Epoxidation of the methamphetamine pyrolysis product, trans-phenylpropene, to trans-phenylpropylene oxide by CYP enzymes and stereoselective glutathione adduct formation

Toxicology and Applied Pharmacology

Volumn 211, Issue 2, 2006, Pages 148-156

  Sanga, Madhu ^a   Younis, Islam R ^a   Tirumalai, Padma S ^a   Bland, Tina M ^a   Banaszewska, Monica ^a   Konat, Gregory W ^a   Tracy, Timothy S ^b   Gannett, Peter M ^a   Callery, Patrick S ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Cytotoxicity; Epoxide; Glutathione; Methamphetamine; Phenylpropene; Pyrolysis

Indexed keywords

BETA METHYLSTYRENE; CINNAMYL ALCOHOL; CYTOCHROME P450 1A2; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; CYTOCHROME P450 INHIBITOR; GLUTATHIONE; METHAMPHETAMINE; PHENYLPROPYLENE; PROPYLENE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

CELL DEATH; CELL DEGENERATION; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONFERENCE PAPER; CONJUGATION; CONTROLLED STUDY; CYTOTOXICITY; ENANTIOMER; EPOXIDATION; GLIA CELL; HUMAN; HUMAN CELL; INCUBATION TIME; LIVER MICROSOME METABOLISM; METABOLIC ACTIVATION; PYROLYSIS; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TRANS ISOMER;

ALKENES; ANIMALS; BINDING SITES; CATTLE; CELL LINE, TUMOR; CELL SIZE; CELL SURVIVAL; CHROMATOGRAPHY, LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; CYTOSOL; ENZYME INHIBITORS; EPOXY COMPOUNDS; GLUTATHIONE; HUMANS; ISOENZYMES; MASS SPECTROMETRY; METHAMPHETAMINE; MICROSOMES, LIVER; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PROPANOLS; STEREOISOMERISM; STYRENES; TIME FACTORS;

EID: 32544445151     PISSN: 0041008X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.taap.2005.06.017     Document Type: Conference Paper

References (37)

