Mutagenic potential of adenine N6 adducts of monoepoxide and diolepoxide derivatives of butadiene

Environmental and Molecular Mutagenesis

Volumn 35, Issue 1, 2000, Pages 48-56

  Carmical, J Russ ^a   Nechev, Lubomir V ^b,c   Harris, Constance M ^b,c   Harris, Thomas M ^b,c   Lloyd, R Stephen ^a  

^a UNIVERSITY OF TEXAS MEDICAL BRANCH   (United States)

^b VANDERBILT UNIVERSITY   (United States)

^c VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

1,3 butadiene adducts; Deoxyoligonucleotides; E. coli polymerases; Mutagenesis; Stereoselectivity

Indexed keywords

1,2 EPOXY 3 BUTENE; ADENINE NUCLEOTIDE; BUTADIENE DIEPOXIDE; DNA; DNA POLYMERASE;

ARTICLE; BACTERIOPHAGE; CARCINOGENESIS; DNA ADDUCT; DNA MODIFICATION; DNA REPLICATION; DRUG DNA INTERACTION; EPOXIDATION; ESCHERICHIA COLI; GENETIC TRANSFECTION; HYDROLYSIS; MUTAGENICITY; ONCOGENE N RAS; PLAQUE FORMING CELL; STEREOISOMERISM;

ADENINE; BASE SEQUENCE; BUTADIENES; DNA; EPOXY COMPOUNDS; GENES, RAS; GLYCOLS; HUMANS; MUTAGENS;

EID: 0033998873     PISSN: 08936692     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2280(2000)35:1<48::AID-EM7>3.0.CO;2-C     Document Type: Article

References (29)

