In Vitro Antioxidant Properties of 2-Imino-benzimidazole and 1,3-Thiazolo[3,2-a]benzimidazolone Derivative
Abstract
Antioxidant properties of 2-[2-imino-5-nitro-3-(2-oxo-2-phenylethyl)-2,3-dihydro-1H-benzimdazol-1-yl]-1-phenylethanone (compound 1) and 2-(4-fluorobenzylidene)-6-(phenylcarbonyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one (compound 2) were evaluated in vitro. Compounds 1 and 2 did not show significant radical scavenging activity. It has been suggested that antioxidant strategies should not be based on direct scavengers, but rather on the potentiation of endogenous antioxidant defenses, or on the reduction of the sources of reactive species. Although missing direct scavenging mechanism, the assayed compounds (1 and 2) as evidenced inhibitors of xanthine oxidase and dipeptidyl peptidase-4 might act antioxidatively by other mechanisms.
References
Apak R, Özyürek M, Güçlü K, Çapanoğlu E. Antioxidant activity/capacity measurement. 1. Classification, physicochemical principles, mechanisms, and electron transfer (ET)-based assays. Journal of Agricultural and Food Chemistry 2016; 64: 997-1027. (https://pubs.acs.org/doi/10.1021/acs.jafc.5b04739)
Pinchuk I, Shoval H, Dotan Y, Lichtenberg D. Evaluation of antioxidants: scope, limitations and relevance of assays. Chemistry and Physics of Lipids 2012; 165: 638-647. (https://doi.org/10.1016/j.chemphyslip.2012.05.003)
Togliatto G, Lombardo G, Brizzi MF. The future challenge of reactive oxygen species (ROS) in hypertension: from bench to bed side. International Journal of Molecular Sciences 2017; 18: 1988. (https://doi.org/10.3390/ijms18091988)
Battelli MG, Polito L, Bolognesi A. Xanthine oxidoreductase in atherosclerosis pathogenesis: not only oxidative stress. Atherosclerosis 2014; 237: 562-567. (http://dx.doi.org/10.1016/j.atherosclerosis.2014.10.006)
George J, Struthers AD. Role of urate, xanthine oxidase and the effects of allopurinol in vascular oxidative stress. Vascular Health and Risk Management 2009; 5: 265-272. (https://doi.org/10.2147/VHRM.S4265)
Cadenas E, Packer L, editors. Handbook of antioxidants. Second edition revised and expanded. Marcel Dekker, Inc, 2002.
Haida Z, Hakiman M. A comprehensive review on the determination of enzymatic assay and nonenzymatic antioxidant activities. Food Science and Nutrition 2019; 7: 1555-1563. (https://doi.org/10.1002/fsn3.1012)
Mavrova AT, Yancheva D, Anastassova N, Anichina K, Zvezdanovic J, Djordjevic A, Markovic D, Smelcerovic A. Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles. Bioorganic and Medicinal Chemistry 2015; 23: 6317-6326. (https://doi.org/10.1016/j.bmc.2015.08.029)
Brand-Williams W, Cuvelier ME, Berset CL. Use of a free radical method to evaluate antioxidant activity. LWT - Food science and Technology 1995; 28: 25-30. (https://doi.org/10.1016/S0023-6438(95)80008-5)
Miliauskas G, Venskutonis PR, Van Beek TA. Screening of radical scavenging activity of some medicinal and aromatic plant extracts. Food Chemistry 2004; 85: 231-237. (https://doi.org/10.1016/j.foodchem.2003.05.007)
Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine 1999; 26: 1231-1237. (https://doi.org/10.1016/S0891-5849(98)00315-3)
Arts MJ, Haenen GR, Voss HP, Bast A. Antioxidant capacity of reaction products limits the applicability of the Trolox Equivalent Antioxidant Capacity (TEAC) assay. Food and Chemical Toxicology 2004; 42: 45-49. (https://doi.org/10.1016/j.fct.2003.08.004)
Apak R, Güclü K, Özyürek M, Celik SE. Mechanism of antioxidant capacity assays and the CUPRAC (cupric ion reducing antioxidant capacity) assay. Microchimica Acta 2008; 160: 413-419. (https://doi.org/10.1007/s00604-007-0777-0)
Benzie IF, Strain JJ. Ferric reducing/antioxidant power assay: direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods in Enzymology 1999; 299: 15-27. (https://doi.org/10.1016/S0076-6879(99)99005-5)
Vijayalakshmi M, Ruckmani K. Ferric reducing anti-oxidant power assay in plant extract. Bangladesh Journal of Pharmacology 2016; 11: 570-572. (https://doi.org/10.3329/bjp.v11i3.27663)
Gulcin İ. Antioxidants and antioxidant methods: an updated overview. Archives of Toxicology 2020; 94: 651-715. (https://doi.org/10.1007/s00204-020-02689-3)
Feigelson P. The inhibition of xanthine oxidase in vitro by trace amounts of l-ascorbic acid. Journal of Biological Chemistry 1952; 197: 843-850. (https://www.jbc.org/content/197/2/843.full.pdf)
Roumeliotis S, Roumeliotis A, Dounousi E, Eleftheriadis T, Liakopoulos V. Dietary antioxidant supplements and uric acid in chronic kidney disease: a review. Nutrients 2019; 11: 1911. (https://doi.org/10.3390/nu11081911)
Tomovic K, Ilic BS, Smelcerovic Z, Miljkovic M, Yancheva D, Kojic M, Mavrova AT, Kocic G, Smelcerovic A. Benzimidazole-based dual dipeptidyl peptidase-4 and xanthine oxidase inhibitors. Chemico-Biological Interactions 2020; 315: 108873. (https://doi.org/10.1016/j.cbi.2019.108873)
Steven S, Münzel T, Daiber A. Exploiting the pleiotropic antioxidant effects of established drugs in cardiovascular disease. International Journal of Molecular Sciences 2015; 16: 18185-18223. (https://doi.org/10.3390/ijms160818185)
Szocs K. Endothelial dysfunction and reactive oxygen species production in ischemia/reperfusion and nitrate tolerance. General Physiology and Biophysics 2004; 23: 265-296.
Pickering RJ, Rosado CJ, Sharma A, Buksh S, Tate M, de Haan JB. Recent novel approaches to limit oxidative stress and inflammation in diabetic complications. Clinical and Translational Immunology 2018; 7: e1016. (https://doi.org/10.1002/cti2.1016)