Covalent binding to DNA in vitro of 2',3'-oxides derived from allylbenzene analogs

Drug Metabolism and Disposition

Volumn 24, Issue 9, 1996, Pages 1020-1027

  Luo, Gang ^a,b   Guenthner, Thomas M ^a  

^a UNIVERSITY OF ILLINOIS   (United States)

^b NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BENZENE DERIVATIVE; DNA; EPOXIDE; EPOXIDE HYDROLASE; ESTRAGOLE; SAFROLE;

ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARCINOGEN DNA INTERACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; COVALENT BOND; DNA ADDUCT; DNA BINDING; EPOXIDATION; MALE; MASS SPECTROMETRY; METABOLITE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

ANIMALS; ANISOLES; BENZENE DERIVATIVES; DEOXYGUANOSINE; DNA; DNA ADDUCTS; EPOXIDE HYDROLASES; EPOXY COMPOUNDS; GUANOSINE; GUINEA PIGS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICE; SAFROLE;

ANIMALIA;

EID: 0029809858     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Y. T. Woo, D. Y. Lai, J. C. Arcos, and M. F. Aigus: Safrole, estragole, and related compounds. In "Chemical Induction of Cancer: Structural Bases and Biological Mechanisms," vol. IIIc, pp. 267-319. Academic Press, New York, 1988.
2. A. B. Swanson, E. C. Miller, and J. A. Miller: The side chain epoxide and hydroxylation of the hepatocarcinogens safrole and estragole and related compounds by rat and mouse microsomes. Biochim. Biophys. Acta 673, 504-516 (1981).
3. E. W. Boberg, E. C. Miller, J. A. Miller, A. Poland, and A. Liem: Strong evidence from studies with brachymorphic mice and pentachlorophenol that 1′-hydroxysafrole is the major ultimate electrophilic and carcinogenic metabolite of safrole in mouse liver. Cancer Res. 43, 5163-5173 (1983).
4. 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, 737-744 (1980).
5. W. G. Stillwell, M. J. Carman, L. Bell, and M. G. Horning: The metabolism of safrole and safrole 2′,3′-epoxide in the rat and guinea pig. Drug Metab. Dispos. 2, 489-498 (1974).
6. G. Luo and T. M. Guenthner: Metabolism of allylbenzene 2′,3′-oxide and estragole 2′,3′-oxide in the isolated perfused rat liver. J. Pharmacol. Exp. Ther. 272, 588-596 (1995).
7. A. B. Swanson, D. A. Chambliss, J. C. Blomquist, E. C. Miller, and J. A. Miller: The mutagenicities of safrole, estragole, eugenol, trans-anethole, and some of their known or possible metabolites for Salmonella typhimurium mutants. Mutat. Res. 60, 143-153 (1979).
8. M. A. El-Tantawy and B. D. Hammock: The effect of hepatic microsomal and cytosolic subcellular fractions on the mutagenic activity of epoxide-containing compounds in the Salmonella assay. Mutat. Res. 79, 59-71 (1980).
9. E. C. Miller, A. B. Swanson, D. H. Phillips, T. F. Fletcher, and J. A. Miller: Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Res. 43, 1124-1134 (1983).
10. K. Savela, A. Hesso, and K. Hemminki: Characterization of reaction products between styrene oxide and deoxynucleosides and DNA. Chem.-Biol. Interact. 60, 235-246 (1986).
11. F. Latif, R. C. Moschel, K. Hemminki, and A. Dipple: Styrene oxide as a stereochemical probe for the mechanism of aralkylation at different sites on guanosine. Chem. Res. Toxicol. 1, 364-369 (1988).
12. C. de Meester, F. Poncelet, M. Roberfroid, J. Rondelet, and H. Mercier: Mutagenicity of styrene and styrene oxide. Mutat. Res. 56, 147-152 (1977).
13. V. Ponomarkov, J. R. P. Cabral, J. Wahrendorf, and D. Galendo: A carcinogenicity study of styrene-7,8 oxide in rats. Cancer Lett. 24, 95-101 (1984).
14. G. Luo, M. K. Qato, and T. M. Guenthner: Hydrolysis of the 2′,3′-allylic epoxides of allylbenzene, estragole, and safrole by both microsomal and cytosolic epoxide hydrolases. Drug Metab. Dispos. 20, 440-445 (1992).
15. G. Luo and T. M. Guenthner: Detoxication of the 2′,3′-epoxide metabolites allylbenzene and estragole: conjugation with glutathione. Drug Metab. Dispos. 22, 731-737 (1994).
16. K. Ota and B. D. Hammock: Cytosolic and microsomal epoxide hydrolases: differential properties in mammalian liver. Science 207, 1479-1481 (1980).
