Thiolytic chemistry of alternative precursors to the major metabolite of the cancer chemopreventive oltipraz

Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9406-9413

  Navamal, Mettachit ^a   McGrath, Colleen ^a   Stewart, Jennifer ^a   Blans, Patrick ^a   Villamena, Frederick ^b   Zweier, Jay ^b   Fishbein, James C ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

^b JOHNS HOPKINS ASTHMA AND ALLERGY CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DECOMPOSITION; ESTERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; SYNTHESIS (CHEMICAL);

REACTION FLUX; THIOLYTIC CHEMISTRY;

CHEMOTHERAPY;

7 METHYL 6,8 BIS(METHYLDISULFANYL)PYRROLO[1,2 A]PYRAZINE; ALCOHOL; DRUG METABOLITE; ESTER DERIVATIVE; GLUTATHIONE; MESYLIC ACID; METHANETHIOSULFONIC ACID[(6 (METHANESULFONYLSULFANYL) 7 METHYL)PYRROLO[1,2 A]PYRAZIN 8 YL]ESTER; OLTIPRAZ; PYRAZINE DERIVATIVE; THIOESTER; THIOL DERIVATIVE; THIOMETHYL; UNCLASSIFIED DRUG;

ARTICLE; CANCER PREVENTION; CHEMISTRY; CHEMOPROPHYLAXIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS;

ALGORITHMS; ANTICARCINOGENIC AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; GLUTATHIONE; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRAZINES; SULFHYDRYL COMPOUNDS;

EID: 0037184764     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020588n     Document Type: Article

References (31)

