Dose-response relationships for/V7-(2-hydroxyethyl) guanine induced by low-dose [14C]ethylene oxide: Evidence for novel mechanism of endogenous adduct formation

Cancer Research

Volumn 69, Issue 7, 2009, Pages 3052-3059

  Marsden, Debbie A ^a   Jones, Donald J L ^a   Britton, Robert G ^a   Ognibene, Ted ^b   Ubick, Esther ^b   Johnson, George E ^c   Farmer, Peter B ^a   Brown, Karen ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

^c SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOCYCLOPROPANECARBOXYLIC ACID; 7 (2 HYDROXYETHYL)GUANINE; BIOLOGICAL MARKER; CARBON 14; DNA; ETHYLENE OXIDE; NUCLEOTIDE; 1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID; AMINO ACID; CARBON; DIAGNOSTIC AGENT; DRUG DERIVATIVE; GUANINE; N(7) HYDROXYETHYLGUANINE; N(7)-HYDROXYETHYLGUANINE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CARCINOGENICITY; CONTROLLED STUDY; DNA DAMAGE; DOSE RESPONSE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IN VIVO STUDY; LIQUID CHROMATOGRAPHY; LIVER; LOW DRUG DOSE; MALE; MAMMAL CELL; MUTAGENICITY; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; RAT; RISK ASSESSMENT; SPLEEN; STOMACH; TANDEM MASS SPECTROMETRY; ANIMAL; BIOSYNTHESIS; DNA ADDUCT; FISCHER 344 RAT; METABOLISM; TISSUE DISTRIBUTION;

AMINO ACIDS, CYCLIC; ANIMALS; BIOLOGICAL MARKERS; CARBON RADIOISOTOPES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA ADDUCTS; DOSE-RESPONSE RELATIONSHIP, DRUG; ETHYLENE OXIDE; GUANINE; MALE; OXIDATIVE STRESS; RATS; RATS, INBRED F344; TANDEM MASS SPECTROMETRY; TISSUE DISTRIBUTION;

EID: 66149087753     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-08-4233     Document Type: Article

References (46)

