Antioxidant activity evaluation of derivatives with 6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine scaffold

Authors

  • N. Yu. Slyvka Lesya Ukrainka Volyn National University 13, Voli Ave., Lutsk, Ukraine, 43025 Author
  • S. M. Holota Lesya Ukrainka Volyn National University 13, Voli Ave., Lutsk, Ukraine, 43025; Danylo Halytsky Lviv National Medical University 69, Pekarska Str., Lviv, Ukraine, 79010 Author
  • L. M. Saliyeva Lesya Ukrainka Volyn National University 13, Voli Ave., Lutsk, Ukraine, 43025 Author
  • E. M. Kadykalo Lesya Ukrainka Volyn National University 13, Voli Ave., Lutsk, Ukraine, 43025 Author
  • M. A. Kolishetska Danylo Halytsky Lviv National Medical University 69, Pekarska Str., Lviv, Ukraine, 79010 Author
  • M. V. Vovk Institute of Organic Chemistry, NAS of Ukraine 5, Murmanska Str., Kyiv, Ukraine, 02660 Author

DOI:

https://doi.org/10.7124/bc.000A74

Keywords:

6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine, antiradical/scavenging activity, DPPH, IC50, SAR

Abstract

Aim. Study of antioxidant (antiradical) activity of 6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine derivatives. Methods. In vitro study of antiradical/scavenging activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals inhibition assay; IC50 values determination. Results. The series of 29 modified derivatives of 6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine were evaluated for their ability to scavenge DPPH radicals in conditions close to physiological at 5 mM concentration and for the most promising compounds the IC50 values were determined using the serial dilutions method. The structure - antiradical activity correlations were performed and possible mechanisms of action were discussed. Conclusions. Tested 6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine derivatives possess a moderate level of antiradical/scavenging activity.

References

Sies H, Jones DP. Reactive oxygen species (ROS) as pleiotropic physiological signalling agents. Nat Rev Mol Cell Biol. 2020; 21(7):363-83.

Zarkovic N. Roles and functions of ROS and RNS in cellular physiology and pathology. Cells. 2020; 9(3):767.

Cherkas A, Holota S, Mdzinarashvili T, Gabbianelli R, Zarkovic N. Glucose as a major antioxidant: when, what for and why it fails? Antioxidants (Basel). 2020; 9(2):140.

Rossetti AC, Paladini MS, Riva MA, Molteni R. Oxidation-reduction mechanisms in psychiatric disorders: A novel target for pharmacological intervention. Pharmacol Ther. 2020; 210:107520.

Cherkas A, Golota S, Guéraud F, Pichler Ch, Nersesyan A, Abrahamovych O, Krupak V, Bugiichyk V, Yatskevych O, Pliatsko M, Eckl P, Knasmüller S. A Helicobacter pylori-associated insulin resistance in asymptomatic sedentary young men does not correlate with inflammatory markers and urine levels of 8-iso-PGF2-α or 1,4-dihydroxynonane mercapturic acid. Arch Physiol Biochem. 2018; 124(3):275-85.

Jaganjac M, Milkovic L, Gegotek A, Cindric M, Zarkovic K, Skrzydlewska E, Zarkovic N. The relevance of pathophysiological alterations in redox signaling of 4-hydroxynonenal for pharmacological therapies of major stress-associated diseases. Free Radic Biol Med. 2020; 157:128-53.

Camara AK, Lesnefsky EJ, Stowe DF. Potential therapeutic benefits of strategies directed to mitochondria. Antioxid Redox Signal. 2010; 13(3):279-347.

Kurutas EB. The importance of antioxidants which play the role in cellular response against oxidative/nitrosative stress: current state. Nutr J. 2016; 15(1):71.

Daiber A, Chlopicki S. Revisiting pharmacology of oxidative stress and endothelial dysfunction in cardiovascular disease: Evidence for redox-based therapies. Free Radic Biol Med. 2020; 157:15-37.

Liu ZQ. Bridging free radical chemistry with drug discovery: A promising way for finding novel drugs efficiently. Eur J Med Chem. 2020; 189:112020.

Haider K, Haider MR, Neha K, Yar MS. Free radical scavengers: An overview on heterocyclic advances and medicinal prospects. Eur J Med Chem. 2020; 204:112607.

Zhang HY, Yang DP, Tang GY. Multipotent antioxidants: From screening to design. Drug Discov Today. 2006; 11(15-16):749-54.

Ney Y, Nasim JM, Kharma A, Youssef LA, Jacob C. Small molecule catalysts with therapeutic potential. Molecules. 2018; 23(4):765.

Bielitza M, Belorgey D, Ehrhardt K, Johann L, Lanfranchi DA, Gallo V, Schwarzer E, Mohring F, Jortzik E, Williams DL, Becker K, Arese P, Elhabiri M, Davioud-Charvet E. Antimalarial NADPH-consuming redox-cyclers as superior glucose-6-phosphate dehydrogenase deficiency copycats. Antioxid Redox Signal. 2015; 22(15):1337-51.

Pappa A, Franco R, Schoneveld O, Galanis A, Sandaltzopoulos R, Panayiotidis MI. Sulfur-containing compounds in protecting against oxidant-mediated lung diseases. Curr Med Chem. 2007; 14(24):2590-6.

Mukwevho E, Ferreira Z, Ayeleso A. Potential role of sulfur-containing antioxidant systems in highly oxidative environments. Molecules. 2014; 19(12):19376-89.

Gaucher C, Boudier A, Bonetti J, Clarot I, Leroy P, Parent M. Glutathione: antioxidant properties dedicated to nanotechnologies. Antioxidants (Basel). 2018; 7(5):62.

Sahiba N, Sethiya A, Soni J, Agarwal DK, Agarwal S. Saturated five-membered thiazolidines and their derivatives: from synthesis to biological applications. Top Curr Chem (Cham). 2020; 378(2):34.

Farouk EM, Mohamed AB, Fawzi FM. An overview on synthetic 2-aminothiazole-based compounds associated with four biological activities. Molecules. 2021;26(5):1449.

Saliyeva LM, Holota SM, Grozav AM, Yakovychuk ND, Lukashchuk MM, Marushko LP, Slyvka NY, Vovk MV. Synthesis, the antiexudative and antimicrobial activity of 6-arylidene substituted imidazo[2,1-b]thiazoles. J Org Pharm Chem. 2021;19(2):29-35.

Saliyeva L, Slyvka N, Holota S, Grozav A, Yakovychuk N, Litvinchuk M, Vovk M. Synthesis and Evaluation of Bioactivity of 6-[(2-Pyridinyloxy)](benzo)imidazo[2,1-b][1,3]thiazine derivatives. Biointerface Res Appl Chem. 2022; 12(4):5031-44.

Saliyeva L, Holota S, Grozav A, Yakovychuk N, Litvinchuk M, Slyvka N, Vovk M. Synthesis and evaluation of antimicrobial and anti-inflammatory activity of 6-aryliden-2-methyl-2,3-dihydroimidazo[2,1-b][1,3]thiazoles. Biointerface Res Appl Chem. 2022; 12(1):292-303.

Brand-Williams W, Cuvelier M, Berset C. Use of a free radical method to evaluate antioxidant activity. LWT - Food Sci Technol. 1995; 28(1):25-30.

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Published

2022-12-01

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Section

Bioorganic Chemistry