Inhibitors of Helicobacter pylori α-and β-Carbonic Anhydrases as Novel Drugs for Gastroduodenal Diseases

Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications

Volumn , Issue , 2009, Pages 359-374

  Nishimori, Isao ^a   Takeuchi, Hiroaki ^a   Supuran, Claudiu T ^b  

^a KOCHI MEDICAL SCHOOL   (Japan)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Inhibitors of helicobacter pylori and carbonic anhydrases; Kinetic and inhibition properties of and CAs from H. pylori; Subcellular localization and biological function of and CAs in H. pylori

Indexed keywords

EID: 84889495845     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470508169.ch17     Document Type: Chapter

References (46)

1. Marshall, B. J.; Warren, J. R. Unidentified curved bacilli in the stomach of patients with gastritis and peptic ulceration. Lancet 1984, 1, 1311-13115.
2. Penston, J. G.; McColl, K. E. Eradication of Helicobacter pylori: an objective assessment of current therapies. Br. J. Clin. Pharmacol. 1997, 43, 223-243.
3. Suerbaum, S.; Michetti, P. Helicobacter pylori infection. N. Engl. J. Med. 2002, 347, 1175-1186.
4. Bytzer, P.; O'Morain, C. Treatment of Helicobacter pylori. Helicobacter 2005, 10 (Suppl. 1), 40-46.
5. Lam, S. K.; Talley, N. J. Report of the 1997 Asia Pacific Consensus Conference on the management of Helicobacter pylori infection. J. Gastroenterol. Hepatol. 1998, 13, 1-12.
6. Huang, J. Q.; Hunt, R. H. Treatment after failure: the problem of ''non-responders''. Gut 1999, 45 (Suppl. 1), I40-I44.
7. Laheij, R. J.; Rossum, L. G.; Jansen, J. B.; Straatman, H.; Verbeek, A. L. Evaluation of treatment regimens to cure Helicobacter pylori infection: a meta-analysis. Aliment. Pharmacol. Ther. 1999, 13, 857-864.
8. Fischbach, L. A.; van Zanten, S.; Dickason, J. Meta-analysis: the efficacy, adverse events, and adherence related to first-line anti-Helicobacter pylori quadruple therapies. Aliment. Pharmacol. Ther. 2004, 20, 1071-1082.
9. Gisbert, J. P.; Pajares, J. M. Helicobacter pylori therapy: first-line options and rescue regimen. Dig. Dis. 2001, 19, 134-143.
10. Chi, C. H.; Lin, C. Y.; Sheu, B. S.; Yang, H. B.; Huang, A. H.;Wu, J. J. Quadruple therapy containing amoxicillin and tetracycline is an effective regimen to rescue failed triple therapy by overcoming the antimicrobial resistance of Helicobacter pylori. Aliment. Pharmacol. Ther. 2003, 18, 347-353.
11. Lamouliatte, H.; Mégraud, F.; Delchier, J. C.; Bretagne, J. F.; Courillon-Mallet, A.; De Korwin, J. D.; Fauchére, J. L.; Labigne, A.; Fléjou, J. F.; Barthelemy, P.;Multicentre Study Group. Second-line treatment for failure to eradicate Helicobacter pylori: a randomized trial comparing four treatment strategies. Aliment. Pharmacol. Ther. 2003, 18, 791-797.
12. Mantzaris, G. J.; Petraki, K.; Archavlis, E.; Amberiadis, P.; Christoforidis, P.; Kourtessas, D.; Chiotakakou, E.; Triantafyllou,G. Omeprazole triple therapy versus omeprazole quadruple therapy for healing duodenal ulcer and eradication of Helicobacter pylori infection: a 24-month follow-up study. Eur. J. Gastroenterol. Hepatol. 2002, 14, 1237-1243.
13. Sachs, G.; Weeks, D. L.; Wen, Y.;: Marcus, E. A.; Scott,D. R. Acid acclimation by Helicobacter pylori. Physiology (Bethesda) 2005, 20, 429-438.
14. Marcus,E. A.; Moshfegh, A. P.; Sachs, G.; Scott,D. R. The periplasmic a-carbonic anhydrase activity of Helicobacter pylori is essential for acid acclimation. J. Bacteriol. 2005, 187, 729-738.
15. Stähler, F. N.; Ganter, L.; Lederer, K.; Kist, M.; Bereswill, S. Mutational analysis of the Helicobacter pylori carbonic anhydrases. FEMS Immunol. Med. Microbiol. 2005, 44, 183-189.
