The α and β classes carbonic anhydrases from Helicobacter pylori as novel drug targets

Current Pharmaceutical Design

Volumn 14, Issue 7, 2008, Pages 622-630

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

^a KOCHI MEDICAL SCHOOL   (Japan)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Acetazolamide; Carbonic anhydrase; Gastric acid; H. pylori; Inhibitor; Methazolamide; Urease

Indexed keywords

ACETAZOLAMIDE; ALUMINUM HYDROXIDE; AMOXICILLIN; ANTIBIOTIC AGENT; BISMUTH SALT; CARBON DIOXIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE ALPHA; CARBONATE DEHYDRATASE BETA; CARBONATE DEHYDRATASE INHIBITOR; CLARITHROMYCIN; ETHOXZOLAMIDE; HISTAMINE H2 RECEPTOR ANTAGONIST; MAGNESIUM CARBONATE; METHAZOLAMIDE; METRONIDAZOLE; PROTON PUMP INHIBITOR; SULPIRIDE; TETRACYCLINE; TOPIRAMATE; UREASE; CARBONATE DEHYDRATASE I; ISOENZYME;

ACCLIMATIZATION; AMINO ACID SEQUENCE; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; BACTERIAL CELL; BACTERIAL GENETICS; BACTERIAL GROWTH; CELLULAR DISTRIBUTION; CYTOPLASM; DRUG EFFICACY; DRUG TARGETING; ENZYME INHIBITION; ERADICATION THERAPY; GASTROINTESTINAL DISEASE; GROWTH INHIBITION; HELICOBACTER INFECTION; HELICOBACTER PYLORI; HUMAN; HYDRATION; IN VITRO STUDY; INTESTINE FLORA; MUCOSA ASSOCIATED LYMPHOID TISSUE LYMPHOMA; NONHUMAN; NUCLEOTIDE SEQUENCE; PATHOGENESIS; PATIENT COMPLIANCE; PRIORITY JOURNAL; RECURRENCE RISK; REVIEW; STOMACH CANCER; STOMACH PH; STOMACH ULCER; TREATMENT DURATION; TREATMENT OUTCOME; ULCER HEALING; UNSPECIFIED SIDE EFFECT; ANIMAL; CHEMISTRY; CLASSIFICATION; DRUG ANTAGONISM; DRUG DELIVERY SYSTEM; ENZYMOLOGY; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; METHODOLOGY; MOLECULAR GENETICS; SYNTHESIS;

AMINO ACID SEQUENCE; ANIMALS; CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; DRUG DELIVERY SYSTEMS; HELICOBACTER PYLORI; HUMANS; ISOENZYMES; MOLECULAR SEQUENCE DATA;

EID: 42149120104     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/138161208783877875     Document Type: Review

References (44)

