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Review

A patent update on therapeutic applications of urease inhibitors (2012–2018)

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Pages 181-189 | Received 26 Nov 2018, Accepted 15 Feb 2019, Published online: 06 Mar 2019

References

  • You ZL, Han X, Zhang GN. Synthesis, crystal structures, and urease inhibitory activities of three novel thiocyanato‐bridged polynuclear schiff base cadmium (ii) complexes. Z Anorg Allg Chem. 2008;634(1):142–146.
  • Sumner JB. The isolation and crystallization of the enzyme urease preliminary paper. J Biol Chem. 1926;69(2):435–441.
  • Mobley H, Island MD, Hausinger RP. Molecular biology of microbial ureases. Microbiol Rev. 1995;59(3):451–480.
  • Zonia LE, Stebbins NE, Polacco JC. Essential role of urease in germination of nitrogen-limited arabidopsis thaliana seeds. Plant Pathol. 1995;107(4):1097–1103.
  • Karplus PA, Pearson MA, Hausinger RP. 70 years of crystalline urease: what have we learned?. Acc Chem Res. 1997;30(8):330–337.
  • Zambelli B, Musiani F, Benini S, et al. Chemistry of ni2+ in urease: sensing, trafficking, and catalysis. Acc Chem Res. 2011;44(7):520–530.
  • Carlini CR, Ligabue-Braun R. Ureases as multifunctional toxic proteins: a review. Toxicon. 2016;110:90–109.
  • Collins CM, D’Orazio SE. Bacterial ureases: structure, regulation of expression and role in pathogenesis. Mol Microbiol. 1993;9(5):907–913.
  • Zhengping W, Van Cleemput O, Demeyer P, et al. Effect of urease inhibitors on urea hydrolysis and ammonia volatilization. Biol Fertil Soils. 1991;11(1):43–47.
  • Maroney MJ, Ciurli S. Nonredox nickel enzymes. Chem Rev. 2013;114(8):4206–4228.
  • Boer JL, Mulrooney SB, Hausinger RP. Nickel-dependent metalloenzymes. Arch Biochem Biophys. 2014;544:142–152.
  • Modolo LV, de Souza AX, Horta LP, et al. An overview on the potential of natural products as ureases inhibitors: a review. J Adv Res. 2015;6(1):35–44.
  • Andrews RK, Dexter A, Blakeley RL, et al. Jack bean urease (ec 3.5. 1.5) viii. On the inhibition of urease by amides and esters of phosphoric acid. J Am Chem Soc. 1986;108(22):7124–7125.
  • Kosikowska P, Berlicki Ł. Urease inhibitors as potential drugs for gastric and urinary tract infections: a patent review. Expert Opin Ther Pat. 2011;21(6):945–957.
  • Biglar M, Soltani K, Nabati F, et al. A preliminary investigation of the jack-bean urease inhibition by randomly selected traditionally used herbal medicine. Iran J Pharm Res. 2012;11(3):831.
  • Li H-Q, Xiao Z-P, Yan T, et al. Amines and oximes derived from deoxybenzoins as Helicobacter pylori urease inhibitors. Eur J Med Chem. 2009;44(5):2246–2251.
  • Ziarani GM, Asadi S, Faramarzi S, et al. Green synthesis and urease inhibitory activity of spiro-pyrimidinethiones/spiro-pyrimidinones-barbituric acid derivatives. Iran J Pharm Res. 2015;14(4):1105.
  • Kobashi K, Hase J, Uehara K. Specific inhibition of urease by hydroxamic acids. Biochim Biophys Acta. 1962;65(2):380–383.
  • Muri EMF, Mishra H, Avery MA, et al. Design and synthesis of heterocyclic hydroxamic acid derivatives as inhibitors of Helicobacter pylori urease. Synth Commun. 2003;33(12):1977–1995.
  • Amtul Z, Siddiqui R, Choudhary M. Chemistry and mechanism of urease inhibition. Curr Med Chem. 2002;9(14):1323–1348.
