Synthesis, cytotoxicity, and QSAR analysis of X-thiophenols in rapidly dividing cells

Chemical Research in Toxicology

Volumn 16, Issue 3, 2003, Pages 276-284

  Verma, Rajeshwar P ^a   Kapur, Sanjay ^a   Barberena, Omar ^a   Shusterman, Alan ^b   Hansch, Corwin H ^a   Selassie, Cynthia D ^a  

^a POMONA COLLEGE   (United States)

^b REED COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE; THIOPHENOL DERIVATIVE;

ANIMAL CELL; ARTICLE; CELL DIVISION; CYTOTOXICITY; LEUKEMIA L 1210; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SYNTHESIS; TOXICITY TESTING;

ANIMALS; ELECTRONS; HYDROGEN-ION CONCENTRATION; INHIBITORY CONCENTRATION 50; KINETICS; LEUKEMIA; MICE; MODELS, MOLECULAR; PHENOLS; PREDICTIVE VALUE OF TESTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; THERMODYNAMICS; TUMOR CELLS, CULTURED;

ANIMALIA;

EID: 0037352125     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx020103q     Document Type: Article

References (44)

1. Soto, A. M., Justicia, H., Wray, J. W., and Sonnenschein, C. (1991) P-Nonyl-Phenol: an estrogenic xenobiotic released from "modified" polystyrene. Environ. Health Perspect. 92, 167-173.
2. Hansch, C., Telzer, B. R., and Zhang, L. (1995) Comparative QSAR in toxicology: examples from teratology and cancer chemotherapy of aniline mustards. Crit. Rev. Toxicol. 25, 67-89.
3. Gao, H., Katzenellenbogen, J. A., Garg, R., and Hansch, C. (1999) Comparative QSAR analysis of estrogen receptor ligands. Chem. Rev. 99, 723-744.
4. Zhang, L., Gao, H., Hansch, C., and Selassie, C. D. (1998) Molecular orbital parameters and QSAR in the analysis of phenol toxicity to leukemia cells. J. Chem. Soc., Perkin Trans. 2 2553-2556.
5. Selassie, C. D., DeSoyza, T. V., Rosario, M., Gao, H., and Hansch, C. (1998) Phenol toxicity in leukemia cells: a radical process? Chem.-Biol. Interact. 113, 175-190.
6. Hansch, C., and Gao, H. (1997) Comparative QSAR: Radical reactions of benzene derivatives in chemistry and biology. Chem. Rev. 97, 2995-3060.
7. Hansch, C., and Zhang, L. (1995) Comparative QSAR: radical toxicity and scavenging. Two different sides of the same coin: SAR QSAR. Environ. Res. 4, 73-82.
8. Selassie, C. D., Shusterman, A. J., Kapur, S., Verma, R. P., Zhang, L., and Hansch, C. (1999) On the toxicity of phenols to fast growing cells. A QSAR model for a radical-based toxicity. J. Chem. Soc., Perkin Trans. 2 2729-2733.
9. Henderson, B. E., Ross, R., and Bernstein, L. (1988) Estrogens as a cause of human cancer: the Richard and Hinda Rosenthal Foundation Award Lecture. Cancer Res. 48, 246-253.
10. Yager, J. D., and Liehr, J. G. (1996) Molecular mechanisms of estrogen carcinogenesis. Annu. Rev. Pharmacol. Toxicol. 36, 203-232.
11. Asadawa, E. M., Hagiwara, A., Takanoshi, S., and Ito, N. (1994) Carcinogenicity 4-methoxyphenol and 4-methylcatechol in F344 rats. Int. J. Cancer 56, 146-152.
12. Food Phytochemicals for Cancer Prevention. I. (1994) (Huang, M.-T., Osawa, T., Ho, C.-T., and Rosen, R. T., Eds.) ACS Symposium 546, American Chemical Society, Washington, DC.
13. Food Phytochemicals for Cancer Prevention. (1994) (Ho, C.-T., Osawa, T., Huang, M.-T., and Rosen, R. T., Eds.) ACS Symposium 547, American Chemical Society, Washington, DC.
14. Flavanoids in Health and Disease. (1998) (Rice-Evans, C. A., and Packer, L., Eds.) Marcell Dekker, New York.
15. Free Radicals and Oxidative Stress: Environment, Drugs and Food Additives. (1995) (Rice-Evans, C., Halliwell, B., and Lunt, G. G., Eds.) Biochemical Society Symposium 61, Portland Press, London.
16. Amrolia, P., Sullivan, S. G., Stern, A., and Munday, R. (1989) Toxicity of aromatic thiols in the human red blood cell. J. Appl. Toxicol. 9, 113-118.
17. Bonifacic', M., and Asmus, K. D. (1976) Free radical oxidation of organic disulfides. J. Phys. Chem. 80, 2426-2430.
18. Asmus, K.-D. (1990) Sulfur-centered free radicals. In Methods in Enzymology, Vol. 186, pp 168-180, Academic Press, New York.
19. Suter, C. M. (1931) Studies in the diphenyl ether series. II. Preparation and structure of some sulfonic acids and related derivatives. J. Am. Chem. Soc. 53, 1112-1116.
