Propylene oxide: Mutagenesis, carcinogenesis and molecular dose

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 380, Issue 1-2, 1997, Pages 179-197

  Ríos Blanco, Melva N ^a   Plna, Kamila ^c   Faller, Thomas ^d   Kessler, Winfried ^d   Håkansson, Krystyna ^c   Kreuzer, Paul E ^d   Ranasinghe, Asoka ^b   Filser, Johannes G ^d   Segerbäck, Dan ^c   Swenberg, James A ^a,b  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

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

^c KAROLINSKA INSTITUTE   (Sweden)

^d INSTITUTE OF EPIDEMIOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

7 (2 HYDROXYETHYL)GUANINE; PROPYLENE OXIDE;

CARCINOGENESIS; DERIVATIZATION; DNA BINDING; DOSIMETRY; DRUG SCREENING; ELECTROPHORESIS; GAS CHROMATOGRAPHY; INHALATION; LIVER; MASS SPECTROMETRY; MUTAGEN TESTING; MUTAGENESIS; NONHUMAN; NOSE MUCOSA; PRIORITY JOURNAL; RESPIRATORY EPITHELIUM; REVIEW; TARGET ORGAN; TECHNIQUE;

ANIMALIA; BACTERIA (MICROORGANISMS); MAMMALIA; RODENTIA;

EID: 19244383235     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(97)00135-8     Document Type: Article

References (70)

