Effects of chemoprotective agents on the metabolic activation of the carcinogenic arylamines PhIP and 4-aminobiphenyl in human and rat liver microsomes

Nutrition and Cancer

Volumn 33, Issue 1, 1999, Pages 46-52

  Hammons, George J ^a   Fletcher, Joyce V ^a   Stepps, Kristy R ^a   Smith, Elijah A ^a   Balentine, Douglas A ^b   Harbowy, Matthew E ^b   Kadlubar, Fred F ^a  

^a Div of Molecular Epidemiology   (United States)

^b UNILEVER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; 3 INDOLEMETHANOL; 4 BIPHENYLAMINE; ALLYL SULFIDE; ANTINEOPLASTIC AGENT; BENZYL ISOTHIOCYANATE; BIOCHANIN A; CAFESTOL; CATECHIN; DAIDZEIN; EQUOL; ETHOXYQUIN; FORMONONETIN; GENISTIN; KAHWEOL; OLTIPRAZ; POLYPHENOL DERIVATIVE; QUERCETIN; TANNIN;

ANIMAL CELL; ARTICLE; HUMAN; HUMAN CELL; HYDROXYLATION; LIVER CARCINOGENESIS; LIVER MICROSOME; LIVER PROTECTION; MALE; NONHUMAN; RAT; TEA;

EID: 0032967185     PISSN: 01635581     EISSN: None     Source Type: Journal    
DOI: 10.1080/01635589909514747     Document Type: Article

References (60)

