Urease inhibitors as potential drugs for gastric and urinary tract infections: a patent review

Bibliography

• Mobley HL, Hausinger RP. Microbial ureases: significance, regulation, and molecular characterization. Microbiol Rev 1989;53:85-108
   PubMedGoogle Scholar
• Krajewska B, Ureases I. Functional, catalytic and kinetic properties: a review. J Mol Cat B 2009;59:9-21
   Google Scholar
• Zerner B. Recent advances in the chemistry of an old enzyme, urease. Bioorg Chem 1991;19:116-31
   Web of Science ®Google Scholar
• Blakeley RL, Treston A, Andrews RK, Nickel(II)-promoted ethanolysis and hydrolysis of N-(2-pyridylmethyl)urea. A model for urease. J Am Chem Soc 1982;104:612-14
   Web of Science ®Google Scholar
• Shaw WHR, Bordeaux JJ. The Decomposition of urea in aqueous media. J Am Chem Soc 1955;77:4729-33
   Web of Science ®Google Scholar
• Callahan BP, Yunan Y, Wolfenden R. The burden borne by urease. J Am Chem Soc 2005;127:10828-9
   PubMed Web of Science ®Google Scholar
• Estiu G, Merz KM Jr. The hydrolysis of urea and the proficiency of urease. J Am Chem Soc 2004;126:6932-44
   PubMedGoogle Scholar
• Karplus PA, Pearson MA, Hausinger RP. 70 Years of crystalline urease: what have we learned? Acc Chem Res 1997;30:330-7
   Web of Science ®Google Scholar
• Mobley HLT, Island MD, Hausinger RP. Molecular biology of microbial ureases. Microbiol Rev 1995;59:451-80
   PubMedGoogle Scholar
• Amtul Z, Atta-ur-Rahman, Siddiqui RA, Chemistry and mechanism of urease inhibition. Curr Med Chem 2002;9:1323-48
   PubMed Web of Science ®Google Scholar
• Benini S, Rypniewski WR, Wilson KS, A new proposal for urease mechanism based on the crystal structures of the native and inhibited enzyme from Bacillus pasteurii: why urea hydrolysis costs two nickels. Struct Fold Des 1999;7:205-16
   Google Scholar
• Jabri E, Carr MB, Hausinger RP, The crystal structure of urease from Klebsiella aerogenes. Science 1995;268:998-1004
   PubMed Web of Science ®Google Scholar
• Pearson MA, Hausinger RP, Karplus PA. Crystallographic studies of the nickel metalloenzyme urease and insights into the catalytic mechanism. J Inorg Biochem 1997;67:179
   Google Scholar
• Dunn BE, Grutter MG. Helicobacter pylori springs another surprise. Nat Struct Biol 2001;8:480-2
   PubMedGoogle Scholar
• Benini S, Rypniewski WR, Wilson KS, The complex of Bacillus pasteurii urease with acetohydroxamate anion from X-ray data at 1.55 A resolution. J Biol Inorg Chem 2000;5:110-18
   PubMed Web of Science ®Google Scholar
• Follmer C. Insights into the role and structure of plant ureases. Phytochemistry 2008;69:18-28
   PubMed Web of Science ®Google Scholar
• Schafer UK, Kaltwasser H. Urease from Staphylococcus saprophyticus: purification, characterization and comparison to Staphylococcus xylosus urease. Arch Microbiol 2008;161:393-9
   Google Scholar
• Pinkse MWH, Maier CS, Kim J-I, Macromolecular assembly of Helicobacter pylori urease investigated by mass spectrometry. J Mass Spectrom 2003;38:315-20
   PubMed Web of Science ®Google Scholar
• McCarty GW, Bremner JM. Production of urease by microbial activity in soils under aerobic and anaerobic conditions. Biol Fertil Soils 1991;11:228-39
   Google Scholar
• Sahrawat KL. Control of urea hydrolysis and nitrification in soil by chemicals. Prospects and problems. Plant Soil 1980;57:335-52
   Web of Science ®Google Scholar
• Bremner JM, Krogmeier MJ. Evidence that the adverse effect of urea fertilizer on seed germination in soil is due to ammonia formed through hydrolysis of urea by soil urease. Proc Natl Acad Sci USA 1989;86:8185-8
