Differences among allelic variants of human glutathione transferase A2-2 in the activation of azathioprine

Chemico-Biological Interactions

Volumn 186, Issue 2, 2010, Pages 110-117

  Zhang, Wei ^a   Modén, Olof ^a   Mannervik, Bengt ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Allelic variants; Azathioprine; Bioactivation; Glutathione transferase; Thiopurine methyltransferase

Indexed keywords

AZATHIOPRINE; GLUTATHIONE TRANSFERASE A2; GLUTATHIONE TRANSFERASE A2 2; GLUTATHIONE TRANSFERASE M1; MERCAPTOPURINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG ACTIVATION; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME POLYMORPHISM; PROTEIN EXPRESSION;

6-MERCAPTOPURINE; ALLELES; AMINO ACID SUBSTITUTION; ANTIMETABOLITES, ANTINEOPLASTIC; AZATHIOPRINE; BASE SEQUENCE; DNA PRIMERS; ENZYME ACTIVATION; ENZYME STABILITY; GENETIC ASSOCIATION STUDIES; GENETIC VARIATION; GLUTATHIONE TRANSFERASE; HUMANS; IMMUNOSUPPRESSIVE AGENTS; ISOENZYMES; KINETICS; MULTIVARIATE ANALYSIS; MUTAGENESIS, SITE-DIRECTED; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

EID: 77953539483     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.04.028     Document Type: Article

References (38)

