Divergent effects of compounds on the hydrolysis and transpeptidation reactions of γ-glutamyl transpeptidase

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 4, 2012, Pages 476-489

  Wickham, Stephanie ^a   Regan, Nicholas ^b   West, Matthew B ^a   Kumar, Vidya Prasanna ^c   Thai, Justin ^b   Li, Pui Kai ^b   Cook, Paul F ^c   Hanigan, Marie H ^a  

^a UNIVERSITY OF OKLAHOMA COLLEGE OF MEDICINE   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

Enzyme; Gamma glutamyl substrates; Inhibition; OU749

Indexed keywords

ACIVICIN; ACYLTRANSFERASE INHIBITOR; DIPEPTIDE; GAMMA GLUTAMYLTRANSFERASE; OU 749; OU 749 DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG POTENCY; DRUG STRUCTURE; ELECTRON; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME MECHANISM; HUMAN; HYDROLYSIS; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL;

DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; GAMMA-GLUTAMYLTRANSFERASE; HUMANS; HYDROLYSIS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; THIADIAZOLES;

EID: 84864069695     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.597748     Document Type: Article

References (45)

1. Hanigan MH. γGlutamyl transpeptidase, a glutathionase: Its expression and function in carcinogenesis. Chem Biol Interact 1998;111-112:333-342.
2. Hanigan MH, Frierson HF Jr. Immunohistochemical detection of γglutamyl transpeptidase in normal human tissue. J Histochem Cytochem 1996;44:1101-1108.
3. Lieberman MW, Wiseman AL, Shi ZZ, Carter BZ, Barrios R, Ou CN et al. Growth retardation and cysteine deficiency in γ-glutamyl transpeptidase-deficient mice. Proc Natl Acad Sci USA 1996;93:7923-7926.
4. Hanigan MH, Frierson HF Jr, Swanson PE, De Young BR. Altered expression of γ-glutamyl transpeptidase in human tumors. Hum Pathol 1999;30:300-305.
5. Ruoso P, Hedley DW. Inhibition of γ-glutamyl transpeptidase activity decreases intracellular cysteine levels in cervical carcinoma. Cancer Chemother Pharmacol 2004;54:49-56.
6. Hanigan MH, Gallagher BC, Townsend DM, Gabarra V. γ-glutamyl transpeptidase accelerates tumor growth and increases the resistance of tumors to cisplatin in vivo. Carcinogenesis 1999; 20:553-559.
7. Hanigan MH, Pitot HC. γ-glutamyl transpeptidase-its role in hepatocarcinogenesis. Carcinogenesis 1985;6:165-172.
8. Lowry MH, McAllister BP, Jean JC, Brown LA, Hughey RP, Cruikshank WW et al. Lung lining fluid glutathione attenuates IL-13-induced asthma. Am J Respir Cell Mol Biol 2008;38:509-516.
9. Ahluwalia GS, Grem JL, Hao Z, Cooney DA. Metabolism and action of amino acid analog anti-cancer agents. Pharmacol Ther 1990;46:243-271.
10. Weiss GR, McGovren JP, Schade D, Kufe DW. Phase I and pharmacological study of acivicin by 24-hour continuous infusion. Cancer Res 1982;42:3892-3895.
11. Earhart RH, Koeller JM, Davis TE, Borden EC, McGovren JP, Davis HL et al. Phase I trial and pharmacokinetics of acivicin administered by 72-hour infusion. Cancer Treat Rep 1983;67:683-692.
12. Fleishman G, Yap HY, Murphy WK, Bodey G. Phase II trial of acivicin in advanced metastatic breast cancer. Cancer Treat Rep 1983;67:843-844.
13. Taylor S, Belt RJ, Joseph U, Haas CD, Hoogstraten B. Phase I evaluation of AT-125 single dose every three weeks. Invest New Drugs 1984;2:311-314.
14. King JB, West MB, Cook PF, Hanigan MH. A novel, species-specific class of uncompetitive inhibitors of γ-glutamyl transpeptidase. J Biol Chem 2009;284:9059-9065.
15. Tate SS, Meister A. Interaction of γ-glutamyl transpeptidase with amino acids, dipeptides, and derivatives and analogs of glutathione. J Biol Chem 1974;249:7593-7602.
16. Tate SS, Meister A. Stimulation of the hydrolytic activity and decrease of the transpeptidase activity of γ-glutamyl transpeptidase by maleate; identity of a rat kidney maleatestimulated glutaminase and γ-glutamyl transpeptidase. Proc Natl Acad Sci USA 1974;71:3329-3333.
17. Castonguay R, Lherbet C, Keillor JW. Kinetic studies of rat kidney γ-glutamyltranspeptidase deacylation reveal a general basecatalyzed mechanism. Biochemistry 2003;42:11504-11513.
18. Keillor JW, Castonguay R, Lherbet C. γ-glutamyl transpeptidase substrate specificity and catalytic mechanism. Meth Enzymol 2005;401:449-467.
19. Han L, Hiratake J, Kamiyama A, Sakata K. Design, synthesis, and evaluation of γ-phosphono diester analogues of glutamate as highly potent inhibitors and active site probes of γ-glutamyl transpeptidase. Biochemistry 2007;46:1432-1447.
20. Lherbet C, Keillor JW. Probing the stereochemistry of the active site of γ-glutamyl transpeptidase using sulfur derivatives of l-glutamic acid. Org Biomol Chem 2004;2:238-245.
