Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism in human hepatic microsomes by ipomeanol analogs - An exploratory study

Cancer Letters

Volumn 129, Issue 2, 1998, Pages 131-138

  Nunes, Maria G ^a   Desai, Dhimant ^a   Koehl, Werner ^b   Spratt, Thomas E ^a   Guengerich, F Peter ^c   Amin, Shantu ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

^b University of Koblenz Landau   (Germany)

^c VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Human liver microsome; Ipomeanol analogs; Metabolism; Nitrosamines

Indexed keywords

4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE; 4 IPOMEANOL; ALKANONE; BENZENE; CARCINOGEN; CYTOCHROME P450; PENTANE;

ARTICLE; CARCINOGENESIS; CLARA CELL; CONTROLLED STUDY; HUMAN; HUMAN CELL; LIVER MICROSOME METABOLISM; METABOLIC ACTIVATION; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS; BIOLOGICAL MARKERS; BIOTRANSFORMATION; BUTANONES; HUMANS; HYDROXYLATION; KETONES; MICROSOMES, LIVER; NITROSAMINES; PENTANES; PYRIDINES; TERPENES;

EID: 0032547014     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-3835(98)00049-4     Document Type: Article

References (45)

1. Wynder E.L., Hoffmann D. Smoking and lung cancer: scientific challenges and opportunities. Cancer Res. 54:1994;5284-5295.
2. Morse M.A., Amin S.G., Hecht S.S., Chung F.-L. Effects of isothiocyanates on tumorigenicity, O6-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung. Cancer Res. 49:1989;2894-2897.
3. Zhang Y., Talalay P., Cho C.G., Posner G.H. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. USA. 89:1992;2399-2403.
4. Morse M.A., Wang C.X., Stoner G.D., Mandal S., Conran P.B., Amin S.G., Hecht S.S., Chung F.-L. Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced DNA adduct formation and tumorigenicity in lung of F344 rats by dietary phenethyl isothiocyanate. Cancer Res. 49:1989;549-553.
5. F.-L. Chung, Chemoprevention of lung carcinogenesis by aromatic isothiocyanates, in: L. Wattenberg, M. Lipkin, C.W. Boone, G.J. Kelloff (Eds.), Cancer Chemoprevention, CRC Press, Boca Raton, FL, 1992, pp. 227-245.
6. Morse M.A., Eklind K.I., Hecht S.S., Jordan K.G., Choi C.-I., Desai D.H., Amin S.G., Chung F.-L. Structure-activity relationships for inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone lung tumorigenesis by arylkyl isothiocyanates in A/J mice. Cancer Res. 51:1991;1846-1850.
7. Jiao D., Eklind K.I., Choi C.-I., Desai D.H., Amin S.G., Chung F.L. Structure-activity relationships of isothiocyanates as mechanism-based inhibitors of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis in A/J mice. Cancer Res. 54:1994;4327-4333.
8. Hecht S.S., Hoffmann D. Tobacco-specific nitrosamines, an important group of carcinogens in tobacco smoke. Carcinogenesis. 9:1988;875-884.
9. Chung F.-L., Wang M., Hecht S.S. Effects of dietary indoles and isothiocyanates on N-nitrosodimethylamine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone α-hydroxylation and DNA methylation in rat liver. Carcinogenesis. 6:1985;539-543.
10. Wattenberg L.W., Coccia J.B. Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone carcinogenesis in mice by D-limonene and citrus fruit oils. Carcinogenesis. 12:1991;115-117.
11. Wargowitch M.J. Diallyl sulfides, a flavor component of garlic (Allium sativum) inhibits dimethylhydrazine-induced colon cancer. Carcinogenesis. 8:1987;487-489.
12. Wang Z.Y., Hong J.Y., Huang M.T., Reuhl K.R., Conney A.H., Yang C.S. Inhibition of N-nitrosodiethylamine- and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced tumorigenesis in A/J mice by green tea and black tea. Cancer Res. 52:1992;1943-1947.
