Importance of a hypervariable active-site residue in human Mu class glutathione transferases catalyzing the bioactivation of chemotherapeutic thiopurine prodrugs

Biochimica et Biophysica Acta - General Subjects

Volumn 1770, Issue 8, 2007, Pages 1098-1103

  Eklund, Birgitta I ^a   Mannervik, Bengt ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Active site mutation; Functional plasticity; Glutathione transferase; Modulated activity; Thiopurine prodrugs

Indexed keywords

6 (2 ACETYLVINYLTHIO)GUANINE; 6 (2 ACETYLVINYLTHIO)PURINE; ALANINE; ENZYME; GLUTATHIONE TRANSFERASE M1; GLUTATHIONE TRANSFERASE M2; GLUTATHIONE TRANSFERASE M4; GLUTATHIONE TRANSFERASE M5; GLYCINE; GUANINE DERIVATIVE; HYDROXYL GROUP; MERCAPTOPURINE; PRODRUG; PROLINE; PURINE DERIVATIVE; SERINE; THREONINE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CATALYSIS; COMPARATIVE STUDY; DRUG ACTIVATION; ENZYME ACTIVITY; POINT MUTATION; PRIORITY JOURNAL; STEREOSPECIFICITY; WILD TYPE;

6-MERCAPTOPURINE; AMINO ACID SUBSTITUTION; ANTIMETABOLITES, ANTINEOPLASTIC; BINDING SITES; CATALYSIS; GLUTATHIONE TRANSFERASE; HUMANS; KINETICS; MOLECULAR STRUCTURE; PRODRUGS; SERINE; SPECTROPHOTOMETRY, ULTRAVIOLET; SUBSTRATE SPECIFICITY;

EID: 34347220501     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbagen.2007.04.001     Document Type: Article

References (26)

