Identification and characterization of 2′-deoxyadenosine adducts formed by isoprene monoepoxides in vitro

Chemical Research in Toxicology

Volumn 24, Issue 7, 2011, Pages 1048-1061

  Begemann, Petra ^a,d   Boysen, Gunnar ^a,b,e   Georgieva, Nadia I ^a   Sangaiah, Ramiah ^a   Koshlap, Karl M ^b   Koc, Hasan ^a,f   Zhang, Daping ^c   Golding, Bernard T ^c   Gold, Avram ^a   Swenberg, James A ^a,b,d  

^a University of North Carolina at Chapel Hill   (United States)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

^c NEWCASTLE UNIVERSITY   (United Kingdom)

^d ENVIRON INTERNATIONAL CORPORATION   (United States)

^e UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^f PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHENYL 2 METHYLOXIRANE; CARBON; DEOXYADENOSINE; DNA BASE; EPOXIDE; ETHYLENE OXIDE; ISOPRENE; PROPEN 2 YLOXIRANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DEAMINATION; DEUTERON NUCLEAR MAGNETIC RESONANCE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MUTAGENICITY; PHYSIOLOGY; ULTRAVIOLET SPECTROSCOPY;

BUTADIENES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYADENOSINES; DNA ADDUCTS; EPOXY COMPOUNDS; HEMITERPENES; MAGNETIC RESONANCE SPECTROSCOPY; PENTANES; TANDEM MASS SPECTROMETRY;

RODENTIA;

EID: 79960485165     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200055c     Document Type: Article

References (60)

