Urinary excretion of morphine and biosynthetic precursors in mice

Proceedings of the National Academy of Sciences of the United States of America

Volumn 107, Issue 18, 2010, Pages 8147-8152

  Grobe, Nadja ^a   Lamshöft, Marc ^b   Orth, Robert G ^c   Dräger, Birgit ^d   Kutchan, Toni M ^a   Zenk, Meinhart H ^a   Spiteller, Michael ^b  

^a DONALD DANFORTH PLANT SCIENCE CENTER   (United States)

^b TU DORTMUND UNIVERSITY   (Germany)

^c Apis Discoveries LLC   (United States)

^d MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Endogenous morphine; High resolution mass spectrometry; Mammalian mophine; Morphine biosynthesis; Stable isotope labeled morphine

Indexed keywords

ALKALOID; CODEINE; DIMETHOXY N METHYL APORPHINE; DIMETHOXY N METHYL MORPHINANDIENONE; DIMETHOXY N METHYL TETRAHYDROBENZYLISOQUINOLINE; DIMETHOXY TETRAHYDROBENZYLISOQUINOLINE; DIMETHOXY TETRAHYDROPROTOBERBERINE; DRUG METABOLITE; ISOQUINOLINE ALKALOID; MONOMETHOXY TETRAHYDROBENZYLISOQUINOLINE; MONOMETHOXY TETRAHYDROPROTOBERBERINE; MORPHINE; OPIATE; ORIPAVINE; PHENOL; RETICULINE; SALUTARIDIN; TETRAHYDROPAPAVEROLINE; TETRAHYDROPROTOBERBERINE (TETRAHYDROXYBERBINE); THEBAINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; ISOTOPE LABELING; MASS SPECTROMETRY; METABOLISM; MOUSE; NONHUMAN; PLANT; PRECURSOR; PRIORITY JOURNAL; RODENT; SIGNAL TRANSDUCTION; STEREOCHEMISTRY; URINALYSIS; URINARY EXCRETION;

ANIMALS; FEMALE; MASS SPECTROMETRY; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; MORPHINANS; MORPHINE; TETRAHYDROPAPAVEROLINE; THEBAINE;

ANIMALIA; MAMMALIA; MUS; PAPAVER SOMNIFERUM; RODENTIA;

EID: 77952338608     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1003423107     Document Type: Article

References (43)

