Cytochrome P450 isoenzymes involved in rat liver microsomal metabolism of californine and protopine

European Journal of Pharmacology

Volumn 485, Issue 1-3, 2004, Pages 69-79

  Paul, Liane D ^a   Springer, Dietmar ^a   Staack, Roland F ^a   Kraemer, Thomas ^a   Maurer, Hans H ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Californine; Cytochrome P450; Liver microsome, rat; Metabolism; Protopine

Indexed keywords

ALKALOID DERIVATIVE; CALIFORNINE; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2C11; CYTOCHROME P450 2C11 ANTIBODY; CYTOCHROME P450 2D1; CYTOCHROME P450 3A2; DRUG METABOLITE; DRUG METABOLIZING ENZYME; FLAVONE DERIVATIVE; HERBACEOUS AGENT; ISOENZYME; KETOCONAZOLE; NAPHTHOFLAVONE; PROTOPINE; QUININE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DEMETHYLATION; DRUG ABUSE; DRUG DETERMINATION; DRUG METABOLISM; ENZYME INHIBITION; ENZYME SUBSTRATE; ESCHSCHOLTZIA; KINETICS; LIVER MICROSOME; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

EID: 1642497558     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2003.11.051     Document Type: Article

References (49)

1. Baldwin S.J., Bloomer J.C., Smith G.J., Ayrton A.D., Clarke S.E., Chenery R.J. Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica. 25:1995;261-270.
2. Boobis A.R., Kahn G.C., Whyte C., Brodie M.J., Davies D.S. Biphasic O-deethylation of phenacetin and 7-ethoxycoumarin by human and rat liver microsomal fractions. Biochem. Pharmacol. 30:1981;2451-2456.
3. Boobis A.R., Sesardic D., Murray B.P., Edwards R.J., Singleton A.M., Rich K.J., Murray S., de-la-Torre R., Segura J., Pelkonen O., Pasanen M., Kobayashi S., Zhi-Guang T., Davies D.S. Species variation in the response of the cytochrome P-450-dependent monooxygenase system to inducers and inhibitors. Xenobiotica. 20:1990;1139-1161.
4. Bourrie M., Meunier V., Berger Y., Fabre G. Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J. Pharmacol. Exp. Ther. 277:1996;321-332.
5. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:1976;248-254.
6. Butler M.A., Iwasaki M., Guengerich F.P., Kadlubar F.F. Human cytochrome P-450PA (P-450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines. Proc. Natl. Acad. Sci. U. S. A. 86:1989;7696-7700.
7. Cheney R.H. Therapeutic potential of eschscholtziae californicae herba. Q. J. Crude Drug. 3:1964;413-416.
8. Cheng Y., Prusoff W.H. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol. 22:1973;3099-3108.
9. Clarke S.E. In vitro assessment of human cytochrome P450. Xenobiotica. 28:1998;1167-1202.
10. Copeland R.A. Kinetics of single-substrate enzyme reactions. Copeland R.A. Enzymes: A Practical Introduction to Structure, Mechanism and Data Analysis. 2000;109-144 Wiley, NY.
11. Duke J.A. CRC Handbook of Medicinal Herbs. 1985;CRC Press, Boca Raton, FL.
12. Gertig H. Alkaloids of Eschscholtzia californica Cham: 3. Preparative separation of alkaloid fractions obtained from benzene root extract. Acta Pol. Pharm. 22:1965;271-279.
13. Ghosal A., Satoh H., Thomas P.E., Bush E., Moore D. Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cDNA-expressed human cytochrome P450. Drug Metab. Dispos. 24:1996;940-947.
14. Gorski J.C., Hall S.D., Jones D.R., Vandenbranden M., Wrighton S.A. Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem. Pharmacol. 47:1994;1643-1653.