1. R.N. Armstrong Glutathione S-transferases: reaction mechanism, structure, and function Chem. Res. Toxicol. 4 1991 131 140
2. S.J. Baldwin, J.C. Bloomer, G.J. Smith, A.D. Ayrton, S.E. Clarke, and R.J. Chenery Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9 Xenobiotica 25 1995 261 270
3. G. Bellucci, C. Chiappe, A. Cordoni, and F. Marioni Substrate enantioselectivity in the rabbit liver microsomal epoxide hydrolase catalyzed hydrolysis of trans and cis 1-phenylpropene oxides. A comparison with styrene oxide Tetrahedron: Asymmetry 4 1993 1160 1163
4. M. Boccellino, F. Cuccovillo, M. Napolitano, N. Sannolo, C. Balestieri, A. Acampora, A. Giovane, and L. Quagliuolo Styrene-7,8-oxide activates a complex apoptotic response in neuronal PC12 cell line Carcinogenesis 24 2003 535 540
5. S.V. Bounds, and J. Caldwell Pathways of metabolism of [1′-14C]-trans-anethole in the rat and mouse Drug Metab. Dispos. 24 1996 717 724
6. D.L. Brown Jr., W. Boda, M.P. Stone, and A.R. Buckpitt High-performance liquid chromatographic assay of cytosolic glutathione S-transferase activity with styrene oxide J. Chromatogr. 231 1982 265 272
7. T.K. Chang, F.J. Gonzalez, and D.J. Waxman Evaluation of triacetyloleandomycin, alfanaphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450 Arch. Biochem. Biophys. 311 1994 437 442
8. E. Dare, R. Tofighi, M.V. Vettori, T. Momoi, D. Poli, T.C. Saido, A. Mutti, and S. Ceccatelli Styrene 7,8-oxide induces caspase activation and regular DNA fragmentation in neuronal cells Brain Res. 933 2002 12 22
9. K.S. De Costa, S.R. Black, B.F. Thomas, J.P. Burgess, and J.M. Mathews Metabolism and disposition of alpha-methylstyrene in rats Drug Metab. Dispos. 29 2001 166 171
10. M. Delaforge, P. Janiaud, P. Levi, and J.P. Morizot Biotransformation of allylbenzene analogues in vivo and in vitro through the epoxide-diol pathway Xenobiotica 10 1980 737 744
11. S.P. de Visser, F. Ogliaro, P.K. Sharma, and S. Shaikh What factors affect the regioselectivity of oxidation by cytochrome p450? A DFT study of allylic hydroxylation and double bond epoxidation in a model reaction J. Am. Chem. Soc. 124 2002 11809 11826
12. E.C. Dietze, E. Kuwano, and B.D. Hammock The interaction of cytosolic epoxide hydrolase with chiral epoxides Int. J. Biochem. 25 1993 43 52
13. F.P. Guengerich Cytochrome P450 oxidations in the generation of reactive electrophiles: epoxidation and related reactions Arch. Biochem. Biophys. 409 2003 59 71
14. F.P. Guengerich, D.H. Kim, and M. Iwasaki Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects Chem. Res. Toxicol. 4 1991 168 179
15. T.M. Guenthner, and G. Luo Investigation of the role of the 2′,3′-epoxidation pathway in the bioactivation and genotoxicity of dietary allylbenzene analogs Toxicology 160 2001 47 58
16. J.D. Hayes, J.U. Flanagan, and I.R. Jowsey Glutathione transferases Annu. Rev. Pharmacol. Toxicol. 45 2005 51 88
17. M.R. Lee, J. Jeng, W.S. Hsaing, and B.H. Hwang Determination of pyrolysis products of smoked methamphetamine mixed with tobacco by tandem mass spectrometry J. Anal. Toxicol. 23 1999 41 45
18. I. Linhart Stereochemistry of styrene biotransformation Drug Metab. Rev. 33 2001 353 367
19. I. Linhart, I. Gut, J. Smejkal, and J. Novak Biotransformation of styrene in mice. Stereochemical aspects Chem. Res. Toxicol. 13 2000 36 44
20. A.D. Marshall, and J. Caldwell Lack of influence of modulators of epoxide metabolism on the genotoxicity of trans-anethole in freshly isolated rat hepatocytes assessed with the unscheduled DNA synthesis assay Food Chem. Toxicol. 34 1996 337 345
21. R.L. Melnick Carcinogenicity and mechanistic insights on the behavior of epoxides and epoxide-forming chemicals Ann. N. Y. Acad. Sci. 982 2002 177 189
22. R.S. Mohan, K. Gavardinas, S. Kyere, and D.L. Whalen Spontaneous hydrolysis reactions of cis- and trans-beta-methyl-4-methoxystyrene oxides (anethole oxides): buildup of trans-anethole oxide as an intermediate in the spontaneous reaction of cis-anethole oxide J. Org. Chem. 65 2000 1407 1413
23. T. Nakajima, E. Elovaara, F.J. Gonzalez, H.V. Gelboin, H. Vaino, and T. Aoyama Characterization of the human cytochrome P450 isozymes responsible for styrene metabolism IARC Sci. Publ. 127 1993 101 108
24. S.V. Otton, H.K. Crewe, M.S. Lennard, G.T. Tucker, and H.F. Woods Use of quinidine inhibition to define the role of the sparteine/debrisoquine cytochrome P450 in metoprolol oxidation by human liver microsomes J. Pharmacol. Exp. Ther. 247 1988 242 247
25. J.D. Peele, and E.O. Oswald Metabolism of naturally occurring propenylbenzene derivatives: III. Allylbenzene, propenyl benzene, and related metabolic products Biochim. Biophys. Acta 497 1977 598 607
26. M.M. Peters, and J. Caldwell Studies on trans-cinnamaldehyde: 1. The influence of dose size and sex on its disposition in the rat and mouse Food Chem. Toxicol. 32 1994 869 876
27. C.J. Rompelberg, H. Verhagen, and P.J. van Bladeren Effects of the naturally occurring alkenylbenzenes eugenol and trans-anethole on drug-metabolizing enzymes in the rat liver Food Chem. Toxicol. 31 1993 637 645
28. M. Sato, M. Hida, and H. Nagase Analysis of pyrolysis products of methamphetamine J. Anal. Toxicol. 28 2004 638 643
29. H. Sekine, and Y. Nakahara Abuse of smoking methamphetamine mixed with tobacco: I. Inhalation efficiency and pyrolysis products of methamphetamine J. Forensic Sci. 32 1987 1271 1280
30. D. Sesardic, A.R. Boobis, B.P. Murray, S. Murray, J. Segura, R. Torre, and D.S. Davies Furafylline is a potent and selective inhibitor of cytochrome P450IA2 in man Br. J. Clin. Pharmacol. 29 1990 651 663
31. Shakleya, D.M., Tarr, S.G., Kraner, J.C., Clay, D.J., Callery, P.S., in press. Potential marker for smoked methamphetamine hydrochloride based on a gas chromatography-mass spectrometry quantification method for trans-phenylpropene. J. Anal. Toxicol.
32. G. Speit, and L. Henderson Review of the in vivo genotoxicity tests performed with styrene Mutat. Res. 589 2005 67 79
33. Tarr, S.G., 2005. Mass spectrometry of metallothionein adducts as candidate biomarkers of styrene oxide and 1-phenylpropylene oxide. Thesis, West Virginia University.
34. R.A. Tschirret-Guth, and P.R. Ortiz de Montellano Protein radicals in myoglobin dimerization and myoglobin-catalyzed styrene epoxidation Arch. Biochem. Biophys. 335 1996 93 101
35. A.D.N. Vaz, D.F. McGinnity, and M.J. Coon Epoxidation of olefins by cytochrome P450: evidence from site-specific mutagenesis for hydroperoxo-iron as an electrophilic oxidant Proc. Natl. Acad. Sci. U.S.A. 95 1998 3555 3560
36. P. Vodicka, M. Koskinen, R. Stetina, P. Soucek, L. Vodickova, Z. Matousu, M. Kuricova, and K. Hemminki The role of various biomarkers in the evaluation of styrene genotoxicity Cancer Detect. Prev. 27 2003 275 284
37. T. Watabe, N. Ozawa, N. Hiratsuka, Y. Saito, and T. Tsurumori Regiospecific glutathione conjugation of alkylarylethylene oxides by hepatic glutathione S-transferase Biochem. Pharmacol. 33 1984 2687 2690