Glyoxalase enzyme system as a potential target for antitumor drug development

Drugs of the Future

Volumn 25, Issue 4, 2000, Pages 385-392

  Creighton, Donald J ^a   Hamilton, Diana S ^a   Kavarana, Malcolm J ^a   Sharkey, Ellyn M ^a   Eiseman, Julie L ^b  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

^b UNIVERSITY OF PITTSBURGH MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; GLYOXALASE; PRODRUG;

ANTINEOPLASTIC ACTIVITY; CANCER THERAPY; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG POTENCY; DRUG TARGETING; ENZYME INHIBITION; HUMAN; NONHUMAN; REVIEW;

EID: 0034082780     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2000.025.04.858665     Document Type: Review

References (37)

1. Thornalley, P.J. Glutathione-dependent detoxification of α oxoaldehydes by the glyoxalase system: Involvement in disease mechanisms and antiproliferative activity of glyoxalase I inhibitors. Chem Biol Interact 1998, 111-112: 137-51.
2. Thornalley, P.J. Advances in glyoxalase research. Glyoxalase expression in malignancy, anti-proliferative effects of methylglyoxal, glyoxalase I inhibitor diesters and S-D-lactoylglutathione, and methylglyoxal-modified protein binding and endocytosis by the advanced glycation end product receptor. Crit Rev Oncol Hematol 1994, 20: 99-128.
3. Vander Jagt, D.L. The glyoxalase system. In: Coenzymes and Cofactors: Glutathione, Vol. 3, Part A. Dolphin, D., Poulson, R., Avramovic, O. (Eds.). John Wiley and Sons: New York 1989, 597-641.
4. Creighton, D.J., Pourmotabbed, T. Glutathione-dependent aldehyde oxidation reactions. In: Molecular Structure and Energetics: Principles of Enzyme Activity, Vol. 9. Liebman, J.F., Greenberg, A. (Eds.). VCH Publishers: New York 1988, 353-86.
5. Creighton, D.J., Murthy, N.S.R.K. Stereochemistry of enzyme-catalyzed reactions at carbon. In: The Enzymes, 3rd Ed., Vol. 19. Sigman, D.S., Boyer, P.D. (Eds.). Academic Press 1990, 323-421.
6. Kalapos, M.P. On the promine/retine theory of cell division: Now and then. Biochim Biophys Acta 1998, 1426: 1-16.
7. Richard, J.P. Kinetic parameters for the elimination reaction catalyzed by triosephosphate isomerase and an estimation of the reaction's physiological significance. Biochemistry 1991, 30: 4581-5.
8. Ranganathan, S., Walsh, E.S., Tew, K.D. Glyoxalase I in detoxification: Studies using a glyoxalase I transfectant cell line. Biochem J 1995, 309: 127-31.
9. Creighton, D.J., Migliorini, M., Pourmotabbed, T., Guha, M. Optimization of efficiency in the glyoxalase pathway. Biochemistry 1988, 27: 7376-84.
10. Shih, M.J., Edinger, J.W., Creighton, D.J. Diffusion-dependent kinetic properties of glyoxalase I and estimates of the steady-state concentrations of glyoxalase pathway intermediates in glycolyzing erythrocytes. Eur J Biochem 1997, 244: 852-7.
11. Griffis, C.E.F., Ong, L.H., Buettner, L., Creighton, D.J. Nonstereospecific substrate usage by glyoxalase I. Biochemistry 1983, 22: 2945-51.
12. Guha, M.K., Vander Jagt, D.L., Creighton, D.J. Diffusion-dependent rates for the hydrolysis reaction catalyzed by glyoxalase II from rat erythrocytes. Biochemistry 1988, 27: 8818-22.
13. Vander Jagt, D.L., Robinson, B., Taylor, K.K., Hunsaker, L.A. Reduction of trioses by NADPH-dependent aldo-keto reductases. Aldose reductase, methylglyoxal, and diabetic complications. J Biol Chem 1992, 267: 4364-9.
14. Reiften, K.A., Schneeder, F.A. A comparative study on proliferation, macromolecular synthesis and energy metabolism of in vitro-grown Ehrlich ascites tumor cells in the presence of glucosone, galactosone and methylglyoxal. J Cancer Res Clin Oncol 1984, 107: 206-10.
15. Ayoub, F.M., Allen, R.E., Thornalley P.J. Inhibition of proliferation of human leukaemia 60 cells by methylglyoxal in vitro. Leuk Res 1993, 17: 397-401.
16. Amicarelli, F., Bucciarelli, T., Poma, A. et al. Adaptive response of human melanoma cells to methylglyoxal injury. Carcinogenesis 1998, 19: 519-23.
17. Okada, A., Kawasaki, Y., Hasuike, Y. et al. Induction of apoptotic cell death by methylglyoxal and 3-deoxyglucosone in macrophage-derived cell lines. Biochem Biophys Res Commun 1996, 225: 219-24.