16. Tomb, J. F.; White, O.; Kerlavage, A. R.; Clayton, R. A.; Sutton, G. G.; Fleischmann, R. D.;Ketchum,K.A.; Klenk, H. P.;Gill, S.;Dougherty,B.A.; Nelson, K.;Quackenbush, J.; Zhou, L.; Kirkness, E. F.; Peterson, S.; Loftus, B.; Richardson, D.; Dodson, R.; Khalak, H. G.; Glodek, A.;McKenney, K.; Fitzegerald, L.M.; Lee, N.; Adams,M. D.; Hickey, E. K.; Berg, D. E.; Gocayne, J. D.; Utterback, T. R.; Peterso, L.;Wallin, E.; Hayes, W. S.; Borodovsky, M.; Karp, P. D.; Smith, H. O.; Fraser, C. M.; Venter, J. C. The complete genome sequence of the gastric pathogen Helicobacter pylori. Nature 1997, 388, 539-547.
17. Alm, R. A.; Ling, L. S.; Moir, D. T.; King, B. L.; Brown, E. D.; Doig, P. C.; Smith, D. R.; Noonan, B.; Guild, B. C.; De Jonge, B. L.; Carmel, G.; Tummino, P. J.; Caruso, A.; Uria-Nickelsen, M.; Mills, D. M.; Ives, C.; Gibson, R.; Merberg, D.; Mills, S. D.; Jiang, Q.; Taylor, D. E.; Vovis, G. F.; Trust, T. J. Genomic-sequence comparison of two unrelated isolates of the human gastric pathogen Helicobacter pylori. Nature 1999, 397, 176-180.
18. Oh, J. D.; Kling-Bäckhed, H.; Giannakis, M.; Xu, J.; Fulton, R. S.; Fulton, L. A.; Cordum, H. S.;Wang, C.; Elliott, G.; Edwards, J.; Mardis, E. R.; Engstrand, L. G.; Gordon, J. I. The complete genome sequence of a chronic atrophic gastritis Helicobacter pylori strain: evolution during disease progression. Proc. Natl. Acad. Sci. USA 2006, 103, 9999-10004.
19. Smith, K. S.; Jakubzick, C.; Whittam, T. S.; Ferry, J. G. Carbonic anhydrase is an ancient enzyme widespread in prokaryotes. Proc. Natl. Acad. Sci. USA 1999, 96, 15184-15189.
20. Supuran, C. T.; Scozzafava, A.; Casini, A. Development of sulfonamide carbonic anhydrase inhibitors. In Carbonic Anhydrases: Its Inhibitors and Activators; Supuran, C. T.; Scozzafava,A.; Conway, J., Eds.; CRC Press: Boca Raton, FL, 2004; pp 67-147.
21. Supuran, C. T.; Scozzafava, A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg. Med. Chem. 2007, 15, 4336-4350.
22. Alterio, V.; De Simone, G.; Monti, S. M.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: inhibition of human, bacterial, and archaeal isozymes with benzene-1,3-disulfonamides: solution and crystallographic studies. Bioorg. Med. Chem. Lett. 2007, 17, 4201-4207.
23. Temperini, C.; Scozzafava, A.; Vullo, D.; Supuran, C. T. Carbonic anhydrase activators. Activation of isozymes I, II, IV, VA, VII, and XIV with L-and D-histidine and crystallographic analysis of their adducts with isoform II: engineering proton-transfer processes within the active site of an enzyme. Chemistry 2006, 12, 7057-7066.
24. Cronk, J. D.; Endrizzi, J. A.; Cronk, M. R.; O'neill, J.W.; Zhang, K. Y. Crystal structure of E. coli beta-carbonic anhydrase, an enzyme with an unusual pH-dependent activity. Protein Sci. 2001, 10, 911-922.
25. Mitsuhashi, S.; Mizushima, T.; Yamashita, E.; Yamamoto, M.; Kumasaka, T.; Moriyama, H.; Ueki,T.; Miyachi, S.; Tsukihara,T. X-ray structure of beta-carbonic anhydrase from the red alga, Porphyridium purpureum, reveals a novel catalytic site for CO2 hydration. J. Biol. Chem. 2000, 275, 5521-5526.
26. Kimber, M. S.; Pai, E. F. The active site architecture of Pisum sativum beta-carbonic anhydrase is a mirror image of that of alpha-carbonic anhydrases. EMBO J. 2000, 19, 1407-1418.
27. Hiltonen, T.; Björkbacka, H.; Forsman, C.; Clarke, A. K.; Samuelsson, G. Intracellular beta-carbonic anhydrase of the unicellular green alga Coccomyxa. Cloning of the cDNA and characterization of the functional enzyme overexpressed in Escherichia coli. Plant Physiol. 1998, 117, 1341-1349.