   PubMed Web of Science ®Google Scholar
• Jacobsen SM, Stickler DJ, Mobley HLT, Complicated catheter associated urinary tract infections due to Escherichia coli and Proteus mirabilis. Clin Microbiol Rev 2008;21:26-59
   PubMed Web of Science ®Google Scholar
• Andersen LP. Colonization and infection by Helicobacter pylori in humans. Helicobacter 2007;12:12-15
   PubMedGoogle Scholar
• Follmer C. Ureases as a target for the treatment of gastric and urinary infections. J Clin Pathol 2010;63:424-30
   PubMed Web of Science ®Google Scholar
• Graham DY, Malaty HM, Evans DG, Epidemiology of Helicobacter pylori in an asymptomatic population in the United States. Effect of age, race, and socioeconomic status. Gastroenterol 1991;100:1495-501
   PubMed Web of Science ®Google Scholar
• Covacci A, Telford JL, Del Giudica G, Helicobacter pylori virulence and genetic geography. Science 1999;284:1328-33
   PubMed Web of Science ®Google Scholar
• Eaton KA, Brooks CL, Morgan DR, Essential role of urease in pathogenesis of gastritis induced by Helicobacter pylori in gnotobiotic piglets. Infect Immun 1991;59:2470-5
   PubMed Web of Science ®Google Scholar
• Phadnis SH, Parlow MH, Levy M, Surface localization of Helicobacter pylori urease and a heat shock protein homolog requires bacterial autolysis. Infect Immun 1996;64:905-12
   PubMed Web of Science ®Google Scholar
• Stingl K, Sltendorf K, Bakker EP. Acid survival of Helicobacter pylori: how does urease activity trigger cytoplasmic pH homeostasis? Trends in Microbiol 2002;10:70-4
   PubMed Web of Science ®Google Scholar
• Mobley HLT, Mendz GL, Hazell SL, editors, Helicobacter pylori. Physiology and Genetics. ASM Press, Washington (DC); 2001
   Google Scholar
• Krishnamurthy P, Parlow M, Zitzer JB, Helicobacter pylori containing only cytoplasmic urease is susceptible to acid. Infect Immun 1998;66:5060-6
   PubMedGoogle Scholar
• Scott DR, Weeks D, Hong C, The role of internal urease in acid resistance of Helicobacter pylori. Gastroenterol 1998;114:58-70
   PubMed Web of Science ®Google Scholar
• Evans DJ Jr, Evans DG, Kirkpatrick SS, Characterization of the Helicobacter pylori urease and purification of its subunits. Microb Pathog 1991;10:15-26
   PubMed Web of Science ®Google Scholar
• Ham NC, Oh ST, Sung JY, Supramolecular assembly and acid resistance of Helicobacter pylori urease. Nat Struct Biol 2001;8:505-9
   PubMedGoogle Scholar
• Hu LT, Foxall PA, Russell R, Purification of recombinant Helicobacter pylori urease apoenzyme encoded by ureA and ureB. Infect Immun 1992;60:2657-66
   PubMedGoogle Scholar
• Park IS, Hausinger RP. Evidence for the presence of urease apoprotein complexes containing UreD, UreF, and UreG in cells that are competent for in vivo enzyme activation. J Bacteriol 1995;177:1947-51
   PubMedGoogle Scholar
• Scott DR, Marcus EA, Weeks DL, Expression of the Helicobacter pylori ureI gene is required for acidic pH activation of cytoplasmic urease. Infect Immun 2000;68:470-7
   PubMedGoogle Scholar
• Rektorschek M, Buhmann A, Weeks D, Acid resistance of Helicobacter pylori depends on the UreI membrane protein and an inner membrane proton barrier. Mol Microb 2000;36:141-52
   PubMedGoogle Scholar
• Skouloubris S, Thiberge J-M, Labigne A, The Helicobacter pylori UreI protein is not involved in urease activity but is essential for bacterial survival in vivo. Infect Immun 1998;66:4517-21
   PubMed Web of Science ®Google Scholar
• Pasteur Institut. Methods of inhibiting Helicobacter pylori. US6190667; 2001