1. International Agency for Research on Cancer (IARC) (1999) Re-Evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide, IARC Monogr. Eval. Carcinog. Risks Hum., Vol. 71, part 3, pp 1015-1025, IARC, Lyon, France.
2. International Agency for Research on Cancer (IARC) (2008) Overall Evaluations of Carcinogenicity to Humans. List of all agents, mixtures and exposures evaluated to date, http://monographs.iarc.fr/ENG/Classification/ crthall.php.
3. National Toxicology Program (NTP) (2005) 11th ROC: Isoprene, Eleventh Report on Carcinogens, Research Triangle Park, NC, http://ntp.niehs.nih.gov/ntp/ roc/eleventh/profiles/s099isop.pdf.
4. World Health Organization (WHO) (2008) The Scientific Basis of Tobacco Product Regulation. Second Report of a WHO Study Group, WHO Technical Report Series No. 951, WHO, Geneva, Switzerland.
5. Graedel, T. E., Hawkins, D. T., and Claxton, L. D. (1986) Atmospheric Chemical Compounds. Sources, Occurrence, and Bioassay, Academic Press, Orlando, FL.
6. Elmenhorst, H. and Harke, H. P. (1968) Volatile components of tobacco smoke. Preparative yield of a gas-phase condensate Z. Naturforsch. B 23 (9) 1271-1272
7. Lofroth, G., Stensman, C., and Brandhorst-Satzkorn, M. (1991) Indoor sources of mutagenic aerosol particulate matter: smoking, cooking and incense burning Mutat. Res. 261 (1) 21-28
8. Wallace, L. A. and Pellizzari, E. D. (1987) Personal air exposures and breath concentrations of benzene and other volatile hydrocarbons for smokers and nonsmokers Toxicol. Lett. 35 (1) 113-116 (Pubitemid 17024014)
9. Leber, A. P. (2001) Overview of isoprene monomer and polyisoprene production processes Chem.-Biol. Interact 135-136, 169-173 (Pubitemid 32530486)
10. Lynch, J. (2001) Occupational exposure to butadiene, isoprene and chloroprene Chem.-Biol. Interact 135-136, 207-214 (Pubitemid 32530488)
11. Sharkey, T. D. (1996) Isoprene synthesis by plants and animals Endeavour 20 (2) 74-78 (Pubitemid 127742905)
12. Kuzma, J., Nemecek-Marshall, M., Pollock, W. H., and Fall, R. (1995) Bacteria produce the volatile hydrocarbon isoprene Curr. Microbiol. 30 (2) 97-103
13. Gelmont, D., Stein, R. A., and Mead, J. F. (1981) Isoprene-the main hydrocarbon in human breath Biochem. Biophys. Res. Commun. 99 (4) 1456-1460 (Pubitemid 12242937)
14. Barrefors, G. and Petersson, G. (1993) Assessment of ambient volatile hydrocarbons from tobacco smoke and from vehicle emissions J. Chromatogr. 643 (1-2) 71-76 (Pubitemid 23221055)
15. NTP (1999) NTP toxicology and carcinogenesis studies of isoprene (CAS No. 78-79-5) in F344/N rats (inhalation studies). Natl. Toxicol. Prog. Technol. Rep. Ser. 486, 1-176.
16. Placke, M. E., Griffis, L., Bird, M., Bus, J., Persing, R. L., and Cox, L. A., Jr. (1996) Chronic inhalation oncogenicity study of isoprene in B6C3F1 mice Toxicology 113 (1-3) 253-262 (Pubitemid 26364101)
17. Melnick, R. L., Sills, R. C., Roycroft, J. H., Chou, B. J., Ragan, H. A., and Miller, R. A. (1994) Isoprene, an endogenous hydrocarbon and industrial chemical, induces multiple organ neoplasia in rodents after 26 weeks of inhalation exposure Cancer Res. 54 (20) 5333-5339 (Pubitemid 24336021)
18. Melnick, R. L., Sills, R. C., Roycroft, J. H., Chou, B. J., Ragan, H. A., and Miller, R. A. (1996) Inhalation toxicity and carcinogenicity of isoprene in rats and mice: comparisons with 1,3-butadiene Toxicology 113 (1-3) 247-252 (Pubitemid 26364100)
19. Hong, H. L., Devereux, T. R., Melnick, R. L., Eldridge, S. R., Greenwell, A., Haseman, J., Boorman, G. A., and Sills, R. C. (1997) Both K-ras and H-ras protooncogene mutations are associated with Harderian gland tumorigenesis in B6C3F1 mice exposed to isoprene for 26 weeks Carcinogenesis 18 (4) 783-789 (Pubitemid 28132468)
20. Sills, R. C., Hong, H. L., Melnick, R. L., Boorman, G. A., and Devereux, T. R. (1999) High frequency of codon 61 K-ras A→T transversions in lung and Harderian gland neoplasms of B6C3F1 mice exposed to chloroprene (2-chloro-1,3-butadiene) for 2 years, and comparisons with the structurally related chemicals isoprene and 1,3-butadiene Carcinogenesis 20 (4) 657-662 (Pubitemid 29151304)
