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Estudio in Silico de la reactividad y propiedades fisicoquímicas de aductos de Epóxido de Eugenol y 2-Metoxi-4-alilideno-2,5-ciclohexadieno-1-ona con glutation en Candida albicans
Study in silico of reactivity and physicochemical properties of adducts of epoxide of eugenol and 2-methoxy-4-allylidene-2,5-ciclohexadiene-1-one with glutation in Candida albicans
DOI:
https://doi.org/10.15446/rev.fac.cienc.v8n1.74214Keywords:
aducto, eugenol, epóxido de eugenol, quinona metilada (es)adduct, eugenol, eugenol epoxide, methylated quinone (en)
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El eugenol es un alilbenceno con actividad antifúngica, diversos estudios han demostrado su capacidad de inhibir el crecimiento de Candida albicans. Se ha propuesto la formación de aductos entre un derivado del eugenol (2-metoxi-4-alilideno-2,5-hexadieno-1-ona) y glutatión como un mecanismo de estrés oxidativo. Asimismo, otro derivado del eugenol, epóxido de eugenol, tiene teóricamente la capacidad para formar aductos. Por lo tanto, este estudio determinó in silicolas propiedades fisicoquímicas de estos aductos y su reactividad en microorganismos aeróbicos. Se encontró que estos aductos tienen baja hidrofobicidad, por lo que, tendrían baja capacidad para atravesar membranas biológicas y por tanto una distribución intracelular. Asimismo, las reacciones químicas que originan estos aductos son termodinámicamente favorables. Por último, estos aductos son susceptibles a modificaciones químicas en microorganismos aeróbicos; estas reacciones podrían ser catalizadas por enzimas como el citocromo P450.
Eugenol is an allylbenzene with antifungal activity, many studies have demonstrated its ability to inhibit the growth of Candida albicans. The formation of adducts between a derivative of eugenol (2-methoxy-4-allylidene-2,5-ciclohexadiene-1-one) and glutathione as a mechanism of oxidative stress has been proposed. Likewise, another eugenol derivative, eugenol epoxide, theoretically has the capacity to form adducts. Therefore, this study determined in silico the physicochemical properties of these adducts and their reactivity in aerobic microorganisms. It was found that these adducts have low hydrophobicity, therefore, they would have low capacity to cross biological membranes and therefore an intracellular distribution. Likewise, the chemical reactions that originate these adducts are thermodynamically favorable. Finally, these adducts are susceptible to chemical modifications in aerobic microorganisms; These reactions could be catalyzed by enzymes such as cytochrome P450.
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