Mutagenicity of stereochemical configurations of 1,2-epoxybutene and 1,2:3,4-diepoxybutane in human lymphblastoid cells

Chemico-Biological Interactions

Volumn 166, Issue 1-3, 2007, Pages 207-218

  Meng, Quanxin ^a   Redetzke, Diana L ^a   Hackfeld, Linda C ^b   Hodge, Richard P ^b   Walker, Dale M ^c   Walker, Vernon E ^c  

^a BATTELLE MEMORIAL INSTITUTE   (United States)

^b UNIVERSITY OF TEXAS MEDICAL BRANCH   (United States)

^c LOVELACE RESPIRATORY RESEARCH INSTITUTE   (United States)

Author keywords

1,3 Butadiene; Epoxy metabolites; Mutagenicity; Stereoisomer

Indexed keywords

1,2 EPOXY 3 BUTENE; 1,3 BUTADIENE; BUTADIENE DIEPOXIDE; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; THYMIDINE KINASE;

ARTICLE; CELL CLONING; CELL SURVIVAL; CHEMICAL CARCINOGENESIS; CHEMICAL MUTAGENESIS; CONTROLLED STUDY; GENE MUTATION; HUMAN; HUMAN CELL; LYMPHOBLASTOID CELL; MUTAGENICITY; STEREOCHEMISTRY;

CELL DEATH; CELL SURVIVAL; DNA; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INDUCTION; EPOXY COMPOUNDS; EXONS; GENOME, HUMAN; GENOMICS; HUMANS; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; LYMPHOCYTES; MUTAGENESIS; MUTAGENICITY TESTS; MUTANT PROTEINS; MUTATION; POLYMERASE CHAIN REACTION; STEREOISOMERISM; THYMIDINE KINASE;

RODENTIA;

EID: 33947110328     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2006.06.001     Document Type: Article

References (36)