1. Marshall BJ, Warren JR. Unidentified curved bacilli in the stomach of patients with gastritis and peptic ulceration. Lancet 1984; 1: 1311-5.
2. Penston JG, McColl KE. Eradication of Helicobacter pylori: An objective assessment of current therapies. Br J Clin Pharmacol 1997; 43: 223-43
3. Suerbaum S, Michetti P. Helicobacter pylori infection. N Engl J Med 2002; 347: 1175-86.
4. Bytzer P, O' Morain C. Treatment of Helicobacter pylori. Helicobacter 2005; 10: 40-6.
5. Lam SK, Talley NJ. Report of the 1997 Asia Pacific Consensus Conference on the management of Helicobacter pylori infection. J Gastroenterol Hepatol 1998; 13: 1-12.
6. Huang, JQ, Hunt RH. Treatment after failure: The problem of "non-responders". Gut 1999; 45: 140-4.
7. Laheij RJ, Rossum LG, Jansen JB, Straatman H, Verbeck AL. Evaluation of treatment regimens to cure Helicobacter pylori infection- a meta-analysis. Aliment Pharmacol Ther 1999; 13: 857-64.
8. Fischbach LA, 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: 1071-82
9. Gisbert JP, Pajares JM. Helicobacter pylori therapy: First-line options and rescue regimen. Dig Dis 2001; 19: 134-43.
10. Chi CH, Lin CY, Sheu BS, Yang HB, Huang AH, Wu JJ. 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: 347-53.
11. Lamouliatte H, Mégraud F, Delchier JC, Bretagne JF, Courillon-Mallet A, De Korwin JD, et al. Second-line treatment for failure to eradicate Helicobacter pylori: A randomized trial comparing four treatment strategies. Aliment Pharmacol Ther 2003; 18: 791-7.
12. Mantzaris GJ, Petraki K, Archavlis E, Amberiadis P, Christoforidis P, Kourtessas D, et at. Omeprazole triple therapy vesus 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: 1237-43.
13. Sachs G, Weeks DL, Wen Y, Marcus EA, Scott DR. Acid acclimation by Helicobacter pylori. Physiology (Bethesda) 2005; 20: 429-38.
14. Marcus EA, Moshfegh AP, Sachs G, Scott, DR. The periplasmic α-carbonic anhydrase activity of Helicobacter pylori is essential for acid acclimation. J Bacteriol 2005; 187: 729-38.
15. Stähler FN, Canter L, Lederer K, Kist NA, Bereswill S. Mutational analysis of the Helicobacter pylori carbonic anhydrases. FEMS Immunol Med Microbiol 2005; 44: 183-9.
16. Tomb JT, White O, Kerlavage AR, Clayton KA, Sutton GG, Fleischmann RD, et al. The complete genome sequence of the gastric pathogen Helicobacter pylori. Nature 1997; 388: 539-47.
17. Alm RA, Ling LS, Moir DT, King BL, Brown ED, Doig PC. et al. Genomic-sequence comparison of two unrelated isolates of the human gastric pathogen Helicobacter pylori. Nature 1999; 397: 176-80.
18. Oh JD, Kling-Bäckhed H, Giannakis M, Xu J, Fulton RS, Fulton LA, et al. 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 KS, Jakubzick C, Whittam TS, Ferry JG. Carbonic anhydrase is an ancient enzyme widespread in prokaryotes. Proc Natl Acad Sci USA 1999; 96: 15184-9.
20. Supuran CT, Scozzafava A, Conway J. Carbonic Anhydrases: Its inhibitors and activators. Boca Raton, CRC Press 2004; 1-363.
21. Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007; 15: 4336-50.
22. Alterio V, De Simone G, Monti SM, Scozzafava A, Supuran CT. 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: 4201-7.
23. Temperini C, Scozzafava A, Vullo D, Supuran CT. Carbonic anhydrase activators. Activation of isozymes I, II, IV, VA, VII, and XIV with 1- 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: 7057-66.
24. Cronk JD, Endrizzi JA, Cronk MR, O'neill JW, Zhang, KY. Crystal structure of E. coli beta-carbonic anhydrase, an enzyme with an unusual pH-dependent activity. Protein Sci 2001; 10: 911-22