15. Gottlieb A.A. Concise Encyclopedia of Legal Herbs and Chemicals with Psychoactive Properties. 2002;. http://www.erowid.org/library/books_online/ legal_highs/legal_highs.shtml.
16. Guedon D., Cappelaere N., Simanek V. HPLC analysis of the main alkaloids from Eschscholtzia californica cham. Phytochem. Anal. 1:1990;77-82.
17. Haensel R., Keller K., Rimpler H., Schneider G. Hagers Handbuch der pharmazeutischen Praxis. 5th ed. 1993;Springer, Berlin.
18. Hiramatsu M., Kumagai Y., Unger S.E., Cho A.K. Metabolism of methylenedioxymethamphetamine: formation of dihydroxymethamphetamine and a quinone identified as its glutathione adduct. J. Pharmacol. Exp. Ther. 254:1990;521-527.
19. Hiroi T., Chow T., Imaoka S., Funae Y. Catalytic specificity of CYP2D isoforms in rat and human. Drug Metab. Dispos. 30:2002;970-976.
20. Hutzler J.M., Tracy T.S. Atypical kinetic profiles in drug metabolism reactions. Drug Metab. Dispos. 30:2002;355-362.
21. Kardos J., Blasko G., Simonyi M. Enhancement of gamma-aminobutyric acid receptor binding by protopine-type alkaloids. Arzneim.-Forsch. 36:1986;939-940.
22. Ko F.N., Wu T.S., Lu S.T., Wu Y.C., Huang T.F., Teng C.M. Antiplatelet effects of protopine isolated from Corydalis tubers. Thromb. Res. 56:1989;289-298.
23. Kobayashi S., Murray S., Watson D., Sesardic D., Davies D.S., Boobis A.R. The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine in the rat is the inverse of that in man. Biochem. Pharmacol. 38:1989;2795-2799.
24. Kobayashi K., Urashima K., Shimada N., Chiba K. Substrate specificity for rat cytochrome P450 (CYP) isoforms: screening with cDNA-expressed systems of the rat. Biochem. Pharmacol. 63:2002;889-896.
25. Kotegawa T., Laurijssens B.E., von Moltke L.L., Cotreau M.M., Perloff M.D., Venkatakrishnan K., Warrington J.S., Granda B.W., Harmatz J.S., Greenblatt D.J. In vitro, pharmacokinetic, and pharmacodynamic interactions of ketoconazole and midazolam in the rat. J. Pharmacol. Exp. Ther. 302:2002;1228-1237.
26. Kraemer T., Maurer H.H. Toxicokinetics of amphetamines: metabolism and toxicokinetic data of designer drugs, of amphetamine, methamphetamine and their N-alkyl derivatives [review]. Ther. Drug Monit. 24:2002;277-289.
27. Kraemer T., Bickeboeller-Friedrich J., Maurer H.H. On the metabolism of the amphetamine-derived antispasmodic drug mebeverine: gas chromatography-mass spectrometry studies on rat liver microsomes and on human urine. Drug Metab. Dispos. 28:2000;339-347.
28. Kronbach T., Mathys D., Umeno M., Gonzalez F.J., Meyer U.A. Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol. Pharmacol. 36:1989;89-96.
29. Lin Y., Lu P., Tang C., Mei Q., Sandig G., Rodrigues A.D., Rushmore T.H., Shou M. Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab. Dispos. 29:2001;368-374.
30. Manske R.H.F., Shin K.H. The alkaloids of papaveraceous plants, LIII. Eschscholtzia californica cham. Can. J. Chem. 43:1965;2180-2182.
31. Maurer H.H. Methods for GC-MS. Pfleger K., Maurer H.H., Weber A. Mass Spectral and GC Data of Drugs, Poisons, Pesticides, Pollutants and their Metabolites, Part 4. 2000;3-241 Wiley, Weinheim.
32. Maurer H.H., Bickeboeller-Friedrich J., Kraemer T., Peters F.T. Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ("Ecstasy"). Toxicol. Lett. 112:2000;133-142.
33. Nakajima M., Kobayashi K., Oshima K., Shimada N., Tokudome S., Chiba K., Yokoi T. Activation of phenacetin O-deethylase activity by alpha-naphthoflavone in human liver microsomes. Xenobiotica. 29:1999;885-898.