1. Huff J.E., Melnick R.L., Solleveld H.A., Haseman J.K., Powers M., and Miller R.A. Multiple organ carcinogenicity of 1,3-butadiene in B6C3F1 mice after 60 weeks of inhalation exposure. Science 227 (1985) 548-549
2. Owen P.E., Glaiser R.J., Gaunt I.F., and Pullinger D.H. Inhalation toxicity studies with 1,3-butadiene. 3. Two-year toxicity/carcinogenicity studies in rats. Am. Ind. Hyg. Assoc. J. 48 (1987) 407-413
3. Melnick R.L., Huff J., Chou B.J., and Miller R. Carcinogenicity of 1,3-butadiene in C57BL/6 × C3H F1 mice at low exposure concentrations. Cancer Res. 50 (1990) 6592-6599
4. Cochrane J.E., and Skopek T.R. Mutagenicity of butadiene and its epoxide metabolites. I. Mutagenic potential of 1,2-epoxybutene 1,2,3,4-diepoxybutane and 3,4-epoxy-1,2-butanediol in cultured human lymphoblasts. Carcinogenesis 15 (1994) 719-723
5. Steen A.-M., Meyer K.G., and Recio L. Analysis of hprt mutations occurring in human TK6 lymphoblastoid cells following exposure to 1,2,3,4-diepoxybutane. Mutagenesis 12 (1997) 61-67
6. Steen A.-M., Meyer K.G., and Recio L. Characterization of hprt mutations following 1,3-epoxy-3-butene exposure of human TK6 cells. Mutagenesis 12 (1997) 359-364
7. 32P-Postlabelling/HPLC assay reveals an enantioselective adduct formation in N7 guanine residues in vivo after 1,3-butadiene inhalation exposure. Carcinogenesis 18 (1997) 439-443
8. Koivisto P., Adler I.-D., Pacchierotti F., and Peltonen K. DNA adducts in mouse testis and lung after inhalation exposure to 1,3-butadiene. Mutat. Res. 397 (1998) 3-10
9. Koivisto P., Kilpeläinen I., Rasanen I., Adler I.-D., Pacchierotti F., and Peltonen K. Butadiene diolepoxide- and diepoxybutane-derived DNA adducts at N7-guanine: a high occurrence of diolepoxide-derived adducts in mouse lung after 1,3-butadiene exposure. Carcinogenesis 20 (1999) 1253-1259
10. Koivisto P., and Peltonen K. N7-guanine adducts of the epoxy metabolites of 1,3-butadiene in mice lung. Chem. Biol. Interact. 135-136 (2001) 363-372
11. Krause R.J., and Elfarra A.A. Oxidation of butadiene monoxide to meso- and (±)-diepoxybutane by cDNA-expressed human cytochrome P45Os and by mouse, rat, and human liver microsomes: evidence for preferential hydration of meso-diepoxybutane in rat and human microsomes. Arch. Biochem. Biophys. 337 (1997) 176-184
12. Nieusma J.L., Claffey D.J., Maniglier-Poulet C., Imiolczyk T., Ross D., and Ruth J.A. Stereochemical aspects of 1,3-butadiene metabolism and toxicity in rat and liver microsomes and freshly isolated rat hepatocytes. Chem. Res. Toxicol. 10 (1997) 450-456
13. Nieusma J.L., Claffey D.J., Ruth J.A., and Ross D. Stereochemical aspects of the conjugation of epoxide metabolites of butadiene with glutathione in rat liver cytosol and freshly isolated rat hepatocytes. Toxicol. Sci. 43 (1998) 102-109
14. Feit P.W. 4-Bismethanesulfonates of the stereoisomeric butanetetraols and related compounds. J. Med. Chem. 7 (1964) 14-17
15. Feit P.W. Synthese der stereoisomeren 1,2;3,4-dioxido-butane. Chem. Ber. 93 (1960) 116-127
16. Claffey D.J. Multigram-scale stereoselective synthesis of meso-1,3-butadiene bisepoxide. Synth. Commun. 32 (2002) 3041-3045
17. Walker V.E., Walker D.M., Meng Q., McDonald J.D., Scott B.R., Bauer M.J., Seilkop S.K., Claffey D.J., Upton P.B., Powley M.W., Swenberg J.A., and Henderson R.F. Genotoxicity of 1,3-butadiene and its epoxy intermediates. HEI Research Report Number, Health Effects Institute (2006), Capitol City Press, Montpelier, VT
18. Martinelli M.J., Vaidyanathan R., Pawlak J.M., Nayyar N.K., Dhokte U.P., Doecke C.W., Zollars L.M.H., Moher E.D., Khau V.V., and Kosmrlj B. Catalytic regioselective sulfonylation of α-chelatable alcohols: scope and mechanistic insight. J. Am. Chem. Soc. 124 (2002) 3578-3585
19. Finn M.G., Sharpless K.B., and Morrison J.D. The mechanism of asymmetric epoxidation with titanium-tartrate catalysts. Asymmetric Synthesis (1985), Academic Press, New York, NY