1. Thier R, Bolt HM. Carcinogenicity and genotoxicity of ethylene oxide: new aspects and recent advances. CrIt Rev Toxicol 2000;30:595-608.
2. NTP. 10th Report on. carcinogens. Research Triangle Park (NC): U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health, National Toxicology Program.; 2002.
3. Hogstedt C, Malmqvist N, Wadman B. Leukaemia in workers exposed to ethylene oxide. JAMA I979;24I: 1132-1133
4. Hogstedt C, Rohlen O, Berndtsson B, Axelson O, Ehrenberg L. A cohort study of mortality and cancer incidence in ethylene oxide production workers. BrJ Ind. Med 1979;36:276-280
5. Hogstedt C, Aringer L, Gustavsson A. Epidemiologic support for ethylene-oxide as a cancer-causing agent. JAMA 1986;255:1575-1578
6. Teta MJ, Sielken RL, Valdez-Flores C. Ethylene oxide cancer risk assessment based on. epidemiological data: application of revised, regulatory guidelines. Risk Analysis 1999;19:1135-1155
7. Coggon D, Harris EC, Poole J, Palmer KT. Mortality of British workers exposed to ethylene oxide: extended follow up of a British cohort. Occup Environ Med 2004; 61:358-362
8. Steenland K, Stayner J, Deddens J. Mortality analyses in. a cohort of 18235 ethylene oxide exposed workers: follow up extended from 1987 to 1998. Occup Environ Med 2004;61:2-7.
9. Hogstedt B, Gullberg B, Hedner K, et al. Chromosome aberrations and micronuclei in bone marrow cells and peripheral blood lymphocytes in humans exposed to ethylene oxide. Heredita» 1983;98:105-113
10. IARC. Some industrial chemicals: ethylene oxide. In: International Agency for Research on Cancer. IARC monographs on the evaluation, of carcinogenic risks to humans, vol.60. Lyon (France): IARC; 1994. p. 73-159.
11. Walker VE1 Fennell TR1 Upton PB1 et al. Molecular dosimetry of ethylene oxide: formation and persis- tence of A?7-(2-hydroxyethyl)guanine in DNA following repeated exposure of rats and mice. Cancer Res I992;52: 4328-4334
12. Li F1 Segal A1 Solomon JJ. In vitro reaction of ethylene oxide with DNA and characterization of DNA adducts. Chem Biol Interact 1992;83:35-54.
13. Takeshlta M1 Chang C-H1 Johnson F1 Will S1 Grollman. AP. Oligonucleotides containing synthetic abaslc sites: model substrates for DNA-polymerases and apurinic apyrimidinic endonucleases. J Biol Chem. 1987;262: 10171-10179
14. Loeb LA1 Preston BD. Mutagenesis by apurinic apyrimidinic sites. Ann Rev Gen. 1986;20:201-230
15. IARC. Some industrial chemicals: ethylene oxide. In: International Agency for Research on. Cancer. IARC monographs on the evaluation of carcinogenic risks to humans, vol.60. Lyon (France): IARC; 1994. p. 45-71.
16. Wu KY, Serieller N1 Ran.asing.he A1 et al. A gas chromatography/electron capture/negative chemical ionization high-resolution mass spectrometry method for analysis of endogenous and exogenous A7- (2-hydroxyet.hyl)guanlne in rodents and Its potential, for human biological monitoring. Chem. Res Toxicol 1999;18:722-729
17. Zhao C1 Hemminki K. The in vivo levels of DNA alkylation products in human lymphocytes are not age dependent: an assay of 7-methyl- and 7-(2-hydro- xyethylj-guanlne DNA adducts. Carcinogenesis 2002;23: 307-310
18. Yong LC1 Schulte PA1 Kao CY1 et al. DNA adducts in granulocytes of hospital workers exposed to ethylene oxide. AmJ Ind Med 2007:50:293-302.
19. Liberman M1 Mapson LW. Genesis and biogenesis of ethylene. Nature 1964;204:343-345
20. Tůrnqvist M1 Gustafsson B1 Kautlainen A1 Harms- Ringdahl M1 Granath F1 Ehrenberg L. Unsaturated lipids and intestinal bacteria as sources of endogenous production, of ethene and ethylene oxide. Carcinogen- esis 1989;10:39-41.
21. Beauchamp C1 Fridovich I. A mechanism for the production of ethylene from methional. The generation of the hydroxyl radical by xanthine oxidase. J Biol Chem 1970;245:4641-4646
22. Henderson L1 Albertini S1 Aardema M. Thresholds in genotoxicity responses. Mut Res 2000;464:123-128
23. Doak SH1 Jenkins GJS1 Johnson GE1 Quick E1 Parry EM1 Parry JM. Mechanistic influences for mutation induction, curves after exposure to DNA-reactive carci- nogens. Cancer Res 2007;67:3904-3911
24. Swenberg JA1 Fryar-Tlta E1 Jeong YC1 et al. Bio- markers in toxicology and risk assessment: informing critical dose-response relationships. Chem Res Toxicol 2008;21:253-265
