In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole
Authorized Users Only
2018
Authors
Đukić, Mirjana
Fesatidou, Mara
Xenikakis, Iakovos

Geronikaki, Athina

Angelova, Violina T.
Savić, Vladimir

Pasić, Marta
Krilović, Branislav
Đukić, Dušan
Gobeljić, Borko

Pavlica, Marina
Đurić, Ana

Stanojević, Ivan
Vojvodić, Danilo

Saso, Luciano

Article (Published version)

Metadata
Show full item recordAbstract
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(5H) 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 alpha-lipoic acid (alpha-LA) were tested. The results of DPPH testing: Vitamin C 94.35%, Vitamin E 2.99% and alpha-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%; alpha-LA 51.36%; compounds: 1 62.11%; 5 66.71%; 9 60.93%; 4, 6 and 7 demonstrated similar to 50%; 3 and 8 displayed similar to 38%; 2 23.51%. By FRAP method, Vitamins E and C showed equal AOA, similar to 100%, unlike alpha-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.
Keywords:
1,3-thiazole, 1,3,4-thiadiazole / Thiazolidinone / DPPH / FRAP / TBARSSource:
Chemico-Biological Interactions, 2018, 286, 119-131Publisher:
- Elsevier Ireland Ltd, Clare
Funding / projects:
DOI: 10.1016/j.cbi.2018.03.013
ISSN: 0009-2797
PubMed: 29574026
WoS: 000429592200015
Scopus: 2-s2.0-85044467819
Collections
Institution/Community
PharmacyTY - JOUR AU - Đukić, Mirjana AU - Fesatidou, Mara AU - Xenikakis, Iakovos AU - Geronikaki, Athina AU - Angelova, Violina T. AU - Savić, Vladimir AU - Pasić, Marta AU - Krilović, Branislav AU - Đukić, Dušan AU - Gobeljić, Borko AU - Pavlica, Marina AU - Đurić, Ana AU - Stanojević, Ivan AU - Vojvodić, Danilo AU - Saso, Luciano PY - 2018 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3154 AB - 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(5H) 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 alpha-lipoic acid (alpha-LA) were tested. The results of DPPH testing: Vitamin C 94.35%, Vitamin E 2.99% and alpha-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%; alpha-LA 51.36%; compounds: 1 62.11%; 5 66.71%; 9 60.93%; 4, 6 and 7 demonstrated similar to 50%; 3 and 8 displayed similar to 38%; 2 23.51%. By FRAP method, Vitamins E and C showed equal AOA, similar to 100%, unlike alpha-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. PB - Elsevier Ireland Ltd, Clare T2 - Chemico-Biological Interactions T1 - In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole VL - 286 SP - 119 EP - 131 DO - 10.1016/j.cbi.2018.03.013 ER -
@article{ author = "Đukić, Mirjana and Fesatidou, Mara and Xenikakis, Iakovos and Geronikaki, Athina and Angelova, Violina T. and Savić, Vladimir and Pasić, Marta and Krilović, Branislav and Đukić, Dušan and Gobeljić, Borko and Pavlica, Marina and Đurić, Ana and Stanojević, Ivan and Vojvodić, Danilo and Saso, Luciano", year = "2018", 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(5H) 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 alpha-lipoic acid (alpha-LA) were tested. The results of DPPH testing: Vitamin C 94.35%, Vitamin E 2.99% and alpha-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%; alpha-LA 51.36%; compounds: 1 62.11%; 5 66.71%; 9 60.93%; 4, 6 and 7 demonstrated similar to 50%; 3 and 8 displayed similar to 38%; 2 23.51%. By FRAP method, Vitamins E and C showed equal AOA, similar to 100%, unlike alpha-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.", publisher = "Elsevier Ireland Ltd, Clare", journal = "Chemico-Biological Interactions", title = "In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole", volume = "286", pages = "119-131", doi = "10.1016/j.cbi.2018.03.013" }
Đukić, M., Fesatidou, M., Xenikakis, I., Geronikaki, A., Angelova, V. T., Savić, V., Pasić, M., Krilović, B., Đukić, D., Gobeljić, B., Pavlica, M., Đurić, A., Stanojević, I., Vojvodić, D.,& Saso, L.. (2018). In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole. in Chemico-Biological Interactions Elsevier Ireland Ltd, Clare., 286, 119-131. https://doi.org/10.1016/j.cbi.2018.03.013
Đukić M, Fesatidou M, Xenikakis I, Geronikaki A, Angelova VT, Savić V, Pasić M, Krilović B, Đukić D, Gobeljić B, Pavlica M, Đurić A, Stanojević I, Vojvodić D, Saso L. In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole. in Chemico-Biological Interactions. 2018;286:119-131. doi:10.1016/j.cbi.2018.03.013 .
Đukić, Mirjana, Fesatidou, Mara, Xenikakis, Iakovos, Geronikaki, Athina, Angelova, Violina T., Savić, Vladimir, Pasić, Marta, Krilović, Branislav, Đukić, Dušan, Gobeljić, Borko, Pavlica, Marina, Đurić, Ana, Stanojević, Ivan, Vojvodić, Danilo, Saso, Luciano, "In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole" in Chemico-Biological Interactions, 286 (2018):119-131, https://doi.org/10.1016/j.cbi.2018.03.013 . .