Novel benzimidazole derivatives as effective inhibitors of prolyl oligopeptidase: synthesis, in vitro and in silico analysis

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References

• 1. Venäläinen JI, Juvonen RO, Männistö PT. Evolutionary relationships of the prolyl oligopeptidase family enzymes. Eur. J. Biochem. 271(13), 2705–2715 (2004).
  MedlineGoogle Scholar
• 2. Svarcbahs R, Julku U, Kilpeläinen T, Kyyrö M, Jäntti M, Myöhänen TT. New tricks of prolyl oligopeptidase inhibitors – a common drug therapy for several neurodegenerative diseases. Biochem. Pharmacol. 161, 113–120 (2019).
  Medline CASGoogle Scholar
• 3. Sauer U, Eikmanns BJ. The PEP–pyruvate–oxaloacetate node as the switch point for carbon flux distribution in bacteria: we dedicate this paper to Rudolf K Thauer, Director of the Max-Planck-Institute for Terrestrial Microbiology in Marburg, Germany, on the occasion of his 65th birthday. FEMS Microbiol. Rev. 29(4), 765–794 (2005).
  Medline CASGoogle Scholar
• 4. Ali H, Ullah K, Siddiqui H et al. Chemical constituents from Parrotia persica – structural derivatization and their potential prolyl endopeptidase inhibition activity. Bioorg. Chem. 96, 103526 (2020).
  Medline CASGoogle Scholar
• 5. Zolotov NN, Schepetkin IA, Voronina TA et al. Therapeutic effect of novel cyanopyrrolidine-based prolyl oligopeptidase inhibitors in rat models of amnesia. Front. Chem. 9, 780958 (2021).
  Medline CASGoogle Scholar
• 6. Song X-Q, Li Q, Zhang J. A double-edged sword: DLG5 in diseases. Biomed. Pharmacother. 162, 114611 (2023).
  Medline CASGoogle Scholar
• 7. Malek M, Wawrzyniak AM, Koch P et al. Inositol triphosphate-triggered calcium release blocks lipid exchange at endoplasmic reticulum–Golgi contact sites. Nat. Commun. 12(1), 2673 (2021).
  Medline CASGoogle Scholar
• 8. Wadhawan M, Ahmad F, Yadav S, Rathaur S. Proteomic analysis reveals differential protein expression induced by inhibition of prolyl oligopeptidase in filarial parasites. Protein J. 41(6), 613–624 (2022). • Introduction and importance of prolyl olegopeptidase (POP) enzyme.
  Medline CASGoogle Scholar
• 9. Alam A, Ali M, Rehman NU et al. Bio-oriented synthesis of novel (S)-flurbiprofen clubbed hydrazone schiff's bases for diabetic management: in vitro and in silico studies. Pharmaceuticals 15(6), 672 (2022).
  Medline CASGoogle Scholar
• 10. Tatum LA, Su X, Aprahamian I. Simple hydrazone building blocks for complicated functional materials. Acc. Chem. Res. 47(7), 2141–2149 (2014).
  Medline CASGoogle Scholar
• 11. Yao X, Zhang R, Lv B et al. Design, synthesis and biological evaluation of thiazole and imidazo [1, 2-a] pyridine derivatives containing a hydrazone substructure as potential agrochemicals. Advanced Agrochem. 2(2), 154–162 (2023).
  CASGoogle Scholar
• 12. Jabeen M. A comprehensive review on analytical applications of hydrazone derivatives. Journal of the Turkish Chemical Society Section A: Chemistry 9(3), 663–698 (2022).
  CASGoogle Scholar
• 13. Sharma P, Sharma D, Sharma A et al. Hydrazone comprising compounds as promising anti-infective agents: chemistry and structure–property relationship. Mater. Today Chem. 18, 100349 (2020).
  CASGoogle Scholar
• 14. Ahmad S, Khan M, Shah MIA et al. Synthetic transformation of 2-{2-fluoro [1, 1′-biphenyl]-4-yl} propanoic acid into hydrazide–hydrazone derivatives: in vitro urease inhibition and in silico study. ACS Omega 7(49), 45077–45087 (2022).
  Medline CASGoogle Scholar
• 15. Su X, Aprahamian I. Hydrazone-based switches, metallo-assemblies and sensors. Chem. Soc. Rev. 43(6), 1963–1981 (2014).
  Medline CASGoogle Scholar
• 16. Zhou J, Guo T, Zhou L et al. The ferroptosis signature predicts the prognosis and immune microenvironment of nasopharyngeal carcinoma. Sci. Rep. 13(1), 1861 (2023).
  Medline CASGoogle Scholar
• 17. Yang Z, Li P, Gan X. Novel pyrazole-hydrazone derivatives containing an isoxazole moiety: design, synthesis, and antiviral activity. Molecules 23(7), 1798 (2018).
  MedlineGoogle Scholar
• 18. Li L, Wang S, Zhou W. Balance cell apoptosis and pyroptosis of caspase-3-activating chemotherapy for better antitumor therapy. Cancers 15(1), 26 (2022).
  MedlineGoogle Scholar
• 19. Sridhar P, Alagumuthu M, Arumugam S, Reddy SR. Synthesis of quinoline acetohydrazide-hydrazone derivatives evaluated as DNA gyrase inhibitors and potent antimicrobial agents. RSC Adv. 6(69), 64460–64468 (2016).
  CASGoogle Scholar
• 20. Parlar S, Erzurumlu Y, Ilhan R, Ballar Kırmızıbayrak P, Alptüzün V, Erciyas E. Synthesis and evaluation of pyridinium-hydrazone derivatives as potential antitumoral agents. Chem. Biol. Drug Des. 92(1), 1198–1205 (2018).
