Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines† †Electronic supplementary information (ESI) available. See DOI: 10.1039/d0md00153h

Continuous flow chemistry improves the yield of the synthesis of a series of delocalized lipophilic triphenylphosphonium cations that induce mitochondrial dysfunction and apoptosis in head and neck tumor cells. Continuous flow chemistry was used for the synthesis of a series of delocalized lipophili...

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Bibliographic Details
Published in:RSC medicinal chemistry 2020-08, Vol.11 (10), p.1210-1225
Main Authors: Catalán, Mabel, Castro-Castillo, Vicente, Gajardo-de la Fuente, Javier, Aguilera, Jocelyn, Ferreira, Jorge, Ramires-Fernandez, Ricardo, Olmedo, Ivonne, Molina-Berríos, Alfredo, Palominos, Charlotte, Valencia, Marcelo, Domínguez, Marta, Souto, José A., Jara, José A.
Format: Article
Language:English
Subjects:
Chemistry
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Summary:Continuous flow chemistry improves the yield of the synthesis of a series of delocalized lipophilic triphenylphosphonium cations that induce mitochondrial dysfunction and apoptosis in head and neck tumor cells. 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.
ISSN:2632-8682
DOI:10.1039/d0md00153h