Display options
Cite
Spasov A, Ozerov A, Vassiliev P, et al. Synthesis and multifaceted pharmacological activity of novel quinazoline NHE-1 inhibitors. Sci Rep. 2021;11(1):24380doi: 10.1038/s41598-021-03722-w.
Spasov, A., Ozerov, A., Vassiliev, P., Kosolapov, V., Gurova, N., Kucheryavenko, A., Naumenko, L., Babkov, D., Sirotenko, V., Taran, A., Litvinov, R., Borisov, A., Klochkov, V., Merezhkina, D., Miroshnikov, M., Uskov, G., & Ovsyankina, N. (2021). Synthesis and multifaceted pharmacological activity of novel quinazoline NHE-1 inhibitors. Scientific reports, 11(1), 24380. https://doi.org/10.1038/s41598-021-03722-w
Spasov, Alexander, et al. "Synthesis and multifaceted pharmacological activity of novel quinazoline NHE-1 inhibitors." Scientific reports vol. 11,1 (2021): 24380. doi: https://doi.org/10.1038/s41598-021-03722-w
Spasov A, Ozerov A, Vassiliev P, Kosolapov V, Gurova N, Kucheryavenko A, Naumenko L, Babkov D, Sirotenko V, Taran A, Litvinov R, Borisov A, Klochkov V, Merezhkina D, Miroshnikov M, Uskov G, Ovsyankina N. Synthesis and multifaceted pharmacological activity of novel quinazoline NHE-1 inhibitors. Sci Rep. 2021 Dec 21;11(1):24380. doi: 10.1038/s41598-021-03722-w. PMID: 34934125.
Copy Download .nbib Format: NLM
Share it on

Sci Rep. 2021 Dec 21;11(1):24380. doi: 10.1038/s41598-021-03722-w.

Synthesis and multifaceted pharmacological activity of novel quinazoline NHE-1 inhibitors.

Scientific reports

Alexander Spasov, Alexander Ozerov, Pavel Vassiliev, Vadim Kosolapov, Natalia Gurova, Aida Kucheryavenko, Ludmila Naumenko, Denis Babkov, Viktor Sirotenko, Alena Taran, Roman Litvinov, Alexander Borisov, Vladlen Klochkov, Darya Merezhkina, Mikhail Miroshnikov, Georgy Uskov, Nadezhda Ovsyankina

Affiliations

  1. Department of Pharmacology & Bioinformatics, Volgograd State Medical University, Volgograd, Russia, 400131.
  2. Scientific Center for Innovative Drugs, Volgograd State Medical University, Volgograd, Russia, 400087.
  3. Department of Pharmaceutical & Toxicological Chemistry, Volgograd State Medical University, Volgograd, Russia, 400131.
  4. Department of Pharmacology & Bioinformatics, Volgograd State Medical University, Volgograd, Russia, 400131. [email protected].
  5. Scientific Center for Innovative Drugs, Volgograd State Medical University, Volgograd, Russia, 400087. [email protected].

PMID: 34934125 DOI: 10.1038/s41598-021-03722-w

Abstract

The Na

© 2021. The Author(s).