1. Teschemacher H, Opheim KE, Cox BM, Goldstein A (1975) A peptide-like substance from pituitary that acts like morphine. 1. Isolation. Life Sci 16:1771-1776.
2. Goldstein A, et al. (1985) Morphine and other opiates from beef brain and adrenal. Proc Natl Acad Sci USA 82:5203-5207. (Pubitemid 16242829)
3. Weitz CJ, Lowney LI, Faull KF, Feistner G, Goldstein A (1986) Morphine and codeine from mammalian brain. Proc Natl Acad Sci USA 83:9784-9788.
4. Gintzler AR, Levy A, Spector S (1976) Antibodies as a means of isolating and characterizing biologically active substances: Presence of a non-peptide, morphine-like compound in the central nervous system. Proc Natl Acad Sci USA 73:2132-2136.
5. Oka K, Kantrowitz JD, Spector S (1985) Isolation of morphine from toad skin. Proc Natl Acad Sci USA 82:1852-1854.
6. Donnerer J, Oka K, Brossi A, Rice KC, Spector S (1986) Presence and formation of codeine and morphine in the rat. Proc Natl Acad Sci USA 83:4566-4567. (Pubitemid 16057090)
7. Donnerer J, et al. (1987) Chemical characterization and regulation of endogenous morphine and codeine in the rat. J Pharmacol Exp Ther 242:583-587. (Pubitemid 17143493)
8. Hazum E, et al. (1981) Morphine in cow and human milk: Could dietary morphine constitute a ligand for specific morphine (μ) receptors?. Science 213:1010-1012.
9. Rowell FJ, Spark P, Rich CG (1982) Non-peptide morphine-like compounds in vertebrate brain tissue and food. Brit J Pharmacol 77:461P.
10. Poeaknapo C, Schmidt J, Brandsch M, Dräger B, Zenk MH (2004) Endogenous formation of morphine in human cells. Proc Natl Acad Sci USA 101:14091-14096. (Pubitemid 39305035)
11. Boettcher C, Fellermeier M, Boettcher C, Dräger B, Zenk MH (2005) How human neuroblastoma cells make morphine. Proc Natl Acad Sci USA 102:8495-9500. (Pubitemid 40862764)
12. Muller A, et al. (2008) Endogenous morphine in SH-SY5Y cells and the mouse cerebellum. PLoS One 3:e1641.
13. Matsubara K, Fukushima S, Akane A, Kobayashi S, Shiono H (1992) Increased urinary morphine, codeine and tetrahydropapaveroline in Parkinsonian patient undergoing L-3,4-dihydroxyphenylalanine therapy: A possible biosynthetic pathway of morphine from L-3,4-dihydroxyphenylalanine in humans. J Pharmacol Exp Ther 260:974-978.
14. Mikus G, et al. (1994) Endogenous codeine and morphine in poor and extensive metabolisers of the CYP2D6 (debrisoquine/sparteine) polymorphism. J Pharmacol Exp Ther 268:546-551. (Pubitemid 24085844)
15. Hofmann U, et al. (1999) Highly sensitive gas chromatographic-tandem mass spectrometric method for the determination of morphine and codeine in serum and urine in the femtomolar range. J Chromatogr B 727:81-88. (Pubitemid 29189278)
16. Sandler M, Bonham Carter S, Hunter KR, Stern GM (1973) Tetrahydroisoquinoline alkaloids: In vivo metabolites of L-dopa in man. Nature 241:439-443.
17. Turner AJ, Baker KM, Algeri S, Frigerio A, Garattini S (1974) Tetrahydropapaveroline: Formation in vivo and in vitro in rat brain. Life Sci 14:2247-2257.
18. Cashaw JL, Geraghty CA, McLaughlin BR, Davis VE (1987) A method for determination of subpicomole concentrations of tetrahydropapaveroline in rat brain by high-performance liquid chromatography with electrochemical detection. Anal Biochem 162:274-282. (Pubitemid 17064326)
19. Geraghty CA, Cashaw JL (1989) Method for the identification of tetrahydropapaveroline using the Pictet-Spengler condensation reaction and high-performance liquid-chromatography. J Chromatogr 489:399-403.
20. Sällström Baum S, Hill R, Kiianmaa K, Rommelspacher H (1999) Effect of ethanol on (R)- and (S)-salsolinol, salsoline, and THP in the nucleus accumbens of AA and ANA rats. Alcohol 18:165-169. (Pubitemid 29368324)
21. Sango K, et al. (2000) Enantio-selective occurrence of (S)-tetrahydropapaveroline in human brain. Neurosci Lett 283:224-226. (Pubitemid 30168973)
22. Collins MA (2004) Tetrahydropapaveroline in Parkinson's disease and alcoholism: A look back in honor of Merton Sandler. Neurotoxicology 25:117-120.
23. Barton DHR, Cohen T (1957) Some biogenetic aspects of phenol oxidation "Festschrift Prof. Dr. Arthur Stoll" (Birkhäuser, Basel).
24. Grobe N, et al. (2009) Mammalian cytochrome P450 enzymes catalyze the phenol-coupling step in endogenous morphine biosynthesis. J Biol Chem 284:24425-24431.
25. Brochmann-Hanssen E (1984) A second pathway for the terminal steps in the biosynthesis of morphine. Planta Med 50:343-345.
26. Davis VE, Walsh MJ (1970) Alcohol, amines and alkaloids: A possible biochemical basis for alcohol addiction. Science 167:1005-1007.
27. Cashaw JL (1993) Tetrahydropapaveroline in brain regions of rats after acute ethanol administration. Alcohol 10:133-138.
28. Cashaw JL (1993) Determination of tetrahydropapaveroline in the urine of Parkinsonian patients receiving L-dopa-carbidopa (Sinemet) therapy by high-performance liquid chromatography. J Chromatogr 613:267-273.
29. Barton DHR, et al. (1965) Investigations on the biosynthesis of morphine alkaloids. J Chem Soc 2423-2438.
30. Lenz R, Zenk MH (1995) Acetyl coenzyme A:salutaridinol-7-O- acetyltransferase from Papaver somniferum plant cell cultures - The enzyme catalyzing the formation of thebaine in morphine biosynthesis. J Biol Chem 270:31091-31096. (Pubitemid 26018394)
31. Fisinger U (1998) Untersuchungen zur Morphinbiosynthese in der Ratte Rattus rattus L. und im Schlafmohn Papaver somniferum L.. PhD dissertation (Ludwig-Maximilians-University, Munich).
32. Millgate AG, et al. (2004) Analgesia: Morphine-pathway block in top1 poppies. Nature, (NPG Macmillan, London), 431, pp 413-414.
33. Mannering GJ, Dixon AC, Baker EM, Asami T (1954) The in vivo liberation of morphine from codeine in man. J Pharmacol Exp Ther 111:142-146.
34. Adler TK, Fujimoto JW, Way EL, Baker EM (1955) The metabolic fate of codeine in man. J Pharmacol Exp Ther 114:251-262.
35. Dayer P, Desmeules J, Leemann T, Striberni R (1988) Bioactivation of the narcotic drug codeine in human liver is mediated by the polymorphic monooxygenase catalyzing debrisoquine-4-hydroxylation (cytrochrome P-450 dbl/bufI). Biochem Biophys Res Commun 152:411-416.
36. Chen ZR, Somogyi AA, Bochner F (1988) Polymorphic O-demethylation of codeine. Lancet 2:914-915.
37. Eichelbaum M, Gross AS (1990) The genetic polymorphism of debrisoquine/sparteine metabolism - clinical aspects. Pharmacol Ther 46:377-394. (Pubitemid 20108523)
38. Misra AL, Pontani RB, Mule SJ (1974) Pharmacokinetics and metabolism of [3H] thebaine. Xenobiotica 4:17-32.
39. Yamano S, Takahashi A, Todaka T, Toki S (1997) In vivo and in vitro formation of morphinone from morphine in rat. Xenobiotica 27:645-656.
40. Todaka T, Ishida T, Kita H, Narimatsu S, Yamano S (2005) Bioactivation of morphine in human liver: Isolation and identification of morphinone, a toxic metabolite. Biol Pharm Bull 28:1275-1280.
41. Taurog A, Dorris M, Doerge DR (1994) Evidence for a radical mechanism in peroxidase-catalyzed coupline. I. Steady-state experiments with various peroxidases. Arch Biochem Biophys 315:82-89.
42. Kodaira H, Spector S (1988) Transformation of thebaine to oripavine, codeine, and morphine by rat liver, kidney, and brain microsomes. Proc Natl Acad Sci USA 85:1267-1271. (Pubitemid 18073990)
43. Nikolaev VO, et al. (2007) Live cell monitoring of μ-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors. J Biol Chem 282:27126-27132.