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Volumn 39, Issue 11, 2011, Pages 1998-2002

Investigation on the enantioselectivity of the sulfation of the methylenedioxymethamphetamine metabolites 3,4-dihydroxymethamphetamine and 4-hydroxy-3-methoxymethamphetamine using the substrate-depletion approach

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIHYDROXYMETHAMPHETAMINE; 3,4 METHYLENEDIOXYAMPHETAMINE DERIVATIVE; 4 HYDROXY 3 METHOXYMETHAMPHETAMINE; SULFOTRANSFERASE; SULFOTRANSFERASE 1A1; SULFOTRANSFERASE 1A3; SULFOTRANSFERASE 1E1; UNCLASSIFIED DRUG;

EID: 80054723956     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.041129     Document Type: Article
Times cited : (16)

References (29)
  • 1
    • 0033386744 scopus 로고    scopus 로고
    • Glutathione and N-acetylcysteine conjugates of alpha-methyldopamine produce serotonergic neurotoxicity: Possible role in methylenedioxyamphetamine- mediated neurotoxicity
    • DOI 10.1021/tx990084t
    • Bai F, Lau SS, and Monks TJ (1999) Glutathione and N-acetylcysteine conjugates of alpha-methyldopamine produce serotonergic neurotoxicity: possible role in methylenedioxyamphetamine- mediated neurotoxicity. Chem Res Toxicol 12:1150-1157. (Pubitemid 30013524)
    • (1999) Chemical Research in Toxicology , vol.12 , Issue.12 , pp. 1150-1157
    • Bai, F.1    Lau, S.S.2    Monks, T.J.3
  • 2
    • 0032866401 scopus 로고    scopus 로고
    • The use of heterologously expressed drug metabolizing enzymes- state of the art and prospects for the future
    • DOI 10.1016/S0163-7258(99)00028-5, PII S0163725899000285
    • Crespi CL and Miller VP (1999) The use of heterologously expressed drug metabolizing enzymes - state of the art and prospects for the future. Pharmacol Ther 84:121-131. (Pubitemid 29488547)
    • (1999) Pharmacology and Therapeutics , vol.84 , Issue.2 , pp. 121-131
    • Crespi, C.L.1    Miller, V.P.2
  • 3
    • 0033621476 scopus 로고    scopus 로고
    • X-ray crystal structure of human dopamine sulfotransferase, SULT1A3. Molecular modeling and quantitative structure-activity relationship analysis demonstrate a molecular basis for sulfotransferase substrate specificity
    • DOI 10.1074/jbc.274.53.37862
    • Dajani R, Cleasby A, Neu M, Wonacott AJ, Jhoti H, Hood AM, Modi S, Hersey A, Taskinen J, Cooke RM, et al. (1999) X-ray crystal structure of human dopamine sulfotransferase, SULT1A3. Molecular modeling and quantitative structure-activity relationship analysis demonstrate a molecular basis for sulfotransferase substrate specificity. J Biol Chem 274:37862-37868. (Pubitemid 30026852)
    • (1999) Journal of Biological Chemistry , vol.274 , Issue.53 , pp. 37862-37868
    • Dajani, R.1    Cleasby, A.2    Margarete, N.3    Wonacott, A.J.4    Jhoti, H.5    Hood, A.M.6    Modi, S.7    Hersey, A.8    Taskinen, J.9    Cooke, R.M.10    Manchee, G.R.11    Coughtrie, M.W.H.12
  • 4
    • 4544314351 scopus 로고    scopus 로고
    • Neurotoxicity of MDMA (ecstasy): The limitations of scaling from animals to humans
    • de la Torre R and Farré M (2004) Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. Trends Pharmacol Sci 25:505-508.
    • (2004) Trends Pharmacol Sci , vol.25 , pp. 505-508
    • De La Torre, R.1    Farré, M.2
  • 6
    • 33745683233 scopus 로고    scopus 로고
    • Ecstasy: Are animal data consistent between species and can they translate to humans?
    • Easton N and Marsden CA (2006) Ecstasy: are animal data consistent between species and can they translate to humans? J Psychopharmacol 20:194-210.