1. Maltzman J.S., Koretzky G.A. Azathioprine: old drug, new actions. J. Clin. Invest. 2003, 111(8):1122-1124.
2. Van Scoik K.G., Johnson C.A., Porter W.R. The pharmacology and metabolism of the thiopurine drugs 6-mercaptopurine and azathioprine. Drug Metab. Rev. 1985, 16(1-2):157-174.
3. Elion G.B. The George Hitchings and Gertrude Elion lecture. The pharmacology of azathioprine. Ann. N. Y. Acad. Sci. 1993, 685:400-407.
4. Louis E., Belaiche J. Optimizing treatment with thioguanine derivatives in inflammatory bowel disease. Best Pract. Res. Clin. Gastroenterol. 2003, 17(1):37-46.
5. Karran P. Thiopurines, DNA damage, DNA repair and therapy-related cancer. Br. Med. Bull. 2006, 79-80:153-170.
6. Gearry R.B., Barclay M.L. Azathioprine and 6-mercaptopurine pharmacogenetics and metabolite monitoring in inflammatory bowel disease. J. Gastroenterol. Hepatol. 2005, 20(8):1149-1157.
7. Coulthard S., Hogarth L. The thiopurines: an update. Invest. New Drugs 2005, 23(6):523-532.
8. Lyttle M.H., Satyam A., Hocker M.D., Bauer K.E., Caldwell C.G., Hui H.C., Morgan A.S., Mergia A., Kauvar L.M. Glutathione-S-transferase activates novel alkylating agents. J. Med. Chem. 1994, 37(10):1501-1507.
9. Morgan A.S., Sanderson P.E., Borch R.F., Tew K.D., Niitsu Y., Takayama T., Von Hoff D.D., Izbicka E., Mangold G., Paul C., Broberg U., Mannervik B., Henner W.D., Kauvar L.M. Tumor efficacy and bone marrow-sparing properties of TER286, a cytotoxin activated by glutathione S-transferase. Cancer Res. 1998, 58(12):2568-2575.
10. Cozzi P., Beria I., Caldarelli M., Geroni C., Mongelli N., Pennella G. Cytotoxic α-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety. Bioorg. Med. Chem. Lett. 2000, 10(11):1273-1276.
11. Eklund B.I., Moberg M., Bergquist J., Mannervik B. Divergent activities of human glutathione transferases in the bioactivation of azathioprine. Mol. Pharmacol. 2006, 70(2):747-754.
12. Kurtovic S., Grehn L., Karlsson A., Hellman U., Mannervik B. Glutathione transferase activity with a novel substrate mimics the activation of the prodrug azathioprine. Anal. Biochem. 2008, 375(2):339-344.
13. 5-androstene-3, 17-dione catalyzed by human glutathione transferase A1-1. J. Biol. Chem. 2001, 276(15):11698-11704.
14. Kurtovic S., Shokeer A., Mannervik B. Diverging catalytic capacities and selectivity profiles with haloalkane substrates of chimeric alpha class glutathione transferases. Protein Eng. Des. Sel. 2008, 21(5):329-341.
15. Widersten M., Björnestedt R., Mannervik B. Involvement of the carboxyl groups of glutathione in the catalytic mechanism of human glutathione transferase A1-1. Biochemistry 1996, 35(24):7731-7742.
16. Nilsson L.O., Edalat M., Pettersson P.L., Mannervik B. Aromatic residues in the C-terminal region of glutathione transferase A1-1 influence rate-determining steps in the catalytic mechanism. Biochim. Biophys. Acta 2002, 1598(1-2):199-205.
17. Krzanowski W.J. Principles of Multivariate Analysis: A User's Perspective 2000, Oxford University Press, New York.
18. Kurtovic S., Mannervik B. Identification of emerging quasi-species in directed enzyme evolution. Biochemistry 2009, 48(40):9330-9339.
19. Weinshilboum R., Wang L. Pharmacogenomics: bench to bedside. Nat. Rev. Drug Discov. 2004, 3(9):739-748.
20. Wang L., Weinshilboum R. Thiopurine S-methyltransferase pharmacogenetics: insights, challenges and future directions. Oncogene 2006, 25(11):1629-1638.
21. Jackson A.P., Hall A.G., McLelland J. Thiopurine methyltransferase levels should be measured before commencing patients on azathioprine. Br. J. Dermatol. 1997, 136(1):133-134.
22. Leipold G., Schutz E., Haas J.P., Oellerich M. Azathioprine-induced severe pancytopenia due to a homozygous two-point mutation of the thiopurine methyltransferase gene in a patient with juvenile HLA-B27-associated spondylarthritis. Arthritis Rheum. 1997, 40(10):1896-1898.
23. Colombel J.F., Ferrari N., Debuysere H., Marteau P., Gendre J.P., Bonaz B., Soule J.C., Modigliani R., Touze Y., Catala P., Libersa C., Broly F. Genotypic analysis of thiopurine S-methyltransferase in patients with Crohn's disease and severe myelosuppression during azathioprine therapy. Gastroenterology 2000, 118(6):1025-1030.
24. Takatsu N., Matsui T., Murakami Y., Ishihara H., Hisabe T., Nagahama T., Maki S., Beppu T., Takaki Y., Hirai F., Yao K. Adverse reactions to azathioprine cannot be predicted by thiopurine S-methyltransferase genotype in Japanese patients with inflammatory bowel disease. J. Gastroenterol. Hepatol. 2009, 24(7):1258-1264.
25. Lo H.W., Ali-Osman F. Genetic polymorphism and function of glutathione S-transferases in tumor drug resistance. Curr. Opin. Pharmacol. 2007, 7(4):367-374.
26. McIlwain C.C., Townsend D.M., Tew K.D. Glutathione S-transferase polymorphisms: cancer incidence and therapy. Oncogene 2006, 25(11):1639-1648.
27. Johansson A.S., Mannervik B. Interindividual variability of glutathione transferase expression. Interindividual Variability in Human Drug Metabolism 2001, 460-519. Taylor & Francis, London. G.M. Pacifici, O. Pelkonen (Eds.).
28. Morel F., Rauch C., Coles B., Le Ferrec E., Guillouzo A. The human glutathione transferase alpha locus: genomic organization of the gene cluster and functional characterization of the genetic polymorphism in the hGSTA1 promoter. Pharmacogenetics 2002, 12(4):277-286.
29. Xu S., Wang Y., Roe B., Pearson W.R. Characterization of the human class Mu glutathione S-transferase gene cluster and the GSTM1 deletion. J. Biol. Chem. 1998, 273(6):3517-3527.
30. Tetlow N., Board P.G. Functional polymorphism of human glutathione transferase A2. Pharmacogenetics 2004, 14(2):111-116.
31. Silva S.N., Azevedo A.P., Teixeira V., Pina J.E., Rueff J., Gaspar J.F. The role of GSTA2 polymorphisms and haplotypes in breast cancer susceptibility: a case-control study in the Portuguese population. Oncol. Rep. 2009, 22(3):593-598.
32. Tapner M.J., Jones B.E., Wu W.M., Farrell G.C. Toxicity of low dose azathioprine and 6-mercaptopurine in rat hepatocytes. Roles of xanthine oxidase and mitochondrial injury. J. Hepatol. 2004, 40(3):454-463.
33. Coles B.F., Kadlubar F.F. Human alpha class glutathione S-transferases: genetic polymorphism, expression, and susceptibility to disease. Methods Enzymol. 2005, 401:9-42.
34. Ning B., Wang C., Morel F., Nowell S., Ratnasinghe D.L., Carter W., Kadlubar F.F., Coles B. Human glutathione S-transferase A2 polymorphisms: variant expression, distribution in prostate cancer cases/controls and a novel form. Pharmacogenetics 2004, 14(1):35-44.
35. Shen H., Ranganathan S., Kuzmich S., Tew K.D. Influence of ethacrynic acid on glutathione S-transferase pi transcript and protein half-lives in human colon cancer cells. Biochem. Pharmacol. 1995, 50(8):1233-1238.
36. Garcia-Mata R., Conde R.D., Sanllorenti P.M. Contribution of breakdown in the regulation of mouse liver glutathione S-transferase subunits during protein depletion and re-feeding. Biochim. Biophys. Acta 1998, 1448(1):46-50.
37. Marinaki A.M., Ansari A., Duley J.A., Arenas M., Sumi S., Lewis C.M., Shobowale-Bakre el M., Escuredo E., Fairbanks L.D., Sanderson J.D. Adverse drug reactions to azathioprine therapy are associated with polymorphism in the gene encoding inosine triphosphate pyrophosphatase (ITPase). Pharmacogenetics 2004, 14(3):181-187.
38. Stocco G., Martelossi S., Barabino A., Decorti G., Bartoli F., Montico M., Gotti A., Ventura A. Glutathione-S-transferase genotypes and the adverse effects of azathioprine in young patients with inflammatory bowel disease. Inflamm. Bowel Dis. 2007, 13(1):57-64.