On the mechanism of biological activity of hydroquinone derivatives that inhibit tumor cell respiration. A theoretical study

Jorge Soto-Delgado, Victor Bahamonde-Padilla, Ramiro Araya-Maturana, Boris E. Weiss-López

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

A simple mechanism to understand the biological activity of a series of hydroquinone derivatives is proposed. To validate this proposition Gibbs free energies of formation of the different species involved were calculated. The calculations were performed using density functional theory (DFT) at B3LYP/6-31++G(2df,p) level of theory, including solvation effect. The results show that two important variables to examine are the equilibrium phenol-phenoxide and the solvation energy of neutral species, since the balance between both variables affects the capability of the molecules to cross membranes. Once the molecule crossed the membrane, the formation of radical species shows a qualitative correlation with the magnitude of IC50 values. This provides a reasonable criterion to search for more efficient anticancer drug.

Original languageEnglish
Pages (from-to)97-101
Number of pages5
JournalComputational and Theoretical Chemistry
Volume1013
DOIs
Publication statusPublished - 1 Jun 2013

Keywords

  • Antitumoral drugs
  • Antitumoral mechanism
  • DFT calculation
  • Hydroquinone
  • Tumor cell respiration

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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