    • (2006) J Psychopharmacol , vol.20 , pp. 194-210
    • Easton, N.1    Marsden, C.A.2
  • 7
    • 0032779463 scopus 로고    scopus 로고
    • Stereospecific analysis and enantiomeric disposition of 3,4- methylenedioxymethamphetamine (ecstasy) in humans
    • Fallon JK, Kicman AT, Henry JA, Milligan PJ, Cowan DA, and Hutt AJ (1999) Stereospecific analysis and enantiomeric disposition of 3,4- methylenedioxymethamphetamine (Ecstasy) in humans. Clin Chem 45:1058-1069. (Pubitemid 29340544)
    • (1999) Clinical Chemistry , vol.45 , Issue.7 , pp. 1058-1069
    • Fallon, J.K.1    Kicman, A.T.2    Henry, J.A.3    Milligan, P.J.4    Cowan, D.A.5    Hutt, A.J.6
  • 8
    • 33645961595 scopus 로고    scopus 로고
    • The impact of in vitro binding on in vitro-in vivo extrapolations, projections of metabolic clearance and clinical drug-drug interactions
    • Grime K and Riley RJ (2006) The impact of in vitro binding on in vitro-in vivo extrapolations, projections of metabolic clearance and clinical drug-drug interactions. Curr Drug Metab 7:251-264.
    • (2006) Curr Drug Metab , vol.7 , pp. 251-264
    • Grime, K.1    Riley, R.J.2
  • 9
    • 0035664224 scopus 로고    scopus 로고
    • The pharmacology and toxicology of "ecstasy" (MDMA) and related drugs
    • Kalant H (2001) The pharmacology and toxicology of "ecstasy" (MDMA) and related drugs. CMAJ 165:917-928.
    • (2001) CMAJ , vol.165 , pp. 917-928
    • Kalant, H.1
  • 10
    • 0036129441 scopus 로고    scopus 로고
    • Toxicokinetics of amphetamines: Metabolism and toxicokinetic data of designer drugs, amphetamine, methamphetamine, and their N-alkyl derivatives
    • DOI 10.1097/00007691-200204000-00009
    • Kraemer T and Maurer HH (2002) Toxicokinetics of amphetamines: metabolism and toxicokinetic data of designer drugs, of amphetamine, methamphetamine and their N-alkyl derivatives. Ther Drug Monit 24:277-289. (Pubitemid 34248035)
    • (2002) Therapeutic Drug Monitoring , vol.24 , Issue.2 , pp. 277-289
    • Kraemer, T.1    Maurer, H.H.2
  • 11
    • 0029789280 scopus 로고    scopus 로고
    • On the metabolism and the toxicological analysis of methylenedioxyphenylalkylamine designer drugs by gas chromatography-mass spectrometry
    • Maurer HH (1996) On the metabolism and the toxicological analysis of methylenedioxyphenylalkylamine designer drugs by gas chromatography-mass spectrometry. Ther Drug Monit 18:465-470.
    • (1996) Ther Drug Monit , vol.18 , pp. 465-470
    • Maurer, H.H.1
  • 12
    • 0034653801 scopus 로고    scopus 로고
    • Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ('Ecstasy')
    • DOI 10.1016/S0378-4274(99)00207-6, PII S0378427499002076
    • Maurer HH, Bickeboeller-Friedrich J, Kraemer T, and Peters FT (2000) Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ('Ecstasy'). Toxicol Lett 112: 133-142. (Pubitemid 30138114)
    • (2000) Toxicology Letters , vol.112-113 , pp. 133-142
    • Maurer, H.H.1    Bickeboeller-Friedrich, J.2    Kraemer, T.3    Peters, F.T.4
  • 13
    • 67449103235 scopus 로고    scopus 로고
    • Enantioselectivity in the methylation of the catecholic phase-I metabolites of methylenedioxy designer drugs and their capability to inhibit COMT catalyzed dopamine 3-methylation
    • Meyer MR and Maurer HH (2009) Enantioselectivity in the methylation of the catecholic phase-I metabolites of methylenedioxy designer drugs and their capability to inhibit COMT catalyzed dopamine 3-methylation. Chem Res Toxicol 22:1205-1211.
    • (2009) Chem Res Toxicol , vol.22 , pp. 1205-1211
    • Meyer, M.R.1    Maurer, H.H.2
  • 14
    • 54349126394 scopus 로고    scopus 로고
    • The role of human hepatic cytochrome P450 isozymes in the metabolism of racemic 3,4-methylenedioxy-methamphetamine and its enantiomers
    • Meyer MR, Peters FT, and Maurer HH (2008) The role of human hepatic cytochrome P450 isozymes in the metabolism of racemic 3,4-methylenedioxy- methamphetamine and its enantiomers. Drug Metab Dispos 36:2345-2354.