   Google Scholar
• Burne RA, Chen YM. Bacterial ureases in infectious diseases. Microb Infect 2000;2:533-42
   PubMed Web of Science ®Google Scholar
• Hinman F. Directional growth of renal calculi. J Urol 1979;121:700-5
   PubMedGoogle Scholar
• Bichler K-H, Eipper E, Naber K, Urinary infection stones. Int J Antimicrob Agents 2002;19:488-98
   PubMed Web of Science ®Google Scholar
• Musher DM, Griffith DP, Yawn D, Role of Urease in pyelonephritis resulting from urinary tract infection with Proteus. J Infect Dis 1975;131:177-81
   PubMedGoogle Scholar
• Nicolle LE. Epidemiology of urinary tract infections. Clin Microb News 2002;24:135-40
   Google Scholar
• Samtoy B, DeBeukelaer MM. Ammonia encephalopathy secondary to urinary tract infection with Proteus mirabilis. Pediatrics 1980;65:294-7
   PubMed Web of Science ®Google Scholar
• Nicolle LE. Uncomplicated urinary tract infection in adults including uncomplicated Pyelonephritis. Urol Clin North Am 2008;35:1-12
   PubMed Web of Science ®Google Scholar
• Hellerstein S. Antibiotic treatment for urinary tract infections in pediatric patients. Minerva Pediatr 2003;55:395-406
   PubMedGoogle Scholar
• Kobashi K, Hase J, Uehare K. Specific inhibition of urease by hydroxamic acids. Biochim Biophys Acta 1962;65:380-3
   PubMed Web of Science ®Google Scholar
• Fishbein WN, Carbone PP. Urease Catalysis: II. Inhibition of the enzyme by hydroxyurea, hydroxylamine, and acetohydroxamic acid. J Biol Chem 1965;240:2407-14
   PubMed Web of Science ®Google Scholar
• Kobashi K, Hase J, Komai T. Evidence for the formation of an inactive urease-hydroxamic acid complex. Biochem Biophys Res Commun 1966;23:34-8
   PubMedGoogle Scholar
• Hase J, Kobashi K. Inhibition of Proteus vulgaris urease by hydroxamic acids. J Biochem (Tokyo) 1967;62:293-9
   PubMed Web of Science ®Google Scholar
• Blakeley RL, Hinds JA, Kunze HE, Jack bean urease (EC 3.5.1.5). Demonstration of a carbamoyl-transfer reaction and inhibition by hydroxamic acids. Biochemistry 1969;8:1991-2000
   PubMed Web of Science ®Google Scholar
• Kobashi K, Kumaki K, Hase J. Effect of acyl residues of hydroxamic acids on urease inhibition. Biochim Biophys Acta 1971;227:429-41
   PubMedGoogle Scholar
• Kumaki K, Tomoka S, Kobashi K, Structure-activity correlations between hydroxamic acids and their inhibitory powers on urease activity. I. A quantitative approach to the effect of hydrophobic character of acyl residue. Chem Pharm Bull 1972;20:1599-606
   PubMedGoogle Scholar
• Griffith DP, Musher DM. Method and composition for treating urinary tract infections US4024256; 1977
   Google Scholar
• Griffith DP, Gibson JR, Clinton CW, Acetohydroxamic acid: clinical studies of a urease inhibitor in patients with staghorn renal calculi. J Urol 1978;119:9-15
   PubMed Web of Science ®Google Scholar
• Griffith DP, Musher DM. Acetohydroxamic acid. Potential use in urinary infection caused by urea-splitting bacteria. Urology 1975;5:299-302
   Google Scholar
• Griffith DP, Khonsari F, Skurnick JH, A randomized trial of acetohydroxamic acid for the treatment and prevention of infection-induced urinary stones in spinal cord injury patients. J Urol 1988;140:318-24
   PubMed Web of Science ®Google Scholar
• Williams JJ, Rodman JS, Peterson CM. A randomized double-blind study of acetohydroxamic acid in struvite nephrolithiasis. N Engl J Med 1984;311:760-4
   PubMed Web of Science ®Google Scholar
