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 Fuenteb
    • Jocelyn Aguilerac
    • Jorge Ferreiraa
    • Ricardo Ramires-Fernandezd
    • Ivonne Olmedoe
    • Alfredo Molina-Berríosc
    • Charlotte Palominosa
    • Marcelo Valenciaa
    • Marta Domínguezf
    • José A. Souto*f
    • José A. Jara*c
    • *Corresponding authors
    • aClinical and Molecular Pharmacology Program, Institute of Biomedical Sciences (ICBM), Faculty of Medicine, Universidad de Chile, Santiago, Chile
    • bDepartment of Organic and Physical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, Universidad de Chile, Santos Dumont 964, Santiago 8380494, Chile
    • cInstitute for Research in Dental Sciences (ICOD), Faculty of Dentistry, Universidad de Chile, Santiago, Chile
    • dDentistry School, Universidad Mayor, Santiago 8340585, Chile
    • ePhysiopathology Program, Institute of Biomedical Sciences (ICBM), Faculty of Medicine, Universidad de Chile, Santiago 8380453, Chile
    • fDepartamento de Química Orgánica, Facultad de Química, CINBIO and IIS Galicia Sur, Universidade de Vigo, Vigo, Spain

    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.

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