γ-(Monophenyl)phosphono glutamate analogues as mechanism-based inhibitors of γ-glutamyl transpeptidase

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 17, 2006, Pages 6043-6054

  Han, Liyou ^a   Hiratake, Jun ^a   Tachi, Norihito ^a   Suzuki, Hideyuki ^a   Kumagai, Hidehiko ^a   Sakata, Kanzo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

(Monophenyl)phosphono glutamate analogues; Glutamyl transpeptidase; Mechanism based inhibitor; Phosphonylation

Indexed keywords

ACIVICIN; ENZYME INHIBITOR; GAMMA GLUTAMYLTRANSFERASE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG DETERMINATION; DRUG HYDROLYSIS; DRUG INHIBITION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INACTIVATION; ENZYME INHIBITION; ESCHERICHIA COLI; PHASE TRANSITION; STRUCTURE ANALYSIS;

ESCHERICHIA COLI; GAMMA-GLUTAMYLTRANSFERASE; GLUTAMIC ACID; HUMANS; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS;

ESCHERICHIA COLI;

EID: 33746047636     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.05.008     Document Type: Article

References (62)

1. Taniguchi N., and Ikeda Y. Adv. Enzymol. Rel. Areas Mol. Biol. 72 (1998) 239
2. Hiratake J., Suzuki H., and Kumagai H. In: Barrett A.J., Rawlings N.D., and Woessner J.F. (Eds). Handbook of Proteolytic Enzymes. 2nd ed. (2004), Elsevier, Amsterdam 2090-2094
3. Zhang H., Forman H.J., and Choi J. Methods Enzymol. 401 (2005) 468
4. Whitfield J.B. Crit. Rev. Clin. Lab. Sci. 38 (2001) 263
5. Hanigan M.H., and Frierson Jr. H.F.J. Histochem. Cytochem. 44 (1996) 1101
6. Hanigan M.H., and Ricketts W.A. Biochemistry 32 (1993) 6302
7. Vincent B.R., Mousset S., and Jacquemin-Sablon A. Eur. J. Biochem. 262 (1999) 873
8. Ruoso P., and Hedley D.W. Cancer Chemother. Pharmacol. 54 (2004) 49
9. Anderson M.E., and Meister A. Proc. Natl. Acad. Sci. U.S.A. 80 (1983) 707
10. Godwin A.K., Meister A., O'Dwyer P.J., Huang C.-S., Hamilton T.C., and Anderson M.E. Proc. Natl. Acad. Sci. U.S.A. 89 (1992) 3070
11. Hanigan M.R., Gallagher B.C., Townsend D.M., and Gabarra V. Carcinogenesis 20 (1999) 553
12. Hanigan M.H. Carcinogenesis 16 (1995) 181
13. Lewis A.D., Hayes J.D., and Wolf C.R. Carcinogenesis 9 (1988) 1283
14. Hanigan M.H., and Pitot H.C. Carcinogenesis 6 (1985) 165
15. Benlloch M., Ortega A., Ferrer P., Segarra R., Obrador E., Asensi M., Carretero J., and Estrela J.M. J. Biol. Chem. 280 (2005) 6950
16. Ortega A.L., Carretero J., Obrador E., Gambini J., Asensi M., Rodilla V., and Estrela J.M. J. Biol. Chem. 278 (2003) 13888
17. Obrador E., Carretero J., Ortega A., Medina I., Rodilla V., Pellicer J.A., and Estrela J.M. Hepatology 35 (2002) 74
18. Pompella A., De Tata V., Paolicchi A., and Zunino F. Biochem. Pharmacol. 71 (2006) 231 and references cited therein
19. Owen A.D., Schapira A.H., Jenner P., and Marsden C.D. Ann. N.Y. Acad. Sci. 786 (1996) 217
20. Sian J., Dexter D.T., Lees A.J., Daniel S., Jenner P., and Marsden S.D. Ann. Neurol. 36 (1994) 356
21. Lee D.-H., Ha M.-H., Kim J.-H., Christiani D.C., Gross M.D., Steffes M., Blomhoff R., and Jacobs D.R. Diabetologia 46 (2003) 359
22. Meisinger C., Löwel H., Heier M., Schneider A., and Thorand B. J. Internal Med. 258 (2005) 527
23. Paolicchi A., Minotti G., Tonarelli P., De Cesare D., Mezzetti A., Dominici S., Comporti M., and Pompella A. J. Invest. Med. 47 (1999) 151