References

  1. Pedersen, S. F. & Counillon, L. The SLC9A-C mammalian Na+/H+ exchanger family: molecules, mechanisms, and physiology. Physiol. Rev. 99, 2015–2113 (2019). - PubMed
  2. Karmazyn, M. NHE-1: still a viable therapeutic target. J. Mol. Cell. Cardiol. 61, 77–82 (2013). - PubMed
  3. Shi, Y., Kim, D., Caldwell, M. & Sun, D. The role of Na(+)/h(+) exchanger isoform 1 in inflammatory responses: maintaining H(+) homeostasis of immune cells. Adv. Exp. Med. Biol. 961, 411–418 (2013). - PubMed
  4. De Vito, P. The sodium/hydrogen exchanger: a possible mediator of immunity. Cell. Immunol. 240, 69–85 (2006). - PubMed
  5. Liu, Y. et al. Activation of microglia depends on Na+/H+ exchange-mediated H+ homeostasis. J. Neurosci. 30, 15210–15220 (2010). - PubMed
  6. Zhang, Y. et al. Amelioration of Lipopolysaccharide-Induced Acute Lung Injury in Rats by Na-H Exchanger-1 Inhibitor Amiloride Is Associated with Reversal of ERK Mitogen-Activated Protein Kinase. BioMed Res. Int. 2018, 1–7 (2018). - PubMed
  7. Ali, A., Ahmad, F. J., Pillai, K. K. & Vohora, D. Evidence of the antiepileptic potential of amiloride with neuropharmacological benefits in rodent models of epilepsy and behavior. Epilepsy. Behav. 5, 322–328 (2004). - PubMed
  8. Gumina, R. J., Newman, P. J. & Gross, G. J. Effect on ex vivo platelet aggregation and in vivo cyclic flow with Na+/H+ exchange inhibition: Gumina, NHE-1 inhibition and platelet aggregation. J. Thromb. Thrombolysis 31, 431–435 (2011). - PubMed
  9. Lee, K.-S. et al. Anti-platelet activity of KR-32560, a novel sodium/hydrogen exchanger-1 inhibitor. Pharmacol. Res. 53, 265–270 (2006). - PubMed
  10. Spasov, A. A. et al. Effect of NHE-1 inhibitors zoniporide and RU-1355 on the hemorheological properties of blood under conditions of brain ischemia in rats. Eksp. Klin. Farmakol. 80, 3–7 (2017). - PubMed
  11. Avila, M. Y., Seidler, R. W., Stone, R. A. & Civan, M. M. Inhibitors of NHE-1 Na+/H+ exchange reduce mouse intraocular pressure. Invest. Ophthalmol. Vis. Sci. 43, 1897–1902 (2002). - PubMed
  12. Lupachyk, S. et al. Na +/H +-exchanger-1 inhibition counteracts diabetic cataract formation and retinal oxidative-nitrative stress and apoptosis. Int. J. Mol. Med. 29, 989–998 (2012). - PubMed
  13. Dreffs, A., Henderson, D., Dmitriev, A. V., Antonetti, D. A. & Linsenmeier, R. A. Retinal pH and acid regulation during metabolic acidosis. Curr. Eye Res. 43, 902–912 (2018). - PubMed
  14. Wu, S. et al. Involvement of Na+/H+ exchanger 1 in advanced glycation end products-induced proliferation of vascular smooth muscle cell. Biochem. Biophys. Res. Commun. 375, 384–389 (2008). - PubMed
  15. Sączewski, F. & Balewski, Ł. Biological activities of guanidine compounds, 2008–2012 update. Expert Opin. Ther. Pat. 23, 965–995 (2013). - PubMed
  16. Jin, L. et al. Synthesis and Na+/H+ exchanger inhibitory activity of benzoylguanidine derivatives. Eur. J. Med. Chem. 46, 4107–4116 (2011). - PubMed
  17. Tang, W. et al. Synthesis of a sodium-hydrogen exchange type 1 Inhibitor: an efficient Cu-catalyzed conjugated addition of a grignard reagent to an acetyl pyridinium salt. Org. Process Res. Dev. 17, 382–389 (2013). - PubMed
  18. Lee, S. et al. (5-Arylfuran-2-ylcarbonyl)guanidines as cardioprotectives through the Inhibition of Na+/H+ exchanger isoform-1. J. Med. Chem. 48, 2882–2891 (2005). - PubMed
  19. Dong, Y. et al. Structure and mechanism of the human NHE1-CHP1 complex. Nat. Commun. 12, 3474 (2021). - PubMed
  20. Hameed, A. et al. Quinazoline and quinazolinone as important medicinal scaffolds: a comparative patent review (2011–2016). Expert Opin. Ther. Pat. 28, 281–297 (2018). - PubMed
  21. Gupta, T. et al. Current perspectives on quinazolines with potent biological activities: a review. Synth. Commun. 48, 1099–1127 (2018). - PubMed
  22. Das, R., Mehta, D. K. & Dhanawat, M. Bestowal of quinazoline Scaffold in anticancer drug discovery. Anticancer Agents Med. Chem. 21, 1350–1368 (2021). - PubMed
  23. Asif, M. Chemical characteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives. Int. J. Med. Chem. 2014, 395637 (2014). - PubMed
