Selected isothiocyanates rapidly induce growth inhibition of cancer cells

Molecular Cancer Therapeutics

Volumn 2, Issue 10, 2003, Pages 1045-1052

  Zhang, Yuesheng ^a   Tang, Li ^a   Gonzalez, Veronica ^a  

^a UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CHEMOKINE; CCL6 PROTEIN, MOUSE; GLYCOPROTEIN P; ISOTHIOCYANIC ACID DERIVATIVE;

APOPTOSIS; ARTICLE; BIOSYNTHESIS; CELL CYCLE; CELL DIFFERENTIATION; CELL DIVISION; CELL MEMBRANE POTENTIAL; CELL STRAIN HL 60; CHEMICAL MODEL; DRUG EFFECT; DRUG RESISTANCE; HUMAN; IC 50; MITOCHONDRION; PATHOLOGY; TIME; TUMOR CELL LINE; WESTERN BLOTTING;

APOPTOSIS; BLOTTING, WESTERN; CELL CYCLE; CELL DIFFERENTIATION; CELL DIVISION; CELL LINE, TUMOR; CHEMOKINES, CC; DRUG RESISTANCE, NEOPLASM; HL-60 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; ISOTHIOCYANATES; MEMBRANE POTENTIALS; MITOCHONDRIA; MODELS, CHEMICAL; P-GLYCOPROTEIN; TIME FACTORS;

EID: 1942451371     PISSN: 15357163     EISSN: 15388514     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

