In vitro antioxidant activity of thiazolidinone derivatives of 1, 3-thiazole and 1, 3, 4-thiadiazole. (25th April 2018)

• Record Type: Journal Article
• Authors: Djukic, Mirjana; Fesatidou, Mara; Xenikakis, Iakovos; Geronikaki, Athina; Angelova, Violina T.; Savic, Vladimir; Pasic, Marta; Krilovic, Branislav; Djukic, Dusan; Gobeljic, Borko; Pavlica, Marina; Djuric, Ana; Stanojevic, Ivan; Vojvodic, Danilo; Saso, Luciano
• Is Part Of: Chemico-biological interactions. Volume 286(2018)
• Page Start: 119
• Page End: 131
• Publication Date: 2018-04-25
• Subjects: 1, 3-thiazole, 1, 3, 4-thiadiazole -- Thiazolidinone -- DPPH -- FRAP -- TBARS; Biochemistry -- Periodicals; Toxicological chemistry -- Periodicals; Biochemistry -- Periodicals; Biologie moléculaire -- Périodiques; Biochimie -- Périodiques; Toxicologie biochimique -- Périodiques; 572
• DOI: 10.1016/j.cbi.2018.03.013
• Languages: English
• ISSNs: 0009-2797

Abstract

Abstract: The initial steps in preclinical drug developing research concern the synthesis of new compounds for specific therapeutic use which needs to be confirmed by in vitro and then in vivo testing. Nine thiazolidinone derivatives (numerically labeled 1 – 9 ) classified as follows: 1, 3-thiazole-based compounds ( 1 and 2 ); 1, 3, 4-thiadiazole based compounds ( 3 and 4 ); substituted 5-benzylideno-2-adamantylthiazol[3, 2-b][1, 2, 4]triazol-6(5 H )ones ( 5–8 ); and an ethylaminothiazole-based chalcone (9 ), were tested for antioxidant activity (AOA) by using three in vitro assays: DPPH (1, 1-diphenyl-2-picrylhydrazyl scavenging capacity test); FRAP (ferric reducing antioxidant power test); and TBARS (thiobarbituric acid reactive substances test). Compounds 1–4 and 9 in particular are newly synthesized compounds. Also, traditional antioxidants Vitamins E and C and α-lipoic acid (α-LA) were tested. The results of DPPH testing: Vitamin C 94.35%, Vitamin E 2.99% and α-LA 1.57%; compounds: 4 33.98%; 2 18.73%; 1 15.62%; 5 6.59%; 3 4.99%; 6–9 demonstrated almost no AOA. The results of TBARS testing (% of LPO inhibition): Vitamin C 62.32%; Vitamin E 36.29%; α-LA 51.36%; compounds: 1 62.11%; 5 66.71%; 9 60.93%; 4, 6 and 7 demonstrated ∼50%; 3 and 8 displayed ∼38%; 2 23.51%. By FRAP method, Vitamins E and C showed equal AOA, ∼100%, unlike α-LA (no AOA), and AOA of the tested compounds (expressed as a fraction of the AOA of Vitamin C) were: 2 and 4 –75%; 8, 3 and 1 –45%; 5–7 and 9 –27%. Different red-ox reaction principles between these assays dictate different AOA outcomes for a single compound. Vitamin C appeared to be the superior antioxidant out of the traditional antioxidants; and compound 4 was superior to other tested thiazolidinone derivatives. Vitamin C appeared to be the superior antioxidant out of the traditional antioxidants; and compound 4 was superior to other tested thiazolidinone derivatives. Phenyl-functionalized benzylidene, amino-carbonyl functional domains and chelating ligand properties of the thiazolidinone derivatives correlated with AOA. Graphical abstract: Highlights: 9 thiazolidinone derivatives were tested for antioxidant activity (AOA). Used in vitro assays: DPPH radical scavenging capacity test, FRAP and TBARS. Accomplished AOA were compared to vitamins C and E and α-lipoic acid. Different AOA for a single compound depends on its structure and test principles. Chelating effect, phenoxy (in benzylidene) and amino-carbonyl groups determine AOA.