24. Ruttmann E., Brant L.J., Concin H., Diem G., Rap K., and Ulmer H. Circulation 112 (2005) 2130
25. Townsend D.M., Tew K.D., and Tapiero H. Biomed. Pharmacother. 57 (2003) 145
26. Allison R.D. Methods Enzymol. 113 (1985) 419
27. Keillor J.W., Ménard A., Castonguay R., Lherbet C., and Rivard C. J. Phys. Org. Chem. 17 (2004) 529
28. Hanka L.J., and Diez A. Antimicrob. Agents Chemother. 3 (1973) 425
29. Gardell S.J., and Tate S.S. FEBS Lett. 122 (1980) 171
30. Stole E., Seddon A.P., Wellner D., and Meister A. Proc. Natl. Acad. Sci. U.S.A. 87 (1990) 1706
31. Smith T.K., Ikeda Y., Fujii J., Taniguchi N., and Meister A. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 2360
32. Jayaram H.N., Cooney D.A., RRyan J.A., Neil G.L., Dion R.L., and Bono V.H. Cancer Chemother. Rep. 59 (1975) 481
33. Zalkin H. Adv. Enzymol. Rel. Areas Mol. Biol. 72 (1998) 87
34. Earhart R.H., and Neil G.L. Adv. Enzyme Regul. 24 (1985) 179
35. Chittur S.V., Klem T.J., Shafer C.M., and Jo Davisson V. Biochemistry 40 (2001) 876
36. Tate S.S., and Meister A. Proc. Natl. Acad. Sci. U.S.A. 74 (1977) 931
37. Tate S.S., and Meister A. Proc. Natl. Acad. Sci. U.S.A. 75 (1978) 4806
38. Stein R.L., DeCicco C., Nelson D., and Thomas B. Biochemistry 40 (2001) 5804
39. London R.E., and Gabel S.A. Arch. Biochem. Biophys. 385 (2001) 250
40. Inoue M., Hiratake J., Suzuki H., Kumagai H., and Sakata K. Biochemistry 39 (2000) 7764
41. Brannigan J.A., Dodson G., Duggleby H.J., Moody P.C.E., Smith J.L., Tomchick D.R., and Murzin A.G. Nature 378 (1995) 416
42. Suzuki H., and Kumagai H. Biochemistry 277 (2002) 43536
43. Hirschmann R., Yager K.M., Taylor C.M., Witherington J., Sprengeler P.A., Phillips B.W., Moore W., and Smith III A.B. J. Am. Chem. Soc. 119 (1997) 8177
44. Inoue M., Hiratake J., and Sakata K. Biosci. Biotechnol. Biochem. 63 (1999) 2248
45. Bartlett P.A., and Lamden L.A. Bioorg. Chem. 14 (1986) 356
46. Thompson G.A., and Meister A. J. Biol. Chem. 252 (1977) 6792
47. Tate S.S., and Meister A. Methods Enzymol. 113 (1985) 400
48. Cook N.D., and Peters T.J. Biochim. Biophys. Acta 832 (1985) 142
49. Suzuki H., Kumagai H., and Tochikura T. J. Bacteriol. 168 (1986) 1325
50. McIntyre T.M., and Curthoys N.P. J. Biol. Chem. 254 (1979) 6499
51. Hengge A.C., and Onyido I. Curr. Org. Chem. 9 (2005) 61
52. Ménard A., Castonguay R., Lherbet C., Rivard C., Roupioz Y., and Keillor J.W. Biochemistry 40 (2001) 12678
53. Tate S.S., and Meister A. Proc. Natl. Acad. Sci. U.S.A. 71 (1974) 3329
54. Thompson G.A., and Meister A. J. Biol. Chem. 254 (1979) 2956
55. Thompson G.A., and Meister A. J. Biol. Chem. 255 (1980) 2109
56. Gardell S.J., and Tate S.S. J. Biol. Chem. 258 (1983) 6198
57. Suzuki H., Hashimoto W., and Kumagai H. J. Bacteriol. 175 (1993) 6038
58. Kosolapoff G.M. J. Am. Chem. Soc. 70 (1948) 1971
59. Chambers J.R., and Isbell A.F. J. Org. Chem. 29 (1964) 832
60. Bradford M.M. Anal. Biochem. 72 (1976) 248
61. Smith G.D., Ding J.L., and Peters T.J. Anal. Biochem. 100 (1979) 136-139
62. Stein R.L., Strimpler A.M., Edwards P.D., Lewis J.J., Mauger R.C., Schwartz J.A., Stein M.M., Trainor D.A., Wildonger R.A., and Zottola M.A. Biochemistry 26 (1987) 2682