Rational design of novel coumarins: A potential trend for antioxidants in cosmetics

Authors

  • Apilak Worachartcheewan Department of Community Medical Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand, Phone: (662) 441-4376; Fax: (662) 441-4380, E-mail: apilak.woa@mahidol.ac.th
  • Veda Prachayasittkul Center of Data Mining and Biomedical Informatics, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand
  • Supaluk Prachayasittkul Center of Data Mining and Biomedical Informatics, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand, E-mail: supaluk@g.swu.ac.th
  • Visanu Tantivit Department of Community Medical Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand
  • Chareef Yeeyahya Department of Community Medical Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand
  • Virapong Prachayasittkikul Department of Clinical Microbiology and Applied Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand

DOI:

https://doi.org/10.17179/excli2019-1903

Keywords:

coumarin, antioxidant activity, rational design, QSAR, MLR

Abstract

Coumarins are well-known for their antioxidant effect and aromatic property, thus, they are one of ingredients commonly added in cosmetics and personal care products. Quantitative structure-activity relationships (QSAR) modeling is an in silico method widely used to facilitate rational design and structural optimization of novel drugs. Herein, QSAR modeling was used to elucidate key properties governing antioxidant activity of a series of the reported coumarin-based antioxidant agents (1-28). Several types of descriptors (calculated from 4 softwares i.e., Gaussian 09, Dragon, PaDEL and Mold2 softwares) were used to generate three multiple linear regression (MLR) models with preferable predictive performance (Q2LOO-CV = 0.813-0.908; RMSELOO-CV = 0.150-0.210; Q2Ext = 0.875-0.952; RMSEExt = 0.104-0.166). QSAR analysis indicated that number of secondary amines (nArNHR), polarizability (G2p), electronegativity (D467, D580, SpMin2_Bhe, and MATS8e), van der Waals volume (D491 and D461), and H-bond potential (SHBint4) are important properties governing antioxidant activity. The constructed models were also applied to guide in silico rational design of an additional set of 69 structurally modified coumarins with improved antioxidant activity. Finally, a set of 9 promising newly design compounds were highlighted for further development. Structure-activity analysis also revealed key features required for potent activity which would be useful for guiding the future rational design. In overview, our findings demonstrated that QSAR modeling could possibly be a facilitating tool to enhance successful development of bioactive compounds for health and cosmetic applications.

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Published

2020-02-26

How to Cite

Worachartcheewan, A., Prachayasittkul, V., Prachayasittkul, S., Tantivit, V., Yeeyahya, C., & Prachayasittkikul, V. (2020). Rational design of novel coumarins: A potential trend for antioxidants in cosmetics. EXCLI Journal, 19, 209–226. https://doi.org/10.17179/excli2019-1903

Issue

Vol. 19 (2020)

Section

Original articles

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