A conceptual framework for predicting the toxicity of reactive chemicals: Modeling soft electrophilicity

SAR and QSAR in Environmental Research

Volumn 17, Issue 4, 2006, Pages 413-428

  Schultz, T W ^a   Carlson, R E ^b   Cronin, M T D ^c   Hermens, J L M ^d   Johnson, R ^e   O'Brien, P J ^f   Roberts, D W ^c   Siraki, A ^g   Wallace, K B ^h   Veith, G D ⁱ  

^a UNIVERSITY OF TENNESSEE   (United States)

^b MD 57 ^*  (United States)

^c LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^d UTRECHT UNIVERSITY   (Netherlands)

^e U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^f UNIVERSITY OF TORONTO   (Canada)

^g NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^h UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

ⁱ International QSAR Foundation   (United States)

Author keywords

Molecular initiating events; QSAR; Reactivity toxicity; Thiol reactivity

Indexed keywords

ASSOCIATION REACTIONS; BIOCHEMISTRY; COMPUTATIONAL CHEMISTRY; INDICATORS (CHEMICAL); INDUSTRIAL CHEMICALS; MOLECULAR GRAPHICS; NUCLEOPHILES; ORGANIC CHEMICALS;

CELLULAR TARGETS; CHEMICAL MODEL; CONCEPTUAL FRAMEWORKS; INITIATING EVENTS; MOLECULAR INITIATING EVENT; QSAR; REACTIVE CHEMICALS; REACTIVITY TOXICITY; THIOL REACTIVITY; TOXIC EFFECT;

TOXICITY;

EID: 33747770746     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/10629360600884371     Document Type: Article

References (34)

1. G.D. Veith. SAR QSAR Environ. Res., 15, 323 (2004).
2. L. Shi, W. Tong, H. Fang, Q. Xie, H. Hong, R. Perkins, J. Wu, M. Tu, R.M. Blair, W.S. Branham, C. Waller, J. Walker, D.M. Sheehan. SAR QSAR Environ. Res., 13, 69 (2002).
3. T.W. Schultz, G.D. Sinks, M.T.D. Cronin. Environ. Toxicol., 17, 14 (2002).
4. H. Hong, W. Tong, Q. Xie, H. Fang, R. Perkins. SAR QSAR Environ. Res., 16, 339 (2005).
5. B.B. Brodie, W.D. Reid, A.K. Cho, G. Sipes, G. Krishna, J.R. Gillette. Proc. Natl. Acad. Sci. USA, 68, 160 (1971).
6. D. Farkas, S.R. Tannenbaum. Curr. Drug Metab., 6, 111 (2005).
7. J.A. Hinson, D.W. Roberts. Annu. Rev. Pharmacol. Toxicol., 32, 471 (1992).
8. O.G. Mekenyan, S.D. Dimitrov, T.S. Pavlov, G.D. Veith. Curr. Pharm. Design., 10, 1273 (2004).
9. A. Jacobs. Understanding Organic Reaction Mechanisms, Cambridge University Press, Cambridge (1997).
10. C.G. Swain, C.B. Scott. J. Am. Chem. Soc., 75, 141 (1953).
11. M. Karelson, V.S. Lobanov, A.R. Katritzky. Chem. Rev., 96, 1027 (1996).
12. B. Cole. Drug Metab. Rev., 15, 1307 (1984-85).
13. S.D. Dimitrov, L.K. Low, G.Y. Patlewicz, P.S. Kern, G.D. Dimitrova, M.H.I. Comber, R.D. Phillips, J. Niemela, P.T. Bailey, O.G. Mekenyan, Chem. Res. Toxicol. in press (2006).
14. J. March. Advanced Organic Chemistry Reactions, Mechanisms, and Structure, fourth, John Wiley & Sons, New York (1992).
15. A. Harder, B.I. Escher, R.P. Schwarzenbach. Environ. Sci. Technol., 37, 4955 (2003).
16. H. Esterbauer, H. Zoolner, N. Scholz. Zeitschrift für Naturforschung, 30c, 466 (1975).
17. E.D. Clarke, D.T. Greenhow, D. Adams. Pestic. Sci., 54, 385 (1998).
18. G.F. Gerberick, J.D. Vassallo, R.E. Bailey, J.G. Chaaney, S.W. Morrall, J.P. Lepoittevin. Toxicol. Sci., 81, 332 (2004).
19. T.W. Schultz, J.W. Yarbrough, E.L. Johnson. SAR QSAR Environ. Res., 16, 313 (2005).
20. R.L. Lipnick. Sci. Total Environ., 109/110, 131 (1991).
21. A.P. Freidig, H.J.M. Verhaar, J.L.M. Hermens. Environ. Toxicol. Chem., 18, 1133 (1999).
22. J. Ferguson. Proc. R. Soc. Lond. B, 127, 387 (1939).
23. M.H. Abraham, G.D. Nielson, Y. Alarie. J. Pharm. Sci., 83, 680 (1994).
24. Y. Alarie, G.D. Nielson, J. Andonian-Haftvan, M.H. Abraham. Toxicol. Appl. Pharmacol., 134, 92 (1995).
25. M. Schaper. Am. Ind. Hyg. Assoc. J., 54, 488 (1993).
26. Y. Alarie, M. Schaper, G.D. Nielson, M.H. Abraham. Arch. Toxicol., 72, 125 (1998).
27. A.O. Aptula, G. Patlewicz, D.W. Roberts. Chem. Res. Toxicol., 18, 1420 (2005).
28. M.P. Payne, P.T. Walsh. J. Chem. Inf. Comput. Sci., 34, 154 (1994).
29. A.O. Aptula, G. Patlewicz, D.W. Roberts, T.W. Schultz. Toxicol. in Vitro, 20, 239 (2006).
30. G. Patlewicz, D.W. Roberts, J.D. Walker. QSAR & Comb. Sci., 22, 196 (2003).
31. P. O'Brien, A.G. Siraki, S. Tafazoli, K. Chan. In Liver Diseases: Biochemical Mechanisms & New Therapeutic Insights, S. Ali, S.L. Friedman, and D.A. Mann (Eds), pp. 531-541, Oxford & IBH Publishing, New Dehli (2005).
32. P.B. Hulbert, N.M. Hamoodi. J. Pharm. Biomed. Anal., 8, 1009 (1990).
33. K. Chan, P. O'Brien, Quantitative structure-activity relationships for the non-enzymic GSH reactivity and hepatocyte cytotoxicity induced by halonitrobenzenes and quinones (unpublished) (2006).
34. D.C. Evans, A.P. Watt, D.A. Nicoll-Griffith, T.A. Baillie. Chem. Res. Toxicol., 17, 3 (2004).