21. Del Monte, M., Citti, L., and Gervasi, P. G. (1985) Isoprene metabolism by liver microsomal mono-oxygenases Xenobiotica 15 (7) 591-597 (Pubitemid 15046468)
22. Chiappe, C., De Rubertis, A., Tinagli, V., Amato, G., and Gervasi, P. G. (2000) Stereochemical course of the biotransformation of isoprene monoepoxides and of the corresponding diols with liver microsomes from control and induced rats Chem. Res. Toxicol. 13 (9) 831-838
23. Bogaards, J. J., Venekamp, J. C., and van Bladeren, P. J. (1996) The biotransformation of isoprene and the two isoprene monoepoxides by human cytochrome P450 enzymes, compared to mouse and rat liver microsomes Chem.-Biol. Interact 102 (3) 169-182 (Pubitemid 27036773)
24. Bogaards, J. J., Venekamp, J. C., Salmon, F. G., and van Bladeren, P. J. (1999) Conjugation of isoprene monoepoxides with glutathione, catalyzed by alpha, mu, pi and theta-class glutathione S-transferases of rat and man Chem.-Biol. Interact 117 (1) 1-14 (Pubitemid 29062894)
25. Buckley, L. A., Coleman, D. P., Burgess, J. P., Thomas, B. F., Burka, L. T., and Jeffcoat, A. R. (1999) Identification of urinary metabolites of isoprene in rats and comparison with mouse urinary metabolites Drug Metab. Dispos. 27 (7) 848-854 (Pubitemid 29297785)
26. Vogelstein, B. and Kinzler, K. W. (1993) The multistep nature of cancer Trends Genet. 9 (4) 138-141 (Pubitemid 23098782)
27. Swenberg, J. A., Richardson, F. C., Boucheron, J. A., and Dyroff, M. C. (1985) Relationships between DNA adduct formation and carcinogenesis Environ. Health Perspect. 62, 177-183 (Pubitemid 16188420)
28. Farmer, P. B. and Singh, R. (2008) Use of DNA adducts to identify human health risk from exposure to hazardous environmental pollutants: the increasing role of mass spectrometry in assessing biologically effective doses of genotoxic carcinogens Mutat. Res. 659 (1-2) 68-76
29. Gervasi, P. G., Citti, L., Del Monte, M., Longo, V., and Benetti, D. (1985) Mutagenicity and chemical reactivity of epoxidic intermediates of the isoprene metabolism and other structurally related compounds Mutat. Res. 156 (1-2) 77-82 (Pubitemid 15097886)
30. Gervasi, P. G. and Longo, V. (1990) Metabolism and mutagenicity of isoprene Environ. Health Perspect. 86, 85-87 (Pubitemid 20298819)
31. Fabiani, R., Rosignoli, P., De, B. A., Fuccelli, R., and Morozzi, G. (2007) DNA-damaging ability of isoprene and isoprene mono-epoxide (EPOX I) in human cells evaluated with the comet assay Mutat. Res. 629 (1) 7-13 (Pubitemid 46483192)
32. Golding, B. T., Cottrell, L., Mackay, D., Zhang, D., and Watson, W. P. (2003) Stereochemical and kinetic comparisons of mono- and diepoxide formation in the in vitro metabolism of isoprene by liver microsomes from rats, mice, and humans Chem. Res. Toxicol. 16 (7) 933-944 (Pubitemid 36899008)
33. Bleasdale, C., Small, R. D., Watson, W. P., Wilson, J., and Golding, B. T. (1996) Studies on the molecular toxicology of buta-1,3-diene and isoprene epoxides Toxicology 113 (1-3) 290-293 (Pubitemid 26364105)
34. Tareke, E., Golding, B. T., Small, R. D., and Tornqvist, M. (1998) Haemoglobin adducts from isoprene and isoprene monoepoxides Xenobiotica 28 (7) 663-672 (Pubitemid 28352418)
35. Begemann, P., Christova-Georgieva, N. I., Sangaiah, R., Koc, H., Zhang, D., Golding, B. T., Gold, A., and Swenberg, J. A. (2004) Synthesis, characterization, and identification of N7-guanine adducts of isoprene monoepoxides in vitro Chem. Res. Toxicol. 17 (7) 929-936 (Pubitemid 38955352)
36. Koskinen, M. and Plna, K. (2000) Specific DNA adducts induced by some mono-substituted epoxides in vitro and in vivo Chem.-Biol. Interact 129 (3) 209-229 (Pubitemid 32008373)
37. Tretyakova, N., Sangaiah, R., Yen, T. Y., Gold, A., and Swenberg, J. A. (1997) Adenine adducts with diepoxybutane: isolation and analysis in exposed calf thymus DNA Chem. Res. Toxicol. 10 (10) 1171-1179 (Pubitemid 27449521)
38. Selzer, R. R. and Elfarra, A. A. (1999) In vitro reactions of butadiene monoxide with single- and double-stranded DNA: characterization and quantitation of several purine and pyrimidine adducts Carcinogenesis 20 (2) 285-292 (Pubitemid 29057562)