13. Xu Y., Ho C.-T., Amin S.G., Han C., Chung F.-L. Nitrosamine-induced lung tumorigenesis in A/J mice by green tea and its major polyphenol as antioxidants. Cancer Res. 52:1992;3875-3879.
14. Hecht S.S., Spratt T.E., Trushin N. Evidence for 4-(3-pyridyl)-4-oxobutylation of DNA in F344 rats treated with the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N-nitrosonornicotine. Carcinogenesis. 9:1988;161-165.
15. Hecht S.S., Young R., Chen C.-H. Metabolism in the F344 rat of 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco-specific carcinogen. Cancer Res. 40:1980;4144-4150.
16. Peterson L.A., Mathew R., Hecht S.S. Quantitation of microsomal α-hydroxylation of the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 51:1991;5495-5500.
17. Peterson L.A., Ng D., Stearns R.A., Hecht S.S. Formation of NADP(H) analogs of tobacco-specific nitrosamines in rat liver and pancreatic microsomes. Chem. Res. Toxicol. 7:1994;599-608.
18. Morse M.A., Eklind K.I., Toussaint M., Amin S.G., Chung F.-L. Characterization of a glucuronide metabolite of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and its dose-dependent excretion in the urine of mice and rats. Carcinogenesis. 11:1990;1819-1823.
19. Carmella S.G., Akerkar S., Hecht S.S. Metabolites of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers' urine. Cancer Res. 53:1993;721-724.
20. Murphy S.E., Spina D.A., Nunes M.G., Pullo D.A. Glucuronidation of 4-(hydroxymethylnitrosamino)-1-(3-pyridyl)-1-butanone, a metabolically activated form of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, by phenobarbital-treated rats. Chem. Res. Toxicol. 8:1995;772-779.
21. Smith T.J., Guo Z., Thomas P.E., Chung F.-L., Morse M.A., Eklind K.I., Yang C.S. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mouse lung microsomes and its inhibition by isothiocyanates. Cancer Res. 50:1990;6817-6822.
22. Devereux T.R., Anderson M.W., Belinsky S.A. Factors regulating activation and DNA alkylation by 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone and nitrosodimethylamine in rat lung and isolated cells, and the relationship to carcinogenicity. Cancer Res. 48:1988;4215-4221.
23. Devereux T.R., Jones K.G., Bend J.R., Fouts J.R., Statham C.N., Boyd M.R. In vitro metabolic activation of the pulmonary toxin, 4-ipomeanol, in nonciliated bronchiolar epithelial (Clara) and alveolar type II cells isolated from rabbit lung. J. Pharmacol. Exp. Ther. 220:1981;223-227.
24. Smith A.C., Barrett D., Stedham M.A., el-Hawari M., Kastello M.D., Grieshaber C.K., Boyd M.R. Preclinical toxicology studies of 4-ipomeanol: a novel candidate for clinical evaluation in lung cancer. Cancer Treatment Rep. 71:1987;1157-1164.
25. Lin J.M., Desai D.H., Morse M.A., Amin S., Hecht S.S. Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone pulmonary metabolism and tumorigenicity in mice by analogs of the investigational chemotherapeutic drug 4-ipomeanol. Chem. Res. Toxicol. 5:1992;674-679.
26. Desai D., Nunes M.G., Chang L., Lin J.-M., Jiao D., Amin S. Ipomeanol analogs as potential chemopreventive agents against in vitro metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Cancer Lett. 97:1995;155-162.
27. Czerwinski M., McLemore T.L., Philpot R.M., Nhamburo P.T., Korzekwa K., Gelboin H.V., Gonzalez F.J. Metabolic activation of 4-ipomeanol by complementary DNA-expressed human cytochromes P-450: evidence for species-specific metabolism. Cancer Res. 51:1991;4636-4638.
28. F.P. Guengerich, Analysis and characterization of enzymes, in: A.W. Hayes (Ed.), Principles and Methods of Toxicology, Raven Press, New York, 1994, pp. 1259-1313.
29. Perella F.W. A practical curve-fitting microcomputer program for the analysis of enzyme kinetic data on IBM-PC compatible computers. Anal. Biochem. 174:1988;437-447.
