Conjugation of isoprene monoepoxides with glutathione, catalyzed by α, μ, π and θ-class glutathione S-transferases of rat and man

Chemico-Biological Interactions

Volumn 117, Issue 1, 1999, Pages 1-14

  Bogaards, Jan J P ^a   Venekamp, Joke C ^a   Salmon, Florence G C ^a   Van Bladeren, Peter J ^a  

^a TNO   (Netherlands)

Author keywords

Glutathione S transferase; Isoprene; Metabolism; Polymorphism

Indexed keywords

CYTOCHROME P450; EPOXIDE; EPOXIDE HYDROLASE; GLUTATHIONE; GLUTATHIONE TRANSFERASE; ISOPRENE;

ARTICLE; CONJUGATE; CONJUGATION; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIVER; LIVER METABOLISM; MOUSE; RAT; XENOBIOTIC METABOLISM;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EPOXY COMPOUNDS; GLUTATHIONE; GLUTATHIONE TRANSFERASE; HUMANS; LIVER; MICE; RATS; RATS, WISTAR; SPECIES SPECIFICITY; SUBCELLULAR FRACTIONS;

EID: 0032922066     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(98)00094-5     Document Type: Article

References (28)

1. 1 mice following two week exposures. Environ. Health Perspect. 86:1990;93-98.
2. Del Monte M., Citti L., Gervasi P.G. Isoprene metabolism by liver microsomal mono-oxygenases. Xenobiotica. 15:1985;591-597.
3. Longo V., Citti L., Gervasi P.G. Hepatic microsomal metabolism of isoprene in various rodents. Toxicol. Lett. 29:1985;33-37.
4. Wistuba D., Weigand K., Peter H. Stereoselectivity of in vitro isoprene metabolism. Chem. Res. Toxicol. 7:1994;336-343.
5. Bogaards J.J.P., Venekamp J.C., van Bladeren P.J. The biotransformation of isoprene and the two isoprene monoepoxides by human cytochrome P450 enzymes, compared to mouse and rat liver microsomes. Chemico-Biol. Interact. 102:1996;169-182.
6. Gervasi P.G., Longo V. Metabolism and mutagenicity of isoprene. Environ. Health Perspect. 86:1990;85-87.
7. Melnick R.L., Sills R.C., Roycroft J.H., Chou B.J., Ragan H.A., Miller R.A. Isoprene, an endogenous hydrocarbon and industrial chemical, induces multiple organ neoplasia in rodents after 26 weeks of inhalation exposure. Cancer Res. 54:1994;5333-5339.
8. Strange R.C., Faulder C.G., Davis B.A., Hume R., Brown J.A.H., Cotton W., Hopkinson D.A. The human glutathione S-transferases: studies on the tissue distribution and genetic variation of the GST1, GST2 and GST3 isozymes. Ann. Hu Genet. 48:1984;11-20.
9. Seidegard J., Pero R.W., Markowitz M.M., Roush G., Miller D.G., Beattie E.J. Isoenzyme(s) of glutathione transferase (class Mu) as a marker for the susceptibility to lung cancer: a follow up study. Carcinogenesis. 11:1990;33-36.
10. Van Ommen B., Bogaards J.J.P., Peters W.H., Blaauboer B., van Bladeren P.J. Quantification of human hepatic glutathione S-transferases. Biochem J. 269:1990;609-613.
11. Ketterer B., Harris J.M., Talaska G., Meyer D.J., Pemble S.E., Taylor J.B., Lang N.P., Kadlubar F.F. The human glutathione S-transferase supergene family, its polymorphism, and its effects on the susceptibility to lung cancer. Environ. Health. Perspect. 98:1992;87-94.
12. Nelson H.H., Wiencke J.K., Christiani D.C., Cheng T.J., Zuo Z.F., Schwartz B.S., Lee B.K., Spitz M.R., Wang M, Xu X., Kelsey K.T. Ethnic differences in the prevalence of the homozygous deleted genotype of glutathione S-transferase theta. Carcinogenesis. 16:1995;1243-1245.
13. Peter H., Deutchmann S., Reichel C., Hallier E. Metabolism of methyl chloride by human erythrocytes. Arch. Toxicol. 63:1989;351-355.
14. Hallier E., Deutchmann S., Reichel C., Bolt H.M., Peter H. A comparative investigation of the metabolism of methyl bromide and methyl iodide in human erythrocytes. Int. Arch. Occup. Environ. Health. 62:1990;221-225.