• Griffith DP, Gleeson MJ, Lee H, Randomized, double-blind trial of Lithostat (acetohydroxamic acid) in the palliative treatment of infection-induced urinary calculi. Eur Urol 1991;20:243-7
   PubMed Web of Science ®Google Scholar
• Bailie NC, Osborne CA, Leininger JR, Teratogenic effect of acetohydroxamic acid in clinically normal beagles. Am J Vet Res 1986;47:2604-11
   PubMedGoogle Scholar
• Kobashi K, Takebe S, Terashima N, Inhibition of urease activity by hydroxamic acid derivatives of amino acids. J Biochem (Tokyo) 1975;77:837-43
   PubMed Web of Science ®Google Scholar
• Munakata K, Tanaka S, Toyoshima S. Theraphy for urolithiasis with hydroxamic acids. I. Synthesis of new N-(aroyl)glycinohydroxamic acid derivatives and related compounds. Chem Pharm Bull 1980;28:2045-51
   Web of Science ®Google Scholar
• Kobashi K, Munakata K, Takebe S, Therapy for urolithiasis by hydroxamic acids. II. Urease inhibitory potency and urinary excretion rate of hippurohydroxamic acid derivatives. J Pharmacobiodyn 1980;3:444-50
   PubMedGoogle Scholar
• Morton Norwich Products, Inc. 2-p-nitro- or p-chlorobenzamido-acetohydroxamic acid. US3787569; 1974
   Google Scholar
• Andersen JA. Benurestat, a urease inhibitor for the therapy of infected ureolysis. Invest Urol 1975;12:381-6
   PubMedGoogle Scholar
• Eisai Co. Ltd. Novel hydroxamic acid derivatives and medicaments for treatment of urolithiasis and pyelonephrosis comprising such derivatives. US4083996; 1978
   Google Scholar
• Munakata K, Mochida H, Kondo S, Mutagenicity of N-acylglycinohydroxamic acids and related compounds. J Pharmacobiodyn 1980;3:557-61
   PubMedGoogle Scholar
• Satoh M, Munakata K, Takeuchi H, Evaluation of effects of novel urease inhibitor, N-(pivaloyl)glycinohydroxamic acid on the formation of an infection bladder stone using a newly designed urolithiasis modell in rats. Chem Pharm Bull 1991;39:894-6
   PubMedGoogle Scholar
• Eisai Co. Ltd. Novel hydroxamic acid compounds, method for preparation thereof and medicaments containing such compounds. US4256765; 1981
   Google Scholar
• Munakata K, Kobashi K, Takebe S, Therapy for urolithiasis by hydroxamic acids. III. Urease inhibitory potency and urinary excretion rate of N-acylglycinohydroxamic acids. J Pharmacobiodyn 1980;3:451-6
   PubMedGoogle Scholar
• Takeuchi H, Okada Y, Kobashi K, Treatment of infected urinary stones in rats by a new hydroxamic acid, “N-(Pivaroyl)glycinohydroxamic acid”. Urol Res 1982;10:217-19
   PubMedGoogle Scholar
• Asahi Chem Ind Co. Ltd. Hydroxamic acid derivative, enzyme inhibitor and antiulcer agent. JP4217950; 1992
   Google Scholar
• Dixon NE, Gazzola C, Watters JJ, Inhibition of jack bean urease (EC 3.5.1.5) by acetohydroxamic acid and by phosphoramidate. Equivalent weight for urease. J Am Chem Soc 1975;97:4130-1
   PubMed Web of Science ®Google Scholar
• Andrews RK, Dexter A, Blakeley RL, 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;108:7124-5
   Web of Science ®Google Scholar
• Morton Norwich Products, Inc. N-[Diaminophosphinyl]arylcarboxamides. US4182881; 1980
   Google Scholar
• Morton Norwich Products, Inc. Phosphorotriamides as urease inhibitors. US4242325; 1980
   Google Scholar
• Morton Norwich Products, Inc. 8-[(4-Aminophenyl)sulfonyl]amino-2-naphthalenyl phosphorodiamidate. US4225526; 1980
   Google Scholar
• Morton Norwich Products, Inc. [[(4-Aminophenyl)sulfonyl]amino]phenyl phosphorodiamidates. US4222948; 1980
   Google Scholar
• Takeda Chemical Industries Ltd. Phosphorylamides, their preparation and use. US5840917; 1998
   Google Scholar