1. Svensson K., Osterman-Golkar S. Kinetics of metabolism of propene and covalent binding to macromolecules in the mouse. Toxicol. Appl. Pharmacol. 73:1984;363-372.
2. Törnqvist M., Kautiainen A., Gatz R.N., Ehrenberg L. Hemoglobin adducts in animals exposed to gasoline and diesel exhausts. 1. Alkenes J. Appl. Toxicol. 8(3):1988;159-170.
3. Bootman J., Logde D.C., Whalley H.E. Mutagenic activity of propylene oxide in bacterial and mammalian systems. Mutat. Res. 67:1979;101-112.
4. Guttenplan J.B., Kosinska W., Chung F.L. Mutagenic activities and specificities of biologically and environmentally significant epoxides. Environ. Mol. Mutagen. 23(Suppl. 23):1994;23.
5. Migliore L., Rossi A.M., Loprieno N. Mutagenic action of structurally related alkene oxides on Schizosaccharomyces pombe: The influence, in vitro, of mouse-liver metabolizing system. Mutat. Res. 102:1982;425-437.
6. McGregor D., Brown A.G., Cattanach P., Edwards I., McBride D., Riach C., Shepherd W., Caspary W.J. Responses of the L5178Y mouse lymphoma forward mutation assay. V. Gases and vapors Environ. Mol. Mutagen. 17:1991;122-129.
7. Zamora P.O., Benson J.M., Li A.P., Brooks A.L. Evaluation of an exposure system using cells grown on collagen gels for detecting highly volatile mutagens in the CHO/HGPRT mutation assay. Environ. Mutagen. 5:1983;795-801.
8. Agurell E., Cederberg H., Hedenskog M., Rannug U. Chemically induced changes in the spectrum of amplifications of the human minisatellite MS1 integrated in chromosome III of a haploid yeast strain. Mol. Gen. Genet. 242:1994;137-144.
9. Agurell E., Cederberg H., Ehrenberg L., Lindahl-Kiessling K., Rannug U., Törnqvist M. Genotoxic effects of ethylene oxide and propylene oxide: a comparative study. Mutat. Res. 250:1991;229-237.
10. Tucker J.D., Xu J., Stewart J., Baciu P.C., Ong T. Detection of sister chromatid exchanges induced by volatile genotoxicants. Teratog. Carcinog. Mutagen. 6:1986;15-21.
11. Pero R.W., Bryngelsson T., Widegren B., Högstedt B., Welinder H. A reduced capacity for unscheduled DNA synthesis in lymphocytes from individuals exposed to propylene oxide and ethylene oxide. Mutat. Res. 104:1982;193-200.
12. Pero R.W., Osterman-Golkar S., Högstedt B. Unscheduled DNA synthesis correlated to alkylation of hemoglobin in individuals occupationally exposed to propylene oxide. Cell Biol. Toxicol. 1(4):1985;309-314.
13. Jorritsma U., Cornet M., Van Hummelen P., Bolt H.M., Vercruysse A., Kirsch-Volders M., Rogiers V. Comparative mutagenicity of 2-methylpropene (isobutene), its epoxide 2-methyl-1,2-epoxypropane and propylene oxide in the in vitro micronucleus test using human lymphocytes. Mutagenesis. 10(2):1995;101-104.
14. Dean B.J., Hodson-Walker G. An in vitro chromosome assay using cultured rat-liver cells. Mutat. Res. 64:1979;329-337.
15. Zhang L., Jenssen D. Studies on intrachromosomal recombination in SP5/V79 Chinese hamster cells upon exposure to different agents related to carcinogenesis. Carcinogenesis. 15(10):1994;2303-2310.
16. Kolman A., Dušinská M. Comparison of propylene oxide and epichlorohydrin effects in two transformation tests (C3H/10T1/2 and SHE cells). Toxicol. Lett. 81:1995;213-221.
17. Hardin B.D., Schuler R.L., McGinnis P.M., Niemeier R.W., Smith R.J. Evaluation of propylene oxide for mutagenic activity in 3 in vivo test systems. Mutat. Res. 117:1983;337-344.
18. Lynch D.W., Lewis T.R., Moorman W.J., Burg J.R., Gulati D.K., Kaur P., Sabharwal P.S. Sister-chromatid exchanges and chromosome aberrations in lymphocytes from monkeys exposed to ethylene oxide and propylene oxide by inhalation. Toxicol. Appl. Pharmacol. 76:1984;85-95.
19. Farooqi Z., Törnqvist M., Ehrenberg L., Natarajan A.T. Genotoxic effects of ethylene oxide and propylene oxide in mouse bone marrow cells. Mutat. Res. 288:1993;223-228.
20. Maples K.R., Dahl A.R. Blood levels of propylene oxide during propylene inhalation and effect on hepatic and nasal cytochrome P-450 concentrations. Drug Metab. Dispos. 19(4):1991;835-837.
21. 1 mice. Toxicol. Appl. Pharmacol. 76:1984;288-295.
22. Golka K., Peter H., Denk B., Filser J.G. Pharmacokinetics of propylene and its reactive metabolite propylene oxide in Sprague-Dawley rats. Arch. Toxicol. Suppl. 13:1989;240-242.