39. Zhao, C., Vodicka, P., Sram, R. J., and Hemminki, K. (2000) Human DNA adducts of 1,3-butadiene, an important environmental carcinogen Carcinogenesis 21 (1) 107-111 (Pubitemid 30064151)
40. Barlow, T., Takeshita, J., and Dipple, A. (1998) Deamination and Dimroth rearrangement of deoxyadenosine-styrene oxide adducts in DNA Chem. Res. Toxicol. 11 (7) 838-845 (Pubitemid 28350734)
41. Kowalczyk, A., Harris, C. M., and Harris, T. M. (2001) Synthesis and characterization of oligodeoxynucleotides containing an N1 beta-hydroxyalkyl adduct of 2′-deoxyinosine Chem. Res. Toxicol. 14 (6) 746-753 (Pubitemid 32565725)
42. Rodriguez, D. A., Kowalczyk, A., Ward, J. B., Jr., Harris, C. M., Harris, T. M., and Lloyd, R. S. (2001) Point mutations induced by 1,2-epoxy-3-butene N1 deoxyinosine adducts Environ. Mol. Mutagen. 38 (4) 292-296 (Pubitemid 34052163)
43. Harwood, L. M., Casy, G., and Sherlock, J. (1990) A simple laboratory procedure for preparation of (1-methylethenyl)oxirane (3,4-epoxyisoprene) Synth. Commun. 20, 1287-1292
44. Singer, B. and Grunberger, D. (1983) Molecular Biology of Mutagenesis and Carcinogenesis Plenum Press, New York.
45. Tretyakova, N., Lin, Y., Sangaiah, R., Upton, P. B., and Swenberg, J. A. (1997) Identification and quantitation of DNA adducts from calf thymus DNA exposed to 3,4-epoxy-1-butene Carcinogenesis 18 (1) 137-147 (Pubitemid 28134627)
46. 6-adenosine adducts and N1-inosine adducts formed by the reaction of butadiene monoxide with adenosine: evidence for the N1-adenosine adducts as major initial products Chem. Res. Toxicol. 9 (5) 875-881
47. Esmans, E. L., Broes, D., Hoes, I., Lemiere, F., and Vanhoutte, K. (1998) Liquid-chromatography-mass spectrometry in nucleoside, nucleotide and modified nucleotide characterization J. Chromatogr., A 794, 109-127 (Pubitemid 28083605)
48. Plavec, J. and Tong, W. (1993) How do the gauche and anomeric effects drive the pseudorotational equilibrium of the pentofuranose moiety of nucleosides? J. Am. Chem. Soc. 115, 9734-9746
49. Ippel, J. H., Wijrnenga, S. S., de Jong, R., Heus, H. A., Hilbers, C. W., de Vroom, E., van der Marel, G. A., and van Boom, J. H. (1996) Heteronuclear scalar couplings in the bases and sugar rings of nucleic acids: their determinationand application in assignment and conformational analysis Magn. Reson. Chem. 34, S156-Sl76
50. Günther, H. (1995) NMR Spectroscopy, John Wiley and Sons, New York.
51. Boysen, G., Pachkowski, B. F., Nakamura, J., and Swenberg, J. A. (2009) The formation and biological significance of N7-guanine adducts Mutat. Res. 678 (2) 76-94
52. Watson, W. P., Cottrell, L., Zhang, D., and Golding, B. T. (2001) Metabolism and molecular toxicology of isoprene Chem.-Biol. Interact 135-136, 223-238 (Pubitemid 32530490)
53. Ellis, M. K., Golding, B. T., and Watson, W. P. (1984) Intrinsic reactivities in the alkylations of protected amino-acids by (R)-methyloxirane and (S)-methyloxirane J. Chem. Soc., Perkin Trans. 2, 1737-1743
54. Qian, C. and Dipple, A. (1995) Different mechanisms of aralkylation of adenosine at the 1- and N6-positions Chem. Res. Toxicol. 8 (3) 389-395
55. Carrell, H. L., Glusker, J. P., Moschel, R. C., Hudgins, W. R., and Dipple, A. (1981) Crystal structure of a carcinogen:nucleoside adduct Cancer Res. 41 (6) 2230-2234 (Pubitemid 11111421)
56. Martin, F. H., Castro, M. M., Abloul-ela, F., and Tinoco, I., Jr. (1985) Base pairing involving deoxyinosine: implications for probe design Nucleic Acids Res. 13 (24) 8927-8938
57. Case-Green, S. C. and Southern, E. M. (1994) Studies on the base pairing properties of deoxyinosine by solid phase hybridisation to oligonucleotides Nucleic Acids Res. 22 (2) 131-136 (Pubitemid 24160926)
58. 6-deoxyadenosine intrastrand cross-links in mammalian cells Chem. Res. Toxicol. 15 (12) 1572-1580 (Pubitemid 36008204)
59. 6 adducts of monoepoxide and diolepoxide derivatives of butadiene Environ. Mol. Mutagen. 35 (1) 48-56 (Pubitemid 30112453)
60. 6-(2,3,4-trihydroxybutyl)-2′-deoxyadenosyl DNA Adduct of butadiene diol epoxide with deoxyguanosine: formation of a dA(anti) ·dG(anti) pairing interaction Chem. Res. Toxicol. 18 (2) 145-153 (Pubitemid 40256232)