• Faraci WS, Yang BV, O'Rourke D, Inhibition of Helicobacter pylori urease by phenyl phosphorodiamidates: mechanism of action. Bioorg Med Chem 1995;3:605-10
   PubMed Web of Science ®Google Scholar
• Pope AJ, Toseland CD, Rushant B, Effect of potent urease inhibitor, fluorofamide, on Helicobacter sp. in vivo and in vitro. Dig Dis Sci 1998;43:109-19
   PubMed Web of Science ®Google Scholar
• Vassiliou S, Grabowiecka A, Kosikowska P, Design, synthesis and evaluation of novel organophosphorus inhibitors of bacterial ureases. J Med Chem 2008;51:5736-44
   PubMedGoogle Scholar
• Vassiliou S, Kosikowska P, Grabowiecka A, Computer-aided optimization of phosphinic inhibitors of bacterial ureases. J Med Chem 2010;53:5597-606
   PubMed Web of Science ®Google Scholar
• Shaw WHR, Raval DN. The inhibition of urease by methylurea. J Am Chem Soc 1961;83:2866-8
   Google Scholar
• Uesato S, Hashimoto Y, Nishino M, N-Substituted hydroxyureas as urease inhibitors. Chem Pharm Bull (Tokyo) 2002;50:1280-2
   PubMed Web of Science ®Google Scholar
• Sivapriya K, Suguna P, Banerjee A, Facile one-pot synthesis of thio and selenourea derivatives: a new class of potent urease inhibitors. Bioorg Med Chem Lett 2007;17:6387-91
   PubMed Web of Science ®Google Scholar
• Perveen Shahnaz. Process for the preparation of “Urchym” a urease and alpha-chymotrypsin enzyme inhibitory drug. US221214; 2008
   Google Scholar
• Zaborska W, Kot M, Superata K. Inhibition of Jack Bean urease by 1,4-benzoquinone and 2,5-dimethyl-1,4-benzoquinone. Evaluation of the inhibition mechanism. J Enzyme Inh Med Chem 2002;17:247-53
   PubMed Web of Science ®Google Scholar
• Tanaka T, Kawase M, Tani S. Urease inhibitory activity of simple a,b-unsaturated ketones. Life Sci 2003;73:2985-90
   PubMed Web of Science ®Google Scholar
• Ashiralieva A, Kleiner D. Polyhalogenated benzo- and naphthoquinones are potent inhibitors of plant and bacterial ureases. FEBS Lett 2003;555:367-70
   PubMed Web of Science ®Google Scholar
• Kleiner D, Ashiralieva A. Use of quinones and their derivatives as urease inhibitors, particularly for treating infections with urease-producing bacteria, e.g., Helicobacter pylori. DE10333448; 2005
   Google Scholar
• BIO21 KK. Urease inhibitor composition, food and beverage and cosmetics containing the same. JP070229; 2007
   Google Scholar
• Ichimaru Pharcos, Inc. Urease inhibitor. JP2006193477; 2006
   Google Scholar
• Nagase Co. Ltd. Urease inhibitor. JP2006219376; 2006
   Google Scholar
• Nagase Co. Ltd. Urease inhibitor. JP2006241039; 2006
   Google Scholar
• Yakult Honsha Co. Ltd. Urease activity inhibitor. JP48844; 2003
   Google Scholar
• Xiao Z-P, Shi D-H, Li H-Q, Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease. Bioorg Med Chem 2007;15:3703-10
   PubMed Web of Science ®Google Scholar
• Tanaka T, Kawase M, Tani S. aHydroxyketones as− inhibitors of urease. Bioorg Med Chem 2004;12:501-5
   PubMed Web of Science ®Google Scholar
• Jishou University. 1,2-diphenylethane type urease inhibitor and synthesis and applications thereof. CN101665413; 2010
   Google Scholar
• Xiao ZP, Ma TW, Fu WC, The synthesis, structure and activity evaluation of pyrogallol and catechol derivatives as Helicobacter pylori urease inhibitors. Eur J Med Chem 2010;45:5064-70
   PubMed Web of Science ®Google Scholar
• Dajani EZ, Klamut MJ. Novel therapeutic approaches to gastric and duodenal ulcers: an update. Expert Opin Invest Drugs 2000;9:1537-44
   PubMed Web of Science ®Google Scholar
• Nagaya H, Satoh H, Kubo K, Possible mechanism for the inhibition of gastric (H+/K+)-adenosine triphosphatase by the proton pump inhibitor AG-1749. J Pharmacol Exp Ther 1989;248:799-805
