Efaects of isothiocyanates on cytochrome P-450 1A1 and 1A2 activity and on the mutagenicity of heterocyclic amines

Anticancer Research

Volumn 16, Issue 6 B, 1996, Pages 3597-3602

  Hamilton, Solomon M ^a   Teel, Robert W ^a  

^a LOMA LINDA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Chemoprevention; Cytochrome P 450; EROD; Heterocyclic amines; Isothiocyanates; MROD; Mutagenesis

Indexed keywords

BENZYL ISOTHIOCYANATE; CYTOCHROME P450; ETHOXYRESORUFIN; HETEROCYCLIC AMINE; ISOTHIOCYANIC ACID DERIVATIVE; PHENETHYL ISOTHIOCYANATE; PHENYL ISOTHIOCYANATE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DEMETHYLATION; DOSE RESPONSE; ENZYME INHIBITION; HAMSTER; LIVER MICROSOME; MALE; MUTAGENESIS; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL; SALMONELLA TYPHIMURIUM;

ANIMALS; CARBOLINES; CRICETINAE; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; IMIDAZOLES; ISOTHIOCYANATES; MALE; MESOCRICETUS; MUTAGENICITY TESTS; MUTAGENS; QUINOLINES; QUINOXALINES; SALMONELLA TYPHIMURIUM; THIOCYANATES;

