Reactions of glutathione with carcinogenic esters of N-arylhydroxamic acids

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1302-1308

  Novak, Michael ^a   Lin, Jing ^a  

^a MIAMI UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOBIPHENYL DERIVATIVE; CARCINOGEN; FLUORENE DERIVATIVE; GLUTATHIONE; HYDROXAMIC ACID DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG DETOXIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0029876347     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9534563     Document Type: Article

References (43)

1. Kosower, N. S.; Kosower, E. M. In International Review of Cytology: Bourne, G. H., Danielli, J. F., Jeon, K. W., Eds.; Academic Press: New York, 1978; Vol. 54, pp 109-160.
2. Meister, A. In Coenzymes and Cofactors Volume III: Glutathione; Dolphin, D., Poulson, R., Avramovic, O., Eds.; Wiley: New York, 1989; Part A, pp 367-474.
3. Kosower, E. M. In Coenzyme and Cofactors Volume III: Glutathione; Dolphin, D., Poulson, R., Avramovic, O., Eds.: Wiley: New York, 1989; Part A, pp 103-146.
4. Chasseaud, L. F. In Advances in Cancer Research: Klein, G., Weihhouse, S., Eds.: Academic Press: New York, 1979; Vol. 29, pp 175-274.
5. Moldéus, P.; Jernström, B. In Functions of Glutathione: Biochemical, Physiological, Toxicological, and Clinical Aspects; Larsson, A., Orrenius, S., Holmgren, A., Mannervik, B., Eds.; Raven Press: New York, 1983; pp 99-108.
6. (a) van den Goorbergh, J. A. M.; Meerman, J. H. N.; de Wit, H.; Mulder, G. J. Carcinogenesis 1985, 6, 1635-1640.
7. (b) Beland, F. A.; Miller, D. W.; Mitchum, R. K. J. Chem. Soc., Chem. Commun. 1983, 30-31.
8. Meerman, J. H. N.; Beland, F. A.; Ketterer, B.; Srai, S. K. S.; Bruins, A. P.; Mulder, G. J. Chem.-Biol. Interact. 1982, 39, 149-168.
9. (a) Novak, M.; Kennedy, S. A. J. Am. Chem. Soc. 1995, 117, 574-575.
10. (b) Novak, M.; Kennedy, S. A.; Kolb, B., to be submitted to J. Am. Chem. Soc.
11. (a) Novak, M.; Kahley, M. J.; Eiger, E.; Helmick, J. S.; Peters, H. E. J. Am. Chem. Soc. 1993, 115, 9453-9460.
12. (b) Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; Swanegan, L. A. J. Am. Chem. Soc. 1994, 116, 11626-11627.
13. Davidse, P. A.; Kahley, M. J.; McClelland, R. A.; Novak, M. J. Am. Chem. Soc. 1994, 116, 4513-4514.
14. Rabenstein, D. L. J. Am. Chem. Soc. 1973, 95, 2797-2803. Cheesman, B. V.; Arnold, A. P.; Rabenstein, D. L. J. Am. Chem. Soc. 1988, 110, 6359-6364.
15. Rabenstein, D. L. J. Am. Chem. Soc. 1973, 95, 2797-2803. Cheesman, B. V.; Arnold, A. P.; Rabenstein, D. L. J. Am. Chem. Soc. 1988, 110, 6359-6364.
16. -]
17. Extinction coefficients for 16-18 indicate that we could have detected a 4% overall yield of these materials equally distributed among the three of them.
18. Novak, M.; Helmick, J. S.; Oberlies, N.; Rangappa, K. S.; Clark, W. M.; Swenton, J. S. J. Org. Chem. 1993, 58, 867-878.
19. Kazanis, S.; McClelland, R. A. J. Am. Chem. Soc. 1992, 114, 3052-3059. Bolton, J. L.; McClelland, R. A. J. Am. Chem. Soc. 1989, 111, 8172-8181.
20. Kazanis, S.; McClelland, R. A. J. Am. Chem. Soc. 1992, 114, 3052-3059. Bolton, J. L.; McClelland, R. A. J. Am. Chem. Soc. 1989, 111, 8172-8181.
21. Although 11 and 12 are stable under neutral or mildly alkaline pH conditions, they do undergo rapid dehydration at pH 2 (Novak, M.; Lin, J., work in progress). The greater driving force for aromatization of 20 may reduce the activation barrier so that dehydration of 20 occurs under the reaction conditions.
22. Panda, M.; Novak, M.; Magonski, J. J. Am. Chem. Soc. 1989, 111, 4524-4525.
23. Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; James, T. G. J. Org. Chem. 1995, 60, 8294-8304.
24. Humphreys, W. G.; Kadlubar, F. F.; Guengerich, F. P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 8278-8282.
25. Novak, M.; Rangappa, K. S. J. Org. Chem. 1992, 57, 1285-1290. Novak, M.; Ranaappa, K. S.; Manitsas, R. K. J. Org. Chem. 1993, 58, 7813-7821.
26. Novak, M.; Rangappa, K. S. J. Org. Chem. 1992, 57, 1285-1290. Novak, M.; Ranaappa, K. S.; Manitsas, R. K. J. Org. Chem. 1993, 58, 7813-7821.
27. Fleming, I., Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976; pp 34-37.
