Formation of deaminated products in styrene oxide reactions with deoxycytidine

Chemical Research in Toxicology

Volumn 12, Issue 10, 1999, Pages 883-886

  Barlow, Thomas ^a,b   Dipple, Anthony ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYCYTIDINE; DEOXYURIDINE; STYRENE OXIDE;

ARTICLE; CARCINOGENESIS; CHEMICAL REACTION; DEAMINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; MUTAGENESIS; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

AMIDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; DEOXYCYTIDINE; DEOXYURIDINE; DNA ADDUCTS; EPOXY COMPOUNDS; HYDROGEN BONDING; MUTAGENS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 0032706342     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990070n     Document Type: Article

References (26)

1. Vainio, H., Norppa, H., Hemminki, K., and Sorsa, M. (1982) in Biological Reactive Intermediates, 2. Chemical Mechanisms and Biological Effects, Part A (Snyder, R., Parke, D. V., Kocsis, J., Jollow, D. J., Gibson, G. G., and Witmer, C. M., Eds.) pp 257-274, Plenum Publishing Corp., New York.
2. Sugiura, K., and Goto, M. (1981) Mutagenicities of styrene oxide derivatives on bacterial test systems: relationship between mutagenic potencies and chemical reactivity. Chem.-Biol. Interact. 35, 71-91.
3. McConnell, E. E., and Swenberg, J. A. (1994) Review of styrene and styrene oxide long-term animal studies. Crit. Rev. Toxicol. 24 (Suppl. S1), S49-S55.
4. Latif, F., Moschel, R. C., Hemminki, K., and Dipple, A. (1988) Styrene oxide as a stereochemical probe for the mechanism of aralkylation at different sites on guanosine. Chem. Res. Toxicol. 1, 364-369.
5. 6-substituted guanosine products resulting from reaction of guanosine with styrene oxide. J. Org. Chem. 51, 2952-2955.
6. Hemminki, K., Paasivirta, J., Kurkirinne, T., and Virkki, L. (1980) Alkylation products of DNA bases by simple epoxides. Chem.-Biol. Interact. 30, 259-270.
7. 32P-postlabeling of DNA adducts of styrene-exposed lamination workers. Carcinogenesis 14, 2059-2061.
8. Hemminki, K., and Hesso, A. (1984) Reaction products of styrene oxide with guanosine in aqueous media. Carcinogenesis 5, 601-607.
9. Savela, K., Hesso, A., and Hemminki, K. (1986) Characterization of reaction products between styrene oxide and deoxynucleosides and DNA. Chem.-Biol. Interact. 60, 235-246.
10. Hemminki, K., and Vodicka, P. (1995) Styrene: from characterisation of DNA adducts to application in styrene-exposed lamination workers. Toxicol. Lett. 77, 153-161.
11. 32P-postlabelling in DNA and human embryonal lung fibroblasts (HEL). Carcinogenesis 17, 801-808.
12. Hemminki, K., and Suni, R. (1984) Formation of phosphodiesters in thymidine monophosphate by styrene oxide. Toxicol. Lett. 21, 59-63.
13. Savela, K., and Hemminki, K. (1986) Reaction products of styrene oxide with deoxynucleosides and DNA in vitro. Arch. Toxicol. (Suppl. 9), 281-285.
14. Vodicka, P., and Hemminki, K. (1988) Identification of alkylation products of styrene oxide in single-and double-stranded DNA. Carcinogenesis 9, 1657-1660.
15. Barlow, T., Ding, J., Vouros, P., and Dipple, A. (1997) Investigation of hydrolytic deamination of 1-(2-hydroxy-1-phenylethyl)-adenosine. Chem. Res. Toxicol. 10, 1247-1249.
16. Barlow, T., Takeshita, J., and Dipple, A. (1998) Deamination and Dimroth rearrangement of deoxyadenosine-styrene oxide adducts in DNA. Chem. Res. Toxicol. 11, 838-845.
17. 6-positions. Chem. Res. Toxicol. 8, 389-395.
18. Finneman, J. I., Kim, H., Harris, C. M., and Harris, T. M. (1997) Mechanistic studies of the reaction of styrene oxide with adenine in an oligonucleotide. 213th National ACS Meeting, Division of Chemical Toxicology, San Antonio, TX, April 6-11 (abstract).
19. Kim, H., Harris, C. M., and Harris, T. M. (1996) Studies of the mechanisms of adduction of 2′-deoxyadenosine with optically active styrene oxide. 212th National ACS Meeting, Division of Chemical Toxicology, Boston, MA, August 25-30, p 54 (abstract).
20. Solomon, J. J., Mukai, F., Fedyk, J., and Segal, A. (1988) Reactions of propylene oxide with 2′-deoxynucleosides and in vitro with calf thymus DNA. Chem.-Biol. Interact. 67, 275-294.
21. Li, F., Segal, A., and Solomon, J. J. (1992) In vitro reaction of ethylene oxide with DNA and characterization of DNA adducts. Chem.-Biol. Interact. 83, 35-54.
22. Solomon, J. J., Singh, U. S., and Segal, A. (1993) In vitro reactions of 2-cyanoethylene oxide with calf thymus DNA. Chem.-Biol. Interact. 88, 115-135.
23. 3-deoxyuridine adducts of butadiene monoxide. Arch. Biochem. Biophys. 343, 63-72.
24. Singer, B. (1975) UV spectral characteristics and acidic dissociation constants of 280 alkyl bases, nucleosides, and nucleotides. In Handbook of Biochemistry and Molecular Biology: Nucleic Acids (Fasman, G. D., Ed.) pp 409-449, CRC Press, Cleveland, OH.
25. Fujii, T., Saito, T., and Terahara, N. (1986) Purines XXVII. Hydrolytic deamination versus Dimroth rearrangement in the 9-substituted adenine ring: Effect of an omega-hyroxyalkyl group at the 1-position. Chem. Pharm. Bull. 34, 1094-1107.
26. Barlow, T., and Dipple, A. (1998) Aralkylation of guanosine with para-substituted styrene oxides. Chem. Res. Toxicol. 11, 44-53.