Abiotic sulfhydryl reactivity: A predictor of aquatic toxicity for carbonyl-containing α,β-unsaturated compounds

Chemical Research in Toxicology

Volumn 20, Issue 3, 2007, Pages 558-562

  Yarbrough, Jason W ^a   Schultz, T Wayne ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 PENTEN 3 ONE; ACROLEIN; ACRYLIC ACID BUTYL ESTER; ACRYLIC ACID ETHYL ESTER; ACRYLIC ACID ISOPENTYL ESTER; ACRYLIC ACID PENTYL ESTER; ACRYLIC ACID PROPARGYL ESTER; ACRYLIC ACID PROPYL ESTER; ACRYLIC ACID VINYL ESTER; ALDEHYDE DERIVATIVE; ALPHA,BETA UNSATURATED ESTER; CROTONALDEHYDE; ESTER DERIVATIVE; ETHYL CROTONIC ACID ESTER; ETHYL METHACRYLATE; ETHYL PROPIOLIC ACID ESTER; GLUTATHIONE DERIVATIVE; KETONE DERIVATIVE; METHACRYLIC ACID ISOPROPYL ESTER; METHACRYLIC ACID METHYL ESTER; METHACRYLIC ACID PROPYL ESTER; METHACRYLIC ACID VINYL ESTER; METHYL 2 OCTENOIC ACID ESTER; METHYL CROTONIC ACID ESTER; METHYL PROPIOLIC ACID ESTER; METHYL TETROLIC ACID ESTER; METHYL TIGLATE; THIOL DERIVATIVE; TRIPEPTIDE GLUTATHIONE; UNCLASSIFIED DRUG; VINYL CROTONIC ACID ESTER;

ABIOTIC STRESS; AQUATIC ENVIRONMENT; ARTICLE; CONTROLLED STUDY; ELECTROPHILIC STRESS; HYDROPHOBICITY; NONHUMAN; POPULATION GROWTH; TETRAHYMENA PYRIFORMIS; TOXICITY;

ACROLEIN; ALDEHYDES; ALGORITHMS; ANIMALS; DATA INTERPRETATION, STATISTICAL; ESTERS; GLUTATHIONE; KETONES; KINETICS; METHYLMETHACRYLATE; ORGANIC CHEMICALS; SULFHYDRYL COMPOUNDS; TETRAHYMENA PYRIFORMIS;

TETRAHYMENA PYRIFORMIS;

EID: 34047274393     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx600344a     Document Type: Article

References (25)