  • Kot M, Zaborska W, Orlinska K. Inhibition of jack bean urease by n-(n-butyl) thiophosphorictriamide and n-(n-butyl) phosphorictriamide: determination of the inhibition mechanism. J Enzym Inhib. 2001;16(6):507–516.
  • Todd MJ, Hausinger R. Competitive inhibitors of klebsiella aerogenes urease. Mechanisms of interaction with the nickel active site. J Biol Chem. 1989;264(27):15835–15842.
  • Mishra H, Parrill AL, Williamson JS. Three-dimensional quantitative structure-activity relationship and comparative molecular field analysis of dipeptide hydroxamic acid Helicobacter pylori urease inhibitors. Antimicrob Agents Chemother. 2002;46(8):2613–2618.
  • Dixon NE, Hinds JA, Fihelly AK, et al. Jack bean urease (ec 3.5. 1.5). Iv. The molecular size and the mechanism of inhibition by hydroxamic acids. Spectrophotometric titration of enzymes with reversible inhibitors. Can J Biochem. 1980;58(12):1323–1334.
  • Fishbein WN. Urease inhibitors for hepatic coma: inhibition of 14c-urea hydrolysis in mice by alkyl hydroxamates: I. Methodology; acetohydroxamic acid. Biochem Med. 1967;1(2):111–128.
  • Kobashi K, Kumaki K, Hase J. Effect of acyl residues of hydroxamic acids on urease inhibition. Biochim Biophys Acta (BBA)-Enzymol. 1971;227(2):429–441.
  • Smith PT, King AD Jr, Goodman N. Isolation and characterization of urease from Aspergillus niger. Microbiology. 1993;139(5):957–962.
  • Prakash O, Upadhyay LSB. Inhibition of water melon (Citrullus vulgaris) urease by fluoride. J Plant Biochem Biotechnol. 2004;13(1):61–64.
  • Barboza‐Silva E, Castro A, Marquis R. Mechanisms of inhibition by fluoride of urease activities of cell suspensions and biofilms of Staphylococcus epidermidis, Streptococcus salivarius, Actinomyces naeslundii and of dental plaque. Oral Microbiol Immunol. 2005;20(6):323–332.
  • Abdullah MA, Abuo-Rahma GE-DA, Abdelhafez E-SM, et al. Design, synthesis, molecular docking, anti-proteus mirabilis and urease inhibition of new fluoroquinolone carboxylic acid derivatives. Bioorg Chem. 2017;70:1–11.
  • Morris NS, Stickler DJ. The effect of urease inhibitors on the encrustation of urethral catheters. Urol Res. 1998;26(4):275–279.
  • Benini S, Ciurli S, Nolting HF, et al. X‐ray absorption spectroscopy study of native and phenylphosphorodiamidate‐inhibited Bacillus pasteurii urease. Eur J Biochem. 1996;239(1):61–66.
  • Rauf A, Nazish KA, Nasim F-U, et al. Synthesis of novel cyanoacetamides derivatives and their urease inhibition studies. Eur J Chem. 2015;6(2):163–168.
  • Rauf A, Shahzad S, Bajda M, et al. Design and synthesis of new barbituric-and thiobarbituric acid derivatives as potent urease inhibitors: structure activity relationship and molecular modeling studies. Bioorg Med Chem. 2015;23(17):6049–6058.
  • Rahim F, Ali M, Ullah S, et al. Development of bis-thiobarbiturates as successful urease inhibitors and their molecular modeling studies. Chin Chem Lett. 2016;27(5):693–697.
  • Rauf MK, Talib A, Badshah A, et al. Solution-phase microwave assisted parallel synthesis of n, n′-disubstituted thioureas derived from benzoic acid: biological evaluation and molecular docking studies. Eur J Med Chem. 2013;70:487–496.
