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

Resultado de la investigación: Article

4 Citas (Scopus)

Resumen

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.

Idioma originalEnglish
Páginas (desde-hasta)97-101
Número de páginas5
PublicaciónComputational and Theoretical Chemistry
Volumen1013
DOI
EstadoPublished - 1 jun 2013

Huella dactilar

Cell Respiration
Solvation
respiration
activity (biology)
Bioactivity
solvation
Tumors
Theoretical Models
tumors
Cells
membranes
Derivatives
Membranes
Molecules
energy of formation
Gibbs free energy
Phenol
phenols
Inhibitory Concentration 50
Density functional theory

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Biochemistry
  • Condensed Matter Physics

Citar esto

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On the mechanism of biological activity of hydroquinone derivatives that inhibit tumor cell respiration. A theoretical study. / Soto-Delgado, Jorge; Bahamonde-Padilla, Victor; Araya-Maturana, Ramiro; Weiss-López, Boris E.

En: Computational and Theoretical Chemistry, Vol. 1013, 01.06.2013, p. 97-101.

Resultado de la investigación: Article

TY - JOUR

T1 - On the mechanism of biological activity of hydroquinone derivatives that inhibit tumor cell respiration. A theoretical study

AU - Soto-Delgado, Jorge

AU - Bahamonde-Padilla, Victor

AU - Araya-Maturana, Ramiro

AU - Weiss-López, Boris E.

PY - 2013/6/1

Y1 - 2013/6/1

N2 - 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.

AB - 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.

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KW - Antitumoral mechanism

KW - DFT calculation

KW - Hydroquinone

KW - Tumor cell respiration

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DO - 10.1016/j.comptc.2013.03.007

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