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Volumn 33, Issue 4, 2009, Pages 190-197

Biotechnological synthesis of the designer drug metabolite 4′-hydroxymethyl-α-pyrrolidinohexanophenone in fission yeast heterologously expressing human cytochrome P450 2D6 - A versatile alternative to multistep chemical synthesis

Author keywords

[No Author keywords available]

Indexed keywords

4' HYDROXYMETHYL ALPHA PYRROLIDINOHEXANOPHENONE; CYTOCHROME P450 2D6; CYTOCHROME REDUCTASE; DESIGNER DRUG; DRUG METABOLITE; UNCLASSIFIED DRUG;

EID: 66349096061     PISSN: 01464760     EISSN: 01464760     Source Type: Journal    
DOI: 10.1093/jat/33.4.190     Document Type: Article
Times cited : (21)

References (32)
  • 2
    • 0142165136 scopus 로고    scopus 로고
    • Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4′methyl-alpha- pyrrolidinopropiophenone (MPPP) studied in urine using gas chromatography-mass spectrometry
    • D. Springer, G. Fritschi, and H.H. Maurer. Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4′methyl-alpha-pyrrolidinopropiophenone (MPPP) studied in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 796: 253-266 (2003).
    • (2003) J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. , vol.796 , pp. 253-266
    • Springer, D.1    Fritschi, G.2    Maurer, H.H.3
  • 3
    • 0037097028 scopus 로고    scopus 로고
    • Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-alpha-pyrrolidinopropiophenone in urine using gas chromatography-mass spectrometry
    • D. Springer, F.T. Peters, G. Fritschi, and H.H. Maurer. Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-alpha-pyrrolidinopropiophenone in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 773: 25-33 (2002).
    • (2002) J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. , vol.773 , pp. 25-33
    • Springer, D.1    Peters, F.T.2    Fritschi, G.3    Maurer, H.H.4
  • 4
    • 0142091104 scopus 로고    scopus 로고
    • Metabolism and toxicological detection of the new designer drug 4′-methoxy-alpha-pyrrolidinopropiophenone studied in rat urine using gas chromatography- Mass spectrometry
    • D. Springer, G. Fritschi, and H.H. Maurer. Metabolism and toxicological detection of the new designer drug 4′-methoxy-alpha- pyrrolidinopropiophenone studied in rat urine using gas chromatography- mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 793: 331-342 (2003).
    • (2003) J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. , vol.793 , pp. 331-342
    • Springer, D.1    Fritschi, G.2    Maurer, H.H.3
  • 5
    • 0142122818 scopus 로고    scopus 로고
    • Metabolism and toxicological detection of the new designer drug 3′,4′-methylenedioxy- alpha-pyrrolidinopropiophenone studied in urine using gas chromatography-mass spectrometry
    • D. Springer, G. Fritschi, and H.H. Maurer. Metabolism and toxicological detection of the new designer drug 3′,4′-methylenedioxy- alpha-pyrrolidinopropiophenone studied in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 793: 377-388 (2003).
    • (2003) J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. , vol.793 , pp. 377-388
    • Springer, D.1    Fritschi, G.2    Maurer, H.H.3
  • 6
    • 34248140784 scopus 로고    scopus 로고
    • Mass spectral and NMR spectral data of two new designer drugs with an alpha-aminophenone structure: 4′-methyl-alpha-pyrrolidinohexanophenone and 4′-methyl-alpha-pyrrolidinobutyrophenone
    • F. Westphal, T. Junge, P. Rosner, G. Fritschi, B. Klein, and U. Girreser. Mass spectral and NMR spectral data of two new designer drugs with an alpha-aminophenone structure: 4′-methyl-alpha-pyrrolidinohexanophenone and 4′-methyl-alpha-pyrrolidinobutyrophenone. Forensic Sci. Int. 169: 32-42 (2007).
    • (2007) Forensic Sci. Int. , vol.169 , pp. 32-42
    • Westphal, F.1    Junge, T.2    Rosner, P.3    Fritschi, G.4    Klein, B.5    Girreser, U.6
  • 7
    • 24044529175 scopus 로고    scopus 로고
    • Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-alpha-pyrrolidinobutyrophenone (MPBP) in urine using gas chromatography-mass spectrometry