   PubMedGoogle Scholar
• Sjostrom JE, Kuhler T, Larsson H. Basis for the selective antibacterial activity in vitro of proton pump inhibitors against Helicobacter spp. Antimicrob Agents Chemother 1997;41:1797-801
   PubMed Web of Science ®Google Scholar
• Kühler TC, Fryklund J, Bergman N, Structure-activity relationship of omeprazole and analogs as Helicobacter pylori urease inhibitors. J Med Chem 1995;38:4906-16
   PubMed Web of Science ®Google Scholar
• Takeda Chemical Industries Ltd. Urease inhibitor. JP7025767; 1995
   Google Scholar
• Nagata K, Satoh H, Iwahi T, Potent inhibitory action of the gastric proton pump inhibitor lansoprazole against urease activity of Helicobacter pylori: unique action selective for H. pylori cells. Antimicrob Agents Chemother 1993;37:769-74
   PubMed Web of Science ®Google Scholar
• Tsuchiya M, Imamura L, Park J-B, Helicobacter Pylori urease inhibition by rabeprazole, a proton pump inhibitor. Biol Pharm Bull 1995;18:1053-6
   PubMed Web of Science ®Google Scholar
• Eisai Co. Ltd. Antiurease agent. JP7118153; 1995
   Google Scholar
• Haessle AB. Substituted pyridylsulfinylbenzimidazoles having gastric acid secretion properties, pharmaceutical preparations containing same, and intermediates for their preparation. EU5129; 1978
   Google Scholar
• Takeda Chemical Industries Ltd. Pyridine derivatives and their production. EU174726; 1986
   Google Scholar
• Eisai Co. Ltd. Pyridine derivatives, pharmaceutical compositions comprising the same, the use of the same for the manufacture of medicaments having therapeutic or preventative value, and a process for preparing the same. EU268956; 1988
   Google Scholar
• Nippon Chemiphar Co. Benzimidazole derivatives. DE3531487; 1986
   Google Scholar
• Toa Eiyo Ltd. Cycloheptenopyridine derivatives, process for preparation thereof and antiulcer agents containing the same. EU434999; 1991
   Google Scholar
• Ems SA. Antibacterial and/or antiprotozoal nitromidazole derivative compounds with urease inhibitor activity, process for preparing these compounds and use in pharmaceutical compositions and medicines. US072929; 2007
   Google Scholar
• Otsuka Pharma Co. Ltd. Urease inhibitors. US058952; 2004
   Google Scholar
• Kajiwara M. Urease inhibitors. US060482; 2003
   Google Scholar
• Amtul Z, Rasheed M, Choudhary MI, Kinetics of novel competitive inhibitors of urease enzymes by a focused library of oxadiazoles/thiadiazoles and triazoles. Biochem Biophys Res Comm 2004;319:1053-63
   PubMed Web of Science ®Google Scholar
• Viamet Pharmaceuticals, Inc. Metallo-hydrolase inhibitors using metal binding moietes in combination with targeting moieties. US256082; 2010
   Google Scholar
• Chen W, Li Y, Cui Y, Synthesis, molecular docking and biological evaluation of Schiff base transition metal complexes as potential urease inhibitors. Eur J Med Chem 2010;45:4473-8
   PubMed Web of Science ®Google Scholar
• You Z-L, Ni L-L, Shi D-H, Synthesis, structures, and urease inhibitory activities of three copper(II) and zinc(II) complexes with 2-{[2-(2-hydroxyethylamino)ethylimino]methyl}-4-nitrophenol. Eur J Med Chem 2010;45:3196-9
   PubMed Web of Science ®Google Scholar
• You Z-L, Zhang L, Shi D-H, Synthesis, crystal structures and urease inhibitory activity of copper(II) complexes with Schiff bases. Inorg Chem Commun 2010;13:996-8
   Web of Science ®Google Scholar
• Griffith DP. Urease stones. Urol Res 1979;7:215-21
   PubMedGoogle Scholar