34. Omura T., Sato R. The carbon monoxide-binding pigment of liver micosomes: I. Evidence for its hemoprotein nature. J. Biol. Chem. 239:1964;2370-2378.
35. Ono S., Hatanaka T., Hotta H., Satoh T., Gonzalez F.J., Tsutsui M. Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica. 26:1996;681-693.
36. Paul L.D., Maurer H.H. Studies on the metabolism and toxicological detection of the Eschscholtzia californica alkaloids californine and protopine in urine using gas chromatography-mass spectrometry. J. Chromatogr., B, Biomed. Sci. Appl. 789:2003;43-57.
37. Raetsch C. Enzyklopädie der Psychoaktiven Pflanzen. 1998;Wissenschaftliche Verlagsgesellschaft, Stuttgart.
38. Rolland A., Fleurentin J., Lanhers M.C., Younos C., Misslin R., Mortier F., Pelt J.M. Behavioural effects of the American traditional plant Eschscholzia californica: sedative and anxiolytic properties. Planta Med. 57:1991;212-216.
39. Rolland A., Fleurentin J., Lanhers M.C., Misslin R., Mortier F. Neurophysiological effects of an extract of Eschscholzia californica Cham. (Papaveraceae). Phytother. Res. 15:2001;377-381.
40. Sesardic D., Boobis A.R., Edwards R.J., Davies D.S. A form of cytochrome P450 in man, orthologous to form d in the rat, catalyses the O-deethylation of phenacetin and is inducible by cigarette smoking. Br. J. Clin. Pharmacol. 26:1988;363-372.
41. Sesardic D., Edwards R.J., Davies D.S., Thomas P.E., Levin W., Boobis A.R. High affinity phenacetin O-deethylase is catalysed specifically by cytochrome P450d (P450IA2) in the liver of the rat. Biochem. Pharmacol. 39:1990;489-498.
42. Shimada T., Mimura M., Inoue K., Nakamura S., Oda H., Ohmori S., Yamazaki H. Cytochrome P450-dependent drug oxidation activities in liver microsomes of various animal species including rats, guinea pigs, dogs, monkeys, and humans. Arch. Toxicol. 71:1997;401-408.
43. Siegel R.K. Herbal intoxication. Psychoactive effects from herbal cigarettes, tea, and capsules. JAMA. 236:1976;473-476.
44. Song L.S., Ren G.J., Chen Z.L., Chen Z.H., Zhou Z.N., Cheng H. Electrophysiological effects of protopine in cardiac myocytes: inhibition of multiple cation channel currents. Br. J. Pharmacol. 129:2000;893-900.
45. Soucek P., Gut I. Cytochromes P-450 in rats: structures, functions, properties and relevant human forms. Xenobiotica. 22:1992;83-103.
46. Ustunes L., Laekeman G.M., Gozler B., Vlietinck A.J., Ozer A., Herman A.G. In vitro study of the anticholinergic and antihistaminic activities of protopine and some derivatives. J. Nat. Prod. 51:1988;1021-1022.
47. Vincieri F.F., Celli S., Mulinacci N., Speroni E. An approach to the study of the biological activity of Eschscholtzia californica Cham. Pharmacol. Res. Commun. 20(Suppl. 5):1988;41-44.
48. Xu B.Q., Aasmundstad T.A., Bjorneboe A., Christophersen A.S., Morland J. Ethylmorphine O-deethylation in isolated rat hepatocytes. Involvement of codeine O-demethylation enzyme systems. Biochem. Pharmacol. 49:1995;453-460.
49. Xu B.Q., Aasmundstad T.A., Christophersen A.S., Morland J., Bjorneboe A. Evidence for CYP2D1-mediated primary and secondary O-dealkylation of ethylmorphine and codeine in rat liver microsomes [published erratum appears in Biochem. Pharmacol. 1997 Jun 15;53(12):1945]. Biochem. Pharmacol. 53:1997;603-609.