  • Babu TMC, Rajesh SS, Bhaskar BV, et al. Molecular docking, molecular dynamics simulation, biological evaluation and 2d qsar analysis of flavonoids from syzygium alternifolium as potent anti-Helicobacter pylori agents. RSC Adv. 2017;7(30):18277–18292.
  • Zhou J-T, Li C-L, Tan L-H, et al. Inhibition of Helicobacter pylori and its associated urease by palmatine: investigation on the potential mechanism. PLoS one. 2017;12(1):e0168944.
  • Tan L, Li C, Chen H, et al. Epiberberine, a natural protoberberine alkaloid, inhibits urease of Helicobacter pylori and jack bean: susceptibility and mechanism. Eur J Pharm Sci. 2017;110:77–86.
  • Aslam MAS, Mahmood S-U, Shahid M, et al. Synthesis, biological assay in vitro and molecular docking studies of new schiff base derivatives as potential urease inhibitors. Eur J Med Chem. 2011;46(11):5473–5479.
  • Arshad T, Khan KM, Rasool N, et al. 5-bromo-2-aryl benzimidazole derivatives as non-cytotoxic potential dual inhibitors of α-glucosidase and urease enzymes. Bioorg Chem. 2017;72:21–31.
  • Menteşe E, Bektaş H, Sokmen BB, et al. Synthesis and molecular docking study of some 5, 6-dichloro-2-cyclopropyl-1h-benzimidazole derivatives bearing triazole, oxadiazole, and imine functionalities as potent inhibitors of urease. Bioorg Med Chem Lett. 2017;27(13):3014–3018.
  • Qazi SU, Rahman SU, Awan AN, et al. Semicarbazone derivatives as urease inhibitors: synthesis, biological evaluation, molecular docking studies and in-silico adme evaluation. Bioorg Chem. 2018;79:19–26.
  • Hameed A, Khan KM, Zehra ST, et al. Synthesis, biological evaluation and molecular docking of n-phenyl thiosemicarbazones as urease inhibitors. Bioorg Chem. 2015;61:51–57.
  • Isaac IO, al-Rashida M, Rahman SU, et al. Acridine-based (thio) semicarbazones and hydrazones: synthesis, in vitro urease inhibition, molecular docking and in-silico adme evaluation. Bioorg Chem. 2019;82:6–16.
  • Uesato S, Hashimoto Y, Nishino M, et al. N-substituted hydroxyureas as urease inhibitors. Chem Pharm Bull. 2002;50(9):1280–1282.
  • Choudhary MI, Khan A, Khan KM et al.. Schiff bases of thiazoles: a new class of ureases inhibitors; 2016. US 9,447,057 B2.
  • Corsello SM, Bittker JA, Liu Z, et al. The drug repurposing hub: a next-generation drug library and information resource. Nat Med. 2017;23(4):405.
  • Khan JAJ, Choudhary MI, Al-Ghamdi MAA et al.. 4-[2-(dipropylamino) ethyl]-1, 3-dihydro-2h-indol-2-one (ropinirole) a new inhibitor of jack bean urease enzyme: an example of drug repurposing; 2017. US 2017/0252323 A1.
  • Khan JAJ, Choudhary MI, Al-Ghamdi MAA et al.. Drug repositioning: urease inhibitory activity of (2s)-1-[(2s)-2-methyl-3-sulfanylpropanoyl] pyrrolidine-2-carboxylic acid (captopril); 2017. US 9688628 B1.
  • Hoekstra WJ, Schotzinger RJ, Gustafson GD. Metalloenzyme inhibitor compounds; 2015. US 8,940,735 B2.
  • Hoekstra WJ, Yates CM, Rafferty SW. Metalloenzyme inhibitor compounds; 2014. WO 2014/117090 Al.
  • Hoekstra WJ, Schotzinger RJ, Rafferty SW. Metalloenzyme inhibitor compounds; 2013. WO 2013/109998 Al.
  • Hoekstra WJ, Rafferty SW, Yates CM et al.. Metalloenzyme inhibitor compounds; 2012. WO 2012/177603 A2.
  • Radel RJ. Thiophosphoryl triamide as a urease inhibitor; 1985. 06/745,051.

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