1. Garner, RC, Martin, CN, and Clayson, DB: Carcinogenic aromatic amines and related compounds. In Chemical Carcinogens, 2nd ed, CE Searle (ed). Washington, DC: Am Chem Soc, 1984, vol 1, pp 175-276. (Monogr 182)
2. Eisenbrand, G, and Tang, W: Food-borne heterocyclic amines. Chemistry, formation, occurrence and biological activities. A literature review. Toxicology 84, 1-82, 1993.
3. Sugimura, T, and Wakabayashi, K: Heterocyclic amines: new mutagens and carcinogens in cooked foods. Adv Exp Med Biol 283, 569-578, 1991.
4. Weisburger, JH: Heterocyclic amines in cooked foods: possible human carcinogens. Cancer Res 53, 2422-2424, 1993.
5. Felton, JS, and Knize, MG: Occurrence, identification, and bacterial mutagenicity of heterocyclic amines in cooked food. Mutat Res 259, 205-217, 1991.
6. Sugimura, T: Carcinogenicity of mutagenic heterocyclic amines formed during the cooking of meats. Mutat Res 150, 33-41, 1985.
7. Manabe, S, Tohyama, K, Wada, O, and Aramaki, T: Detection of a carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), in cigarette smoke condensate. Carcinogenesis 12, 1945-1947, 1991.
8. Manabe, S, Suzuki, H, Wada, O, and Ueki, A: Detection of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in beer and wine. Carcinogenesis 14, 899-901, 1993.
9. Ito, N, Hasegawa, R, Sano, M, Tamano, S, Esumi, H, et al.: A new colon and mammary carcinogen in cooked food, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Carcinogenesis 12, 1503-1506, 1991.
10. Ushiyama, H, Wakabayashi, M, Hirose, H, Itoh, T, Sugimura, T, et al.: Presence of carcinogenic heterocyclic amines in urine of healthy volunteers eating a normal diet, but not of inpatients receiving parenteral alimentation. Carcinogenesis 12, 1417-1422, 1991.
11. Lynch, AM, Knize, MG, Boobis, AR, Gooderham, NJ, Davis, DS, et al.: Intra-and interindividual variability in systemic exposure in humans to 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, carcinogens present in cooked beef. Cancer Res 52, 6216-6223, 1992.
12. Lin, D, Lay, JO, Bryant, MS, Malaveille, C, Friesen, H, et al.: Analysis of 4-aminobiphenyl-DNA adducts in human urinary bladder and lung by alkaline hydrolysis and negative ton gas chromatography. Environ Health Perspect 102, 11-16, 1994.
13. Schiffman, MH, Andrews, AW, Van Tassell, RL, Smith, L, Daniel, J, et al.: Case-control study of colorectal cancer and fecal mutagenicity. Cancer Res 49, 3420-3424, 1989.
14. Lang, NP, Butler, MA, Massengill, J, Lawson, M, Stotts, RC, et al.: Rapid metabolic phenotypes for acetyltransferase and cytochrome P4501A2 and putative exposure to food-borne heterocyclic amines increase the risk for colorectal cancer of polyps. Cancer Epidemiol Biomarkers Prev 3, 675-682, 1994.
15. Sinha, R, Rothman, N, Brown, ED, Mark, SD, Hoover, RN, et al.: Pan-fried meat containing high levels of heterocyclic aromatic amines but low levels of polycyclic aromatic hydrocarbons induces cytochrome P4501A2 activity in humans. Cancer Res 54, 6154-6159, 1994.
16. Radomski, JL: The primary aromatic amines: their biological properties and structure-activity relationships. Annu Rev Pharmacol Toxicol 19, 129-157, 1979.
17. Bryant, MS, Vineis, P, Skipper, PL, and Tannenbaum, SR: Hemoglobin adducts of aromatic amines: association with smoking status and type of tobacco. Proc Natl Acad Sci USA 85, 9788-9791, 1988.
18. Talaska, G, Al-Juburi, AZSS, and Kadlubar, FF: Smoking related carcinogen-DNA adducts in biopsy samples of urinary bladder: identification of N-(deoxyguanosin-8-yl)-4-aminobipnenyl as a major adduct. Proc Natl Acad Sci USA 88, 5350-5354, 1991.
19. Block, G, Patterson, B, and Subar, A: Fruit, vegetables and cancer prevention. A review of the epidemiological evidence. Nutr Cancer 18, 1-29, 1992.
20. Yamane, T, Hagiwara, N, Tateishi, M, Akachi, S, Kim, M, et al.: Inhibition of azoxymethane-induced colon carcinogenesis in rat by green tea polyphenol fraction. Jpn J Cancer Res 82, 1336-1339, 1991.