20. Gao Y., Hanson R.M., Klunder J.M., Ko S.Y., Masamuni H., and Sharpless K.B. Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization. J. Am. Chem. Soc. 109 (1987) 5765-5780
21. Crawford R.J., Lutener S.B., and Cockcroft R.D. The thermally induced rearrangements of 2-vinyloxirane. Can. J. Chem. 54 (1976) 3364-3376
22. Meng Q., Su T., Olivero O.A., Poirier M.C., Shi X., Ding X., and Walker V.E. Relationship between DNA incorporation, mutant frequency, and loss of heterozygosity at the TK locus in human lymphoblastoid cells exposed to 3′-azido-3′-deoxythymidine. Toxicol. Sci. 54 (2000) 322-329
23. Gibbs A.R., Nguyen P.N., Edward A., Civitello A.B., and Caskey C.T. Multiplex DNA deletion detection and exon sequencing of the hypoxanthine-guanine phosphoribosyltransferase gene in Lesch-Nyhan families. Genomics 7 (1990) 235-244
24. Meng Q., Walker D.M., Scott R.S., Seilkop S.K., Aden J.K., and Walker V.E. Characterization of Hprt mutations in cDNA and genomic DNA of T-cell mutants from control and 1,3-butadiene-exposed male B6C3F1 mice and F344 rats. Environ. Mol. Mutagen. 43 (2004) 75-92
25. Meng Q., Walker D.M., Olivero O.A., Shi X., Antiochos B.B., Poirier M.C., and Walker V.E. AZT-ddI coexposure potentiates DNA incorporation of AZT and mutagenesis in human cells. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 12667-12671
26. Sussman H.E., Olivero O.A., Meng Q., Pietras S.M., Poirier M.C., O'Neill J.P., Finette B.A., Bauer M.J., and Walker V.E. Genotoxicity of 3′-azido-3′-deoxythymidine in the human lymphoblastoid cell line, TK6: relationships between DNA incorporation, mutant frequency, and spectrum of deletion mutations in HPRT. Mutat. Res. 429 (1999) 249-259
27. Meng Q., Wisse L.A., Hackfeld L.C., and Hodge R.P. (2R,3S)-3-epoxybutane-1,2-diol is significantly more cytotoxic and mutagenic than other stereoisomers of 3-epoxybutane-1,2-diol in TK6 cells. The Health Effects Institute Annual Conference (2005) 34
28. Richardson K.A., Peters M.M., Megens R.H., van Elburg P.A., Golding B.T., Boogaard P.J., Watson W.P., and van Sittert N.J. Identification of novel metabolites of butadiene monoepoxide in rats and mice. Chem. Res. Toxicol. 11 (1998) 1543-1555
29. Meng Q., Su T., O'Neill J.P., and Walker V.E. Molecular analysis of mutations at the HPRT and TK loci of human lymphoblastoid cells after combined treatments with 3′-azido-3′-deoxythymidine and 2′,3′-dideoxyinosinedagger. Environ. Mol. Mutagen. 39 (2002) 282-295
30. Park S., Hodge J., Anderson C., and Tretyakova N. Guanine-adenine DNA cross-linking by 1,2,3,4-diepoxybutane: potential basis for biological activity. Chem. Res. Toxicol. 17 (2004) 1638-1651
31. V.E. Walker, Q. Meng, In vivo mutation of the endogenous hprt genes of mice and rats by 1,3-butadiene and its metabolites, in: HEI Research Report 92, 1,3-Butadiene: Cancer, Mutations, and Adducts, Health Effect Institute, Cambridge, MA, 2000, pp 89-139.
32. Perez H.L., Lahdetie J., Landin H., Kilpelainen I., Koivisto P., Peltonen K., and Osterman-Golkar S. Haemoglobin adducts of epoxybutanediol from exposure to 1,3-butadiene or butadiene epoxides. Chem. Biol. Interact. 105 (1997) 181-198
33. Boogaard P.J., van Sittert N.J., Watson W.P., and de Kloe K.P. A novel DNA adduct, originating from 1,2-epoxy-3,4-butanediol, is the major DNA adduct after exposure to [2,3-(14)C]-1,3-butadiene,[4-(14)C]-1,2-epoxy-3-butane. Chem. Biol. Interact. 135-136 (2001) 687-693
34. Swenberg J.A., Koc H., Upton P.B., Georguieva N., Ranasinghe A., Walker V.E., and Henderson R. Using DNA and hemoglobin adducts to improve the risk assessment of butadiene. Chem. Biol. Interact. 135-136 (2001) 387-403
35. Boogaard P.J., de Kloe K.P., Booth E.D., and Watson W.P. DNA adducts in rats and mice following exposure to [4-14C]-1,2-epoxy-3-butene and to [2,3-14C]-1,3-butadiene. Chem. Biol. Interact. 148 (2004) 69-92
36. Booth E.D., Kilgour J.D., Robinson S.A., and Watson W.P. Dose responses for DNA adduct formation in tissues of rats and mice exposed by inhalation to low concentrations of 1,3-[2,3-[(14)C]]-butadiene. Chem. Biol. Interact. 147 (2004) 195-211