1. This work was supported by The National Institutes of Health, National Cancer Institute, through Grant RO1 CA91032.
2. Clapper, M. L. Pharmacol. Ther. 1998, 78, 17-27.
3. Ansher, S. S.; Dolan, P.; Bueding, E. Food Chem. Toxicol. 1986, 24, 405-415.
4. Kensler, T. W.; Groopman, J. D.; Sutter, T. R.; Curphey, T. J.; Roebuck, B. D. Chem. Res. Toxicol. 1999, 12, 113-126.
5. Wilkinson, J.; Clapper, M. L. Proc. Soc. Exp. Biol. Med. 1997, 216, 192-200.
6. Camoirano, A.; Bagnasco, M.; Bennicelli, C.; Cartiglia, C.; Wang, J. B.; Zhang, B. C.; Zhu, Y. R.; Qian, G. S.; Egner, P. A.; Jacobson, L. P.; Kensler, T. W.; De Flora, S. Cancer Epidemiol., Biomarkers Prev. 2001, 10, 775-783.
7. Jacobson, L. P.; Zhang, B. C.; Zhu, Y. R.; Wang, J. B.; Wu, Y.; Zhang, Q. N.; Yu, L. Y.; Qian, G. S.; Kuang, S. Y.; Li, Y. F.; Fang, X.; Zarba, A.; Chen, B.; Enger, C.; Davidson, N. E.; Gorman, M. B.; Gordon, G. B.; Prochaska, H. J.; Egner, P. A.; Groopman, J. D.; Munoz, A.; Helzlsouer, K. J.; Kensler, T. W. Cancer Epidemiol., Biomarkers Prev. 1997, 6, 257-265.
8. Kensler, T. W.; He, X.; Otieno, M.; Egner, P. A.; Jacobson, L. P.; Chen, B.; Wang, J. S.; Zhu, Y. R.; Zhang, B. C.; Wang, J. B.; Wu, Y.; Zhang, Q. N.; Qian, G. S.; Kuang, S. Y.; Fang, X.; Li, Y. F.; Yu, L. Y.; Prochaska, H. J.; Davidson, N. E.; Gordon, G. B.; Gorman, M. B.; Zarba, A.; Enger, C.; Munoz, A.; Helzlsouer, K. J.; et al. Cancer Epidemiol., Biomarkers Prev. 1998, 7, 127-134.
9. Benson, A. B. J. Cell Biochem. Suppl. 1993, 17F, 278-291.
10. Wang, J. S.; Shen, X.; He, X.; Zhu, Y. R.; Zhang, B. C.; Wang, J. B.; Qian, G. S.; Kuang, S. Y.; Zarba, A.; Egner, P. A.; Jacobson, L. P.; Munoz, A.; Helzlsouer, K. J.; Groopman, J. D.; Kensler, T. W. J. Natl. Cancer Inst. 1999, 17, 347-354.
11. Egner, P. A.; Kensler, T. W.; Prestera, T.; Talalay, P.; Libby, A. H.; Joyner, H. H.; Curphey, T. J. Carcinogenesis 1994, 15, 177-181.
12. Prochaska, H. J.; Talalay, P. Cancer Res. 1988, 48, 4776-4782.
13. Davidson, N. E.; Egner, P. A.; Kensler, T. W. Cancer Res. 1990, 50, 2251-2255.
14. Kensler, T. W.; Primiano, T.; Sutter, T. R.; Egner, P. A.; Dolan, P. M.; Groopman, J. D.; Curphey, T. J.; Roebuck, B. D. Proc. Int. Symp. Nat. Antioxid. 1996, 243-250.
15. Maxuitenko, Y. Y.; Libby, A. H.; Joyner, H. H.; Curphey, T. J.; MacMillan, D. L.; Kensler, T. W.; Roebuck, B. D. Carcinogenesis 1998, 19, 1609-1615.
16. Kim, W.; Gates, K. S. Chem. Res. Toxicol. 1997, 10, 296-301.
17. Bieder, A.; Decouvelaere, B.; Gaillard, C.; Depaire, H.; Heusse, D.; Ledoux, C.; Lemar, M.; LeRoy, J. P.; Raynaud, L.; Snozzi, C.; Gregoire, J. Arzneim.-Forsch. 1983, 33, 1289-1297.
18. O'Dwyer, P. J.; Clayton, M.; Halbherr, T.; Myers, C. B.; Yao, K. Clin. Cancer Res. 1997, 3, 783-791.
19. Fleury, M. B.; Largeron, M. Tetrahedron 1985, 41, 3705-3715.
20. Largeron, M.; Martens, T.; Fleury, M. B. Tetrahedron Lett. 1987, 43, 3421-3428.
21. Armarego, W. L. F. J. Chem. Soc. 1965, 2778-2787.
22. Grimshaw, C. E.; Whistler, R. L.; Cleland, W. W. J. Am. Chem. Soc. 1979, 101, 1521-1532.
23. Wilson, J. M.; Bayer, R. J.; Hupe, D. J. J. Am. Chem. Soc. 1977, 99, 7922-7926.
24. Freter, R.; Pohl, E. R.; Wilson, J. M.; Hupe, D. J. J. Org. Chem. 1979, 44, 1771-1774.
25. Whitesides, G. M.; Lilburn, J. E.; Szajewski, R. P. J. Org. Chem. 1977, 42, 332-338.
26. Szajewski, R. P.; Whitesides, G. M. J. Am. Chem. Soc. 1980, 102, 2011-2026.
27. Smith, D. J.; Maggio, E. T.; Kenyon, G. L. Biochemistry 1975, 14, 766-771.
28. Roberts, D. D.; Lewis, S. D.; Ballou, D. P.; Olson, S. T.; Shafer, J. A. Biochemistry 1986, 25, 5595-5601.
29. Klaassen, C. D. Casarett and Doul's Toxicology, the Basic Science of Poisons, 5th Ed.; McGraw-Hill: New York, 1996.
30. Carmichael, A. J.; Makino, K.; Riesz, P. Radiat. Res. 1984, 100, 222-234.
31. Halliwell, B.; Gutteridge, J. M. Free Radicals in Biology and Medicine, 3rd Ed.; Oxford Science Publications: Oxford, U.K., 1998.