25. Brown K1 Tompkins EM1 White INH. Applications of accelerator mass spectrometry for pharmacological, and toxicological research. Mass Spectrom Rev 2006; 25:127-145
26. Marsden DA1 Jones DJL1 Lamb JH1 Tompkins E1 Farmer PB1 Brown K. Determination of endogenous and exogenously derived A7-(2-.hydroxyethyl)guanine adducts in ethylene oxide treated rats. Chem Res Toxicol 2007;20:290-299
27. Brown K1 Dingley KH1 Turteltaub KW. Accelerator mass spectrometry for biomedical research. Methods Enzym ol 2005;402:423-443
28. Ognibene TJ, Bench G, Brown TA, Peaslee GF, Vogel JS. A new accelerator mass spectrometry system for C- quantification. of biochemical samples. Int J Mass Spectrom 2002;218:255-264
29. C via accelerator mass spectro- metry. Anal Chem 2003;75:2192-2196
30. Carpenter SP, Lasker JM, Rauey JL. Expression, induction, and catalytic activity of the ethanol-lnducible cytochrome P450 (CYP2E1) in human fetal liver and hepatocytes. Mol Pharmacol 1996;49:260-268
31. Jones DJL, Lim CK, Ferry, DR, Gescher A. Determi- nation of quercetin in human plasma by HPLC with spectrophotometric or electrochemical detection. Biomed Chromatogr 1998;12:232-235
32. Fennell TR, Brown CD. A physiologically based pharmacokinetic model for ethylene oxide in mouse, rat and human. Toxicol Appl Pharmacol 2001;173: 161-175
33. Brugnone F, Perbelllni L, Faccini GB, Pasinl F, Bartolucci GB, DeRosa E. Ethylene oxide exposure: biological monitoring by analysis of alveolar air and blood. Int Arch Occup Environ Health 1986;58:105-112
34. Liberman M, Kunlshi AT, Mapson LW, Wardale DA. Stimulation of ethylene production, in apple tissue slices by methionine. Plant Physiol 1966;41:376-382
35. Gaillard T, Hulme AC, Rhodes MJC, Wooltorton LSC. Enzymic conversion of linolenic acid to ethylene by extracts of apple fruits. FEBS Lett 1968;1:283-286
36. Mapson LW, March JF, Rhodes MJC, Wooltorton. LSC. A comparative study of the ability of methionine or linolenic acid to act as precursors of ethylene in plant tissues. Biochem J 1970;117:473-479
37. Katoh T, Higashi K, Inoue N, Tanaka I. Lipid peroxidation and the metabolism of glutathione in rat liver and brain following ethylene oxide inhalation. Toxicology 1989;58:1-9.
38. Celi, I, Suzek H. Effects of subacute treatment of ethylene glycol on serum marker enzymes and erythro- cyte and tissue antioxidant defense systems and lipid peroxidation in rats. Chem. Biol Interact 2007; 167: 145-152
39. Kadiiska MB, Mason. RP. Ethylene glycol generates free radical metabolites in rats: an. ESR in vivo spin trapping Investigation. Chem Res Toxicol 2000;13:1187-91.
40. Adams DO, Yang SF. Ethylene biosynthesis: identification, of 1-aminocyclopropane-I-carboxylic acid as an intermediate in the conversion of methionine to ethylene. Proc Natl Acad Sei U S A 1979;76:170-174
41. Apelbaum A, Wang SY, Burgoon AC, Baker JE, Liberman M. Inhibition of the conversion of 1-amino- cyclopropan.e-1-carboxylic acid to ethylene by structural analogs, inhibitors of electron transfer, uncouplers of oxidative phosphorylation, and free radical scavengers. Plant Physiol 1981;67:74-79
42. Boiler T, Hemer RC, Ken.de H. Assay for and enzymatic formation of an ethylene precursor, 1- aminocyclopropane-1-carboxyiic acid. Planta 1979;145: 293-303.
43. Ghattas W Gaudin. C, Giorgi M, Rockenbauer A, Simaan AJ, Réglier M. ACC-oxidase like activity of a copper (H)-ACC complex in the presence of hydrogen peroxide. Detection of a reaction intermediate at low temperature. Chem Commun. 2006;1027-1029
44. Bousquet JF, Thimann KV. Lipid peroxidation forms ethylene from 1-aminocyclopropane-l-carboxylic acid and may operate in leaf senescence. Proc Natl. Acad Sci USA 1984;81:1724-1727
45. Pirrung MC. Mechanism, of a lipoxygenase model for ethylene biosynthesis. Biochemistry 1986;25:.l14-9.
46. Petritis K, Koukala G, Koussissi E, Elfakir C, Dreux M, Dourtoglou V. The simultaneous determination of 1- aminocyclopropane-1-carboxylic acid and cyclopro- pane-l.l-dicarboxylic acid in Lycoperslcum esculentum by high-performance liquid chromatography-electro- spray tandem mass spectrometry. Phytochem Anal 2003;14:347-351