Metabolism of myosmine in wistar rats

Drug Metabolism and Disposition

Volumn 33, Issue 11, 2005, Pages 1648-1656

  Zwickenpflug, Wolfgang ^a   Tyroller, Stefan ^a   Richter, Elmar ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 PYRIDYLACETIC ACID; 3' HYDROXYMYOSMINE; 4 HYDROXY 1 (3 PYRIDYL) 1 BUTANONE; 4 OXO 4 (3 PYRIDYL)BUTYRIC ACID; ALKALOID DERIVATIVE; DRUG METABOLITE; KETONE DERIVATIVE; MYOSMINE; NICOTINYL ALCOHOL; NITROSONORNICOTINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; FECES ANALYSIS; FEMALE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; NITROSATION; NONHUMAN; PRIORITY JOURNAL; QUANTUM YIELD; RADIOACTIVITY; RAT; RISK ASSESSMENT; TOBACCO; ULTRAVIOLET SPECTROSCOPY; URINARY EXCRETION;

ALKALOIDS; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; FECES; FEMALE; KETO ACIDS; MALE; PYRIDINES; RATS; RATS, WISTAR; TIME FACTORS; TOBACCO;

ANIMALIA; MALUS X DOMESTICA; NICOTIANA TABACUM; RATTUS NORVEGICUS;

EID: 27544464502     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.104.003087     Document Type: Article

References (36)