20. Sheley, C. F. (1978) A convenient synthesis of 4-alkyl and 4-cyano thiophenols. Mol. Cryst. Liq. Cryst. 44, 193-196.
21. 3.
22. 3.
23. Protiva, M., Rajsner, M., Adlerova, E., Seidlova, V., and Vejdelek, Z. J. (1964) Neurotropic and psychotropic substances. I. New types of 6, 11-dihydrodibenzo (b,e) thiepine derivatives and analogues. Collect. Czech. Chem. Commun. 29, 2161-2181; (1964) Chem. Abstr. 62, 524a.
24. Protiva, M., Rajsner, M., Adlerova, E., Seidlova, V., and Vejdelek, Z. J. (1964) Neurotropic and psychotropic substances. I. New types of 6, 11-dihydrodibenzo (b,e) thiepine derivatives and analogues. Collect. Czech. Chem. Commun. 29, 2161-2181; (1964) Chem. Abstr. 62, 524a.
25. Kuliev, A. M., Kuliev, A. B., and Mamedov, F. N. (1964) Synthesis of alkylthiophenols. Zh. Obshch. Khim 34, 993-995; (1964) Chem. Abstr. 60, 15761e.
26. Kuliev, A. M., Kuliev, A. B., and Mamedov, F. N. (1964) Synthesis of alkylthiophenols. Zh. Obshch. Khim 34, 993-995; (1964) Chem. Abstr. 60, 15761e.
27. Rajsner, M., Seidlova, V., and Protiva, M. (1962) Homologues and halogen derivatives of prothiadine with substituents in the benzene nuclei. Cesk. Farm. 11, 451-456; (1963) Chem. Abstr. 59, 2773f.
28. Rajsner, M., Seidlova, V., and Protiva, M. (1962) Homologues and halogen derivatives of prothiadine with substituents in the benzene nuclei. Cesk. Farm. 11, 451-456; (1963) Chem. Abstr. 59, 2773f.
29. Teruaki, M., and Tadashi, E. (1967) The Oxidation of Thiols and their Lead Salts. Bull. Chem. Soc. Jpn. 40, 2388-2391.
30. C-QSAR Program, BioByte Corp., Claremont, CA 91711.
31. Mason, R. P., and Holtzman, J. L. (1975) The mechanism of microsomal and mitrochondrial nitrodeductase. Electron spin resonance evidence for nitroaromatic free radical intermediates. Biochemistry 14, 1626-1632.
32. Selassie, C. D., Garg, R., Kapur, S., Kurup, A., Verma, R. P., Mekapati, S. B., and Hansch, C. (2002) Comparative QSAR and the radical toxicity of various functional groups. Chem. Rev. 102, 2585-2605.
33. Fu, Y., Lin, B.-L., Song, K.-S., Liu, L., and Guo, Q.-X. (2002) Substituent effects on the S-H bond dissociation energies of thiophenols. J. Chem. Soc., Perkin Trans. 2 1223-1230.
34. Larson, A. G., Holm, A. H., Roberson, M., and Daasbjerg, K. (2001) Substituent effects on the oxidation and reduction potentials of phenylthiyl radicals in acetonitrile. J. Am. Chem. Soc. 123, 1723-1729.
35. Armstrong, D. A., Sun, Q., and Schuler, R. H. (1996) Reduction potentials and kinetics of electron-transfer reactions of phenylthiyl radicals: comparison with phenoxyl radicals. J. Phys. Chem. 100, 9892-9899.
36. Tripathi, G. N. R., Sun, Q., Armstrong, D. A., Chipman, D. M., Schuler, R. H. (1992) Resonance Raman spectra and structure of phenylthiyl radical. J. Phys. Chem. 96, 5344-5350.
37. Bordwell, F. G., Zhang, X.-M., Satish, A. V., and Cheng, J. P. (1994) Assessment of the importance of changes in ground-state energies on the bond dissociation enthalopies of the O-H bonds in phenols and the S-H bonds in thiophenols. J. Am. Chem. Soc. 116, 6605-6610.
38. Misra, H. P. (1974) Generation of superoxide free radical during the autoxidation of thiols. J. Biol. Chem. 249, 2151-2155.
39. Marklund, S., and Marklund, G. (1974) Involvement of the superoxide anion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase. Eur. J. Biochem. 47, 469-474.
40. Maria, P. D., Fini, A., and Hall, F. M. (1973) Thermodynamic acid dissociation constants of aromatic thiols. J. Chem. Soc., Perkin Trans. 2 1969-1971.
41. Munday, R. (1985) Toxicity of Aromatic Disulfides. I. Generation of superoxide radical and hydrogen peroxide by aromatic disulfides in vitro. J. Appl. Toxicol. 5, 402-408.
42. Bowden, K. (1995) Reaction constants and reaction mechanisms. Org. React. 29, 19-26.
43. Hansch, C., Leo, A., and Taft, R. W. (1991) A survey of Hammett substituent constants and resonance and field parameters. Chem. Rev. 91, 165-195.
44. oct from structure. Chem. Rev. 93, 1281-1305.