21. Narisawa, T, and Fukaura, Y: A very low dose of green tea polyphenols in drinking water prevents N-methyl-N-nitrosourea-induced colon carcinogenesis in F344 rats. Jpn J Cancer Res 84, 1007-1009, 1993.
22. Yin, P, Zhao, J, Cheng, S, Zhu, Q, Liu, Z, et al.: Experimental studies of the inhibitory effects of green tea catechin on mice large intestinal cancers induced by 1,2-dimethylhydrazine. Cancer Lett 79, 33-38, 1994.
23. Stoner, GD, and Mukhtar, H: Polyphenols as cancer chemopreventive agents. J Cell Biochem 22, 169-180, 1995.
24. Katiyar, SK, and Mukhtar, H: Tea in chemoprevention of cancer -epidemiologic and experimental studies. Int J Oncol 8, 221-238, 1996.
25. Sugic, S, Okamoto, K, Olumura, A, Tanaka, T, and Mori, H: Inhibitory effects of benzyl thiocyanate and benzyl isothiocyanate on methyl azoxymethanol acetate-induced intestinal carcinogenesis in rats. Carcinogenesis 15, 1555-1560, 1994.
26. Wargovich, MJ: Diallyl sulfide, a flavor component of garlic (Allium sativum), inhibits dimethylhydrazine-induced colon cancer. Carcinogenesis 8, 487-489, 1987.
27. Sumiyoshi, H, and Wargovich, MJ: Chemoprevention of 1,2-dimethylhydrazine-induced colon cancer in mice by naturally occurring organosulfur compounds. Cancer Res 50, 5084-5087, 1990.
28. Reddy, BS, Rao, CV, Rivenson, A, and Kelloff, G: Chemoprevention of colon carcinogenesis by organosulfur compounds. Cancer Res 53, 3493-3498, 1993.
29. Guo, D, Schut, HAJ, Davis, CD, Snyderwine, EG, Bailey, GS, et al.: Protection by chlorophyllin and indole-3-carbinol against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced DNA adducts and colonic aberrant crypts in the F344 rat. Carcinogenesis 16, 2931-2937, 1995.
30. Deschner, EE, Ruperto, J, Wong, G, and Newmark, HL: Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neoplasia. Carcinogenesis 12, 1193-1196, 1991.
31. Ito, N, and Imaida, K: Strategy of research for cancer-chemoprevention. Teratog Carcinog Mutagen 12, 79-95, 1992.
32. Wattenberg, LW, Lam, LK, and Fladmoe, AV: Inhibition of chemical carcinogen-induced neoplasia by coumarins and α-angelicalactone. Cancer Res 39, 1651-1654, 1979.
33. 1 binding to DNA in vivo in rats fed phenolic antioxidants, ethoxyquin and a dithiothione. Carcinogenesis 6, 759-763, 1985.
34. Liu, J, Lin, RI, and Milner, JA: Inhibition of 7, 12-dimethylbenz[a]anthracene-induced mammary tumors and DNA adducts by garlic powder. Carcinogenesis 13, 1847-1851, 1992.
35. Miller, EG, McWhorter, K, Rivera-Hidalgo, F, Wright, JM, Hirsbrunner, P, et al.: Kahweol and cafestol: inhibitors of hamster buccal pouch carcinogenesis. Nutr Cancer 15, 41-46, 1991.
36. Kensler, TW, Egner, PA, Dolan, PM, Groopman, JD, and Roebuck, BD: Mechanism of protection against aflatoxin tumorigenicity in rats fed 5-(2-pyrazinyl)-4-methyl-1,2-dithiol-3-thione (oltipraz) and related 1,2-dithiol-3-thiones and 1,2-dithiol-3-ones. Cancer Res 47, 4271-4277, 1987.
37. Stavric, B: Antimutagens and anticarcinogens in foods. Food Chem Toxicol 32, 79-90, 1994.
38. Wolfgang, WH, McDaniel, LP, Kaderlik, KR, Teitel, CH, Lang, NP, et al.: Chemoprotection against the formation of colon DNA adducts from the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the rat. Mutat Res 376, 115-122, 1997.
39. McManus, ME, Felton, JS, Knize, MG, Burgess, WM, Roberts Thomson, S, et al.: Activation of the food-derived mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by rabbit and human liver microsomes and purified forms of cytochrome P-450. Carcinogenesis 10, 357-363, 1989.
40. Wallin, H, Mikalsen, A, Guengerich, FP, Ingelraan-Sundberg, M, Solberg, KE, et al.: Differential rates of metabolic activation and detoxication of the food mutagen 2-amino-1-methyl-6-phenylimi-dazo[4,5-b]pyridine by different cytochrome P450 enzymes. Carcinogenesis 11, 489-492, 1990.