1. Fenwick, G. R., Heaney, R. K., and Mullin, W. J. Glucosinolates and their breakdown products in food and food plants. Crit. Rev. Food Sci. Nutr., 18: 123-201, 1983.
2. Fahey, J. W., Zalcmann, A. T., and Talalay, P. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry, 56: 5-51, 2001. (Pubitemid 32063165)
3. Ioannou, Y. M., Burka, L. T., and Matthews, H. B. Allyl isothiocyanate: comparative disposition in rats and mice. Toxicol. Appl. Pharmacol., 75: 173-181, 1984. (Pubitemid 14026428)
4. Gorler, K., Krumbiegel, G., Mennicke, W. H., and Siehl, H. U. The metabolism of benzyl isothiocyanate and its cysteine conjugate in guinea-pigs and rabbits. Xenobiotica, 12: 535-542, 1982. (Pubitemid 13236309)
5. Chung, F. L., Morse, M. A., Eklind, K. I., and Lewis J. Quantitation of human uptake of the anticarcinogen phenethyl isothiocyanate after a watercress meal. Cancer Epidemiol., Biomarkers & Prev., 1: 383-388, 1992.
6. Zhang, Y., Talalay, P., Cho, C. G., and Posner, G. H. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. USA, 89: 2399-2403, 1992.
7. Fahey, J. W., Zhang, Y., and Talalay, P. Broccoli sprouts: an exceptionally rich source of inducers of enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. USA, 94: 10367-10372, 1997. (Pubitemid 27407048)
8. Shapiro, T. A., Fahey, J. W., Wade, K. L., Stephenson, K. K., and Talalay, P. Human metabolism and excretion of cancer chemoprotective glucosinolates and isothiocyanates of cruciferous vegetables. Cancer Epidemiol., Biomarkers & Prev., 7: 1091-1100, 1998. (Pubitemid 29001665)
9. Shapiro, T. A., Fahey, J. W., Wade, K. L., Stephenson, K. K., and Talalay, P. Chemoprotective glucosinolates and isothiocyanates of broccoli sprouts: metabolism and excretion in humans. Cancer Epidemiol., Biomarkers & Prev., 10: 501-508, 2001. (Pubitemid 32701637)
10. Getahun, S. M. and Chung, F. L. Conversion of glucosinolates to isothiocyanates in humans after ingestion of cooked watercress. Cancer Epidemiol., Biomarkers & Prev., 8: 447-451, 1999. (Pubitemid 29230550)
11. Zhang, Y. and Talalay, P. Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms. Cancer Res., 54: 1976s-1981s, 1994. (Pubitemid 24132159)
12. Hecht, S. S. Chemoprevention by isothiocyanates. J. Cell. Biochem., Suppl., 22: 195-209, 1995.
13. Hecht, S. S. Chemoprevention of cancer by isothiocyanates, modifiers of carcinogen metabolism. J. Nutr., 129: 769s-774s, 1999.
14. Conaway, C. C., Yang, Y. M., and Chung, F. L. Isothiocyanates as cancer chemopreventive agents: their biological activities and metabolism in rodents and humans. Curr. Drug Metab., 3: 233-255, 2002. (Pubitemid 34625038)
15. London, S. J., Yuan, J. M., Chung, F. L., Gao, Y. T., Coetzee, G. A., Ross, R. K., and Yu, M. C. Isothiocyanates, glutathione S-transferase M1 and T1 polymorphisms, and lung-cancer risk: a prospective study of men in Shanghai, China. Lancet, 356: 724-729, 2000. (Pubitemid 30663242)
16. Spitz, M. R., Duphorne, C. M., Detry, M. A., Pillow, P. C., Amos, C. I., Lei, L., de Andrade, M., Gu, X., Hong, W. K., and Wu, X. Dietary intake of isothiocyanates: evidence of a joint effect with glutathione S-transferase polymorphisms in lung cancer risk. Cancer Epidemiol., Biomarkers & Prev., 9: 1017-1020, 2000.
17. Lin, H. J., Zhou, H., Dai, A., Huang, H. F., Lin, J. H., Frankl, H. D., Lee, E. R., and Haile, R. W. Glutathione transferase GSTT1, broccoli, and prevalence of colorectal adenomas. Pharmacogenetics, 12: 175-179, 2002. (Pubitemid 34298921)
18. Chiao, J. W., Chung, F. L., Kancherla, R., Ahmed, T., Mittelman, A., and Conaway, C. C. Sulforaphane and its metabolite mediate growth arrest and apoptosis in human prostate cancer cells. Int. J. Oncol., 20: 631-636, 2002.
19. Yang, Y. M., Conaway, C. C., Chiao, J. W., Wang, C. X., Amin, S., Whysner, J., Dai, W., Reinhardt, J., and Chung, F. L. Inhibition of benzo(a)pyrene-induced lung tumorigenesis in A/J mice by dietary N-acetylcysteine conjugates of benzyl and phenethyl isothiocyanates during the postinitiation phase is associated with activation of mitogen-activated protein kinases and p53 activity and induction of apoptosis. Cancer Res., 62: 2-7, 2002. (Pubitemid 34073975)
20. Jiao, D., Smith, T. J., Yang, C. S., Pittman, B., Desai, D., Amin, S., and Chung, F. L. Chemopreventive activity of thiol conjugates of isothiocyanates for lung tumorigenesis. Carcinogenesis, 18: 2143-2147, 1997. (Pubitemid 28134741)
21. Brusewitz, G., Cameron, B. D., Chasseaud, L. F., Gorler, K., Hawkins, D. R., Koch, H., and Mennicke, W. H. The metabolism of benzyl isothiocyanate and its cysteine conjugate. Biochem. J., 162: 99-107, 1977. (Pubitemid 8017353)
22. Mennicke, W. H., Gorler, K., and Krumbiegel, G. Metabolism of some naturally occurring isothiocyanates in the rat. Xenobiotica, 13: 203-207, 1983. (Pubitemid 13035796)
23. Mennicke, W. H., Gorler, K., Krumbiegel, G., Lorenz, D., and Rittmann, N. Studies on the metabolism and excretion of benzyl isothiocyanate in man. Xenobiotica, 18: 441-447, 1988.
24. Baillie, T. A. and Slatter, J. G. Glutathione: a vehicle for the transport of chemically reactive metabolites in vivo. Acc. Chem. Res., 24: 264-270, 1991.
25. Bruggeman, I. M., Temmink, J. H. M., and van Bladeren, P. J. Glutathione- and cysteine-mediated cytotoxicity of allyl and benzyl isothiocyanate. Toxicol. Appl. Pharmacol., 83: 349-359, 1986. (Pubitemid 16079420)
