Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide and Benzyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide
Abstract
In this research, 0, 25, 50, 100, 200 and 400 mg/L (ppm) concentrations of 2-aminoimidazolines (cyclohexyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide (CHX) and benzyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide (BNZ)) were applied to baker's yeast (Saccharomyces cerevisiae) glutathione reductase (GR). Since the inhibition constant (Ki) (43 ± 2 nM) and 50 % inhibition concentration (IC50) (947 mg/L =3.13×10-3 M) values of BNZ were found to be smaller than the Ki (59 ± 17 nM) and IC50 (1461 mg/L =4.95×10-3 M) values of CHX. At imidazoline concentrations of 400 mg/L, CHX reduced GR activity by 16.07 %, while BNZ reduced GR activity by 21.96 %. BNZ inhibited GR more than CHX. In addition, molecular docking results also support the experimental data. CHX and BNZ inhibited GR enzyme activity as competitively.
Keywords
Supporting Institution
No Supporting Institution
Project Number
No funding
Ethical Statement
The study is complied with research and publication ethics
Thanks
The authors thank to the Departments of Chemistry and Biology, Faculty of Science and Letters, Adıyaman University, for providing the opportunity to use their laboratories and thank ADYUMLAB for measurement of 2-aminoimidazolines concentrations.
References
- A. M. S. El-Sharief, A. M. Al-Amri, and S. Y. Al-Raqa, “Halogenated, alkylated and new types of imidazolidine, pyrrolidine, imidazotriazine and thienoimidazole derivatives with biological and antitumor activities,” J. Sulphur Chem., vol. 27, no. 3, pp. 245–263, 2006. https://doi.org/10.1080/17415990600631316
- C. Dardonville, P. Goya, I. Rozas, A. Alsasua, M. I. Martín, and M. J. Borrego, “New aromatic iminoimidazolidine derivatives as alpha1-adrenoceptor antagonists: a novel synthetic approach and pharmacological activity,” Bioorg. Med. Chem., vol. 8, no. 7, pp. 1567–1577, 2000.https://doi.org/10.1016/S0968-0896(00)00089-4
- A. R. Katritzky and B. V. Rogovoy, “Recent developments in guanylating agents,” Arkivoc, vol. 2005, no. 4, pp. 49–87, 2005. https://doi.org/10.3998/ark.5550190.0006.406
- A. Işık, U. Acar Çevik, B. N. Sağlık, and Y. Özkay, “Synthesis, characterization, and molecular docking study of some novel imidazole derivatives as potential antifungal agents,” J. Heterocycl. Chem., vol. 56, no. 1, pp. 142–152, 2019. https://doi.org/10.1002/jhet.3388
- G. Mariappan, R. Hazarika, F. Alam, R. Karki, U. Patangia, and S. Nath, “Synthesis and biological evaluation of 2-substituted benzimidazole derivatives,” Arab. J. Chem., vol. 8, no. 5, pp. 715–719, 2015. http://dx.doi.org/10.1016/j.arabjc.2011.11.008
- H. Majed and F. W. Askar, “Synthesis and biological evaluation of new Benzimidazole derivatives,” Al-Mustansiriyah J. Sci., vol. 29, no. 1, pp. 107–113, 2018. https://doi.org/10.23851/mjs.v29i1.127
- M. Farag, W. M. Abdel-Mageed, O. Basudan, and A. El-Gamal, “Persicaline, A new antioxidant sulphur-containing imidazoline alkaloid from Salvadora persica roots,” Molecules, vol. 23, no. 2, 2018. https://doi.org/10.3390/molecules23020483
- D. R. Bazanov et al., “2,4,5-Tris(alkoxyaryl)imidazoline derivatives as potent scaffold for novel p53-MDM2 interaction inhibitors: Design, synthesis, and biological evaluation,” Bioorg. Med. Chem. Lett., vol. 29, no. 16, pp. 2364–2368, 2019. https://doi.org/10.1016/j.bmcl.2019.06.007
Details
Primary Language
English
Subjects
Enzymes
Journal Section
Research Article
Publication Date
December 31, 2025
Submission Date
July 12, 2025
Acceptance Date
October 17, 2025
Published in Issue
Year 2025 Volume: 14 Number: 4
APA
Karadağ, H., & Genç, M. (2025). Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide and Benzyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, 14(4), 2386-2394. https://doi.org/10.17798/bitlisfen.1740818
AMA
1.Karadağ H, Genç M. Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide and Benzyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi. 2025;14(4):2386-2394. doi:10.17798/bitlisfen.1740818
Chicago
Karadağ, Hasan, and Murat Genç. 2025. “Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-Dihydro-1H-Imidazol-2-Yl)amine Hydroiodide and Benzyl-(4,5-Dihydro-1H-Imidazol-2-Yl)amine Hydroiodide”. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi 14 (4): 2386-94. https://doi.org/10.17798/bitlisfen.1740818.
EndNote
Karadağ H, Genç M (December 1, 2025) Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide and Benzyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi 14 4 2386–2394.
IEEE
[1]H. Karadağ and M. Genç, “Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide and Benzyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide”, Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 14, no. 4, pp. 2386–2394, Dec. 2025, doi: 10.17798/bitlisfen.1740818.
ISNAD
Karadağ, Hasan - Genç, Murat. “Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-Dihydro-1H-Imidazol-2-Yl)amine Hydroiodide and Benzyl-(4,5-Dihydro-1H-Imidazol-2-Yl)amine Hydroiodide”. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi 14/4 (December 1, 2025): 2386-2394. https://doi.org/10.17798/bitlisfen.1740818.
JAMA
1.Karadağ H, Genç M. Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide and Benzyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi. 2025;14:2386–2394.
MLA
Karadağ, Hasan, and Murat Genç. “Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-Dihydro-1H-Imidazol-2-Yl)amine Hydroiodide and Benzyl-(4,5-Dihydro-1H-Imidazol-2-Yl)amine Hydroiodide”. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 14, no. 4, Dec. 2025, pp. 2386-94, doi:10.17798/bitlisfen.1740818.
Vancouver
1.Hasan Karadağ, Murat Genç. Competitive Inhibition of Glutathione Reductase Activity by Cyclohexyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide and Benzyl-(4,5-dihydro-1H-imidazol-2-yl)amine hydroiodide. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi. 2025 Dec. 1;14(4):2386-94. doi:10.17798/bitlisfen.1740818