23. Dunkelberg H. Carcinogenicity of ethylene oxide and 1,2-propylene oxide upon intragastric administration to rats. Br. J. Cancer. 46:1982;924-933.
24. IARC Monographs on the evaluation of the carcinogenic risk of chemicals to humans, vol. 36, Allyl compounds, aldehydes, epoxides and peroxides, Lyon, 1985, pp. 227-243.
25. Dunkelberg H. On the oncogenic activity of ethylene oxide and propylene oxide in mice. Br. J. Cancer. 39:1979;588-589.
26. Lynch D.W., Lewis T.R., Moorman W.J., Burg J.R., Groth D.H., Khan A., Ackerman L.J., Cockrell B.Y. Carcinogenic and toxicologic effects of inhaled ethylene oxide and propylene oxide in F344 rats. Toxicol. Appl. Pharmacol. 76:1984;69-84.
27. 1 mice inhaling propylene oxide for up to two years. J. Natl. Cancer Inst. 77(2):1986;573-582.
28. Toxicology and carcinogenesis studies of propylene oxide in F344/N rats and B6C3F1 mice (Inhalation Studies), NTP TR267, US Dept. of Health and Human Services, Public Health Service, National Institutes of Health, Research Triangle Park, NC, 1985.
29. Sellakumar A.R., Snyder C.A., Albert R.E. Inhalation carcinogenesis of various alkylating agents. J. Natl. Cancer Inst. 79(2):1987;285-289.
30. Kuper C.F., Reuzel P.G.J., Feron V.J., Verschuuren H. Chronic inhalation toxicity and carcinogenicity study of propylene oxide in Wistar rats. Food Chem. Toxicol. 26(2):1988;159-167.
31. Eldridge S.R., Bogdanffy M.S., Jokinen M.P., Andrews L.S. Effects of propylene oxide on nasal epithelial cell proliferation in F344 rats. Fundam. Appl. Toxicol. 27:1995;25-32.
32. Segerbäck D. Alkylation of DNA and hemoglobin in the mouse following exposure to ethene and ethene oxide in vivo. Chem. Biol. Interact. 45:1983;139-151.
33. Farmer P.B., Bailey E., Gorf S.M., Törnqvist M., Osterman-Golkar S., Kautiainen A., Lewis-Enright D.P. Monitoring human exposure to ethylene oxide by the determination of hemoglobin adducts using gas chromatography-mass spectrometry. Carcinogenesis. 7:1986;637-640.
34. Svensson K., Olofsson K., Osterman-Golkar S. Alkylation of DNA and hemoglobin in the mouse following exposure to propene and propylene oxide. Chem. Biol. Interact. 78:1991;55-66.
35. Farmer P.B., Gorf S.M., Bailey E. Determination of hydroxypropylhistidine in haemoglobin as a measure of exposure to propylene oxide using high resolution gas chromatography mass spectrometry. Biomed. Mass Spectrom. 9(2):1982;69-71.
36. Osterman-Golkar S., Bailey E., Farmer P.B., Gorf S.M., Lamb J.H. Monitoring exposure to propylene oxide through the determination of hemoglobin alkylation. Scand. J. Work Environ. Health. 10:1984;99-102.
37. Bailey E., Farmer P.B., Shuker D.E.G. Estimation of exposure to alkylating carcinogens by the GC-MS determination of adducts to hemoglobin and nucleic acids bases in urine. Arch. Toxicol. 60:1987;187-191.
38. Kautiainen A., Törnqvist M. Monitoring exposure to simple epoxides and alkenes through gas chromatographic determination of hemoglobin adducts. Int. Arch. Occup. Environ. Health. 63:1991;27-31.
39. Kautiainen A., Midtvedt T., Törnqvist M. Intestinal bacteria and endogenous production of malonaldehyde and alkylators in mice. Carcinogenesis. 14(12):1993;2633-2636.
40. Törnqvist M., Almberg J., Nilsson S., Osterman-Golkar S. Tissue dose of ethylene oxide from occupational exposure to ethene in fruit stores. Scand. J. Work. Environ. Health. 15:1989;436-438.
41. M. Törnqvist, L. Ehrenberg, Approaches to risk assessment of automotive engine exhausts, in: Vainio, H., Sorsa, M., McMichael, A.J. (Eds.), Complex mixtures and cancer risk, IARC Publication 104, International Agency for Research on Cancer, Lyon, 1990, pp. 277-287.
42. Eide I., Hagemann R., Zahlsen K., Tareke E., Törnqvist M., Kumar R., Vodicka P., Hemminki K. Uptake, distribution, and formation of hemoglobin and DNA adducts after inhalation of C2-C8 1-alkenes (olefins) in the rat. Carcinogenesis. 16(7):1995;1603-1609.
43. Lawley P.D., Jarman M. Alkylation by propylene oxide of deoxyribonucleic acid, adenine, guanosine and deoxyguanylic acid. Biochem. J. 126:1972;893-900.
44. Hemminki K., Paasivirta J., Kurkirinne T., Virkki L. Alkylation products of DNA bases by simple epoxides. Chem. Biol. Interact. 30:1980;259-270.
