The inhibition of tyrosinase by some aryl butenes: A desired activity or a side effect to avoid

Abstract Inhibitory effects on the monophenolase activity of tyrosinase of some aryl butenes derivatives, having moderate to excellent inhibitory activity on MDA-MB-231 breast cancer cell, have been examined. The results show that the substitution of the phenol group by other functional moieties or its removal (unsubstituted phenyl) makes the loss of the tyrosinase inhibition effect of the compounds. Interestingly, the protection of the phenol group of the compounds by a sugar (glucose) led to the loss of the inhibitory activity on tyrosinase but maintained the antitumor activity. The tyrosinase inhibiting potential is considered as a side effect as it leads to depigmentation. Some ferrocenyl aryl butene compounds behave as reversible inhibitors of tyrosinase and kinetic analyses showed that the inhibition type of three derivatives compounds was competitive and another compound was non-competitive. Moreover, the compounds 8 and 19 were found to be the most potent inhibitors of tyrosinase activity among these compounds with IC 50 values of 20 and 25 μM, respectively. However, compound 18 was the most effective compound against MDA-MB-231 tumoral cells with an IC 50 value of 0.86 μM; it could be used as an anticancer drug without interfering with tyrosinase activity and pigmentation process. Conclusively, if some compounds are excellent candidates for cosmetics, others showed strong antitumor activity without depigmentation side effect.