Abstract
In this work, 11 novel compounds based on vaniline and benzylidenehydrazine structure were synthesized with various substituents on phenyl aromatic ring of the molecule and evaluated as tyrosinase inhibitors. These new derivatives showed significant anti-tyrosinase activities, among which 4i demonstrated to be the most potent compound, with IC50 values of 1.58 µM . The structure–activity relationship study of the novel constructed analogs was fully discussed. Kinetic study of compound 4i showed uncompetitive inhibition towards tyrosinase. Furthermore, the high potency of 4i was supported theoretically by molecular docking evaluations.
Highlights
Melanin as the main dark macromolecular pigment is responsible for skin color and plays an important role in the protection of the skin against UV light induced damage [1]
Design of novel vaniline‐benzylidenehydrazine hybrid Tyrosine (Tyr), (Fig. 1, A) is one of the natural ligands of tyrosinase and modified synthetic derivatives of tyrosine have been proved to exhibit potent anti-tyrosinase activity [14]
The presence of phenolic structural features may help in the designing of more potent tyrosinase inhibitors
Summary
Melanin as the main dark macromolecular pigment is responsible for skin color and plays an important role in the protection of the skin against UV light induced damage [1]. The major problem happened in food products including impairing the color, losing nutrition, texture and flavor. This unusual process results from the action of a group of enzymes especially tyrosinase (EC 1.14.18.1) as the rate-limiting enzyme which widely distributed in bacteria, fungi, plants and humans [3, 4]. Despite a large number of reported tyrosinase inhibitors, due to limitations of tyrosinase antagonism including safety and low efficacy, designing of new tyrosinase inhibitors is high demand [14, 15]
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