    • F.T. Peters, M.R. Meyer, G. Fritschi, and H.H. Maurer. Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-alpha-pyrrolidinobutyrophenone (MPBP) in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 824: 81-91 (2005).
    • (2005) J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. , vol.824 , pp. 81-91
    • Peters, F.T.1    Meyer, M.R.2    Fritschi, G.3    Maurer, H.H.4
  • 8
    • 0037420911 scopus 로고    scopus 로고
    • New designer drug 4′-methyl-alpha-pyrrolidinohexanophenone: Studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry
    • D. Springer, F.T. Peters, G. Fritschi, and H.H. Maurer. New designer drug 4′-methyl-alpha-pyrrolidinohexanophenone: studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 789: 79-91 (2003).
    • (2003) J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. , vol.789 , pp. 79-91
    • Springer, D.1    Peters, F.T.2    Fritschi, G.3    Maurer, H.H.4
  • 9
    • 0017035206 scopus 로고
    • Role of central catecholamines in the psychostimulant activity of pyrovalerone
    • in French
    • J.P. Fauquet, E. Morel, C. Demarty, and J.R. Rapin. Role of central catecholamines in the psychostimulant activity of pyrovalerone. Arch. Int. Pharmacodyn. Ther. 224: 325-337 (1976) (in French).
    • (1976) Arch. Int. Pharmacodyn. Ther. , vol.224 , pp. 325-337
    • Fauquet, J.P.1    Morel, E.2    Demarty, C.3    Rapin, J.R.4
  • 10
    • 0018164876 scopus 로고
    • Effects of pyrovalerone on peripheral noradrenergic mechanisms
    • A. Servin, J.P. Fauquet, C. Jacquot, and J.R. Rapin. Effects of pyrovalerone on peripheral noradrenergic mechanisms. Biochem. Pharmacol. 27: 1693-1694 (1978).
    • (1978) Biochem. Pharmacol. , vol.27 , pp. 1693-1694
    • Servin, A.1    Fauquet, J.P.2    Jacquot, C.3    Rapin, J.R.4
  • 11
    • 33144477907 scopus 로고    scopus 로고
    • 1-(4- Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors
    • P.C. Meltzer, D. Butler, J.R. Deschamps, and B.K. Madras. 1-(4- Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: a promising class of monoamine uptake inhibitors. J. Med. Chem. 49: 1420-1432 (2006).
    • (2006) J. Med. Chem. , vol.49 , pp. 1420-1432
    • Meltzer, P.C.1    Butler, D.2    Deschamps, J.R.3    Madras, B.K.4
  • 12
    • 0011276062 scopus 로고
    • Comparative pharmacological study of a new central stimulant, 1-p-tolyl-1-oxo-2-pyrrolidino-n-pentane HCl
    • in German
    • G. Stille, H. Ackermann, E. Eichenberger, and H. Lauener. Comparative pharmacological study of a new central stimulant, 1-p-tolyl-1-oxo-2-pyrrolidino- n-pentane HCl. Arzneimittelforschung 13: 871-877 (1963) (in German).
    • (1963) Arzneimittelforschung , vol.13 , pp. 871-877
    • Stille, G.1    Ackermann, H.2    Eichenberger, E.3    Lauener, H.4
  • 13
    • 0001594153 scopus 로고
    • Compound 84/F 1983 compared with D-amphetamine and placebo in regard to effects on human performance
    • A.R. Holliday, R.B. Morris, and R.P. Sharpley. Compound 84/F 1983 compared with D-amphetamine and placebo in regard to effects on human performance. Psychopharmacologia 6: 192-200 (1964).
    • (1964) Psychopharmacologia , vol.6 , pp. 192-200
    • Holliday, A.R.1    Morris, R.B.2    Sharpley, R.P.3
  • 14
    • 0013855128 scopus 로고
    • Experimental psychological differentiation of the effect of 2 psychostimulants (F-1983 and amphetamine) in humans
    • H. Heimann and G. Lukàcs. Experimental psychological differentiation of the effect of 2 psychostimulants (F-1983 and amphetamine) in humans. Psychopharmacologia 8: 79-90 (1965) (in German).
    • (1965) Psychopharmacologia , vol.8 , pp. 79-90
    • Heimann, H.1    Lukàcs, G.2
  • 15
    • 0017122856 scopus 로고
    • The psychotropic effect of the Pyrovalerone (F-1983), placebo, the milieu therapy and mental condition of the patients in forensic psychiatry
    • S. Söderholm, N.M. Viukari, and R. Rimón. The psychotropic effect of the Pyrovalerone (F-1983), placebo, the milieu therapy and mental condition of the patients in forensic psychiatry. Nervenarzt 47: 88-93 (1976) (in German).
    • (1976) Nervenarzt , vol.47 , pp. 88-93
    • Söderholm, S.1    Viukari, N.M.2    Rimón, R.3
  • 16
    • 0015870524 scopus 로고
