In Silico Approach to Inhibition of Tyrosinase by Ascorbic Acid Using Molecular Docking Simulations

Title:In Silico Approach to Inhibition of Tyrosinase by Ascorbic Acid Using Molecular Docking Simulations

Volume: 14 Issue: 12

Author(s): F. Sezer Senol, M. Tareq Hassan Khan, Gurdal Orhan, Erdem Gurkas, Ilkay Erdogan Orhan, Nese Subutay Oztekin and Fikri Ak

Affiliation:

Keywords: Ascorbic acid, in silico, in vitro, molecular docking, tyrosinase inhibition, vitamin C.

Abstract: Current evidence suggests that endogenous dopamine may act as a neurotoxin following its oxidation to an oquinone and reaction with cellular thiols, which are neutoxic, which may occur spontaneously or via reaction with tyrosinase or some other enzymes. Tyrosinase (E.C. 1.14.18.1) with two cupper ions coordinated by three histidines is a bifunctional enzyme that catalyses both the hydroxylation of tyrosine to L-DOPA and the consequent oxidation of the resulting catechol-containing species to an o-quinone. Therefore, tyrosinase may play a role in neuromelanin formation in the brain and could be central to dopamine neurotoxicity by contributing to the neurodegeneration associated with Parkinson’s disease. In the present study, inhibitory effect of ascorbic acid against tyrosinase has been investigated and it has shown a remarkable inhibitory effect in in vitro assays. Then, the in silico-based experiments established through molecular docking calculations and scoring, docking search algorithm, and data plotting indicated that ascorbic acid is strong inhibitor of tyrosinase by interacting with four amino acid units (histidine 263, serine 282, phenylalanine 264, and valin 283) in the active site of the enzyme. The compound also had two long distant hydrogen bindings with Cu1 and Cu2 with distances of 3.57 and 3.41 A, respectively, through its O5 atom.

Cite this article as:

Senol Sezer F., Khan Tareq Hassan M., Orhan Gurdal, Gurkas Erdem, Orhan Erdogan Ilkay, Oztekin Subutay Nese and Ak Fikri, In Silico Approach to Inhibition of Tyrosinase by Ascorbic Acid Using Molecular Docking Simulations, Current Topics in Medicinal Chemistry 2014; 14 (12) . https://dx.doi.org/10.2174/1568026614666140610121253