17. 32P postlabeling analysis of adducts formed between DNA and safrole 2′,3′-epoxide: absence of adduct formation in vivo. Toxicol. Lett. 75, 201-207 (1995).
18. T. M. Guenthner and F. Oesch: Identification and characterization of a new epoxide hydrolase from mouse liver microsomes. J. Biol. Chem. 258, 15054-15061 (1983).
19. A. Y. Lu, D. Ryan, D. M. Jerina, J. W. Daly, and W. Levin: Liver microsomal epoxide hydrase: solubilization, purification, and characterization. J. Biol. Chem. 250, 8283-8288 (1975).
20. O. H. Lowry, N. J. Rosebrough, A. L. Fair, and R. J. Randall: Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275 (1951).
21. 32P-postlabeling analysis. Carcinogenesis 9, 1055-1060 (1988).
22. P. D. Lawley and P. Brookes: Further studies on the alkylation of nucleic acids and their constituent nucleotides. Biochem. J. 89, 127-138 (1963).
23. K. Hemminki, J. Paasivirta, T. Kurkirinne, and L. Virkki: Alkylation products of DNA bases by simple epoxides. Chem.-Biol. Interact. 30, 259-270 (1980).
24. D. H. Phillips, J. A. Miller, E. C. Miller, and B. Adams: Structures of the DNA adducts formed in mouse liver after administration of the proximate hepatocarcinogen 1′-hydroxyestragole. Cancer Res. 41, 176-186 (1981).
25. 2 atom of adenine residues as sites for covalent binding of metabolically activated 1′-hydroxy-safrole to mouse liver DNA in vivo. Cancer Res. 41, 2664-2671 (1981).
26. E. Van Den Eeckhout, A. De Bruyn, H. Pepermans, E. L. Esmans, I. Vryens, J. Claerebout, M. Claeys, and J. E. Sinsheimer: Adduct formation identification between phenylglycidyl ether and 2′-deoxyadenosine and thymidine by chromatography, mass spectrometry and nuclear magnetic resonance spectroscopy. J. Chromatogr. 504, 113-128 (1990).
27. D. A. R. Williams: "Nuclear Magnetic Resonance Spectroscopy," pp. 202-203. Mowthorpe, Chichester, 1986.
28. 2 atoms of guanine. Chem. Res. Toxicol. 5, 479-490 (1992).
29. 2-(2-oxoethyl)guanine. Chem. Res. Toxicol. 6, 635-648 (1993).
30. F. Z. Sheabar, M. L. Morningstar, and G. N. Wogan: Peracylation of nucleosides with methionine: foundation for a method to detect carcinogen adducts. Chem. Res. Toxicol. 7, 650-658 (1994).
31. 13C couplings. J. Magn. Reson. 57, 314-318 (1984).
32. P. O. Wislocki, P. Borchert, J. A. Miller, and E. C. Miller: The metabolic activation of the carcinogen 1′-hydroxysafrole in vivo and in vitro and the electrophilic reactivities of possible ultimate carcinogens. Cancer Res. 36, 1686-1695 (1976).
33. K. Hemminki: Nucleic acid adducts of chemical carcinogens and mutagens. Arch. Toxicol. 52, 249-285 (1983).
34. P. Brookes and P. D. Lawley: The alkylation of guanosine and guanylic acid. J. Chem. Soc. 1961, 3923-3928 (1961).
35. F. Li, A. Segal, and J. J. Solomon: In vitro reaction of ethylene oxide with DNA and characterization of DNA adducts. Chem.-Biol. Interact. 83, 35-54 (1992).
36. L. Ehrenberg, K. D. Hiesche, S. Osterman-Golkar, and I. Wennberg: Evaluation of genetic risk of alkylating agents: tissue dose in the mouse from air contaminated with ethylene oxide. Mutat. Res. 24, 83-103 (1974).
37. J. S. Paul and M. A. Pavelka: Covalent binding of a carcinogenic epoxide to DNA in vitro. Fed. Proc. 30, 448 (abstr.) (1971).
38. K. Hemminki and A. Hesso: Reaction products of styrene oxide with guanosine in aqueous media. Carcinogenesis 5, 601-607 (1984).
39. B. R. Smith and I. R. Bend: Metabolism and toxicity of benzo[a]pyrene 4,5-oxide in the isolated perfused rat liver. Toxicol. Appl. Pharmacol. 49, 313-321 (1979).
40. B. R. Smith, J. Van Anda, J. R. Fouts, and J. R. Bend: Estimation of styrene 7,8-oxide-detoxifying potential of epoxide hydrolase in glutathione-depleted, perfused rat livers. J. Pharmacol. Exp. Ther. 227, 491-498 (1983).
41. J. Caldwell, V. S. W. Chan, A. D. Marshall, G. Hasheminejad, and S. V. J. Bounds: 1′-hydroxylation is the only metabolic pathway of simple alkenylbenzenes involved in their genotoxicity. Toxicologist 12, 56 (abstr.) (1992).