    • A controlled evaluation of pyrovalerone in chronically fatigued volunteers
    • J. Goldberg, G. Gardos, and J.O. Cole. A controlled evaluation of pyrovalerone in chronically fatigued volunteers. Int. Pharmacopsychiatry 8: 60-69 (1973).
    • (1973) Int. Pharmacopsychiatry , vol.8 , pp. 60-69
    • Goldberg, J.1    Gardos, G.2    Cole, J.O.3
  • 17
    • 0011364919 scopus 로고
    • Clinical studies of a new psycho-stimulant (F-1983)
    • H. Heinmann and K. Vetter. Clinical studies of a new psycho-stimulant (F-1983). Schweiz. Med. Wochenschr. 95: 306-309 (1965) (in German).
    • (1965) Schweiz. Med. Wochenschr. , vol.95 , pp. 306-309
    • Heinmann, H.1    Vetter, K.2
  • 18
    • 0016579853 scopus 로고
    • Abuse of pyrovalerone by drug addicts
    • Paris
    • P. Deniker, H. Loo, H. Cuche, and J.M. Roux. Abuse of pyrovalerone by drug addicts. Ann. Med. Psychol. (Paris) 2: 745-748 (1975) (in French).
    • (1975) Ann. Med. Psychol. , vol.2 , pp. 745-748
    • Deniker, P.1    Loo, H.2    Cuche, H.3    Roux, J.M.4
  • 19
    • 0014792608 scopus 로고
    • The metabolism of pyrovalerone hydrochloride
    • W. Michaelis, J.H. Russel, and O. Schindler. The metabolism of pyrovalerone hydrochloride. J. Med. Chem. 13: 497-503 (1970).
    • (1970) J. Med. Chem. , vol.13 , pp. 497-503
    • Michaelis, W.1    Russel, J.H.2    Schindler, O.3
  • 20
    • 0030572975 scopus 로고    scopus 로고
    • Identification of a pyrovalerone metabolite in the rat by gas chromatography-mass spectrometry and determination of pyrovalerone by gas chromatography-nitrogen-phosphorus detection
    • D.S. Lho, J. Lee, S. Kim, J. Park, and H.S. Shin. Identification of a pyrovalerone metabolite in the rat by gas chromatography-mass spectrometry and determination of pyrovalerone by gas chromatography-nitrogen-phosphorus detection. J. Chromatogr. B Biomed. Sci. Appl. 687: 253-259 (1996).
    • (1996) J. Chromatogr. B Biomed. Sci. Appl. , vol.687 , pp. 253-259
    • Lho, D.S.1    Lee, J.2    Kim, S.3    Park, J.4    Shin, H.S.5
  • 21
    • 0029837492 scopus 로고    scopus 로고
    • Detection and identification of pyrovalerone and its hydroxylated metabolite in the rat
    • H.S. Shin, Y.S. Shin, S. Lee, and B.B. Park. Detection and identification of pyrovalerone and its hydroxylated metabolite in the rat. J. Anal. Toxicol. 20: 568-572 (1996).
    • (1996) J. Anal. Toxicol. , vol.20 , pp. 568-572
    • Shin, H.S.1    Shin, Y.S.2    Lee, S.3    Park, B.B.4
  • 22
    • 10344253335 scopus 로고
    • Identification of the new metabolites of pyrovalerone by various derivatization methods in the rat urine
    • H. Shin and J. Park. Identification of the new metabolites of pyrovalerone by various derivatization methods in the rat urine. Korean Biochem. J. 27: 357-361 (1994).
    • (1994) Korean Biochem. J. , vol.27 , pp. 357-361
    • Shin, H.1    Park, J.2
  • 23
    • 0042025298 scopus 로고    scopus 로고
    • Identification of the cytochrome P450 enzymes involved in the metabolism of 4′-methyl-(alpha)-pyrrolidinopropiophenone, a novel scheduled designer drug, in human liver microsomes
    • D. Springer, L.D. Paul, R.F. Staack, T. Kraemer, and H.H. Maurer. Identification of the cytochrome P450 enzymes involved in the metabolism of 4′-methyl-(alpha)-pyrrolidinopropiophenone, a novel scheduled designer drug, in human liver microsomes. Drug Metab. Dispos. 31: 979-982 (2003).
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 979-982
    • Springer, D.1    Paul, L.D.2    Staack, R.F.3    Kraemer, T.4    Maurer, H.H.5
  • 24
    • 37549045269 scopus 로고    scopus 로고
    • Identification of cytochrome P450 enzymes involved in the metabolism of 4′-methyl-pyrrolidino-butyrophenone (MPBP), a new designer drug, in human liver microsomes
    • F.T. Peters, M.R. Meyer, D.S. Theobald, and H.H. Maurer. Identification of cytochrome P450 enzymes involved in the metabolism of 4′-methyl- pyrrolidino-butyrophenone (MPBP), a new designer drug, in human liver microsomes. Drug Metab. Dispos. 36: 163-168 (2008).
    • (2008) Drug Metab. Dispos. , vol.36 , pp. 163-168
    • Peters, F.T.1    Meyer, M.R.2    Theobald, D.S.3    Maurer, H.H.4