EID: 0030519429     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. Suaimura T, Sato S and Wakabayashi K: Mutagen/carcinogens in pyrolysates of amino acids and proteins in cooked foods. Heterocyclic aromatic amines. In: Chemical Induction of Cancer, Structural Bases and Biological Mechanism, Vol. 3c, Ed. by Y.T. Woo, D.Y. Lai, J.C. Acros and M.F. Argus, pp. 681-710, Academic Press. San Diego, CA, 1988.
2. Suaimura T and Wakabayashi K: Mutagens and Carcinogens in food. In: Mutagens and Carcinogens in the Diet. Ed. by M.W. Pariza, H. V. Aeschbacher, J.S. Felton and S. Sato pp. 1-18, Wiley-Liss, Inc., New York, 1990.
3. Kiaugawa K and Kato T: Formation of mutagens, 2-amino-3,4,8-trimethyl-imidazo [4.5-t] quinoxaline (4.8-DiMeIOx) in heated fish meats. Mutat Res 179: 5-14, 1987.
4. Knaze MG, Happa JA, Healy SK and Felton JS: Identification of the mutagenic quinoxaline isomers from fried ground beef. Mutat Res 178:25-32, 1978.
5. Eiaenbrand G and Tang W: Food-borne heterocyclic amines. Chemistry, formation, occurance and biological activities. A literature review. Toxicology 84: 1-82, 1993.
6. Maasukura N, Kawachi T, Morino K, Ohgaki H, Sugimura T and Takayama S: Carcinogenicity in mice of mutagenic compounds from tryptophan pyrolysates. Science 213: 346-347, 1981.
7. Hoaaka S, Matsushima T, Hirono O and Sugimura T: Carcinogenic activity of 3-amino-1-methyl-SH-pyrido [4,3-b] indole (Trp-P-2), a pyrolysis product of tryptophan. Cancer Lett 13: 21-28, 1981.
8. Ohaaki H, Hasegawa H, Kato T, Suenaga M, Sato S, Takayama S and Sugimura, T: Carcinogenicities in mice and rats of IQ, MeIQ, MeIQx, Proc. Int. Symp. PrincessTakamatsu CancerRes.Fund, 16th: 97-105, 1983.
9. Ohaaki H, Matsukura N, Morino K, Kawachi T, Sugimura T and Takayam S: Carcinogenicity in mice of mutagenic compounds from glutamic acid and soyabean globin pyrolyzatcs. Carcinogenesis 5: 815-819, 1984.
10. Esami H, Ohgaki H, Kohzen E, Takayama S and Sugimura T: Induction of lymphoma in CDF, mice by the food mutagen, 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine. Jpn J Cancer Res 80: 1176-1178, 1989.
11. Ita N, Hasegawa R, Sano M, Tamano S, Esumi H, Takayama S and Sugimura T: A new colon and mammary carcinogen in cooked food, 2-aminol-methyl-6-phenyl-imidazo-[4.5-b] pyridine (PhIP). Carcinogenesis 12: 1503-1506, 1991.
12. Taaayama S, Nakatsuru Y, Masuda M, Ohgaki H, Sato S and Sugimura T: Demonstration of Carcinogenicity in F344 rats of 2-amino-3-methyl-imidazo [4,5-f] quinoline from broiled sardine, fried beef, and beef extract. Gann 75: 467-470, 1984.
13. Ohaaki H, Kusama K., Matsukura N, Morino K, Hasegawa H, Sato S, Takayama S and Sugimura T: Carcinogenicity in mice of a mutagenic compound 2-amino-3-methyl-imidazao [4,5-f] quinoline, from broiled sardine, cooked beef and beef extract. Carcinogenesis 5: 921-924, 1984.
14. Snaderwine EG, Schut AJ, Adamson RH, Thorgeirsson UP and Thorgeirsson SS: Metabolic activation and genotoxicity of heterocyclic arylamines.Cancer Res 52: 2099s-2102s, 1992.
15. Yamazao Y, Ahu-Zeid M, Manabe S, Toyama S and Kato R: Metabolic activation of 2-amino-3,8-dimethylimidazo [4,5-f] quinoxaline by rat liver microsomes and purified cytochrome P-450. Carcinogencsis 9: 105-109, 1988.
16. Mcaanusl ME, Felton JS, Knize MG, Burgess WM, Roberts-Thompson S, Pond SM, Stupans I and Veronese ME: Activation offood 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.
17. Shamada T, Iwasaki M, Martin MV and Guengerich FP: Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens by umu gene response in Salmonella typhimurium TA 1535/psk1002. Cancer Res 46: 3218-3228, 1988.
18. Kaao R: Metabolic activation of mutagenic heterocyclic aromatic amines from protein pyrolysates. CRC Crit Rev Toxicol 16: 307-348, 1986.
19. Yaaazoe Y, Shimada M, Shinohara A, Saito K, Kamataki T and Kato R: Catalysis of the covalent binding of 3-hydroxyamino-1-methyl-SH-pyrido [4,5-b] indole to DNA by L-proline and adenosine triphosphate-dependent enzymes in rat hepatic cytosol. Cancer Res 45: 2495-2500, 1985.
20. Shanohara A, Saito K, Yamazoe Y, Kamataki T and Kato R: DNA binding of N-hydroxy-Trp-P-2 and N-hydroxy-Glu-P-1 by acetyl-CoA dependent enzyme in mammalian liver cytosol. Carcinogenesis 6: 305-307, 1985.