26. Conaway, C. C., Krzeminski, J., Amin, S., and Chung, F. L. Decomposition rates of isothiocyanate conjugates determine their activity as inhibitors of cytochrome p450 enzymes. Chem. Res. Toxicol., 14: 1170-1176, 2001. (Pubitemid 32911454)
27. Xu, K. and Thornalley, P. J. Studies on the mechanism of the inhibition of human leukemia cell growth by dietary isothiocyanates and their cysteine adducts in vitro. Biochem. Pharmacol., 60: 221-231, 2000. (Pubitemid 30312950)
28. Gamet-Payrastre, L., Li, P., Lumeau, S., Cassar, G., Dupont, M. A., Chevolleau, S., Gasc, N., Tulliez, J., and Terce, F. Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells. Cancer Res., 60: 1426-1433, 2000. (Pubitemid 30152017)
29. Musk, S. R. and Johnson, I. T. Allyl isothiocyanate is selectively toxic to transformed cells of the human colorectal tumour line HT29. Carcinogenesis, 14: 2079-2083, 1993. (Pubitemid 23311435)
30. Fimognari, C., Nusse, M., Cesari, R., Iori, R., Cantelli-Forti, G., and Hrelia, P. Growth inhibition, cell-cycle arrest and apoptosis in human T-cell leukemia by the isothiocyanate sulforaphane. Carcinogenesis, 23: 581-586, 2002. (Pubitemid 34498494)
31. Srivastava, S. K., Xiao, D., Lew, K. L., Kokkinakis, D. M., Hershberger, P. A., Johnson, C. S., and Trump, D. L. Allyl isothiocyanate inhibits growth of PC-3 human prostate cancer xenografts in vivo in nude mice. Proc. Am. Assoc. Cancer Res. (93rd AACR Annual Meeting), 43: 1108, 2002.
32. Adesida, A., Edwards, L. G., and Thornalley, P. J. Inhibition of human leukaemia 60 cell growth by mercapturic acid metabolites of phenylethyl isothiocyanate. Food Chem. Toxicol., 34: 385-392, 1996. (Pubitemid 26153180)
33. Zhang, Y., Wade, K. L., Prestera, T., and Talalay, P. Quantitative determination of isothiocyanates, dithiocarbamates, carbon disulfide and related thiocarbonyl compounds by cyclocondensation assay with 1,2-benzenedithiol. Anal. Biochem., 239: 160-167, 1996. (Pubitemid 26268798)
34. Zhang, Y. and Callaway, E. C. High cellular accumulation of sulphoraphane, a dietary anticarcinogen, is followed by rapid transporter-mediated export as a glutathione conjugate. Biochem. J., 364: 301-307, 2002. (Pubitemid 34538974)
35. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods, 65: 55-63, 1983. (Pubitemid 14203433)
36. Finucane, D. M., Waterhouse, N. J., Amarante-Mendes, G. P., Cotter, T. G., and Green, D. R. Collapse of the inner mitochondrial transmembrane potential is not required for apoptosis of HL60 cells. Exp. Cell Res., 251: 166-174, 1999. (Pubitemid 29406530)
37. Dressler, L. G. and Bartow, S. A. DNA flow cytometry in solid tumors, practical aspects and clinical application. Semin. Diagn. Pathol., 6: 55-82, 1989. (Pubitemid 19066163)
38. Kawaii, S., Tomono, Y., Katase, E., Ogawa, K., and Yano, M. Effect of coumarins on HL-60 cell differentiation. Anticancer Res., 20: 2505-2512, 2000. (Pubitemid 30614460)
39. Suh, N., Luyengi, L., Fong, H. H. S., Kinghorn, D., and Pezzuto, J. M. Discovery of natural product chemopreventive agents utilizing HL-60 cell differentiation as a model. Anticancer Res., 13: 233-240, 1995.
40. Ye, L., Dinkova-Kostova, A., Wade, K. L., Zhang, Y., Shapiro, T. A., and Talalay, P. Quantitative determination of dithiocarbamates in human plasma, serum, erythrocytes and urine: pharmacokinetics of broccoli sprout isothiocyanates in humans. Clin. Chim. Acta, 316: 43-53, 2002. (Pubitemid 34028187)
41. Eklind, K. I., Morse, M. A., and Chung, F. L. Distribution and metabolism of the natural anticarcinogen phenethyl isothiocyanate in A/J mice. Carcinogenesis, 11: 2033-2036, 1990. (Pubitemid 20375952)
42. Kassahun, K., Davis, M., Hu, P., Martin, B., and Baillie, T. Biotransformation of the naturally occurring isothiocyanate sulforaphane in the rat: identification of phase 1 metabolites and glutathione conjugates. Chem. Res. Toxicol., 10: 1228-1233, 1997. (Pubitemid 27524827)
43. Conaway, C. C., Jiao, D., Kohri, T., Liebes, L., and Chung, F. L. Disposition and pharmacokinetics of phenethyl isothiocyanate and 6-phenylhexyl isothiocyanate in F344 rats. Drug Metab. Dispos., 27: 13-20, 1999. (Pubitemid 29060994)
44. Budihardjo, I., Oliver, H., Lutter, M., Luo, X., and Wang, X. Biochemical pathways of caspase activation during apoptosis. Annu. Rev. Cell Dev. Biol., 15: 269-290, 1999. (Pubitemid 32250377)
45. Nakagawa, T., Zhu, H., Morishima, N., Li, E., Xu, J., Yankner, B. A., and Yuan, J. Caspase-12 mediates endoplasmic-reticulum-specific apoptosis and cytotoxicity by amyloid-β. Nature, 403: 98-103, 2000. (Pubitemid 30038529)
46. Baker, S. J. and Reddy, E. P. Modulation of life and death by the TNF receptor superfamily. Oncogene, 17: 3261-3270, 1998. (Pubitemid 29043978)
47. Xiao, D., Srivastava, S. K., Zeng, Y., Hershberger, P. A., Johnson, C. S., Trump, D. L., and Singh, S. V. Allyl isothiocyanate suppresses in vitro proliferation of PC-3 and LNCaP human prostate cancer cells by inducing apoptosis and mediating G2/M arrest. Proc. Am. Assoc. Cancer Res. (93rd AACR Annual Meeting), 43: 641, 2002.
48. Lea, M. A., Randolph, V. M., Lee, J. E., and DesBordes, C. Induction of histone acetylation in mouse erythroleukemia cells by some organosulfur compounds including allyl isothiocyanate. Int. J. Cancer, 92: 784-789, 2001. (Pubitemid 32467365)