  24. Ozerov, A. et al. Pyrimidine derivatives of N-acetylguanidine: novel inhibitors of sodium-hydrogen exchanger 1. Heterocycles 96, 1101 (2018). - PubMed
  25. Petrov, V. I. et al. Derivatives of quinazolin-4(3h)-one inhibiting sodium-hydrogen exchange. RU2654062C2 (2018). - PubMed
  26. Wang, W., Sasaki, H., Chien, D. S. & Lee, V. H. Lipophilicity influence on conjunctival drug penetration in the pigmented rabbit: a comparison with corneal penetration. Curr. Eye Res. 10, 571–579 (1991). - PubMed
  27. Kidron, H., Vellonen, K.-S., del Amo, E. M., Tissari, A. & Urtti, A. Prediction of the corneal permeability of drug-like compounds. Pharm. Res. 27, 1398–1407 (2010). - PubMed
  28. Nagai, R., Murray, D. B., Metz, T. O. & Baynes, J. W. Chelation: a fundamental mechanism of action of AGE inhibitors, AGE breakers, and other inhibitors of diabetes complications. Diabetes 61, 549–559 (2012). - PubMed
  29. Hauh-Jyun, C. C. & Cerami, A. Mechanism of inhibition of advanced glycosylation by aminoguanidine in Vitro. J. Carbohydr. Chem. 12, 731–742 (1993). - PubMed
  30. Litvinov, R., Usmiyanova, L. E., Klimenko, D. R. & Gontareva, A. V. Paradoxal activity of aminoguanidine in the model of glycoxidation with copper cations. J. Volgogr. State Med. Univ. 75, 159–165 (2020). - PubMed
  31. Lal, B. et al. Tricyclic guanidine derivatives as sodium-proton exchange inhibitors. WO2006051476 (2006). - PubMed
  32. Spasov, A. A., Gurova, N. A. & Kharitonova, M. V. Structure and physiological role of NHE1 and pharmacological regulation of its activity. Eksp. Klin. Farmakol. 76, 43–48 (2013). - PubMed
  33. Gurova, N. A., Spasov, A. A., Timofeeva, A. S., Zheltova, A. A. & Fedorchuk, V. I. Cardioprotective properties of zoniporide studied on experimental ischemia and reperfusion models in rat myocardium. Eksp. Klin. Farmakol. 76, 17–19 (2013). - PubMed
  34. Spasov, A. A. et al. Neuroprotective properties of a new inhibitor of Na+/H+ exchanger (compound RU-1355) on the model of focal ischemia in rats. Eksp. Klin. Farmakol. 79, 3–7 (2016). - PubMed
  35. Spasov, A. A., Gurova, N. A., Timofeeva, A. S. & Sorokin, S. M. Experimental study of the antiarrhythmic properties of zoniporide. Eksp. Klin. Farmakol. 77, 13–17 (2014). - PubMed
  36. Mao, D. et al. Synthesis and Na(+)/H(+) exchanger-1 inhibitory activity of substituted (quinolinecarbonyl)guanidine derivatives. Chem. Biodivers. 6, 1727–1736 (2009). - PubMed
  37. Lee, S., Yi, K. Y., Youn, S. J., Lee, B. H. & Yoo, S. (2-Aryl-5-methylimidazol-4-ylcarbonyl)guanidines and (2-aryl-5-methyloxazol-4-ylcarbonyl)guanidines as NHE-1 inhibitors. Bioorg. Med. Chem. Lett. 19, 1329–1331 (2009). - PubMed
  38. du Sert, N. P. et al. Reporting animal research: explanation and elaboration for the ARRIVE guidelines 20. PLOS Biol. 18, e3000411 (2020). - PubMed
  39. Kusumoto, K. et al. In vitro and in vivo pharmacology of a structurally novel Na+-H+ exchange inhibitor, T-162559. Br. J. Pharmacol. 135, 1995–2003 (2002). - PubMed
  40. Rosskopf, D. Sodium-hydrogen exchange and platelet function. J. Thromb. Thrombolysis 8, 15–24 (1999). - PubMed
  41. Vassiliev, P. M. et al. Consensus Drug Design Using IT Microcosm. In Application of Computational Techniques in Pharmacy and Medicine 17, 369–431 (2014). - PubMed
  42. Hilbe, J. M. Statistica 7. Am. Stat. 61, 91–94 (2007). - PubMed
  43. Anisimova, V. A. et al. Synthesis and pharmacological activity of 3-(2,2,2-trichloro-1- hydroxyethyl)imidazo [1, 2-a]benzimidazole dihydrochlorides. Pharm. Chem. J. 43, 491–494 (2009). - PubMed
  44. Pease, M. E., Hammond, J. C., Quigley, H. A. Manometric calibration and comparison of TonoLab and TonoPen tonometers in rats with experimental glaucoma and in normal mice. J. Glaucoma 15, 512–519 (2006). - PubMed
  45. Marcus, A. J. et al. Data on the effects of imidazo[1,2-a]benzimidazole and pyrimido[1,2-a]benzimidazole compounds on intraocular pressure of ocular normotensive rats. Data Brief 18, 523–554 (2018). - PubMed
  46. Steru, L., Chermat, R., Thierry, B. & Simon, P. The tail suspension test: a new method for screening antidepressants in mice. Psychopharmacology 85, 367–370 (1985). - PubMed

Publication Types

Grant support