28. Calculations at the SCF76-31G*//3-21G level show that the charge densities on 7a and 7b are highest at the ortho and para carbons of the ring proximal to N. Novak, M.; Lin, J.; Vandewater, A., to be submitted to J. Org. Chem.
29. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochem. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182; American Chemical Society; Washington, D.C., 1984; Vol. 1, pp 175-276. Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19-30. Kadlubar, F. F.; Beland, F. A. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series 283; American Chemical Society: Washington, D.C., 1985; pp 341-370.
30. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochem. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182; American Chemical Society; Washington, D.C., 1984; Vol. 1, pp 175-276. Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19-30. Kadlubar, F. F.; Beland, F. A. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series 283; American Chemical Society: Washington, D.C., 1985; pp 341-370.
31. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochem. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182; American Chemical Society; Washington, D.C., 1984; Vol. 1, pp 175-276. Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19-30. Kadlubar, F. F.; Beland, F. A. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series 283; American Chemical Society: Washington, D.C., 1985; pp 341-370.
32. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochem. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182; American Chemical Society; Washington, D.C., 1984; Vol. 1, pp 175-276. Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19-30. Kadlubar, F. F.; Beland, F. A. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series 283; American Chemical Society: Washington, D.C., 1985; pp 341-370.
33. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochem. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182; American Chemical Society; Washington, D.C., 1984; Vol. 1, pp 175-276. Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19-30. Kadlubar, F. F.; Beland, F. A. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series 283; American Chemical Society: Washington, D.C., 1985; pp 341-370.
34. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochem. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182; American Chemical Society; Washington, D.C., 1984; Vol. 1, pp 175-276. Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19-30. Kadlubar, F. F.; Beland, F. A. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series 283; American Chemical Society: Washington, D.C., 1985; pp 341-370.
35. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochem. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182; American Chemical Society; Washington, D.C., 1984; Vol. 1, pp 175-276. Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19-30. Kadlubar, F. F.; Beland, F. A. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series 283; American Chemical Society: Washington, D.C., 1985; pp 341-370.
36. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochem. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182; American Chemical Society; Washington, D.C., 1984; Vol. 1, pp 175-276. Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19-30. Kadlubar, F. F.; Beland, F. A. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series 283; American Chemical Society: Washington, D.C., 1985; pp 341-370.
37. - in the vicinity of DNA. Smoluk, G. D.; Fahey, R. C.; Ward, J. F. Radiat. Res. 1988, 114, 3-10.
38. Loretz, L. J.; Pariza, M. W. Carcinogenesis 1984, 5, 895-899.
39. Novak, M.; Roy, A. K. J. Org. Chem. 1985, 50, 571-580.
40. Smith, B. A.; Springfield, J. R.; Gutman, H. R. Carcinogenesis 1986, 7, 405-411.
41. Novak, M.; Brodeur, B. J. Org. Chem. 1984, 49, 1142-1144.
42. Novak, M.; Pelecanou, M.; Roy, A. K.; Andronico, A. F.; Plourde, F. M.; Olefirowicz, T. M.; Curtin, T. J. J. Am. Chem. Soc. 1984, 106, 5623-5631.
43. Leaper, J. M. F. J. Am. Chem. Soc. 1931, 53, 1981-1894.