1. Byrne JL, Marshall CJ. 1998. The molecular pathophysiology of myeloid leukaemias: ras revisited. Br J Haematol 100:256-264.
2. Chary P, Latham GJ, Robberson DL, Kim SJ, Han S, Harris CM, Harris TM, Lloyd RS. 1995. In vivo and in vitro replication consequences of stereoisomeric benzo[a]pyrene-7,8-dihydrodiol 9,10-epoxide adducts on adenine N6 at the second position of N-ras codon 61. J Biol Chem 270:4990-5000.
3. Cochrane JE, Skopek TR. 1994. 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 15:713-717.
4. Gay P, Contamine D. 1993. Study of the ref(2)P locus of Drosophila melanogaster. II. Genetic studies of the 37DF region. Mol Gen Genet 239:361-370.
5. Harris CM, Zhou L, Strand EA, Harris TM. 1991. New strategy for the synthesis of oligodeoxynucleotides bearing adducts at exocyclic amino sites of purine nucleosides. J Am Chem Soc 113:4328-4329.
6. Kim H-Y, Nechev L, Zhou L, Tamura R, Harris CM, Harris TM. 1998. Synthesis and adduction of fully deprotected oligodeoxynucleotides containing 6-chloropurine. Tetrahedron Lett 39:6803-6806.
7. Koc H, Tretyakova NY, Walker VE, Henderson RF, Swenberg JA. 1999. Molecular dosimetry of N-7 guanine adduct formation in mice and rats exposed to 1,3-butadiene. Chem Res Toxicol 12:566-574.
8. Koivisto P, Kilpelainen I, Rasanen I, Adler, I-D, Pacchierotti F, Peltonen K. 1999. 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 20:1253-1259.
9. Krause RJ, Elfarra AA. 1997. Oxidation of butadiene monoxide to mesoand (±)-diepoxybutane by cDNA-expressed human cytochrome P450s and by mouse, rat and human liver microsomes: evidence for preferential hydration of meso-diepoxybutane in rat and human liver microsomes. Arch Biochem Biophys 337:176-184.
10. Latham GJ, Zhou L, Harris CM, Harris TM, Lloyd RS. 1993. The replication fate of R- and S-styrene oxide adducts on adenine N6 is dependent on both the chirality of the lesion and the local sequence context. J Biol Chem 268:23427-23434.
11. Latham GJ, McNees AG, De Corte B, Harris CM, Harris TM, O'Donnell M, Lloyd RS. 1996. Comparison of the efficiency of synthesis past single bulky DNA adducts in vivo and in vitro by the polymerase III holoenzyme. Chem Res Toxicol 9:1167-1175.
12. Lawrence CW, Borden A, Banerjee SK, LeClerc JE. 1990. Mutation frequency and spectrum resulting from a single abasic site in a single-stranded vector. Nucleic Acids Res 18:2153-2157.
13. 32P-postlabelling. Carcinogenesis 15:1903-1910.
14. 32P-postlabeling assay of DNA adducts from 1,2,3,4-diepoxybutane, the most genotoxic metabolite of 1,3-butadiene: in vitro methodological studies and in vivo dosimetry. Mutat Res 371:87-104.
15. Macaluso M, Larson R, Delzell E, Sathiakumar N, Hovinga M, Julian J, Muir D, Cole P. 1996. Leukemia and cumulative exposure to butadiene, styrene and benzene among workers in the synthetic rubber industry. Toxicology 113:190-202.
16. McNees AG, O'Donnell M, Horton PH, Kim HY, Kim SJ, Harris CM, Harris TM, Lloyd RS. 1997. Lack of correlation between in vitro and in vivo replication of precisely defined benz-a-anthracene adducted DNAs. J Biol Chem 272:33211-33219.
17. Nieusma JL, Claffey DJ, Koop DR, Chen W, Peter RM, Nelson SD, Ruth JA, Ross D. 1998. Oxidation of 1,3-butadiene to (R)- and (S)-butadiene monoxide by purified recombinant cytochrome P450 2E1 from rabbit, rat and human. Toxicol Lett 95:123-129.
18. Recio L, Meyer KG. 1995. Increased frequency of mutations at A:T base pairs in the bone marrow of B6C3F1 lacI transgenic mice exposed to 1,3-butadiene. Environ Mol Mutagen 26:1-8.
19. Recio L, Sisk S, Meyer K, Pluta L. Bond JA. 1996. Mutagenicity and mutational spectra of 1,3-butadiene in the bone marrow of B6C3F1 lacI transgenic mice. Toxicology 113:106-111.
20. Sambrook J, Fritsch EF, Maniatis T. 1989. Molecular cloning: a labratory manual, 2nd ed. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory.
21. Seaton MJ, Follansbee MH, Bond JA. 1995. Oxidation of 1,2-epoxy-3-butene to 1,2,3,4-diepoxybutane by cDNA-expressed human cytochromes P450 2E1 and 3A4 and human, mouse and rat liver microsomes. Carcinogenesis 16:2287-2293.
22. Selzer RR, Elfarra AA. 1996. Synthesis and biochemical characterization of N1-, N2-, and N7-guanosine adducts of butadiene monoxide. Chem Res Toxicol 9:126-132.
23. Selzer RR, Elfarra AA. 1997. Characterization of four N-3-thymidine adducts formed in vitro by the reaction of thymidine and butadiene monoxide. Carcinogenesis 18:1993-1998.
24. Sisk SC, Pluta LJ, Bond JA, Recio L. 1994. Molecular analysis of lacI mutants from bone marrow of B6C3F1 transgenic mice following inhalation exposure to 1,3-butadiene. Carcinogenesis 15:471-477.
25. Steen AM, Meyer KG, Recio L. 1997a. Analysis of hprt mutations occurring in human TK6 lymphoblastoid cells following exposure to 1,2,3,4-diepoxybutane. Mutagenesis 12:61-67.
26. Steen AM, Meyer KG, Recio L. 1997b. Characterization of hprt mutations following 1,2-epoxy-3-butene exposure of human TK6 cells. Mutagenesis 12:359-364.
27. Tretyakova N, Lin Y, Sangaiah R, Upton PB, Swenberg JA. 1997a. Identification and quantitation of DNA adducts from calf thymus DNA exposed to 3,4-epoxy-1-butene. Carcinogenesis 18:137-147.
28. Tretyakova N, Sangaiah R, Yen TY, Gold A, Swenberg JA. 1997b. Adenine adducts with diepoxybutane: isolation and analysis in exposed calf thymus DNA. Chem Res Toxicol 10:1171-1179.
29. Tretyakova N, Sangaiah R, Yen TY, Swenberg JA. 1997c. Synthesis, characterization, and in vitro quantitation of N-7-guanine adducts of diepoxybutane. Chem Res Toxicol 10:779-785.