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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.

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.

SUBMITTER: Catalan M 

PROVIDER: S-EPMC7652000 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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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.

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

RSC medicinal chemistry 20200819 10

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 intrace  ...[more]