28. Strop, P.; Smith,K. S.; Iverson, T.M.; Ferry, J. G.; Rees,D. C. Crystal structure of the ''cab''-type beta class carbonic anhydrase from the archaeon Methanobacterium thermoautotrophicum. J. Biol. Chem. 2001, 276, 10299-10305.
29. Smith, K. S.; Ferry, J.G. Prokaryotic carbonic anhydrases. FEMS Microbiol. Rev. 2000, 24, 335-366.
30. Chirica, L. C.; Elleby, B.; Lindskog, S.; Cloning, expression and some properties of alphacarbonic anhydrase from Helicobacter pylori. Biochim. Biophys. Acta. 2001, 1544, 55-63.
31. Nishimori, I.; Minakuchi, T.; Morimoto, K.; Sano, S.; Onishi, S.; Takeuchi, H.; Vullo, D.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors:DNAcloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs. J. Med. Chem. 2006, 49, 2117-2126.
32. Nishimori, I.; Vullo, D.; Minakuchi, T.; Morimoto, K.; Onishi, S.; Scozzafava, A.; Supuran,C. T. Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori. Bioorg. Med. Chem. Lett. 2006, 16, 2182-2188.
33. Nishimori, I.; Minakuchi, T.; Kohsaki, T.; Onishi, S.; Takeuchi, H.; Vullo, D.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from Helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 3585-3594.
34. Nishimori, I.; Onishi, S.; Takeuchi, H.; Supuran, C. T. The alpha and beta classes carbonic anhydrases from Helicobacter pylori as novel drug targets. Curr. Pharm. Des. 2008, 14, 622-630.
35. Chirica, L. C.; Petersson, C.; Hurtig, M.; Jonsson, B. H.; Borén,T.; Lindskog, S. Expression and localization of alpha-and beta-carbonic anhydrase in Helicobacter pylori. Biochim. Biophys. Acta. 2002, 1601, 192-199.
36. Guilloton, M. B.; Korte, J. J.; Lamblin, A. F.; Fuchs, J. A.; Anderson, P. M. Carbonic anhydrase in Escherichia coli. A product of the cyn operon. J. Biol. Chem. 1992, 267, 3731-3734.
37. Scott, D. R.; Weeks, D.; Hong, D. C.; Postius, S.; Melchers, K.; Sachs, G. The role of internal urease in acid resistance of Helicobacter pylori. Gastroenterology 1998, 114, 58-70.
38. Puscas, I. Treatment of gastroduodenal ulcers with carbonic anhydrase inhibitors. Ann. N.Y. Acad. Sci. 1984, 429, 587-591.
39. Valean, S.; Vlaicu, R.; Ionescu, I. Treatment of gastric ulcer with carbonic anhydrase inhibitors. Ann. N.Y. Acad. Sci. 1984, 429, 597-600.
40. Davenport, H. The mechanisms of acid secretion. Gastroenterology 1968, 54 (Suppl. 4), 702-705.
41. Penton, J. G.; McColl, K. E. Eradication of Helicobacter pylori: an objective assessment of current therapies. Br. J. Clin. Pharmacol. 1997, 43, 223-243.
42. Morishita, S.; Nishimori, I.; Minakuchi, T.; Onishi, S.; Takeuchi, H.; Sugiura, T.;Vullo, D.; Scozzafava, A.; Supuran,C. T. Cloning, polymorphism and inhibition of b-carbonic anhydrase of Helicobacter pylori. J. Gastroenterol. 2008, 43, 849-857.
43. Shahidzadeh, R.; Opekun, A.; Shiotani, A.; Graham, D.Y. Effect of the carbonic anhydrase inhibitor, acetazolamide, on Helicobacter pylori infection in vivo: a pilot study. Helicobacter 2005, 10, 136-138.
44. Andrutis, K. A.; Fox, J. G.; Schauer, D. B.; Marini, R. P.; Murphy, J. C.; Yan, L.; Solnick, J. V. Inability of an isogenic urease-negative mutant strain of Helicobacter mustelae to colonize the ferret stomach. Infect. Immun. 1995, 63, 3722-3725.
45. Eaton, K. A.; Krakowka, S. Effect of gastric pH on urease-dependent colonization of gnotobiotic piglets by Helicobacter pylori. Infect. Immun. 1994, 62, 3604-3607.
46. Takeuchi, H.; Nakazawa, T.; Okamoto, T.; Shirai, M.; Kimoto, M.; Nishioka, M.; Con, S. A.; Morimoto, N.; Sugiura, T. Cell elongation and cell death of Helicobacter pylori is modulated by the disruption of cdrA (cell division-related gene A). Microbiol. Immunol. 2006, 50, 487-497.