Urease inhibitory activity of simple α,β-unsaturated ketones

Life Sciences

Volumn 73, Issue 23, 2003, Pages 2985-2990

  Tanaka, Toru ^a   Kawase, Masami ^a   Tani, Satoru ^a  

^a JOSAI UNIVERSITY   (Japan)

Author keywords

Jack bean urease; Urease inhibitor; , Unsaturated ketones

Indexed keywords

2 CYCLOHEPTEN 1 ONE; 2 CYCLOHEXENONE; 2 PYRONE DERIVATIVE; 5,6 DIHYDRO 2H PYRAN 2 ONE; ACETOHYDROXAMIC ACID; CYCLOHEPTENE; CYCLOPENTENONE; DITHIOTHREITOL; HYDROXYUREA; KETONE DERIVATIVE; MERCAPTOETHANOL; UNCLASSIFIED DRUG; UREASE; UREASE INHIBITOR;

ARTICLE; CHEMICAL BOND; DRUG SCREENING; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; MICHAEL ADDITION;

CANAVALIA ENSIFORMIS; PHASEOLUS (ANGIOSPERM);

EID: 0141756326     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0024-3205(03)00708-2     Document Type: Article

References (21)

1. Amtul Z., Atta-ur-Rahman, Siddiqui R.A., Choudhary M.I. Chemistry and mechanism of urease inhibition. Current Medicinal Chemistry. 9:2002;1323-1348.
2. Chien C., Kirollos K.S., Linderman R.J., Dauterman W.C. α,β-Unsaturated carbonyl compounds: inhibition of rat liver glutathione S-transferase isozymes and chemical reaction with reduced glutathione. Biochimica Biophysica Acta. 1204:1994;175-180.
3. Dixon M., Webb E.C. Enzyme inhibition and activation. Dixon M., Webb E.C. Enzyme. 3rd ed. 1979;332-344 Academic Press, New York.
4. Faraci W.S., Yang B.V., O'Rourke D., Spencer R.W. Inhibition of Helicobacter pylori urease by pheny phosphorodiamidates: mechanism of action. Bioorganic Medicinal Chemistry. 3(5):1995;605-610.
5. Hitosugi N., Hatsukari I., Ohno R., Hashimoto K., Mihara S., Mizukami S., Nakamura S., Sakagami H., Nagasaka H., Matsumoto I., Kawase M. Comparative analysis of apoptosis-inducing activity of codeine and codeinone. Anesthesiology. 98:2003;643-650.
6. Kawase M., Sakagami H., Furuya K., Kikuchi H., Nishikawa H., Motohashi N., Morimoto Y., Varga A., Molnar J. Cell death-inducing activity of opiates in human oral tumor cell lines. Anticancer Research. 22:2002;211-214.
7. Khan H., Harris R.J., Barna T., Craig D.H., Bruce N.C., Munro A.W., Moody P.C.E., Scrutton N.S. Kinetic and structural basis of reactivity of pentaerythritol tetranitrate reductase with NADPH, 2-cyclohexenone, nitroesters, and nitroaromatic explosives. Journal of Biological Chemistry. 277(24):2002;21906-21912.
8. Kuhler T.C., Fryklund J., Bergman N.-A., Weilitz J., Lee A., Larsson H. Structure-activity relationship of omeprazole and analogues as Helicobacter pylori urease inhibitors. Journal of Medicinal Chemistry. 38:1995;4906-4916. and the references cited therein.
9. Lee K.-H., Huang E.-S., Piantadosi C., Pagano J.S., Geissman T.A. Cytotoxicity of sesquiterpene lactones. Cancer Research. 31:1971;1649-1654.
10. Lee K.-H., Waddell T.G., Hadgraft R.I., Ruffner C.G., Weidner I. Sesquiterpene antitumor agents: inhibitors of cellular metabolism. Science. 196:1977;533-536.
11. Maria A.O.M., Donadel O., Wendel G.H., Guzman J.A., Guerrerio E., Giordnano O.S. Gastric anti-ulcer activity of several α, β-unsaturated carbonyl compounds in rats. Biological Pharmaceutical Bulletin. 23(5):2000;555-557.
12. Mobley H.L.T., Hausinger R.P. Microbial ureases: significance, regulation, and molecular characterization. Microbiological Reviews. 53(1):1989;85-108.
13. Mobley H.L.T., Island M.D., Hausinger R.P. Molecular biology of microbial ureases. Microbiological Reviews. 59(3):1995;451-480.
14. Murakami A., Takahashi D., Kinoshita T., Koshimizu K., Kim H.W., Yoshihiro A., Nakamura Y., Jiwajinda S., Terao J., Ohigashi H. Zerumbone, a Southeast Asian ginger sesquiterpene, markedly suppresses free radical generation, proinflammatory protein production, and cancer cell proliferation accompanied by apoptosis: the α,β-unsaturated carbonyl group is a prerequisite. Carcinogesis. 23(5):2002;795-802.
15. Nagata K., Satoh H., Iwahi T., Shimoyama T., Tamura T. Potent inhibitory action of the gastric proton pump inhibitor, lansoprazole, against urease activity of Helicobacter pylori: unique action selective for H. pylori cells. Antimicrobial Agents Chemotherapy. 37(4):1993;769-774.
16. Odake S., Morikawa T., Tsuchiya M., Imamura L., Kobashi K. Inhibition of Helicobacter pylori urease activity by hydroxamic acid derivatives. Biological Pharmaceutcal Bulletin. 17(10):1994;1329-1332. and the references cited therein.
17. Park J.-B., Imamura L., Kobashi K. Kinetic studies of Helicobacter pylori urease inhibition by a novel proton pump inhibitor, rabeprazole. Biological Pharmaceutical Bulletin. 19(2):1996;182-187. and the references cited therein.
18. Pope A.J., Toseland N., Rushant B., Richardson S., McVey M., Hills J. Effect of potent urease inhibitor, fluorofamide, on Helicobacter sp. in vivo and in vitro. Digestive Diseases Sciences. 43(1):1998;109-119.
19. Uesato S., Hashimoto Y., Nishino M., Nagaoka Y., Kuwajima H. N-Substituted hydroxyureas as urease inhibitors. Chemical Parmaceutical Bulletin. 50(9):2002;1280-1282. and the references cited therein.
20. van Lersel M.L., Ploemen J.P., Lo Bello M., Federici G., van Bladeren P.J. Interaction of α,β-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1. Chemico-Biological Interactions. 108(1-2):1997;67-78.
21. van Slyke D.D., Archibald R.M. Manomeric, titrimetric and colorimetric methods for measurement of urease activity. Journal of Biological Chemistry. 154:1944;623-642.