Comparative QSAR evidence for a free-radical mechanism of phenol-induced toxicity

Chemico-Biological Interactions

Volumn 127, Issue 1, 2000, Pages 61-72

  Hansch, Corwin ^a   McKarns, Susan C ^b   Smith, Carr J ^c   Doolittle, David J ^c  

^a POMONA COLLEGE   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

^c R J REYNOLDS TOBACCO COMPANY   (United States)

Author keywords

Free radicals; Hammett +; Hydrophobicity; Phenols; Premarin; QSAR

Indexed keywords

CONJUGATED ESTROGEN; PHENOL DERIVATIVE;

ANIMAL CELL; ARTICLE; CANCER RISK; CYTOTOXICITY; DISSOCIATION; EPITHELIUM CELL; HYDROPHOBICITY; NONHUMAN; PARTITION COEFFICIENT; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT;

ANIMALS; CELL LINE; CELL MEMBRANE; EPITHELIAL CELLS; FREE RADICALS; L-LACTATE DEHYDROGENASE; LIVER; PHENOLS; RATS; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 0034659106     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(00)00171-X     Document Type: Article

References (30)

1. Huang M.-T., Osawa T., Ho C.-T, Rosen R.T. Food Phytochemicals for Cancer Prevention. I:1994;American Chemical Society, Washington, DC.
2. Ho C.-T., Osawa T., Huang M.-T., Rosen R.T. Food Phytochemicals for Cancer Prevention. II:1994;American Chemical Society, Washington, DC.
3. Rice-Evans C.A., Packer L. Flavonoids in Health and Disease. 1998;Marcel Dekker, New York.
4. BioByte Corporation, 201 West 4th Street, Suite 204, Claremont, CA 91711.
5. Selassie C.D., DeSoyza T.V., Rosario M., Gao H., Hansch C. Phenol toxicity to leukemia cells: a radical process? Chem. Biol. Interactions. 113:1998;175-190.
6. Hansch C., Leo A. QSAR in metabolism. Heller S.R. Exploring QSAR, Fundamentals and Applications in Chemistry and Biology. 1995;299-343 American Chemical Society, Washington, DC.
7. Rozman K.K., Klaasen C.D. Absorption, distribution and excretion of toxicants. Klaassen C.D. Casarett & Doull's Toxicology. Fifth Edition:1996;91-112 McGraw-Hill, New York.
8. Parkinson A. Biotransformation of xenobiotics. Klaassen C.D. Casarett & Doull's Toxicology. Fifth Edition:1996;113-186 McGraw-Hill, New York.
9. Hoffmann G.R. Genetic toxicology. Klaassen C.D. Casarett & Doull's Toxicology. Fifth Edition:1996;269-300 McGraw-Hill, New York.
10. Hansch C., Bjorkroth J.P., Leo A. Hydrophobicity and CNS agents. On the principle of minimal hydrophobicity in drug design. J. Pharm. Sci. 76:1987;663-686.
11. Hansch C., Leo A. QSAR of nonspecific toxicity. Heller S.R. Exploring QSAR, Fundamentals and Applications in Chemistry and Biology. 1995;169-221 American Chemical Society, Washington, DC.
12. Huijgen H.J., Sanders G.T.B., Koster R.W., Vreeken J., Bossuyl P.M.M. The clinical value of lactate dehydrogenase in serum: a quantitative review. Eur. J. Clin. Chem. Clin. Biochem. 35(8):1997;569-579.
13. McKarns S.C., Hansch C., Caldwell W.S., Morgan W.T., Moore S.K., Doolittle D.J. Correlation between hydrophobicity of short-chain aliphatic alcohols and their ability to alter plasma membrane integrity. Fund. Appl. Toxicol. 36:1997;62.
14. Hansch C., Gao H. Comparative QSAR: radical reactions of benzene derivatives in chemistry and biology. Chem. Rev. 97:1997;2995.
15. Tsao M.S., Smith J.D., Nelson K.G., Grisham J.W. A diploid epithelial cell line from normal adult rat liver with phenotypic properties of 'oval' cells. Expt. Cell Res. 154:1984;38.
16. Byler R.M., Sherman N.A., Wallner J.S., Horwitz L.D. Hydrogen peroxide in cultured cardiac myocytes is iron dependent. Am. J. Physiol. 266:1994;121-127.
17. Hansch C., Leo A., Hoekman D. Exploring QSAR. Hydrophobic, Electronic and Steric Constants. 1995;American Chemical Society, Washington, DC.
18. Selassie C.D., Shusterman A.J., Kapur S., Verma R.P., Zhang L., Hansch C. On the toxicity of phenols to fast growing cells. A QSAR model for a radical-based toxicity. J. Chem. Soc. Perkin Tran. 2:1999;2729.
19. Oglesby L.A., Eborn-McCoy M.T., Logsdon T.R., Copeland F., Beyer P.E., Kavlock R.J. In vitro embryotoxicity of a series of para-substituted phenols: structure, activity and correlation with in vivo data. Teratology. 45(1):1992;1-33.
20. Hansch C., Telzer B.R., Zhang L. Comparative QSAR in toxicology: examples from teratology and cancer chemotherapy of aniline mustards. Crit. Rev. Toxicol. 25:1995;67-89.
21. Kavlock R.J. Structure-activity approaches in the screening of environmental agents for developmental toxicity. Reprod. Toxicol. 7(Suppl. 1):1993;113-116.
22. Richard A.M., Hongslo J.K., Boone P.F., Holme J.A. Structure-activity study of paracetamol analogues: inhibition of replicative DNA synthesis in V79 Chinese hamster cells. Chem. Res. Toxicol. 4(2):1991;151-156.
23. Hansch C, Zhang L. Comparative QSAR: radical toxicity and scavenging. Two different sides of the same coin. SAR QSAR Environ. Res. 4(2-3):1995;73-82.
24. Mukai K., Yokoyama K., Fukuda K., Vemoto Y. Kinetic studies of anti oxidant activity in new tochopherol model compounds in solution. Bull. Chem. Soc. Jpn. 60:1987;2163.
25. Franchi P., Lucarni M., Pedulli G.F., Valgimigli L., Luhelli B. Reactivity of substituted phenols toward alkyl radicals. J. Am. Chem. Soc. 121:1999;507.
26. Pritchard K.I. Estrogen/hormone replacement therapy and the etiology of breast cancer. Recent Results Cancer Res. (Germany). 152:1998;22-31.
27. Willhite L. Osteoporosis in women: prevention and treatment. J. Am. Pharm. Assoc. (Wash). 38(5):1998;614-623.
28. Pitot H.C., Dragan Y.P. Chemical carcinogenesis. Klaassen C.D. Casarett & Doull's Toxicology. Fifth Edition:1996;201-267 McGraw-Hill, New York.
29. Anderson E.L. Carcinogenic assessment group of the US environmental protection agency. Quantitative approaches in use to assess cancer risk. Risk Anal. 3(4):1983;277-295.
30. Cohen S.M., Ellwein L.B. Cell proliferation in carcinogenesis. Science. 249:1990;1007-1011.