Mucochloric acid action on ΦX174 DNA: A comparison to other chlorine- substituted 2(5H)-furanones

Chemical Research in Toxicology

Volumn 10, Issue 2, 1997, Pages 205-210

  LaLonde, Robert T ^a   Ramdayal, Frank ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; FURANONE DERIVATIVE; MUTAGENIC AGENT;

ARTICLE; CHEMICAL ANALYSIS; DNA CLEAVAGE; DNA DAMAGE; DNA DETERMINATION; GENOTOXICITY; MUTAGEN TESTING;

AZIDES; BACTERIOPHAGE PHI X 174; DNA, SUPERHELICAL; DNA, VIRAL; DOSE-RESPONSE RELATIONSHIP, DRUG; FURANS; GLUTATHIONE; METHYL METHANESULFONATE; MUTAGENS; SODIUM AZIDE;

EID: 0031048757     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960123q     Document Type: Article

References (17)

1. Kronberg, L., and Franzen, R. (1993) Determination of chlorinated furanones, hydroxyfuranones, and butenedioic acids in chlorine-treated water and in pulp bleaching liquor. Environ. Sci. Technol. 27, 1811-1818.
2. Holmbom, B. R., Voss, R. H., Mortimer, R. D., and Wong, A. (1984) Fractionation, isolation and chlorination of Ames mutagenic compounds in kraft chlorination effluents. Environ. Sci. Technol. 18, 333-337.
3. LaLonde, R. T., Peräkylä, H., Cook, G. P., and Dence, C. W. (1990) Contribution of the 5-hydroxyl group to the mutagenicity of mucochloric acid. Environ. Toxicol. Chem. 9, 687-691.
4. LaLonde, R. T., and Leo, H. R. (1994) Interactive chlorine-by-bromine and hydrogen-by-hydroxyl group replacement effects in 2(5H)-furanone mutagenicity. Chem. Res. Toxicol. 7, 779-783.
5. 13C NMR chemical shifts as determinants of mutagenicity. Chem. Res. Toxicol. 4, 35-40.
6. LaLonde, R. T., Cook, G. P., Peräkylä, H., Dence, C. W., and Babish, J. C. (1991) Salmonella typhimurium (TA100) mutagenicity of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone and its open-and closed-ring analogs. Environ. Mol. Mutagen. 17, 40-48.
7. Chang, L. W., Daniel, F. B., and DeAngelo, A. B. (1991) DNA strand breaks induced in cultured human and rodent cells by chlorohydroxyfuranones - Mutagens isolated from drinking water. Teratog. Carcinog. Mutag. 11, 103-114.
8. LaLonde, R. T., Leo, H., Peräkylä, H., Dence, C. W., and Farrell, R. P. (1992) Associations of the bacterial mutagenicity of halogenated 2(5H)-furanones with their MNDO-PM3 computed properties and mode of reactivity with sodium borohydride. Chem. Res. Toxicol. 5, 392-400.
9. LaLonde, R. T., and Xie, S. (1992) A study of inactivation reactions of N-acetylcysteine with mucochloric acid, a mutagenic product of the chlorination of humic substance in water. Chem. Res. Toxicol. 5, 618-624.
10. LaLonde, R. T., and Xie, S. (1993) Glutathione and N-acetylcysteine inactivations of mutagenic 2(5H)-furanones from the chlorination of humics in water. Chem. Res. Toxicol. 6, 445-451.
11. LaLonde, R. T., Xie, S., Chamulitrat, W., and Mason, R. P. (1994) Oxidation and radical intermediates associated with glutathione conjugation of mucochloric acid. Chem. Res. Toxicol. 7, 482-486.
12. 6-Adenosinyl)-ethenoadenosine derivatives. Chem. Res. Toxicol. 8, 841-846.
13. Padmapriya, A. A., Just, G., and Lewis, N. G. (1985) Synthesis of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone: A potent mutagen. Can. J. Chem. 63, 828-832.
14. Fishbein, P. L., and Moore, H. W. (1990) 7-Chloro-7-cyanobicyclo-[4.2.0]octan-8-one. In Organic Synthesis (Paquette, L. A., Ed.) Vol. 69, pp 205-211, Organic Synthesis, Inc., Division of Organic Chemistry, American Chemical Society, Indiana University, Bloomington.
15. Kishikawa, H., Jiang, Y-P., Goodisman, J., and Dabrowiak, J. C. (1991) Coupled kinetic analysis of cleavage of DNA by esperamicin and calicheamicin. J. Am. Chem. Soc. 113, 5434-5440.
16. Fletcher, R. (1980) Practical Methods of Optimization, Wiley, Chichester.
17. Ishiguro, Y., LaLonde, R. T., Dence, C. W., and Santodonato, J. F. (1987) Mutagenicity of chlorine-substituted furanones and their inactivation by reaction with nucleophiles. Environ. Toxicol. Chem. 6, 935-946.