On the Pro-oxidant Activity of Curcumin in Lipid Media: A Theoretical Study
DOI:
https://doi.org/10.29356/jmcs.v66i3.1727Keywords:
Oxidative stress, kinetic, DFT, curcumin, pro-oxidantAbstract
Abstract. In the scientific literature can be found experimental evidence on the pro-oxidant capacity of curcumin through its photosensitizer property; it has been related to biological activities such as the antibacterial and antitumor observed in this molecule; however, the pro-oxidant evidence, little is known about the reaction mechanism involved in the photosensitizing property of curcumin. Thus, it was carried out a study on the photosensitizer capacity of curcumin in lipid media employs the density functional theory. The thermodynamic results showed the remarkable capacity of curcumin to reduce itself through the single electron transfer mechanisms. The kinetic results showed that mechanism type II is the main mechanism, and it showed a total reaction rate constant calculated of 1.69 x 1010 M-1 s-1 on the photosensitizer capacity of curcumin in lipid media. The reactions related to the mechanism type I was not feasible; hence, these reactions were not contributed to the photosensitizer capacity of curcumin in lipid media. Finally, these results support the idea that the curcumin in lipid media is a pro-oxidant molecule capable of generating the 1O2 molecule and, consequently, could cause oxidative damage through the photooxidative reactions.
Resumen. En la literatura se puede encontrar evidencia experimental sobre la capacidad pro-oxidante de la curcumina a traves de su propiedad fotosensibilizadora, esta propiedad se ha relacionado con la actividad antibacteriana y antitumoral observada en esta molécula; a pesar de la evidencia experimental, poco se conoce sobre el mecanismo de reacción involucrado en la propiedad fotosensibilizadora de la curcumina. De acuerdo con lo anterior, se llevó a cabo el estudio de la capacidad fotosensibilizadora de curcumina en medio lipídico, empleando la teoría de funcionales de la densidad. Los resultados termodinámicos mostraron la extraordinaria capacidad de la curcumina para reducirse a través de reacciones de transferencia electrónica. Los resultados cinéticos mostraron que el mecanismo tipo II es el más importante en la capacidad fotosensibilizadora de la curcumina en medio lipídico, mostrando una constante de velocidad de 1.69 x 1010 M-1 s-1. La reacción relacionada con el mecanismo tipo I no se lleva a cabo; por lo tanto, estas reacciones no contribuyen en la capacidad fotosensibilizadora de la curcumina en medio lipídico. Finalmente, estos resultados apoyan la idea de que la curcumina en medio lipídico es una molécula prooxidante capaz de inducir el estrés oxidativo por la generación de la molécula de 1O2 y de esta forma, generar daño oxidativo a estructuras celulares importantes a través de reacciones de fotooxidación.
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