Antioksidativna aktivnost derivata N,N’-disupstituisanih benzimidazol-2-tiona: in vitro studija

  • Jelena Lazarevic
  • Jelena Zvezdanović Univerzitet u Nišu, Tehnološki fakultet, Leskovac, Srbija
  • Neda Anastassova Institute of Organic Chemistry with Center of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
  • Anelia Ts. Mavrova Institute of Organic Chemistry with Center of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
  • Denitsa Yancheva Institute of Organic Chemistry with Center of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
  • Andrija Šmelcerović Univerzitet u Nišu, Tehnološki fakultet, Leskovac, Srbija
Ključne reči: antioksidantna aktivnost, lipidna peroksidacija, N,N’-disupstituisani benzimidazol-2-tioni

Sažetak


Antioksidativna aktivnost sedam N,N’-disupstituisanih benzimidazol-2-tiona, sa funkcionalizovanim bočnim nizovima u položajima 1- i 3- estarskim (1-4), odnosno hidrazidnim (5-7) grupama, ispitana je in vitro, metodom lipidne peroksidacije. Jedino hidrazidi 1,3-bis[3-(hidrazinooksi)-3-oksopropil]-1,3-dihidro-2H-benzimidazol-2-tion (5), 1,3-bis[3-(hidrazinooksi)-3-oxopropil]-5-metil-1,3-dihidro-2H-benzimidazol-2-tion (6) i 1,3-bis[3-(hidrazinooksi)-3-oxopropil]-5-benzoil-1,3-dihidro-2H-benzimidazol-2-tion (7) pokazuju dobra antioksidativna svojstva (IC50 < 100 μM), sa najboljim vrednostima inhibicije lipidne peroksidacije (IC50) za jedinjenja  5 (64 ± 10 μM) i 6 (73 ± 29 μM). Pomenuta dva jedinjenja, na osnovu in vitro dobijenih IC50 rezultata, predstavljaju dobru polaznu molekularnu osnovu i obećavajući sturkturni element u razvoju jedinjenja za prevenciju bolesti nastalih kao posledica oksidativnog oštećenja.

Reference

References



  1. Beckhauser TF, Francis-Oliveira J, De Pasquale R. Reactive oxygen species: physiological and physiopathological effects on synaptic plasticity. J Exp Neurosci 2016; 10: 23-48. https://doi.org/10.4137/JEN.S39887

  2. Collin F. Chemical basis of reactive oxygen species reactivity and involvement in neurodegenerative diseases. Int J Mol Sci 2019; 20: 2407. https://doi.org/10.3390/ijms20102407



  1. Ramana KV, Srivastava S, Singhal SS. Lipid peroxidation products in human health and disease 2016, Oxid Med Cell. Longev 2017; 2017: 2163285. https://doi.org/10.1155/2017/2163285



  1. Salahuddin, Shaharyar M, Mazumder A. Benzimidazoles: a biologically active compounds. Arab J Chem 2017;10: S157‐S173. https://doi.org/10.1016/j.arabjc.2012.07.017



  1. Gurer-Orhan H, Orhan H, Suzen S, Püsküllü MO et al. Synthesis and evaluation of in vitro antioxidant capacities of some benzimidazole derivatives. J Enzyme Inhib Med Chem 2006; 2: 241-247. https://doi.org/10.1080/14756360600586031



  1. Kuş C, Ayhan-Kılcıgil G, Özbey S et al. Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4–methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class. Bioorg Med Chem 2008; 16: 4294-4303. https://doi.org/10.1016/j.bmc.2008.02.077

  2. Mavrova A, Yancheva D, Anastassova N et al. Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles. Bioorg Med Chem 2015; 23: 6317-6126. https://doi.org/10.1016/j.bmc.2015.08.029

  3. Shirinzadeh H, Eren B, Gurer-Orhan H et al. Novel indole-based analogs of melatonin: synthesis and in vitro antioxidant activity studies. Molecules 2010; 15: 2187-2202. https://doi.org/10.3390/molecules15042187

  4. Johns JR, Platts JA. Theoretical insight into the antioxidant properties of melatonin and derivatives. Org Biomol Chem 2014; 12: 7820-7827. https://doi.org/10.1039/C4OB01396D



  1. Suzen S. Melatonin and synthetic analogs as antioxidants. Curr Drug Deliv 2013; 10: 71-5. https://doi: 10.2174/1567201811310010013

  2. Anastassova N, Mavrova A, Yancheva D et al. Hepatotoxicity and antioxidant activity of some new N,N′-disubstituted benzimidazole-2-thiones, radical scavenging mechanism and structure-activity relationship. Arab J Chem 2016; 11: 353-369. https://doi.org/10.1016/j.arabjc.2016.12.003

  3. Reina M, Castañeda-Arriaga R, Perez-Gonzalez A et al. A Computer-assisted systematic search for melatonin derivatives with high potential as antioxidants. Melatonin Res 2018; 1: 27-58. https://doi.org/10.32794/mr11250003



  1. Elkamhawy A, Woo J, Gouda NA et al. Melatonin analogues potently inhibit MAO-B and protect PC12 cells against oxidative stress. Antioxidants 2021; 10: 1604. https://doi.org/10.3390/antiox10101604

  2. Kolarević A, Ilić BS, Anastassova N et al. Benzimidazoles as novel deoxyribonuclease I inhibitors. J Cell Biochem 2018; 119: 8937-8948. https://doi.org/10.1002/jcb.27147



  1. Lazarević J, Šmelcerović A, Zvezdanović J et al. Lipid peroxidation inhibition study: A promising case of 1,3-di([1,1'-biphenyl]-3-yl)urea. Chem Biol Interact 2020; 326: 109137. https://doi.org/10.1016/j.cbi.2020.109137

  2. Karadag A, Ozcelik B, Saner S. Review of methods to determine antioxidant capacities. Food Anal Methods 2009; 2: 41-60. https://doi.org/10.1007/s12161-008-9067-7



  1. Galano A, Tan D, Reiter R. Melatonin as a natural ally against oxidative stress: a physicochemical examination. J Pineal Res 2011; 51: 1-16. https://doi:10.1111/j.1600-079X.2011.00916.x

Objavljeno
2025/12/21
Rubrika
Originalni rad / Original article