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

© 2020, Leibniz Research Centre for Working Environment and Human Factors. All rights reserved. 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 relat...

Full description

Saved in:
Bibliographic Details
Main Authors: Apilak Worachartcheewan, Veda Prachayasittikul, Supaluk Prachayasittikul, Visanu Tantivit, Chareef Yeeyahya, Virapong Prachayasittikul
Other Authors: Mahidol University
Format: Article
Published: 2020
Subjects:
Online Access:https://repository.li.mahidol.ac.th/handle/123456789/53525
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Mahidol University
id th-mahidol.53525
record_format dspace
spelling th-mahidol.535252020-03-26T12:13:11Z Rational design of novel coumarins: A potential trend for antioxidants in cosmetics Apilak Worachartcheewan Veda Prachayasittikul Supaluk Prachayasittikul Visanu Tantivit Chareef Yeeyahya Virapong Prachayasittikul Mahidol University Agricultural and Biological Sciences Biochemistry, Genetics and Molecular Biology Pharmacology, Toxicology and Pharmaceutics © 2020, Leibniz Research Centre for Working Environment and Human Factors. All rights reserved. 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), polariza-bility (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. 2020-03-26T04:27:29Z 2020-03-26T04:27:29Z 2020-01-01 Article EXCLI Journal. Vol.19, (2020), 209-226 10.17179/excli2019-1903 16112156 2-s2.0-85080958931 https://repository.li.mahidol.ac.th/handle/123456789/53525 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85080958931&origin=inward
institution Mahidol University
building Mahidol University Library
continent Asia
country Thailand
Thailand
content_provider Mahidol University Library
collection Mahidol University Institutional Repository
topic Agricultural and Biological Sciences
Biochemistry, Genetics and Molecular Biology
Pharmacology, Toxicology and Pharmaceutics
spellingShingle Agricultural and Biological Sciences
Biochemistry, Genetics and Molecular Biology
Pharmacology, Toxicology and Pharmaceutics
Apilak Worachartcheewan
Veda Prachayasittikul
Supaluk Prachayasittikul
Visanu Tantivit
Chareef Yeeyahya
Virapong Prachayasittikul
Rational design of novel coumarins: A potential trend for antioxidants in cosmetics
description © 2020, Leibniz Research Centre for Working Environment and Human Factors. All rights reserved. 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), polariza-bility (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.
author2 Mahidol University
author_facet Mahidol University
Apilak Worachartcheewan
Veda Prachayasittikul
Supaluk Prachayasittikul
Visanu Tantivit
Chareef Yeeyahya
Virapong Prachayasittikul
format Article
author Apilak Worachartcheewan
Veda Prachayasittikul
Supaluk Prachayasittikul
Visanu Tantivit
Chareef Yeeyahya
Virapong Prachayasittikul
author_sort Apilak Worachartcheewan
title Rational design of novel coumarins: A potential trend for antioxidants in cosmetics
title_short Rational design of novel coumarins: A potential trend for antioxidants in cosmetics
title_full Rational design of novel coumarins: A potential trend for antioxidants in cosmetics
title_fullStr Rational design of novel coumarins: A potential trend for antioxidants in cosmetics
title_full_unstemmed Rational design of novel coumarins: A potential trend for antioxidants in cosmetics
title_sort rational design of novel coumarins: a potential trend for antioxidants in cosmetics
publishDate 2020
url https://repository.li.mahidol.ac.th/handle/123456789/53525
_version_ 1763488656396386304