2′-Deoxyguanosine, 2′-deoxycytidine, and 2′- deoxyadenosine adducts resulting from the reaction of tetrahydrofuran with DNA bases

Chemical Research in Toxicology

Volumn 19, Issue 7, 2006, Pages 927-936

  Hermida, Silvia A S ^a   Possari, Ediliz P M ^a   Souza, Denise B ^a   De Arruda Campos, Ivan P ^b   Gomes, Osmar F ^a   Di Mascio, Paolo ^a   Medeiros, Marisa H G ^a   Loureiro, Ana Paula M ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b PAULISTA UNIVERSITY   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYADENOSINE; DEOXYCYTIDINE; DEOXYGUANOSINE; DNA BASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SOLVENT; TETRAHYDROFURAN; UNSPECIFIC MONOOXYGENASE; CARCINOGEN; DEOXYADENOSINE DERIVATIVE; DRUG DERIVATIVE; FURAN DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARCINOGENICITY; CATTLE; CELL CULTURE; CULTURE MEDIUM; CYTOTOXICITY; DNA ADDUCT; DNA DAMAGE; ELECTROSPRAY MASS SPECTROMETRY; GENOTOXICITY; LIVER MICROSOME; MALE; NONHUMAN; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY; THYMUS; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ENZYMOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION REDUCTION REACTION;

ANIMALIA;

ANIMALS; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYADENOSINES; DEOXYCYTIDINE; DEOXYGUANOSINE; DNA ADDUCTS; FURANS; MICROSOMES, LIVER; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RATS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 33746255339     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx060033d     Document Type: Article

References (17)

1. Ong, C. N., Chia, S. E., Phoon, W. H., and Tan, K. T. (1991) Biological monitoring of occupational exposure to tetrahydrofuran. Br. J. Ind. Med. 48, 616-621.
2. Hazardous Substances Data Bank (HSDB) (2003) Database maintained by the National Library of Medicine, available through the MEDLARS system. U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health, Bathesda, MD.
3. Daye, K. J., Groff, J. C., Kirpekar, A. C., and Mazumder, R. (2003) High efficiency degradation of tetrahydrofuran (THF) using a membrane bioreactor: identification of THF-degrading cultures of Pseudonocardia sp. strain M1 and Rhodococcus ruber isolate M2. J. Ind. Microbiol. Biotechnol. 30, 705-714.
4. SenGupta, S., Upadhyaya, H. P., Kumar, A., Naik, P. D., and Bajaj, P. (2005) Detection of OH radical in laser induced photo dissociation of tetrahydrofuran at 193 nm. J. Chem. Phys. 122, 124309.
5. 1H NMR spectroscopic investigation of serum and urine in a case of acute tetrahydrofuran poisoning. J. Anal. Toxicol. 25, 270-274.
6. National Toxicology Program (NTP) (1998) Toxicology and carcinogenesis studies of tetrahydrofuran (CAS No. 109-99-9) in F344/N rats and B6C3F1 mice. Technical Report Series No. 475. NIH Publication No. 98-3965. U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health, Research Triangle Park, NC.
7. Chhabra, R. S., Herbert, R. A., Roycroft, J. H., Chou, B., Miller, R. A., and Renne, R. A. (1998) Carcinogenesis studies of tetrahydrofuran vapors in rats and mice. Toxicol. Sci. 41, 183-188.
8. American Conference of Governmental Industrial Hygienists (ACGIH) (2002). TLVs and BEIs: Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices for 2002, Cincinnati, OH.
9. 2-etheno-2′- deoxyguanosine adduct formation. Chem. Res. Toxicol. 13, 601-609.
10. Loureiro, A. P. M., Campos, I. P. d. A., Gomes, O. F., Di Mascio, P., and Medeiros, M. H. G. (2004) Structural characterization of diastereoisomeric ethano adducts derived from the reaction of 2′-deoxyguanosine with trans,trans-2,4-decadienal. Chem. Res. Toxicol. 17, 641-649.
11. Loureiro, A. P. M., Campos, I. P. d. A., Gomes, O. F., Possari, E. P. M., Di Mascio, P., and Medeiros, M. H. G. (2005) Structural characterization of an etheno-2′-deoxyguanosine adduct modified by tetrahydrofuran. Chem. Res. Toxicol. 18, 290-299.
12. 2+ in the presence of xylenol orange. Comparison with the TBA assay and an iodometric method. Lipids 26, 853-856.
13. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
14. 2-tetrahydropyranyl adducts. Chem. Res. Toxicol. 8, 607-616.
15. 2-etheno-2′-deoxyguanosine. Chem. Res. Toxicol. 18, 1701-1714.
16. Gamer, A. O., Jaeckh, R., Leibold, E., Kaufmann, W., Gembardt, C., Bahnemann, R., and van Ravenzwaay, B. (2002) Investigations on cell proliferation and enzyme induction in male rat kidney and female mouse liver caused by tetrahydrofuran. Toxicol. Sci. 70, 140-149.
17. van Ravenzwaay, B., Gamer, A. O., Leibold, E., and Kaufmann, W. (2003) Effect of cytochrome P-450 inhibition on tetrahydrofuran-induced hepatocellular proliferation in female mice. Arch. Toxicol. 77, 459-464.