41. Zhao, K, Murray, S, Davies, DS, Boobis, AR, and Gooderham, NJ: Metabolism of the food derived mutagen and carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) by human liver microsomes. Carcinogenesis 15, 1285-1288, 1994.
42. Turesky, RJ, Lang, NP, Butler, MA, Teitel, CH, and Kadlubar, FF: Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon. Carcinogenesis 12, 1839-1845, 1991.
43. Mammons, GJ, Milton, D, Stepps, K, Guengerich, FP, Tukey, RH, et al.: Metabolism of carcinogenic heterocyclic and aromatic amines by recombinant human cytochrome P450 enyzmes. Carcinogenesis 18, 851-854, 1997.
44. Apostolides, Z, Balentine, DA, Harbowry, ME, and Weisburger, JH: Inhibition of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) mutagenicity by black and green tea extracts and polyphenols. Mutat Res 359, 159-163, 1996.
45. Guengerich, FP, Wang, P, and Davidson, NK: Estimation of isozymes of microsomal cytochrome P-450 in rats, rabbits, and humans using immunochemical staining coupled with sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Biochemistry 21, 1698-1706, 1982.
46. Lowry, OH, Rosebrough, NJ, Farr, AL, and Randall, RJ: Protein measurement with the Folin phenol reagent J Biol Chem 193, 265-275, 1951.
47. Koley, AP, Buters, JTM, Robinson, RC, Markowitz, A, and Friedman, FK. Differential mechanisms of cytochrome P450 inhibition and activation by α-naphthoflavone. J Biol Chem 272, 3149-3152, 1997.
48. Siess, M-H, Leclerc, J, Canivenc-Lavier, M-C, Rat, P, and Suschetet, M: Heterogenous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes. Toxicol Appl Pharmacol 130, 73-78, 1995.
49. Li, Y, Wang, E, Patten, CJ, Chen, L, and Yang, CS: Effects of flavonoids on cytochrome P450-dependent acetaminophen metabolism in rats and human liver microsomes. Drug Metab Dispos 22, 566-571, 1994.
50. Wrighton, SA, and Stevens, JC: The human hepatic cytochromes P450 involved in drug metabolism. Crit Rev Toxicol 22, 1-21, 1992.
51. Apostolides, Z, Balentine, DA, Harbowy, ME, Hara, Y, and Weisburger, JH: Inhibition of PhIP mutagenicity by catechins, and by theaflavins and gallate esters. Mutat Res 389, 167-172, 1997.
52. Wang, ZY, Das, M, Bickers, DR, and Mukhtar, H: Interaction of epicatechins derived from green tea with rat hepatic cytochrome P-450. Drug Metab Dispos 16, 98-103, 1988.
53. Bu-Abbas, A, Clifford, MN, Walker, R, and Ioannides, C: Marked antimutagenic potential of aqueous green tea extracts: mechanism of action. Carcinogenesis 9, 325-331, 1994.
54. Bu-Abbas, A, Clifford, MN, Walker, R, and Ioannides, C: Selective induction of rat hepatic CYP1 and CYP4 proteins and of peroxisomal proliferation by green tea. Carcinogenesis 15, 2575-2579, 1994.
55. Sohn, OS, Surace, A, Fiala, ES, Richie, JP, Colosimo, S, et al.: Effects of green and black tea on hepatic xenobiotic metabolizing systems in the male F344 rat. Xenobiotica 24, 119-127, 1994.
56. Chen, L, Bondoc, FY, Lee, M-J, Hussin, AHJ, Thomas, PE, et al.: Caffeine induces cytochrome P4501A2: induction of CYP1A2 by tea in rats. Drug Metab Dispos 24, 529-533, 1996.
57. Obermeier, MT, White, RE, and Yang, CS: Effects of bioflavonoids on hepatic P450 activities. Xenobiotica 25, 575-584, 1995.
58. Kaderlik, KR, Minchin, RF, Mulder, GJ, Ilett, KF, Jenson, MD, et al.: Metabolic activation pathway for the formation of DNA adducts of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rat extrahepatic tissues. Carcinogenesis 15, 1703-1709, 1994.
59. Shimada, T, El-Bayoumy, K, Upadhyaya, P, Sutter, TR, Guengerich, FP, et al.: Inhibition of human cytochrome P450-catalyzed oxidations of xenobiotics and procarcinogens by synthetic organoselenium compounds. Cancer Res 57, 4757-4764, 1997.
60. Barcelo, S, Gardiner, J, Gescher, A, and Chipman, JK: CYP2E1-mediated mechanism of anti-genotoxicity of the broccoli constituent sulforaphane. Carcinogenesis 17, 277-282, 1996.