25. Mitsuhashi S, Mizushima T, Yamashita E,Yamamoto M, Kumasaka T, Moriyama H, et al. X-ray structure of beta-carbonic anhydrase from the red alga, Porphyridium purpureum, reveals a novel catalytic site for CO(2) hydration. J Biol Chem 2000; 272: 5521-6.
26. Kimber MS. Pai EF. The active site architecture of Pisum sativum beta-carbonic anhydrase is a mirror image of that of alpha-carbonic anhydrases. EMBO J 2000; 19: 1407-19.
27. Hiltonen T, Björkbacka H, Forsman C, Clarke AK, Samuelsson G. Intracellular beta-carbonic anhydrase of the unicellular green alga Coccomyxa. Cloning of the cdna and characterization of the functionn enzyme overexpressed in Escherichia coli. Plant Physiol 1998; 117: 1341-9.
28. Strop P, Smith KS, Iverson TM, Ferry JG, Rees DC. Crystal structure of the "cab"-type beta class carbonic anhydrase from the archaeon Methanobacterium thermoautotrophicum. J Mol Chem 2001; 276: 10299-305
29. Smith KS, Ferry JG. Prokaryotic carbonic anhydrases. FEMS Microbiol Rev 2000; 24: 335-66.
30. Chirica LC, Elleby B, Lindskog S. Cloning, expression and some properties of alpha-carbonic anhydrase from Helicobacter pylori. Biochim Biophys Acta 2001: 1544: 55-63.
31. Nishimori, I, Minakuchi T, Morimoto K, Sano S, Onishi S, Takeuchi H, et al. Carbonic anhydrase inhibitors: DNA cloning and inhibition studies ot the alpha-carbonic anhydrase from Helicobacter pylori, n new target for developing sulfonamide and sulfamate gastric drugs. J Med Chem 2006; 49: 2117-26.
32. Nishimori I, Vullo D, Minakuchi T, Morimoto K, Oninshi S, Scozzafava A, et al. Carbonic anhydrase inhibitors: Cloning and sulfonamide inhibition studies of a carboxyterminal truncated alphacarbonic anhydrase from Helicobacter pylori. Bioorg Med Chem Lett 2006; 16: 2182-8.
33. Nishimori I, Minakuchi T, Kohsaki T, Onishi S, Takeuchi H, Vullo D, et al. 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: 3585-94.
34. Chirica LC, Petersson C, Hurtig M, Jonsson BH, Borén T, Lindskog S. Expression and localization of alpha- and beta-carbonic, anhydrase in Helicobacter pylori. Biochim Biophys Acta 2002; 1601: 192-9.
35. Guilloton MB, Korte JJ, Lamblin AF, Fuchs JA, Anderson PM. Carbonic anhydrase in Escherichia coli. A product of the cyn operon. J Biol Chem 1992; 267: 3731-4.
36. Scott DR, Weeks D, Hong DC, Postius S, Melchers K, Sachs G. The role of internal urease in acid resistance of Helicobacter pylori. Gastorneterology 1998; 114: 58-70.
37. Puscas I. Treatment of gastroduodenal ulcers with carbonic anhydrase inhibitors. Ann N Y Acad Sci 1984; 429: 587-91.
38. Valean S, Vlaicu R, Ionescu I. Treatment of gastric ulcer with carbonic anhydrase inhibitors. Ann NY Acad Sci 1984; 429: 597-600.
39. Davenport H. The mechanisms of acid secretion. Gastroentrology 1968; 54: 702-5.
40. Penton JG, McColl KE. Eradication of Helicobacter pylori: An objective assessment ol current therapies. Br J Clin Pharmacol 1997; 43: 223-43
41. Shanidzadeh R, Opekun A, Shiotani A, Graham DY. Effect of the carbonic anhydrase inhihitor, acetazolamide, on Helicobacter pylori infection in vivo: A pilot study. Helicobacter 2005; 10: 136-8.
42. Andrutis KA, Fox JG, Schauer DB, Marini RP, Murphy JC, Yan L, et al. Inability of an isogenic urease-negative mutant stain of Helicobacter mustelae to colonize the ferret stomach. Infect Immun 1995; 63: 3722-5.
43. Eaton KA, Krakowka S. Effect of gastric pH on urease-dependent colonization of gnotobiotic piglets by Helicobacter pylori. Infect Immun 1994; 62: 3604-7.
44. Takeuchi H, Nakazawa T, Okamoto T, Shirai M, Kimoto M, Nishioka M, et al. Cell elongation and cell death of helicobacter pylori is modulated by the disruption of cdrA (cell division-related gene A). Microbiol Immunol 2006; 50: 487-97.