Synthesis of isothiocyanate-derived mercapturic acids

European Journal of Medicinal Chemistry

Volumn 38, Issue 7-8, 2003, Pages 729-737

  Vermeulen, Martijn ^a   Zwanenburg, Binne ^b   Chittenden, Gordon J F ^b   Verhagen, Hans ^a,c  

^a TNO   (Netherlands)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^c UNILEVER RESEARCH VLAARDINGEN   (Netherlands)

Author keywords

Biomarker; Glucosinolates; Isothiocyanates; Mercapturic acids; Nucleophilic addition

Indexed keywords

ACETYLCYSTEINE; ACETYLCYSTEINE DERIVATIVE; AMINE; BICARBONATE; BIOLOGICAL MARKER; ISOTHIOCYANIC ACID DERIVATIVE; PHOSGENE; PHTHALIMIDE DERIVATIVE;

ARTICLE; SYNTHESIS; VEGETABLE;

EID: 0043158813     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(03)00141-7     Document Type: Article

References (41)

1. Steinmetz K.A., Potter J.D. Cancer Causes Control. 2:1991;325.
2. Block G., Patterson B., Subar A. Nutr. Cancer. 18:1992;1.
3. Food, nutrition, and the prevention of cancer: a global perspective, World Cancer Research Fund, American Institute for Cancer Research, Washington, DC, 1997.
4. Verhoeven D.T., Goldbohm R.A., van Poppel G., Verhagen H., van den Brandt P.A. Cancer Epidemiol. Biomarkers Prev. 5:1996;733.
5. van Poppel G., Verhoeven D.T., Verhagen H., Goldbohm R.A. Adv. Exp. Med. Biol. 472:1999;159.
6. Voorrips L.E., Goldbohm R.A., van Poppel G., Sturmans F., Hermus R.J., van den Brandt P.A. Am. J. Epidemiol. 152:2000;1081.
7. Kjær A. Fortschritte der Chemie Organische Naturstoffe. 18:1960;122.
8. Fenwick G.R., Heaney R.K., Mullin W.J. Crit. Rev. Food Sci. Nutr. 18:1983;123.
9. Nugon-Baudon L., Rabot S., Wal J.M., Szylit O. J. Sci. Food Agric. 52:1990;547.
10. Krul C.A.M., Humblot C., Philippe C., Vermeulen M., van Nuenen M., Havenaar R., Rabot S. Carcinogenesis. 23:2002;101.
11. Guo Z., Smith T.J., Wang E., Sadrieh N., Ma Q., Thomas P.E., Yang C.S. Carcinogenesis. 13:1992;2205.
12. Sparnins V.L., Venegas P.L., Wattenberg L.W. J. Natl. Cancer Inst. 68:1982;493.
13. Zhang Y., Talalay P. Cancer Res. 58:1998;4632.
14. Hecht S.S. Drug Metabolism Rev. 32:2000;395.
15. Bogaards J.J., Verhagen H., Willems M.I., van Poppel G., van Bladeren P.J. Carcinogenesis. 15:1994;1073.
16. Hecht S.S. J. Cell Biochem. 22:1995;195.
17. Brüsewitz G., Cameron B.D., Chasseaud L.F., Görler K., Hawkins D.R., Koch H., Mennicke W.H. Biochem. J. 162:1977;99.
18. Görler K., Krumbiegel G., Mennicke W.H., Siehl H.U. Xenobiotica. 12:1982;535.
19. Chung F.L., Morse M.A., Eklind K.I. Cancer Res. 52:1992;2719.
20. Mennicke W.H., Görler K., Krumbiegel G., Lorenz D., Rittmann N. Xenobiotica. 18:1988;441.
21. Chung F.L., Morse M.A., Eklind K.I., Lewis J. Cancer Epidemiol. Biomarkers Prev. 1:1992;383.
22. Duncan A.J., Rabot S., Nugon-Baudon L. J. Sci. Food Agric. 73:1997;214.
23. Jiao D., Ho C.T., Foiles P., Chung F.L. Cancer Epidemiol. Biomarkers Prev. 3:1994;487.
24. Tiedink H.G., Davies J.A., van Broekhoven L.W., van der Kamp H.J., Jongen W.M. Food Chem. Toxicol. 26:1988;947.
25. Mithen R.F., Dekker M., Verkerk R., Rabot S., Johnson I.T. J. Sci. Food Agric. 80:2000;967.
26. Shapiro T.A., Fahey J.W., Wade K.L., Stephenson K.K., Talalay P. Cancer Epidemiol. Biomarkers Prev. 10:2001;501.
27. Zhang Y., Talalay P., Cho C.G., Posner G.H. Proc. Natl. Acad. Sci. 89:1992;2399.
28. Kjær A., Rubinstein K., Jensen K.A. Acta Chemica Scandinavica. 7:1953;518.
29. Ettlinger M.G., Hodgkins J.E. J. Am. Chem. Soc. 77:1955;1831.
30. Leoni O., Iori R., Palmieri S., Esposito E., Menegatti E., Cortesi R., Nastruzzi C. Bioorg. Med. Chem. 5:1997;1799.
31. Kjær A., Jensen R.B. Acta Chemica Scandinavica. 10:1956;1365.
32. Gilbert J., Nursten H.E. J. Sci. Food Agric. 23:1972;527.
33. Schmid H., Karrer P. Helv. Chim. Acta. 31:1948;1497.
34. Kjær A., Gmelin R. Acta Chemica Scandinavica. 9:1955;542.
35. Kuhnert N., Holst B., Williamson G. J. Labelled Compounds and Radiopharmaceuticals. 44:2001;347.
36. Mennicke W.H., Görler K., Krumbiegel G. Xenobiotica. 13:1983;203.
37. Ioannou Y.M., Burka L.T., Matthews H.B. Toxicol. Appl. Pharmacol. 75:1984;173.
38. Eklind K.I., Morse M.A., Chung F.L. Carcinogenesis. 11:1990;2033.
39. Jiao D., Conaway C.C., Wang M.H., Yang C.S., Koehl W., Chung F.L. Chem. Res. Toxicol. 9:1996;932.
40. Kassahun K., Davis M., Hu P., Martin B., Baillie T. Chem. Res. Toxicol. 10:1997;1228.
41. Vermeulen M., van Rooijen H.J.M., Vaes W.H.J. J. Agric. Food Chem. 51:2003;3554.