title: INTRACELLULAR ANTIOXIDANT ACTIVITY OF A STREPTOMYCES SP. 8812 SECONDARY METABOLITE, 6,7-DIHYDROXY-3,4-DIHYDROISOQINO- LINE-3-CARBOXYLIC ACID, AND ITS SYNTHETIC DERIVATIVES.
abstract: The aim of this study was to determine the antioxidant properties of 6,7-dihydroxy-3,4-dihydroiso- quinoline-3-carboxylic acid (1) and its derivatives in living cells against reactive forms of oxygen and nitrogen, i.e., hydrogen peroxide and nitric oxide. Four of tested compounds scavenged the reactive form of nitrogen more efficiently or similarly to Trolox (EC50 = 55.80 µM). Two compounds exhibited antioxidant activity against reactive oxygen species better than Trolox (EC50 = 51.88 µM). The most active derivative of 1 was the compound containing an iodine atom at position 8 (6,7-dihydroxy-8-iodo-3,4-dihydroisoquinoline-3-carboxylic acid). Our studies showed that some of the derivatives had the ability to cross the cell membrane and scavenge free radicals inside living cells. Thus, they are able to protect DNA and other cellular structures from the dam- aging effects of reactive oxygen and nitrogen species. In addition, some molecular descriptors of the tested compounds were determined with the use of ICM Pro (Molsoft L.L.C.).
authors.forename: Adam
authors.initials: A
authors.lastname: Guśpiel
authors.forename: Joanna
authors.initials: J
authors.lastname: Ziemska
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Cześcik
authors.forename: Robert
authors.initials: R
authors.lastname: Kawecki
authors.forename: Jolanta
authors.initials: J
authors.lastname: Solecka
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D002839:Chromans / Q000138:chemical synthesis / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000737:chemistry; D006801:Humans; D017382:Reactive Oxygen Species / Q000032:analysis; D013302:Streptomyces / Q000737:chemistry*; D014709:Vero Cells
chemical_list: D000975:Antioxidants; D002839:Chromans; D016166:Free Radical Scavengers; D017382:Reactive Oxygen Species; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid