Molecular docking of gallic acid as anti-photoaging in silico

Keywords: antiphotoaging, gallic acid, in silico, mmp-1, molecular docking

Abstract

Skin aging caused by excessive exposure to ultraviolet is known as photoaging. The mechanism underlying skin photoaging relates to collagen degradation in the extracellular matrix (ECM) by overexpression of matrix metalloproteinases-1 (MMP-1). Gallic acid is a phenolic antioxidant found in many types of plants and can be used as an anti-photoaging agent due to its antioxidant activity. This study aims to determine the potential effect of gallic acid as an anti-photoaging against MMP-1 using in silico molecular docking. The stages included gallic acid structure optimization using the HyperChem 8, preparation of protein target MMP-1 (PDB ID: 966C) using the Chimera1.10.1, validation the molecular docking protocol, and docking gallic acid on MMP-1 with the Autodock 1.5.6. The results showed that gallic acid had an affinity for MMP-1 with a binding energy of -6.0 kcal/mol. There are similar amino acid residues in hydrogen bonds between the native ligand RS2 with MMP-1 and gallic acid with MMP-1, namely ALA 182, LEU 181, and HIS 218. The results suggest that gallic acid has the potential as the anti-photoaging agent through the inhibition of the MMP-1 enzyme.

References

Kammeyer A, Luiten RM. Oxidation events and skin aging. Ageing Res Rev. 2015;21: 16-29. https://doi.org/10.1016/j.arr.2015.01.001

RittiƩ L, Fisher GJ. Natural and sun-induced aging of human skin. Cold Spring Harb Perspect Med. 2015;5: a015370. https://doi.org/10.1101/cshperspect.a015370

Xiao Z, Yang S, Chen J, Li C, Zhou C, Hong P, et al. Trehalose against UVB-induced skin photoaging by suppressing MMP expression and enhancing procollagen I synthesis in HaCaT cells. J Funct Foods. 2020;74: 104198. https://doi.org/10.1016/j.jff.2020.104198

Kahkeshani N, Farzaei F, Fotouhi M, Alavi SS, Bahramsoltani R, Naseri R, et al. Pharmacological effects of gallic acid in health and diseases: A mechanistic review. Iran J Basic Med Sci. 2019;22: 225-237. https://doi.org/10.22038/ijbms.2019.32806.7897

Gao J, Hu J, Hu D, Yang X. A role of gallic acid in oxidative damage diseases: A comprehensive review. Nat Prod Commun. 2019;14: 1934578X1987417. https://doi.org/10.1177/1934578X19874174

Queiroz MF, Sabry DA, Sassaki GL, Rocha HAO, Costa LS. Gallic Acid-Dextran Conjugate: Green Synthesis of a Novel Antioxidant Molecule. Antioxidants (Basel). 2019;8. https://doi.org/10.3390/antiox8100478

Choubey S, Goyal S, Varughese LR, Kumar V, Sharma AK, Beniwal V. Probing gallic acid for its broad spectrum applications. Mini Rev Med Chem. 2018;18: 1283-1293. https://doi.org/10.2174/1389557518666180330114010

Naser W. The cosmetic effects of various natural biofunctional ingredients against skin aging: a review. Int J App Pharm. 2021; 10-18. https://doi.org/10.22159/ijap.2021v13i1.39806

Che DN, Xie GH, Cho BO, Shin JY, Kang HJ, Jang SI. Protective effects of grape stem extract against UVB-induced damage in C57BL mice skin. J Photochem Photobiol B, Biol. 2017;173: 551-559. https://doi.org/10.1016/j.jphotobiol.2017.06.042

Lin X, Li X, Lin X. A review on applications of computational methods in drug screening and design. Molecules. 2020;25. https://doi.org/10.3390/molecules25061375

Jain AN, Nicholls A. Recommendations for evaluation of computational methods. J Comput Aided Mol Des. 2008;22: 133-139. https://doi.org/10.1007/s10822-008-9196-5

Kitchen DB, Decornez H, Furr JR, Bajorath J. Docking and scoring in virtual screening for drug discovery: methods and applications. Nat Rev Drug Discov. 2004;3: 935-949. https://doi.org/10.1038/nrd1549

Du X, Li Y, Xia Y-L, Ai S-M, Liang J, Sang P, et al. Insights into Protein-Ligand Interactions: Mechanisms, Models, and Methods. Int J Mol Sci. 2016;17. https://doi.org/10.3390/ijms17020144

Sastry GM, Adzhigirey M, Day T, Annabhimoju R, Sherman W. Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments. J Comput Aided Mol Des. 2013;27: 221-234. https://doi.org/10.1007/s10822-013-9644-8

Leis S, Zacharias M. ReFlexIn: a flexible receptor protein-ligand docking scheme evaluated on HIV-1 protease. PLoS One. 2012;7: e48008. https://doi.org/10.1371/journal.pone.0048008

Zhao P, Alam MB, Lee S-H. Protection of UVB-Induced Photoaging by Fuzhuan-Brick Tea Aqueous Extract via MAPKs/Nrf2-Mediated Down-Regulation of MMP-1. Nutrients. 2018;11. https://doi.org/10.3390/nu11010060

Hwang E, Park S-Y, Lee HJ, Lee TY, Sun Z-W, Yi TH. Gallic acid regulates skin photoaging in UVB-exposed fibroblast and hairless mice. Phytother Res. 2014;28: 1778-1788. https://doi.org/10.1002/ptr.5198

Girsang E, Ginting C, Lister IN, Widowati W, Wibowo S, Perdana F, et al. In silico Analysis of Phytochemical Compound Found in Snake Fruit (Salacca zalacca) Peel as Anti-aging Agent. Thai Journal of Pharmaceutical Sciences (TJPS). 2019;43: 105-109.

Dewi NLPL, Ginarsih NMA. Molecular Docking Ellagic Acid As An Anti-Photoaging Agent In Silico. Acta Holistica Pharmaciana. 2021;3: 22-30.

Chaikul P, Khat-Udomkiri N, Iangthanarat K, Manosroi J, Manosroi A. Characteristics and in vitro anti-skin aging activity of gallic acid loaded in cationic CTAB niosome. Eur J Pharm Sci. 2019;131: 39-49. https://doi.org/10.1016/j.ejps.2019.02.008

Wu Y-Z, Tsai Y-Y, Chang L-S, Chen Y-J. Evaluation of Gallic Acid-Coated Gold Nanoparticles as an Anti-Aging Ingredient. Pharmaceuticals (Basel). 2021;14. https://doi.org/10.3390/ph14111071

Nam S-H, Park J, Jun W, Kim D, Ko J-A, Abd El-Aty AM, et al. Transglycosylation of gallic acid by using Leuconostoc glucansucrase and its characterization as a functional cosmetic agent. AMB Express. 2017;7: 224. https://doi.org/10.1186/s13568-017-0523-x

Published
2021-12-04
How to Cite
Dewi, N. K. D. P., Suryadewi, K. D., Fitriari, D. M., Andini, K. L., & Laksmiani, N. P. L. (2021). Molecular docking of gallic acid as anti-photoaging in silico. Pharmacy Reports, 1(2), 18. https://doi.org/10.51511/pr.18