4.4 Article

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

Journal

RSC MEDICINAL CHEMISTRY
Volume 11, Issue 10, Pages 1210-1225

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0md00153h

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Funding

  1. U-INICIA grant from the Vicerrectoria de Investigacion y Desarrollo, Universidad de Chile [U-INICIA-2014-82379]
  2. Fondecyt Iniciacion Grant [11180533, 11160281, 11170962]
  3. Fondecyt Regular grant [1180296]

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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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