21. Flammang TJ and Kadlubar FF: Acetyl coenzyme A-dependent metabolic activation of N-hydroxy-3, 2′-dimethyl-4-aminobiphenyl and several carcinogenic N-hydroxy arylamines in relation to tissue and species differences, other acyl donors, and arylhydroxamic acid dependent acyltrasferases. Carcinogenesis 7: 919-926, 1986.
22. Buake MD, Thompson S, Weaver RJ, Wolf CR and Mayer RT: Cytochrome P-450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochemical Pharmacology 48: 923-936, 1994.
23. Buak MD and Mayer RT: Inherent specificities of purified cytochromes P450 and P448 toward biphenyl hydroxylation and ethoxyresorufin deethylation. Drug Metab Dispos 3: 245-253, 1975.
24. Buak MD, Thompson S, Elcombe CR, Halpert J, Haaparanta T and Mayer RT: Ethoxy-penthoxy-and benzyloxyphenoxazones and homologues: a scries of substrates to distinguish between different induced cytochrome P450. Biochem Pharmacol 34:3337-3345, 1985.
25. Roarigues AD and Prough RA: Induction of cytochrome P450 1A1 and 1A2 and measurement of catalytic activities. Methods Enzymol 206: 423-431, 1991.
26. Neaurka PV, Park SS, Thomas PE, Nioms RW and Lubert RA: Methoxyresorufin and benzyloxyresorufin: substrates preferentially metabolised by cytochromes P450 1A2 and 2B, respectively, in the rat and mouse. Biochem Pharmacol 46:933-943, 1993.
27. Waatenberg LW: Inhibition of carcinogenic effects of polycyclic hydrocarbons by benzyl isothiocyanates and related compounds. J Natl Cancer Inst. 58: 395-398, 1977.
28. Moase MA and Stoner GD: Cancer chemoprevention: principles and prospects. Carcinogenesis 14: 1737-1746, 1993.
29. Smath TJ, Guo Z, Li C, Ning SM, Thomas PE and Yang CS: Mechanisms of inhibition of 4-(methylnitrosamino)-1-(3-pyridyl-1-butanone) bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Res 53: 3276-3282, 1993.
30. Smath TJ, Guo Z, Thomas PF, Chung FL, Morse MA, Eklind K and Yang CS: Metabolism of 4-(N-methyl-N-nitrosamino) 1-(3-pyridyl)-1-butunone in mouse lung and its inhibition by isothiocyanates. Cancer Res 50: 6817-6822, 1990.
31. Moase MA, Eklind KI, Hecht SS, Jordan KG, Choi CI, Desai DH, Amin SG and Chung FL: Structure activity relationships for inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone lung tumorigenesis by arylalkyl isothiocyanates in A/J mice. Cancer Res 51:1846-1850, 1991.
32. Staner GD, Morrisey DT, Heur YH, Daniel EM, Galati AJ and Wagner SA: Inhibitory effects of phenyl isothiocyanate on N-nitroso-benzylmethylamine carcinogenesis in the rat esophagus. Cancer Res 51:2063-2068, 1991.
33. Maaon DM and Ames BN: Revised methods for the Salmonella mutagenicitytest. Mutat Res 113: 173-215, 1983.
34. Loary OH, Rosenbrough NJ, Farr AL and Randall RJ: Protein measurement with the folin phenol reagent. J Biol Chem 192: 265-275, 1951.
35. Caa Y, Bonnette D, Nair RV, Ceska O, Ashwood-Smith MJ and DiGiovanni J: Inhibition and inactivation of murine hepatic ethoxy-and phenlhoxyresufurin O-dealkylase by naturally occurring coumarins. Chem Res Toxicol 6: 872-879, 1993.
36. Buak MD and Mayer RT: Ethoxyresofurin: direct fluorimetric assay of a microsomal o-dealkylation which is preferentially inducible by 3methylcholanthrene. Drug Metabolism and Disposition 2: 583-588, 1974.
37. Haailton SM, Zhang Z and Teel RW: Effects of isothiocyanate alkyl chain-length on hamster liver cytochrome P-450 activity. Cancer Letters 82: 217-224, 1994.
38. Neamark HL: A hypothesis for dietary compounds as blocking agents of chemical carcinogenesis: plant phenolics and pyrrole pigments. Nutr Cancer 6: 58-70, 1984.
39. Waatenberg LW: Chemoprevention of cancer. Cancer Res 45: 1-8, 1985.
40. Zhang Y and Talalay P: Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms. Cancer Res 54: 1976-1981, 1994.
41. Staner GD, Siglin JC, Morse MA, Desai DH, Amin SG, Kresty LA, Toburn AL, Heffener EM and Francis DJ: Enhancement of esophageal carcinogenesis in male F344 rats by dietary phenylhexyl isothiocyanate. Carcinogenesis 16: 2473-2476, 1995.
42. Raa CV, Rivenson A, Simi B, Hamid R, Zang E and Ruddy BS: Colon tumor promotion by phenylhexyl isothiocyanate in male F344 rats. Proc Am Assoc Cancer Res 36: 124, 1995.
43. Huang Q, Lawson TA, Chung FL, Morris CR and Mvervish SS: Inhibition by phenylethyl and phenylhexyl isothiocyanates on metabolism of and DNA methylation by N-nitrosomethylamylamine in rats. Carcinogensis 14: 749-754, 1993.