  Medline CASGoogle Scholar
• 21. Khan M, Ahad G, Manaf A et al. Synthesis, in vitro urease inhibitory activity, and molecular docking studies of (perfluorophenyl) hydrazone derivatives. Med. Chem. Res. 28, 873–883 (2019).
  CASGoogle Scholar
• 22. Shahab N, Kong D, Ali M et al. Novel polyhydroquinoline Schiff's base derivatives: synthesis, characterization, in vitro α-glucosidase inhibitory, and molecular docking studies. Research on Chemical Intermediates 1–24 (2023).
  Google Scholar
• 23. Akdağ K, Ünal G, Tok F, Arıcıoğlu F, Temel HE, Kaymakcıoğlu-Koçyiğit B. Synthesis and biological evaluation of some new hydrazone derivatives bearing pyrimidine ring as analgesic and anti-inflammatory agents. Acta Pol. Pharm. 75(5), 1147–1159 (2018).
  CASGoogle Scholar
• 24. Talab F, Ullah S, Alam A et al. Bio-oriented synthesis of novel polyhydroquinoline derivatives as α-glucosidase inhibitor for management of diabetes. ACS Omega 8(7), 6234–6243 (2023).
  Medline CASGoogle Scholar
• 25. Liu Z, Fan B, Zhao J, Yang B, Zheng X. Benzothiazole derivatives-based supramolecular assemblies as efficient corrosion inhibitors for copper in artificial seawater: formation, interfacial release and protective mechanisms. Corros. Sci. 212, 110957 (2023).
  CASGoogle Scholar
• 26. Kalidhar U, Kaur A. An overview on some benzimidazole and sulfonamide derivatives with anti-microbial activity. Res. J. Pharm. Biol. Chem. Sci. 2, 1116–1135 (2011).
  CASGoogle Scholar
• 27. Pathare B, Bansode T. Biological active benzimidazole derivatives. Results Chem. 3, 100200 (2021).
  CASGoogle Scholar
• 28. Li J-D, Wu J, Zhao Y et al. Phenotypic spectrum of idiopathic hypogonadotropic hypogonadism patients with CHD7 variants from a large Chinese cohort. J. Clin. Endocrinol. Metab. 105(5), 1515–1526 (2020).
  Google Scholar
• 29. Walia R, Hedaitullah M, Naaz SF, Iqbal K, Lamba H. Benzimidazole derivatives – an overview. Int. J. Res. Pharm. Chem. 1(3), 565–574 (2011).
  CASGoogle Scholar
• 30. Devivar RV, Kawashima E, Revankar GR et al. Benzimidazole ribonucleosides: design, synthesis, and antiviral activity of certain 2-(alkylthio)-and 2-(benzylthio)-5, 6-dichloro-1-(beta.-D-ribofuranosyl) benzimidazoles. J. Med. Chem. 37(18), 2942–2949 (1994).
  Medline CASGoogle Scholar
• 31. Gellis A, Kovacic H, Boufatah N, Vanelle P. Synthesis and cytotoxicity evaluation of some benzimidazole-4, 7-diones as bioreductive anticancer agents. Eur. J. Med. Chem. 43(9), 1858–1864 (2008).
  Medline CASGoogle Scholar
• 32. Bariwal J, Shah A, Kathiravan M, Somani R, Jagtap J, Jain K. Synthesis and antiulcer activity of novel pyrimidylthiomethyl-and pyrimidylsulfinylmethyl benzimidazoles as potential reversible proton pump inhibitors. Indian Journal of Pharmaceutical Education and Research 42(3), 225–231 (2008).
  Google Scholar
• 33. Alagöz Z, Kus C, Coban T. Synthesis and antioxidant properties of novel benzimidazoles containing substituted indole or 1, 1, 4, 4-tetramethyl-1, 2, 3, 4-tetrahydro-naphthalene fragments. J. Enzyme Inhib. Med. Chem. 20(4), (2005).
  Google Scholar
• 34. Vinodkumar R, Vaidya SD, Kumar BVS, Bhise UN, Bhirud SB, Mashelkar UC. Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2 [4-(4, 4-dimethyl-thiochroman-6-yl-ethynyl)-phenyl)-1H-benzimidazoles. Eur. J. Med. Chem. 43(5), 986–995 (2008). • Chemistry of hydrazones.
  Medline CASGoogle Scholar
• 35. Khan A, Waqas M, Khan M, Halim SA, Rehman NU, Al-Harrasi A. Identification of novel prolyl oligopeptidase inhibitors from resin of Boswellia papyrifera (Del.) Hochst. and their mechanism: virtual and biochemical studies. Int. J. Biol. Macromol. 213, 751–767 (2022). • In vitro POP inhibition methodology.
  Medline CASGoogle Scholar
• 36. Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J. Comput. Chem. 31(2), 455–461 (2010).
  Medline CASGoogle Scholar
• 37. Fülöp V, Szeltner Z, Polgár L. Catalysis of serine oligopeptidases is controlled by a gating filter mechanism. EMBO Rep. 1(3), 277–281 (2000). • Molecular docking methodology.
  MedlineGoogle Scholar
• 38. Nehra N, Tittal RK, Ghule VD. 1, 2, 3-Triazoles of 8-hydroxyquinoline and HBT: synthesis and studies (DNA binding, antimicrobial, molecular docking, ADME, and DFT). ACS Omega 6(41), 27089–27100 (2021).
  Medline CASGoogle Scholar
• 39. Waring MJ. Defining optimum lipophilicity and molecular weight ranges for drug candidates – molecular weight dependent lower log D limits based on permeability. Bioorg. Med. Chem. Lett. 19(10), 2844–2851 (2009).
  Medline CASGoogle Scholar
• 40. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 64, 4–17 (2012). • Druglikeness study.
  Google Scholar