1. Schultz, T. W., Netzeva, T. I., Roberts, D. W., and Cronin, M. T. D. (2005) Structure-toxicity relationships for carbonyl-containing α,β-unsaturated aliphatic chemicals evaluated with Tetrahymena pyriformis. Chem. Res. Toxicol. 17, 330-341.
2. Friedman, M., Cavins, J. F., and Wall, J. S. (1965) Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with α,α-unsaturated compounds. J. Am. Chem. Soc. 87, 3672-3682.
3. Freidig, A. P., Verhaar, H. J. M., and Hermens, J. L. M. (1999) Quantitative structure property relationships for the chemical reactivity of acrylates and methacrylates. Environ. Toxicol. Chem. 18, 1133-1139.
4. Aptula, A. O., Patlewicz, G. Y., and Roberts, D. W. (2005) Skin sensitization: Reaction mechanistic applicability domains for structure-activity relationships. Chem. Res. Toxicol. 18, 1420-1426.
5. Greim, H., Ahlers, J., Bias, R., Broecker, B., Hollander, H., Gelbke, H. P., Jacobi, S., Klimisch, H. J., Mangelsdorf, I., Mayr, W., Schon, N., Stropp, G., Stahnecker, P., Vogel, R., Weber, C., Ziegler-Skylakakis, K., and Bayer, E. (1995) Assessment of structurally related chemicals: Toxicity and ecotoxicity of acrylic acid and acrylic acid alkyl esters (acrylates), methacrylic acid and methacrylic acid alkyl esters (methacrylates). Chemosphere 31, 2637-2659.
6. Osman, R., Namboodiri, K., Weistein, H., and Rabinowitz, J. (1988) Reactivities of acrylic and methacrylic acids in a nucleophilic addition model of their biological activity. J. Am. Chem. Soc. 110, 1701-1707.
7. McCarthy, T. J., Hayes, E. P., Schwartz, C. S., and Witz, G. (1994) The reactivity of selected acrylate esters toward glutathione and deoxyribonucleosides in vitro: Structure-activity relationships. Fundam. Appl. Toxicol. 22, 543-548.
8. Schultz, T. W., Yarbrough, J. W., and Johnson, E. L. (2005) Structure-activity relationships for glutathione reactivity of carbonyl-containing compounds. SAR QSAR Environ. Res. 16, 313-322.
9. Schultz, T. W., and Yarbrough, J. W. (2004) Trends in structure-toxicity for carbonyl-containing α,β-unsaturated compounds. SAR QSAR Environ. Res. 15, 139-146.
10. Papirmeister, B., Feister, A. F., Robinson, S. I., and Ford, R. D. Medical Defense Against Mustard Gas: Toxic Mechanisms and Pharmacological Implications. CRC Press, Boca Raton, FL, 1991.
11. Reed, D. J. (1990) Glutathione: Toxicological Implications. Annu. Rev. Pharmacol. Toxicol. 30, 603-631.
12. Benigni, R., Passerini, L., and Rodomonte, A. (2003) Structure-activity relationships for the mutagenicity and carcinogenicity of simple and alpha-beta unsaturated aldehydes. Environ. Mol. Mutagen. 42, 136-143.
13. Gerberick, G. F., Ryan, C. A., Kern, P. S., Schlatter, H., Dearman, R. J., Kimber, I., Patlewicz, G. Y., and Basketter, D. A. (2005) Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods. Dermatitis 16, 157-202.
14. Schultz, T. W. (1997) TETRATOX: Tetrahymena pyriformis population growth impairment endpoint-A surrogate for fish lethality. Toxicol. Methods 7, 289-309.
15. SAS Institute Inc. (1989) SAS/STAT User's Guide, v. 6, 4th ed., Vol. 2, p 846, SAS, Cary, NC.
16. Cronin, M. T. D. (2003) Quantitative structure-activity relationships for acute aquatic toxicity: the role of mechanism of toxic action in successful modeling. In Quantitative Structure-Activity Relationship (QSAR) Models of Mutagens and Carcinogens (Benigni, R., Ed.) pp 235-258, CRC Press, Boca Raton, FL.
17. Bradbury, S. P., Russom, C. L., Ankley, G. T., Schultz, T. W., and Walker, J. D. (2003) Overview of data and conceptual approaches for derivation of QSARs for ecotoxicological effects of organic chemicals. Environ. Toxicol. Chem. 22, 1789-1798.
18. Bradbury, S. P. (1994) Predicting modes of toxic action from chemical structure: An overview. SAR QSAR Environ. Res. 2, 89-104.
19. Escher, B. I., and Hermens, J. L. M. (2002) Modes of action in ecotoxicology: Their role in body burden, species sensitivity, QSARs, and mixture effects. Environ. Sci. Technol. 36, 4201-4217.
20. Schultz, T. W., Carlson, R. E., Cronin, M. T. D., Hermens, J. L. M., Johnson, R., O'Brien, P. J., Roberts, D. W., Siraki, A., Wallace, K. D., and Veith, G. D. (2006) A conceptual framework for predicting toxicity of reactive chemicals: Models -for soft electrophilicity. SAR QSAR Environ. Res. 17, 413-428.
21. Parson, R. G., and Songstad, J. (1967) Application of the principle of hard and soft acids and bases to organic chemistry. J. Am. Chem. Soc. 89, 1827-1836.
22. Schultz, T. W., and Cronin, M. T. D. (2003) Essential and desirable characteristics of ecotoxicity quantitative structure-activity relationships. Environ. Toxicol. Chem. 22, 599-607.
23. Schultz, T. W., Cronin, M. T. D., Netzeva, T. I., and Aptula, A. O. (2002) Structure-toxicity relationships for aliphatic chemicals evaluated with Tetrahymena pyriformis. Chem. Res. Toxicol. 15, 1602-1609.
24. Aptula, A. O., and Roberts, D. W. (2006) Mechanistic applicability domains for nonanimal-based prediction of toxicological end points: General principles and application to reactive toxicity. Chem. Res. Toxicol. 19, 1097-1105.
25. Bearden, A. P., Sinks, G. D., and Schultz, T. W. (1999) Population growth kinetics of Tetrahymena pyriformis exposed to selected electrophiles. In Environmental Toxicology and Risk Assessment, Vol. 8 (Henshel, D., Black, M. C., and Harrass, M. C., Eds.) ASTM STP 1364, pp 319-328, American Society for Testing and Materials, West Conshohocken, PA.