18. Kang, Y., Edwards, L.G., Thornalley, P.J. Effect of methylglyoxal on human leukaemia 60 cell growth: Modification of DNA, GI growth arrest and induction of apoptosis. Leuk Res 1996, 5: 397-405.
19. Baskaran, S., Balasubramanian, K.A. Toxicity of methylglyoxal towards rat enterocytes and colonocytes. Biochem Int 1990, 212: 166-74.
20. Ray, M., Halder, J., Dutta, S.K., Ray, S. Inhibition of respiration of tumor cells by methylglyoxal and protection of inhibition by lactaldehyde. Int J Cancer 1991, 47: 603-9.
21. White, J.S., Rees, K.R. Inhibitory effects of methylglyoxal on DNA, RNA and protein synthesis in cultured guinea pig keratocytes. Chem Biol Interact 1982, 38: 339-47.
22. Vince, R., Daluge, S. A possible approach to anticancer agents. J Med Chem 1971, 14: 35-7.
23. Vince, R., Daluge, S., Wadd, W.B. Studies on the inhibition ofglyoxalase I by S-substituted giutathiones. J Med Chem 1971, 14: 402-4.
24. Murthy, N.S.R.K., Bakeris, T., Kavarana, M.J., Hamilton, D.S., Lan, Y., Creighton, D.J. S-(N-Aryl-N-hydroxycarbamoyl)glutathione derivatives are tight-binding inhibitors of glyoxalase I and slow substrates for glyoxalase II. J Med Chem 1994, 37: 2161-6.
25. Cameron, A.D., Olin, B., Ridderstrom, M., Mannervik, B., Jones, A. Crystal structure of human glyoxaiase I - Evidence for gene duplication and 3D domain swapping. EMBO 1997, 16: 3386-95.
26. Vince, R., Brownell, J., Akella, L.B. Synthesis and activity of γ-(L-γ-azaglutamyl)-S-(p-brobenzyl)-L-cysteinylglycine: A metabolically stable inhibitor of glyoxalase I. Bioorg Med Chem Lett 1999, 9: 853-6.
27. Hamilton, D.S., Creighton, D.J. Inhibition of glyoxalase I by the enediol mimic S-(N-hydroxy-N-methylcarbamoyl)glutathione: The possible basis of a tumor-selective anticancer strategy. J Biol Chem 1992, 267: 24933-6.
28. Cameron, A.D., Ridderstrom, M., Olin, B., Kavarana, M.J., Creighton, D.J., Mannervik, B. Reaction mechanism of glyoxalase I explored by an X-ray crystallographic analysis of the human enzyme in complex with a transition state analogue. Biochemistry 1999, 38: 13480-90.
29. Ly, H.D., Clugston, S.L., Sampson, P.B., Honek, J.F. Synthesis and kinetic evaluation of hydroxamate-based peptide inhibitors of glyoxalase I. Bioorg Med Chem Lett 1998, 8: 705-10.
30. Lo, T.W.C., Thornalley, P.J. Inhibition of proliferation of human leukemia 60 cells by diethyl esters of glyoxalase inhibitors in vitro. Biochem Pharmacol 1992, 44: 2357-63.
31. Kavarana, M.J., Kovaleva, E.G., Creighton, D.J., Wollman, M.B., Eiseman, J.L. Mechanism-based competitive inhibitors of glyoxalase I: Intracellular delivery, in vitro antitumor activities, and stabilities in human serum and mouse serum. J Med Chem 1999, 42: 221-8.
32. Hamilton, D.S., Kavarana, M.J., Sharkey, E.M., Eiseman, J.L., Creighton, D.J. A new method for rapidly generating inhibitors of glyoxalase I inside tumor cells using S-(N-aryl-N-hydroxycarbamoyl)ethylsulfoxides. J Med Chem 1999, 42: 1823-7.
33. Thornalley, P.J., Ladan, M.J., Ridgeway, S.J.S., Kang, Y. Antitumor activity of S-(p-bromobenzyl)glutathione diesters in vitro: A structure activity study. J Med Chem 1996, 39: 3409-11.
34. Thornalley, P.J., Edwards, L.G., Kang, Y.W. et al. Antitumour activity of S-p-bromobenzy/glutathione cyclopentyl diester in vitro and in vivo. Inhibition of glyoxalase I and induction of apoptosis Biochem Pharmacol 1996, 51: 1365-72.
35. Jerzykowski, T., Winter, R., Matuszewski, W., Piskorska, D. A reevaluation of studies on the distribution of glyoxalases in animal and tumor tissues. Int J Biochem 1978, 9: 853-60.
36. Sharkey, E.M., O'Neill, H.B., Kavarana, M.J., Creighton, D.J., Sentz, D.L., Eiseman, J.L. Pharmacokinetics and anti-tumor properties in tumor-bearing mice of an enediol analogue inhibitor of glyoxalase I. Cancer Chemother Pharmacol 1999, accepted.
37. Ayoub, F., Zaman, M., Thornalley, P., Masters, J. Glyoxalase activities in human tumor cell lines in vitro. Anticancer Res 1993, 13: 151-6.