  • 25
    • 34250716024 scopus 로고    scopus 로고
    • Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fission yeast exemplified for the designer drug metabolite 4′-hydroxymethyl-alpha-pyrrolidinobutyrophenone
    • F.T. Peters, C.A. Dragan, D.R. Wilde, M.R. Meyer, M. Bureik, and H.H. Maurer. Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fission yeast exemplified for the designer drug metabolite 4′-hydroxymethyl-alpha-pyrrolidinobutyrophenone. Biochem. Pharmacol. 74: 511-520 (2007).
    • (2007) Biochem. Pharmacol. , vol.74 , pp. 511-520
    • Peters, F.T.1    Dragan, C.A.2    Wilde, D.R.3    Meyer, M.R.4    Bureik, M.5    Maurer, H.H.6
  • 26
    • 66349112544 scopus 로고    scopus 로고
    • New fission yeast strains expressing human cytochrome P 450 enzymes to be used for biotechnological synthesis of drug metabolites
    • Abstract
    • F.T. Peters, A.E. Schwaninger, C.-A. Dragan, M. Bureik, and H.H. Maurer. New fission yeast strains expressing human cytochrome P 450 enzymes to be used for biotechnological synthesis of drug metabolites [Abstract]. Ther. Drug Monit. 29: 466-467 (2007).
    • (2007) Ther. Drug Monit. , vol.29 , pp. 466-467
    • Peters, F.T.1    Schwaninger, A.E.2    Dragan, C.-A.3    Bureik, M.4    Maurer, H.H.5
  • 28
    • 53549097600 scopus 로고    scopus 로고
    • U.S. Department of Health and Human Services, Center for Drug Evaluation and Research (CDER)
    • U.S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER). Guidance for Industry: Safety Testing of Drug Metabolites. http://www.fda.gov/CDER/GUIDANCE/ 6897fnl.pdf.
    • Guidance for Industry: Safety Testing of Drug Metabolites
  • 29
    • 33646723471 scopus 로고    scopus 로고
    • Establishment of a yeast system that stably expresses human cytochrome P450 reductase: Application for the study of drug metabolism of cytochrome P450s in vitro
    • J. Cheng, D.F. Wan, J.R. Gu, Y. Gong, S.L. Yang, D.C. Hao, and L. Yang. Establishment of a yeast system that stably expresses human cytochrome P450 reductase: application for the study of drug metabolism of cytochrome P450s in vitro. Protein Expr. Purif. 47: 467-476 (2006).
    • (2006) Protein Expr. Purif. , vol.47 , pp. 467-476
    • Cheng, J.1    Wan, D.F.2    Gu, J.R.3    Gong, Y.4    Yang, S.L.5    Hao, D.C.6    Yang, L.7
  • 30
    • 27744441015 scopus 로고    scopus 로고
    • Recombinant production of human micro somal cytochrome P450 2D6 in the methylotrophic yeast Pichia pastoris
    • M. Dietrich, L. Grundmann, K. Kurr, L. Valinotto, T. Saussele, R.D. Schmid, and S. Lange. Recombinant production of human micro somal cytochrome P450 2D6 in the methylotrophic yeast Pichia pastoris. Chembiochem. 6: 2014-2022 (2005).
    • (2005) Chembiochem. , vol.6 , pp. 2014-2022
    • Dietrich, M.1    Grundmann, L.2    Kurr, K.3    Valinotto, L.4    Saussele, T.5    Schmid, R.D.6    Lange, S.7
  • 31
    • 0034282681 scopus 로고    scopus 로고
    • Coexpression of genetically engineered fused enzyme between yeast NADPH-P450 reductase and human cytochrome P450 3A4 and human cytochrome b5 in yeast
    • K. Hayashi, T. Sakaki, S. Kominami, K. Inouye, and Y. Yabusaki. Coexpression of genetically engineered fused enzyme between yeast NADPH-P450 reductase and human cytochrome P450 3A4 and human cytochrome b5 in yeast. Arch. Biochem. Biophys. 381: 164-170 (2000).
    • (2000) Arch. Biochem. Biophys. , vol.381 , pp. 164-170
    • Hayashi, K.1    Sakaki, T.2    Kominami, S.3    Inouye, K.4    Yabusaki, Y.5
  • 32
    • 0027480346 scopus 로고
    • Enhanced in vivo monooxygenase activities of mammalian P450s in engineered yeast cells producing high levels of NADPH-P450 reductase and human cytochrome b5
    • G. Truan, C. Cullin, P. Reisdorf, P. Urban, and D. Pompon. Enhanced in vivo monooxygenase activities of mammalian P450s in engineered yeast cells producing high levels of NADPH-P450 reductase and human cytochrome b5. Gene 125: 49-55 (1993)
    • (1993) Gene , vol.125 , pp. 49-55
    • Truan, G.1    Cullin, C.2    Reisdorf, P.3    Urban, P.4    Pompon, D.5


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