1. Eklund B.I., Moberg M., Bergquist J., and Mannervik B. Divergent activities of human glutathione transferases in the bioactivation of azathioprine. Mol. Pharmacol. 70 (2006) 747-754
2. Eklund B.I., Gunnarsdottir S., Elfarra A.A., and Mannervik B. Human glutathione transferases catalyzing the bioactivation of anticancer thiopurine prodrugs. Biochem. Pharmacol. 73 (2007) 1829-1841
3. Cara C.J., Pena A.S., Sans M., Rodrigo L., Guerrero-Esteo M., Hinojosa J., Garcia-Paredes J., and Guijarro L.G. Reviewing the mechanism of action of thiopurine drugs: towards a new paradigm in clinical practice. Med. Sci. Monit. 10 (2004) 247-254
4. Gunnarsdottir S., and Elfarra A.A. Cytotoxicity of the novel glutathione-activated thiopurine prodrugs cis-AVTP [cis-6-(2-acetylvinylthio)purine] and trans-AVTG [trans-6-(2-acetylvinylthio)guanine] results from the National Cancer Institute's anticancer drug screen. Drug Metab. Dispos. 32 (2004) 321-327
5. Gunnarsdottir S., Rucki M., and Elfarra A.A. Novel glutathione-dependent thiopurine prodrugs: evidence for enhanced cytotoxicity in tumor cells and for decreased bone marrow toxicity in mice. J. Pharmacol. Exp. Ther. 301 (2002) 77-86
6. Castro V.M., Soderström M., Carlberg I., Widersten M., Platz A., and Mannervik B. Differences among human tumor cell lines in the expression of glutathione transferases and other glutathione-linked enzymes. Carcinogenesis 11 (1990) 1569-1576
7. Mannervik B., Castro V.M., Danielson U.H., Tahir M.K., Hansson J., and Ringborg U. Expression of class Pi glutathione transferase in human malignant melanoma cells. Carcinogenesis 8 (1987) 1929-1932
8. Tew K.D., Monks A., Barone L., Rosser D., Akerman G., Montali J.A., Wheatley J.B., and Schmidt Jr. D.E. Glutathione-associated enzymes in the human cell lines of the National Cancer Institute Drug Screening Program. Mol. Pharmacol. 50 (1996) 149-159
9. Lyttle M.H., Satyam A., Hocker M.D., Bauer K.E., Caldwell C.G., Hui H.C., Morgan A.S., Mergia A., and Kauvar L.M. Glutathione-S-transferase activates novel alkylating agents. J. Med. Chem. 37 (1994) 1501-1507
10. 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., and Kauvar L.M. Tumor efficacy and bone marrow-sparing properties of TER286, a cytotoxin activated by glutathione S-transferase. Cancer Res. 58 (1998) 2568-2575
11. Kavanagh J.J., Gershenson D.M., Choi H., Lewis L., Patel K., Brown G.L., Garcia A., and Spriggs D.R. Multi-institutional phase 2 study of TLK286 (TELCYTA, a glutathione S-transferase P1-1 activated glutathione analog prodrug) in patients with platinum and paclitaxel refractory or resistant ovarian cancer. Int. J. Gynecol. Cancer 15 (2005) 593-600
12. Hamilton D.S., Zhang X., Ding Z., Hubatsch I., Mannervik B., Houk K.N., Ganem B., and Creighton D.J. Mechanism of the glutathione transferase-catalyzed conversion of antitumor 2-crotonyloxymethyl-2-cycloalkenones to GSH adducts. J. Am. Chem. Soc. 125 (2003) 15049-15058
13. Saavedra J.E., Srinivasan A., Buzard G.S., Davies K.M., Waterhouse D.J., Inami K., Wilde T.C., Citro M.L., Cuellar M., Deschamps J.R., Parrish D., Shami P.J., Findlay V.J., Townsend D.M., Tew K.D., Singh S., Jia L., Ji X., and Keefer L.K. PABA/NO as an anticancer lead: analogue synthesis, structure revision, solution chemistry, reactivity toward glutathione, and in vitro activity. J. Med. Chem. 49 (2006) 1157-1164
14. Josephy D.P., and Mannervik B. Molecular Toxicology. second ed. (2006), Oxford Univ. Press, Inc, New York
15. Mannervik B., Board P.G., Hayes J.D., Listowsky I., and Pearson W.R. Nomenclature for mammalian soluble glutathione transferases. Methods Enzymol. 401 (2005) 1-8
16. Ivarsson Y., Mackey A.J., Edalat M., Pearson W.R., and Mannervik B. Identification of residues in glutathione transferase capable of driving functional diversification in evolution-A novel approach to protein redesign. J. Biol. Chem. 278 (2003) 8733-8738
17. Ivarsson Y., and Mannervik B. Regio- and enantioselectivities in epoxide conjugations are modulated by residue 210 in Mu class glutathione transferase. Protein Eng. Des. Sel. 18 (2005) 607-616
18. Norrgård M.A., Ivarsson Y., Tars K., and Mannervik B. Alternative mutations of a positively selected residue elicit gain or loss of functionalities in enzyme evolution. Proc. Natl. Acad. Sci. U. S. A. 103 (2006) 4876-4881
19. Johansson A.-S., Bolton-Grob R., and Mannervik B. Use of silent mutations in cDNA encoding human glutathione transferase M2-2 for optimized expression in Escherichia coli. Protein Expr. Purif. 17 (1999) 105-112
20. Widersten M., Huang M., and Mannervik B. Optimized heterologous expression of the polymorphic human glutathione transferase M1-1 based on silent mutations in the corresponding cDNA. Protein Expr. Purif. 7 (1996) 367-372
21. Hansson L., Bolton-Grob R., Widersten M., and Mannervik B. Structural determinants in domain II of human glutathione transferase M2-2 govern the characteristic activities with aminochrome, 2-cyano-1,3- dimethyl-1-nitrosoguanidine, and 1,2-dichloro-4-nitrobenzene. Protein Sci. 8 (1999) 2742-2750
22. Simons P.C., and Vander Jagt D.L. Purification of glutathione S-transferases by glutathione-affinity chromatography. Methods Enzymol. 77 (1981) 235-237
23. W.G. Bardsley, http://www.simfit.man.ac.uk, (2006).
24. Fersht A. Structure and Mechanism in Protein Science. A Guide to Enzyme Catalysis and Protein Folding (1999), Freeman, W.H., New York
25. Patskovsky Y.V., Patskovska L.N., and Listowsky I. Functions of His107 in the catalytic mechanism of human glutathione S-transferase hGSTM1a-1a. Biochemistry 38 (1999) 1193-1202
26. Xiao G., Liu S., Ji X., Johnson W.W., Chen J., Parsons J.F., Stevens W.J., Gillil G.L., and Armstrong R.N. First-sphere and second-sphere electrostatic effects in the active site of a class mu gluthathione transferase. Biochemistry 35 (1996) 4753-4765