Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by cultured monkey lung explants

Drug Metabolism and Disposition

Volumn 28, Issue 1, 2000, Pages 5-9

  Hecht, Stephen S ^a   Trushin, Neil ^b   Chhabra, Saranjit K ^c   Anderson, Lucy M ^c   Nerurkar, Pratibha V ^c  

^a UNIVERSITY OF MINNESOTA   (United States)

^b AMERICAN HEALTH FOUNDATION   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 BUTANONE; NITROSAMINE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; FEMALE; HYDROXYLATION; LUNG PARENCHYMA; METABOLIC ACTIVATION; METABOLISM; MONKEY; NONHUMAN; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; REACTION ANALYSIS;

ANIMALS; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ERYTHROCEBUS PATAS; FEMALE; LUNG; MACACA FASCICULARIS; MALE; NITROSAMINES; ORGAN CULTURE TECHNIQUES; PLANTS, TOXIC; RATS; RATS, INBRED F344; TOBACCO;

ANIMALIA; ERYTHROCEBUS PATAS; MACACA FASCICULARIS; NICOTIANA TABACUM; PRIMATES; RODENTIA;

EID: 0033985433     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Carmella SG, Akerkar S and Hecht SS (1993) Metabolites of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers' urine. Cancer Res 5:721-724.
2. Carmella SG, Akerkar S, Richie JP Jr and Hecht SS (1995) Intraindividual and interindividual differences in metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in smokers' urine. Cancer Epidemiol Biomarkers Prev 4:635-642.
3. Carmella SG, Borukhova A, Akerkar SA and Hecht SS (1997) Analysis of human urine for pyridine-N-oxide metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco-specific lung carcinogen. Cancer Epidemiol Biomarkers Prev 6:113-120.
4. Carmella SG and Hecht SS (1985) High-performance liquid chromatographic analysis of metabolites of the nicotine derived nitrosamines, N′-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Anal Biochem 145:239-244.
5. Castonguay A, Lin D, Stoner GD, Radok P, Furuya K, Hecht SS, Schut HAJ and Klaunig JE (1983b) Comparative carcinogenicity in A/J mice and metabolism by cultured mouse peripheral lung of N′-nitrosonornicotine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and their analogues. Cancer Res 43:1223-1229.
6. Castonguay A, Stoner GD, Schut HAJ and Hecht SS (1983a) Metabolism of tobacco-specific N-nitrosamines by cultured human tissues. Proc Natl Acad Sci USA 80:6694-6697.
7. Castonguay A, Tjälve H, Trushin N, d'Argy R and Sperber G (1985) Metabolism and tissue distribution of tobacco-specific N-nitrosamines in the marmoset monkey (Callithrix jacchus). Carcinogenesis 6:1543-1550.
8. Castonguay A, Tjälve H, Trushin N and Hecht SS (1984) Perinatal metabolism of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in C57B1 mice. J Natl Cancer Inst 72:1117-1126.
9. Doerr-O'Rourke K, Trushin N, Hecht SS and Stoner GD (1991) Effect of phenethyl isothiocyanate on the metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by cultured rat lung tissue. Carcinogenesis 12:1029-1034.
10. Hecht SS (1998) Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chem Res Toxicol 11:559-603.
11. Hecht SS and Hoffmann D (1988) Tobacco-specific nitrosamines, an important group of carcinogens in tobacco and tobacco smoke. Carcinogenesis 9:875-884.
12. Hecht SS and Tricker AR (1999) Nitrosamines derived from nicotine and other tobacco alkaloids, in Analytical Determination of Nicotine and Related Compounds and Their Metabolites (Gorrod JW and Jacob P III eds), Elsevier Publishing Co. Amsterdam, in press.
13. Hecht SS, Trushin N, Reid-Quinn CA, Burak ES, Jones AB, Southers JL, Gombar CT, Carmella SG, Anderson LM and Rice JM (1993) Metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in the patas monkey: Pharmacokinetics and characterization of glucuronide metabolites. Carcinogenesis 14:229-236.
14. Hecht SS, Young R and Chen CB (1980) Metabolism in the F344 rat of 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco specific carcinogen. Cancer Res 40:4144-4150.
15. Hoffmann D, Brunnemann KD, Prokopczyk B and Djordjevic MV (1994) Tobacco-specific N-nitrosamines and areca-derived N-nitrosamines: Chemistry, biochemistry, carcinogenicity, and relevance to humans. J Toxicol Environ Health 41:1-52.
16. Hoffmann D and Hecht SS (1985) Nicotine-derived N-nitrosamines and tobacco related cancer: Current status and future directions. Cancer Res 45:935-944.
17. Lackmann GM, Salzberger U, Töllner U, Chen M, Carmella SG and Hecht SS (1999) Metabolites of a tobacco-specific carcinogen in the urine of newborns. J Natl Cancer Inst 91:459-465.
18. McKennis H, Schwartz SL, Turnbull LB, Tamaki E and Bowman ER (1964) The metabolic formation of γ-(3-pyridyl)-γ-hydroxybutyric acid and its possible intermediary role in the mammalian metabolism of nicotine. J Biol Chem 239:3981-3989.
19. Meger M, Richter E, Zwickenpflug W, Oehlmann C, Hargaden MB, A-Rahim YI and Vessell ES (1999) Metabolism and disposition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in rhesus monkeys. Drug Metab Dispos 27:471-478.
20. Parsons WD, Carmella SG, Akerkar S, Bonilla LE and Hecht SS (1998) A metabolite of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in the urine of hospital workers exposed to environmental tobacco smoke. Cancer Epidemiol Biomarkers Prev 7:257-260.
21. Schrader E, Hirsch-Ernst KI, Richter E and Foth H (1998) Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in isolated rat lung and liver. Naunyn-Schmiedeberg's Arch Pharmacol 357:336-343.
22. Smith T, Liao A, Liu Y, Jones A, Anderson L and Yang CS (1997) Enzymes involved in the bioactivation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in patas monkey lung and liver microsomes. Carcinogenesis 18:1577-1584.
23. Smith TJ, Guo ZY, Gonzalez FJ, Guengerich FP, Stoner GD and Yang CS (1992) 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 52:1757-1763.
24. Smith TJ, Stoner GD and Yang CS (1995) Activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung microsomes by cytochromes P450, lipoxygenase, and hydroperoxides. Cancer Res 55:5566-5573.
25. Staretz ME, Koenig L and Hecht SS (1997) Effects of long term phenethyl isothiocyanate treatment on microsomal metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F344 rats. Carcinogenesis 18:1715-1722.
26. Upadhyaya P, Kenney PMJ, Hochalter JB, Wang M and Hecht SS (1999) Tumorigenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) enantiomers and metabolites in the A/J mouse. Carcinogenesis 20:1577-1582.