21. Thompson GA, Meister A. Hydrolysis and transfer reactions catalyzed by γ-glutamyl transpeptidase; evidence for separate substrate sites and for high affinity of L-cystine. Biochem Biophys Res Commun 1976;71:32-36.
22. Elce JS, Broxmeyer B. γ-Glutamyltransferase of rat kidney. Simultaneous assay of the hydrolysis and transfer reactions with (glutamate-14C)glutathione. Biochem J 1976;153:223-232.
23. Curthoys NP, Hughey RP. Characterization and physiological function of rat renal γ-glutamyltranspeptidase. Enzyme 1979;24:383-403.
24. Allison RD, Meister A. Evidence that transpeptidation is a significant function of γ-glutamyl transpeptidase. J Biol Chem 1981;256:2988-2992.
25. Cook PF, Cleland WW. Enzyme Kinetics and Mechanism. Garland Science, London, New York, 2007.
26. Allison RD. γ-Glutamyl transpeptidase: Kinetics and mechanism. Meth Enzymol 1985;113:419-437.
27. Stole E, Smith TK, Manning JM, Meister A. Interaction of γ-glutamyl transpeptidase with acivicin. J Biol Chem 1994;269:21435-21439.
28. Smith TK, Ikeda Y, Fujii J, Taniguchi N, Meister A. Different sites of acivicin binding and inactivation of γ-glutamyl transpeptidases. Proc Natl Acad Sci USA 1995;92:2360-2364.
29. Ikeda Y, Fujii J, Anderson ME, Taniguchi N, Meister A. Involvement of Ser-451 and Ser-452 in the catalysis of human γ-glutamyl transpeptidase. J Biol Chem 1995;270:22223-22228.
30. Castonguay R, Halim D, Morin M, Furtos A, Lherbet C, Bonneil E et al. Kinetic characterization and identification of the acylation and glycosylation sites of recombinant human γ-glutamyltranspeptidase. Biochemistry 2007;46:12253-12262.
31. Thompson GA, Meister A. Modulation of the hydrolysis, transfer, and glutaminase activities of γ-glutamyl transpeptidase by maleate bound at the cysteinylglycine binding site of the enzyme. J Biol Chem 1979;254:2956-2960.
32. Tate SS, Meister A. Serine-borate complex as a transition-state inhibitor of γ-glutamyl transpeptidase. Proc Natl Acad Sci USA 1978;75:4806-4809.
33. Okada T, Suzuki H, Wada K, Kumagai H, Fukuyama K. Crystal structures of γ-glutamyltranspeptidase from Escherichia coli, a key enzyme in glutathione metabolism, and its reaction intermediate. Proc Natl Acad Sci USA 2006;103:6471-6476.
34. Wada K, Irie M, Suzuki H, Fukuyama K. Crystal structure of the halotolerant γ-glutamyltranspeptidase from Bacillus subtilis in complex with glutamate reveals a unique architecture of the solvent-exposed catalytic pocket. FEBS J 2010;277:1000-1009.
35. Morrow AL, Williams K, Sand A, Boanca G, Barycki JJ. Characterization of Helicobacter pylori γ-glutamyltranspeptidase reveals the molecular basis for substrate specificity and a critical role for the tyrosine 433-containing loop in catalysis. Biochemistry 2007;46:13407-13414.
36. Ikeda Y, Fujii J, Taniguchi N, Meister A. Human γ-glutamyl transpeptidase mutants involving conserved aspartate residues and the unique cysteine residue of the light subunit. J Biol Chem 1995;270:12471-12475.
37. Hanigan MH, Ricketts WA. Extracellular glutathione is a source of cysteine for cells that express γ-glutamyl transpeptidase. Biochemistry 1993;32:6302-6306.
38. Estrela JM, Ortega A, Obrador E. Glutathione in cancer biology and therapy. Crit Rev Clin Lab Sci 2006;43:143-181.
39. Perry RR, Mazetta JA, Levin M, Barranco SC. Glutathione levels and variability in breast tumors and normal tissue. Cancer 1993;72:783-787.
40. Oberli-Schrämmli AE, Joncourt F, Stadler M, Altermatt HJ, Buser K, Ris HB et al. Parallel assessment of glutathione-based detoxifying enzymes, O6-alkylguanine-DNA alkyltransferase and P-glycoprotein as indicators of drug resistance in tumor and normal lung of patients with lung cancer. Int J Cancer 1994;59:629-636.
41. Joncourt F, Oberli-Schrämmli AE, Stadler M, Buser K, Franscini L, Fey MF et al. Patterns of drug resistance parameters in adult leukemia. Leuk Lymphoma 1995;17:101-109.
42. Raderer M, Scheithauer W. Clinical trials of agents that reverse multidrug resistance. A literature review. Cancer 1993;72: 3553-3563.
43. Mulder TP, Manni JJ, Roelofs HM, Peters WH, Wiersma A. Glutathione S-transferases and glutathione in human head and neck cancer. Carcinogenesis 1995;16:619-624.
44. Mena S, Benlloch M, Ortega A, Carretero J, Obrador E, Asensi M et al. Bcl-2 and glutathione depletion sensitizes B16 melanoma to combination therapy and eliminates metastatic disease. Clin Cancer Res 2007;13:2658-2666.
45. Rudin CM, Yang Z, Schumaker LM, VanderWeele DJ, Newkirk K, Egorin MJ et al. Inhibition of glutathione synthesis reverses Bcl-2-mediated cisplatin resistance. Cancer Res 2003;63:312-318.