fernandez, Ricardo; Olmedo, Ivonne; Molina-Berrios, Alfredo; Palominos, Charlotte; Valencia, Marcelo; Dominguez, Marta; Souto, Jose A.; Jara, Jose A.

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.

Más información

Título según WOS: Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines
Título de la Revista: RSC MEDICINAL CHEMISTRY
Volumen: 11
Número: 10
Editorial: ROYAL SOC CHEMISTRY
Fecha de publicación: 2020
Página de inicio: 1210
Página final: 1225
DOI:

10.1039/D0MD00153H

Notas: ISI