1. Baker RR (1999) Smoke chemistry, in Tobacco Production, Chemistry and Technology (Davis DL and Nielsen MT eds) pp. 398-439. Blackwell Science Ltd., Oxford.
2. Barlow RD, Thompson PA, and Stone RB (1987) Simultaneous determination of nicotine, cotinine and five additional nicotine metabolites in the urine of smokers using pre-column derivatization and high-performance liquid chromatography. J Chromatogr 419:375-380.
3. Beckett AH, Gorrod JW, and Jenner P (1971) A possible relation between pKa1 and lipid solubility and the amounts excreted in urine of some tobacco alkaloids given to man. J Pharm Pharmacol 24:115-120.
4. Bencherif M, Byrd G, Caldwell WS, Hayes JR, and Lippiello PM (1997) Pharmacological characterization of RJR-2403: a nicotinic agonist with potential therapeutic benefit in the treatment of Alzheimer's disease. CNS Drug Rev 3:325-345.
5. Brandänge S and Lindblom L (1976) N-Vinyl as N-H protection group. A convenient synthesis of myosmine. Acta Chem Scand 30:39.
6. Brandänge S and Rodriguez B (1983) Ring chain tautomerism of myosmine. Acta Chem Scand Ser B 37:643-644.
7. Denton TT, Zhang X, and Cashman JR (2004) Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. Biochem Pharmacol 67:751-756.
8. Hecht SS (1998) Biochemistry, biology and carcinogenicity of tobacco-specific N-nitrosamines. Chem Res Toxicol 11:559-603.
9. Hecht SS (2003) Tobacco carcinogens, their biomarkers and tobacco-induced cancer. Nat Rev Cancer 3:733-744.
10. Hecht SS, Chen CB, Dong M, Ornaf RM, Hoffmann D, and Tso TC (1977) Chemical studies on tobacco smoke LI: studies on non-volatile nitrosamines in tobacco. Beitr Tabakforsch 9:1-6.
11. Hecht SS, Chen C-H, and Hoffmann D (1980a) Metabolic β-hydroxylation and N-oxidation of N′-nitrosonornicotine. J Med Chem 23:1175-1178.
12. Hecht SS, Lin D, and Chen CB (1981) Comprehensive analysis of urinary metabolites of N′-nitrosonornicotine. Carcinogenesis 2:833-838.
13. Hecht SS, Young R, and Chen CB (1980b) Metabolism in the F344 rat of 4-(N-methyl-Nnitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco-specific carcinogen. Cancer Res 40:4144-4150.
14. Hukkanen J, Jacob P, and Benowitz NL (2005) Metabolism and disposition kinetics of nicotine. Pharmacol Rev 57:79-115.
15. IARC (2004) IARC Monographs Programme Finds Smokeless Tobacco Is Carcinogenic To Humans. Press Release No 154. 2004. Lyon, International Agency for Research on Cancer.
16. Kleinsasser NH, Wallner BC, Harréus UA, Zwickenpflug W, and Richter E (2003) Genotoxic effects of myosmine in human lymphocytes and upper aerodigestive tract epithelial cells. Toxicology 192:171-177.
17. McIntee EJ and Hecht SS (2000) Metabolism of N′-nitrosonornicotine enantiomers by cultured rat esophagus and in vivo in rats. Chem Res Toxicol 13:192-199.
18. McKennis H, Schwartz SL, and Bowman ER (1964a) Alternate routes in the metabolic degradation of the pyrrolidine ring of nicotine. J Biol Chem 239:3990-3996.
19. McKennis H, Schwartz SL, Turnbull LB, Tamaki E, and Bowman ER (1964b) 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.
20. Meacham RH, Bowman ER, and McKennis H (1972) Additional routes in the metabolism of nicotine to 3-pyridylacetate. J Biol Chem 247:902-908.
21. Parviainen MT and Puhakainen EVJ (1990) Nicotine metabolites in the urine of smokers. J Chromatogr 525:193-202.
22. Peterson LA, Thomson NM, Crankshaw DL, Donaldson EE, and Kenney PJ (2001) Interactions between methylating and pyridyloxobutylating agents in A/J mouse lungs: implications for 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis. Cancer Res 61:5757-5763.
23. Pilotti A, Enzell CR, McKennis H, Bowman E, Dufva E, and Holmstedt B (1976) Studies on the identification of tobacco alkaloids, their mammalian metabolites and related compounds by gas chromatography-mass spectrometry. Beitr Tabakforsch 8:339-349.
24. Richter E, Schlöbe D, Hölzle D, and Wilp J (2002) Comparative DNA and hemoglobin adduct formation by dietary myosmine and N′- nitrosonornicotine in rats. Naunyn Schmiedebergs Arch Pharmacol 365 (Suppl 1):R140.
25. Riebe M and Westphal K (1983) Studies on the induction of sister-chromatid exchanges in Chinese hamster ovary cells by various alkaloids. Mutat Res 124:281-286.
26. Riebe M, Westphal K, and Fortnagel P (1982) Mutagenicity testing, in bacterial test systems, of some constituents of tobacco. Mutat Res 101:39-43.
27. Rop PP, Grimaldi F, Oddoze C, and Viala A (1993) Determination of nicotine and its main metabolites in urine by high-performance liquid chromatography. J Chromatogr B 612:302-309.
28. Schepers G, Rustemeier K, Walk R-A, and Hackenberg U (1993) Metabolism of S-nicotine in noninduced and Aroclor-induced rats. Eur J Drug Metab Pharmacokinet 18:187-197.
29. Trushin N and Hecht SS (1999) Stereoselective metabolism of nicotine and tobacco-specific N-nitrosamines to 4-hydroxy-4-(3-pyridyl)butanoic acid in rats. Chem Res Toxicol 12:164-171.
30. Tyroller S and Zwickenpflug W (2005) Peroxidation of myosmine: identification of reaction products and influence of the reaction conditions. Proc Am Assoc Cancer Res 46:500.
31. Tyroller S, Zwickenpflug W, and Richter E (2002) New sources of dietary myosmine uptake from cereals, fruits, vegetables and milk. J Agric Food Chem 50:4909-4915.
32. Tyroller S, Zwickenpflug W, and Richter E (2004) Interactions of different tobacco-alkaloids and TSNA on NNN-metabolism in F344 rats. Proc Am Assoc Cancer Res 45:741.
33. Werle E and Schievelbein H (1961) Tabellen zur Toxikologie, Pharmakologie und Chemie von Inhaltsstoffen des Tabaks und des Tabakrauchs. 1. Mitteilung. Arzneim-Forsch 11:1011-1016.
34. Wilp J, Zwickenpflug W, and Richter E (2002) Nitrosation of dietary myosmine as risk factor of human cancer. Food Chem Toxicol 40:1223-1228.
35. Zwickenpflug W (2000) N-nitrosation of myosmine yields HPB (4-hydroxy-1-(3-pyridyl)-1-butanone) and NNN (N-nitrosonornicotine). J Agric Food Chem 48:392-394.
36. Zwickenpflug W, Meger M, and Richter E (1998) Occurrence of the tobacco alkaloid myosmine in nuts and nut products of Arachus hypogaea and Corylus avellana. J Agric Food Chem 46:2703-2706.