title: Design and synthesis of coumarin-3-acylamino derivatives to scavenge radicals and to protect DNA.
abstract: In this study, a series of coumarin-3-acylamino derivatives containing phenethylamine moiety or tyramine moiety were synthesized and their antioxidant activities were evaluated by Cu(2+)/glutathione(GSH)-, ˙OH- and 2,2'-azobis(2-amidinopropane hydrochloride)(AAPH)-induced oxidation of DNA. It was found that both hydroxyl and ortho-methoxy groups at A ring, hydroxyl group at B ring and peptide bond can enhance the abilities of coumarin-3-acylamino derivatives to protect DNA against ˙OH- and AAPH-induced oxidation. Moreover, these coumarin-3-acylamino derivatives were employed to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+˙)). We found that tyramine moiety, hydroxyl and ortho-methoxy are the key groups to enhance the activities of antioxidants to quench ABTS(+˙). Therefore, tyramine linked with coumarin-3-carboxyl acid which containing hydroxyl and ortho-methoxy exhibited powerful antioxidant abilities.
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China.
authors.forename: Qing-Wen
authors.initials: QW
authors.lastname: Liu
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China.
authors.forename: Ye
authors.initials: Y
authors.lastname: Shi
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China. Electronic address: szg@jlu.edu.cn.
authors.forename: Zhi-Guang
authors.initials: ZG
authors.lastname: Song
authors.affiliation: Key Laboratory for Molecular Enzymology and Engineering, Ministry of Education, Jilin University, Changchun 130012, China.
authors.forename: Ying-Hua
authors.initials: YH
authors.lastname: Jin
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China.
authors.forename: Zai-Qun
authors.initials: ZQ
authors.lastname: Liu
mesh_terms: D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004247:DNA / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D003374:Coumarins; D016166:Free Radical Scavengers; D004247:DNA
keywords: Antioxidant; Coumarin; Coumarin-3-acylamino; DNA; Free radical; Oxidation