30. Staretz M.E., Koenig L.A., Hecht S.S. Effects of long-term dietary phenethyl isothiocyanate on the microsomal metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F-344 rats. Carcinogenesis. 18:1997;1715-1722.
31. Smith T.J., Guo Z., Gonzalez F.J., Guengerich F.P., Stoner G.D., Yang C.S. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in human lung and liver microsomes and cytochromes P-450 expressed in hepatoma cells. Cancer Res. 52:1992;1757-1763.
32. Staretz M.E., Hecht S.S. Effects of phenethyl isothiocyanate on the tissue distribution of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and metabolites in F344 rats. Cancer Res. 55:1995;5580-5588.
33. Guo Z., Smith T.J., Thomas P.E., Yang C.S. Metabolic activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone as measured by DNA alkylation in vitro and its inhibition by isothiocyanates. Cancer Res. 51:1991;4798-4803.
34. Guo Z., Smith T.J., Wang E., Sadrieh N., Ma Q., Thomas P.E., Yang C.S. Effect of phenethyl isothiocyanate, a carcinogenesis inhibitor, on xenobiotic-metabolizing enzymes and nitrosamine metabolism in rats. Carcinogenesis. 13:1992;2205-2210.
35. Guo Z., Smith T.J., Wang E., Eklind K.I., Chung F.-L., Yang C.S. Structure-activity relationship of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis. 14:1993;1167-1173.
36. Doerr-O'Rourke K., Trushin N., Hecht S.S., Stoner G.D. Effect of phenethyl isothiocyanate on the metabolism of tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by cultured rat lung tissue. Carcinogenesis. 12:1991;1029-1034.
37. Murphy S., Heiblum S., King P.G., Bowman D., Davis W.J., Stoner G.D. Effect of phenethyl isothiocyanate on the metabolism of tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by cultured rat oral tissue. Carcinogenesis. 12:1991;957-961.
38. Yamazaki H., Oda Y., Funae Y., Imaoka S., Uni Y., Guengerich F.P., Shimada T. Participation of rat liver cytochrome P450 2E1 in the activation of N-nitrosodimethylamine and N-nitrosodiethylamine to products genotoxic in an acetyltransferase-overexpressing Salmonella typhimurium strain (NM 2009). Carcinogenesis. 13:1992;979-985.
39. Smith T.J., Guo Z., Guengerich F.P., Yang C.S. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by human cytochrome P450 1A2 and its inhibition by phenethyl isothiocyanate. Carcinogenesis. 17:1996;809-813.
40. Crespi C.L., Penman B.W., Gelboin H.V., Gonzales F.J. A tobacco smoke-derived nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), is activated by multiple human cytochrome P450s, including the polymorphic human cytochrome P450 2D6. Carcinogenesis. 12:1991;1197-1201.
41. F.P. Guengerich, in: P.R. Ortiz de Montellano (Ed.), Cytochrome P450, Plenum Press, New York, 1995, pp. 473-535.
42. Thornton-Manning J.R., Nikula K.J., Hotchkiss J.A., Avila K.J., Rohrbacher K.D., Ding X., Dahl A.R. Nasal cytochrome P450 2A: identification, regional localization, and metabolic activity toward hexamethylphosphoramide, a known nasal carcinogen. Toxicol. Appl. Pharmacol. 142:1997;22-30.
43. Hong J.Y., Ding X., Smith T.J., Coon M.J., Yang C.S. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a tobacco-specific carcinogen, by rabbit nasal nitrosomes and cytochrome P450s Nma and Nmb. Carcinogenesis. 13:1992;2141-2144.
44. Staretz M.E., Murphy S.E., Patten C.J., Nunes M.G., Koehl W., Amin S., Koenig L., Guengerich F.P., Hecht S.S. Comparative metabolism of the tobacco smoke carcinogens benzo(a)pyrene, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, and N′-nitrosonornicotine in human hepatic microsomes. Drug Metab. Dispos. 25:1997;154-162.
45. Guengerich F.P., Shimada T. Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem. Res. Toxicol. 4:1991;391-407.