45. Djuric Z., Sinsheimer J.E. Reactivity of propylene oxides towards deoxycytidine and identification of reaction products. Chem. Biol. Interact. 50:1984;219-231.
46. Djuric Z., Hooberman B.H., Rosman L., Sinsheimer J.E. Reactivity of mutagenic propylene oxides with deoxynucleosides and DNA. Environ. Mutagen. 8:1986;369-383.
47. Djuric Z., Sinsheimer J.E. Characterization and quantitation of 3-alkylthymidines from reactions of mutagenic propylene oxides with thymidine. Chem. Biol. Interact. 52:1984;243-253.
48. Solomon J.J., Mukai F., Fedyk J., Segal A. Reactions of propylene oxide with 2′-deoxynucleosides and in vitro with calf thymus DNA. Chem. Biol. Interact. 67:1988;275-294.
49. Solomon J.J., Segal A. DNA adducts of propylene oxide and acrylonitrile epoxide: hydrolytic deamination of 3-alkyl-dCyd to 3-alkyl-dUrd. Environ. Health Perspect. 81:1989;19-22.
50. Segerbäck D., Osterman-Golkar S., Molholt B., Nilsson R. In vivo tissue dosimetry as a basis for cross-species extrapolation in cancer risk assessment of propylene oxide. Regul. Toxicol. Pharmacol. 20:1994;1-14.
51. Snyder C.A., Solomon J.J. The extent and persistence of binding to respiratory mucosal DNA by inhaled tritiated propylene oxide. Cancer Lett. 72:1993;157-161.
52. 3H] formaldehyde. Toxicol. Appl. Pharmacol. 76:1984;26-44.
53. Gupta R.C. Nonrandom binding of the carcinogen N-hydrox-2-acetylaminofluorene to repetitive sequences of rat liver DNA in vivo. Proc. Natl. Acad. Sci. USA. 81:1982;6943-6947.
54. 6-methylguanine formation and persistence in rats. Carcinogenesis. 2:1981;1181-1188.
55. Allam K., Saha M., Giese R.W. Preparation of electrophoric derivatives of N7-(2-hydroxyethyl)guanine, an ethylene oxide DNA adduct. J. Chromatogr. 499:1990;571-578.
56. Plna K., Segerbäck D., Schweda E.K.H. DNA adduct formation by allyl glycidyl ether. Carcinogenesis. 17:1996;1465-1471.
57. 32P-postlabeling method for the detection of 7-alkylguanine adducts formed by the reaction of different 1,2-alkyl epoxides with DNA. Carcinogenesis. 16:1995;483-489.
58. Walker V.E., Fennell T.R., Boucheron J.A., Fedtke N., Ciroussel F., Swenberg J.A. Macromolecular adducts of ethylene oxide: a literature review and a time-course study on the formation of 7-(2-hydroxypropyl)guanine following exposures of rats by inhalation. Mutat. Res. 233:1990;151-164.
59. Mathison B.H., Taylor M.L., Bogdanffy M.S. Dimethyl sulfate uptake and methylation of DNA in rat respiratory tissues following acute inhalation. Fundam. Appl. Toxicol. 28:1995;255-263.
60. K. Plna, personal communication.
61. Walker V.E., Fennell T.R., Upton P.B., Skopek T.R., Prevost V., Shuker D.E.G., Swenberg J.A. Molecular dosimetry of ethylene oxide: Formation and persistence of 7-(2-hydroxypropyl)guanine in DNA following repeated exposures of rats and mice. Cancer Res. 52:1992;4328-4334.
62. Törnqvist M., Gustafsson B., Kautiainen A., Harms-Ringdahl M., Granath F., Ehrenberg L. Unsaturated lipids and intestinal bacteria as sources of endogenous production of ethene and ethylene oxide. Carcinogenesis. 10:1989;39-41.
63. Sagai M., Ichinose T. Age-related changes in lipid peroxidation as measured by ethane, ethylene, butane and pentane in respired gases of rats. Life Sci. 27:1980;731-738.
64. Lieberman M., Mapson L.W. Genesis and biogenesis of ethylene. Nature. 204:1964;343-345.
65. Kessler W., Remmer H. Generation of volatile hydrocarbons from amino acids and proteins by an iron/ascorbate/GSH system. Biochem. Pharmacol. 39:1990;1347-1351.
66. Clemens M.R., Einsele H., Frank H., Remmer H., Waller H.D. Volatile hydrocarbons from hydrogen peroxide-induced lipid peroxidation of erythrocytes and their cell compounds. Biochem. Pharmacol. 32:1983;3877-3878.
67. Boiteux S., Laval J. Coding properties of poly(deoxycytidylic acid) templates containing uracil or apyrimidinic sites: in vitro modulation of mutagenesis by DNA repair enzymes. Biochemistry. 21:1982;6746-6751.
68. Takeshita M., Chang C.N., Johnson F., Will S., Grollman A. Oligodeoxynucleotides containing synthetic abasic sites. J. Biol. Chem. 262:1987;10171-10179.
69. 4-ethano-2′-deoxycytidine, and 3-(2-hydroxyethyl)-2′-deoxyuridine. Chem. Res. Toxicol. 8:1995;157-163.
70. Snow E.T., Singh J., Koenig K.L., Solomon J.J. Propylene oxide mutagenesis at template cytosine residues. Environ. Mol. Mutagen. 23:1994;274-280.