15. Pemble S., Schroeder K.R., Spencer S.R., Meyer D.J., Hallier E., Bolt H.M., Ketterer B., Taylor J.B. Human glutathione S-transferase Theta (GSTT1): cDNA cloning and the characterization of a genetic polymorphism. Biochem. J. 300:1994;271-276.
16. Warholm M., Alexandrie A.K., Hogberg J., Sigvardsson K., Rannug A. Polymorphic distribution of glutathione transferase activity with methyl chloride in human blood. Pharmacogenetics. 4:1994;307-311.
17. Bogaards J.J.P., Venekamp J.C., van Bladeren P.J. Stereoselective conjugation of prostaglandin A2 and prostaglandin J2 with glutathione, catalyzed by the human glutathione S-transferases A1-1, A2-2, M1a-1a and P1-1. Chem. Res. Toxicol. 10:1997;310-317.
18. Ploemen J.H.T.M., Bogaards J.J.P., Veldink G.A., van Ommen B., Jansen D.H.M., van Bladeren P.J. Isoenzyme selective irreversible inhibition of rat and human glutathione S-transferases by ethacrynic acid and two brominated derivatives. Biochem. Pharmacol. 45:1993;633-639.
19. Habig W.H., Pabst M.J., Jakoby W.B. Glutathione S-transferases. The first step in mercapturic acid formation. J. Biol. Chem. 249:1974;7130-7139.
20. Sherratt P.J., Pulford D.J., Pemble S.E., Harrison D.J., Green T., Hayes J.D. Evidence that human class Theta glutathione S-transferase T1-1 can catalyse the activation of dichloromethane, a liver and lung carcinogen in the mouse. Comparison of the tissue distribution of GSTT1-1 with that of class Alpha, Mu, and Pi GST in human. Biochem. J. 326:1997;837-846.
21. Thier R., Taylor J.B., Pemble S.E., Humphreys W.G., Persmark W.G., Ketterer B., Guengerich F. Expression of mammalian glutathione S-transferase 5-5 in Samonella TA1535 leads to baise-pair mutations upon exposure to dihalomethanes. Proc. Natl. Acad. Sci. USA. 90:1993;8576-8580.
22. Ploemen J.H.T.M., Wormhoudt L.W., Haenen G.R.M.M., Oudshoorn M.J., Commandeur J.N.M., Vermouelen N.P.E., de Waziers I., Beaune P.H., Watabe T., van Bladeren P.J. The use of human in vitro metabolic parameters to explore the risk assessment of hazardous compounds: the case of ethylene dibromide. Tox. Appl. Pharmacol. 143:1997;56-69.
23. Fjellstedt T.A., Allen R.H., Duncan B.K., Jaboby W.B. Enzymatic conjugation of epoxides with glutathione. J. Biol. Chem. 248:1973;3702-3707.
24. Bogaards J.J.P., Van Ommen B., Van Bladeren P.J. An improved method for the separation and quantification of glutathione S-transferase subunits in rat tissue using high-performance liquid chromatography. J. Chromatogr. 474:1989;435-440.
25. Sharer J.E., Elfarra A.A. S-(2-Hydroxy-3-buten-1-yl)glutathione and S-(1-Hydroxy-3-buten-2-yl)glutathione are in vivo metabolises of butadiene monoxide: detection and quantitation in bile. Chem. Res. Toxicol. 5:1992;787-790.
26. Perella F.W. EZ-FIT: A practical curve-fitting microcomputer program for the analysis of enzyme kinetic data on IBM-PC compatible computers. Anal. Biochem. 174:1988;437-447.
27. Sharer J.E., Duescher R.J., Elfarra A.A. Formation, stability, and rearrangements of the glutathione conjugates of butadiene monoxide: evidence for the formation of stable sulfurane intermediates. Chem. Res. Toxicol. 4:1991;430-436.
28. Elfarra A.A., Sharer J.E., Duescher R.J. Synthesis and characterization of N-acetyl-L-cysteine S-conjugates of butadiene monoxide and their detection and quantitation in urine of rats and mice given butadiene monoxide. Chem. Res. Toxicol. 8:1995;68-76.