    • (2008) Drug Metab Dispos , vol.36 , pp. 2345-2354
    • Meyer, M.R.1    Peters, F.T.2    Maurer, H.H.3
  • 15
    • 0030951385 scopus 로고    scopus 로고
    • 2,5-bis-(glutathion-S-yl)-alpha-methyldopamine, a putative metabolite of (±)-3,4-methylenedioxyamphetamine, decreases brain serotonin concentrations
    • DOI 10.1016/S0014-2999(97)00044-7, PII S0014299997000447
    • Miller RT, Lau SS, and Monks TJ (1997) 2,5-Bis-(glutathion-S-yl)-alpha- methyldopamine, a putative metabolite of (±)-3,4- methylenedioxyamphetamine, decreases brain serotonin concentrations. Eur J Pharmacol 323:173-180. (Pubitemid 27152268)
    • (1997) European Journal of Pharmacology , vol.323 , Issue.2-3 , pp. 173-180
    • Miller, R.T.1    Lau, S.S.2    Monks, T.J.3
  • 16
    • 4143053372 scopus 로고    scopus 로고
    • The Role of Metabolism in 3,4-(±)-Methylenedioxyamphetamine and 3,4-(±)-Methylenedioxymethamphetamine (Ecstasy) toxicity
    • DOI 10.1097/00007691-200404000-00008
    • Monks TJ, Jones DC, Bai F, and Lau SS (2004) The role of metabolism in 3,4-(+)- methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity. Ther Drug Monit 26:132-136. (Pubitemid 38501206)
    • (2004) Therapeutic Drug Monitoring , vol.26 , Issue.2 , pp. 132-136
    • Monks, T.J.1    Jones, D.C.2    Bai, F.3    Lau, S.S.4
  • 18
    • 0035987898 scopus 로고    scopus 로고
    • Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach
    • DOI 10.1124/dmd.30.7.831
    • Obach RS and Reed-Hagen AE (2002) Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos 30:831-837. (Pubitemid 34671096)
    • (2002) Drug Metabolism and Disposition , vol.30 , Issue.7 , pp. 831-837
    • Obach, R.S.1    Reed-Hagen, A.E.2
  • 19
    • 25444497716 scopus 로고    scopus 로고
    • Drug testing in blood: Validated negative-ion chemical ionization gas chromatographic-mass spectrometric assay for enantioselective measurement of the designer drugs MDEA, MDMA, and MDA and its application to samples from a controlled study with MDMA
    • DOI 10.1373/clinchem.2005.052746
    • Peters FT, Samyn N, Lamers CT, Riedel WJ, Kraemer T, de Boeck G, and Maurer HH (2005) Drug testing in blood: validated negative-ion chemical ionization gas chromatographic-mass spectrometric assay for enantioselective determination of the designer drugs MDEA, MDMA, and MDA and its application to samples from a controlled study with MDMA. Clin Chem 51:1811-1822. (Pubitemid 41368171)
    • (2005) Clinical Chemistry , vol.51 , Issue.10 , pp. 1811-1822
    • Peters, F.T.1    Samyn, N.2    Lamers, C.T.J.3    Riedel, W.J.4    Kraemer, T.5    De Boeck, G.6    Maurer, H.H.7
  • 20
    • 4143098459 scopus 로고    scopus 로고
    • Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine)
    • Pizarro N, Farré M, Pujadas M, Peiró AM, Roset PN, Joglar J, and de la Torre R (2004) Stereochemical analysis of 3,4- methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine). Drug Metab Dispos 32:1001-1007. (Pubitemid 39096061)
    • (2004) Drug Metabolism and Disposition , vol.32 , Issue.9 , pp. 1001-1007
    • Pizarro, N.1    Farre, M.2    Pujadas, M.3    Peiro, A.Ma.4    Roset, P.N.5    Joglar, J.6    De La, T.R.7
  • 21
    • 70350319524 scopus 로고    scopus 로고
    • Quantitative evaluation of the expression and activity of five major sulfotransferases (SULTs) in human tissues: The SULT "pie."
    • Riches Z, Stanley EL, Bloomer JC, and Coughtrie MW (2009) Quantitative evaluation of the expression and activity of five major sulfotransferases (SULTs) in human tissues: the SULT "pie." Drug Metab Dispos 37:2255-2261.
    • (2009) Drug Metab Dispos , vol.37 , pp. 2255-2261
    • Riches, Z.1    Stanley, E.L.2    Bloomer, J.C.3    Coughtrie, M.W.4
  • 22
    • 79958193497 scopus 로고    scopus 로고
    • Development and validation of LC-HRMS and GC-NICI-MS methods for stereoselective determination of MDMA and its phase I and II metabolites in human urine
    • Schwaninger AE, Meyer MR, Huestis MA, and Maurer HH (2011a) Development and validation of LC-HRMS and GC-NICI-MS methods for stereoselective determination of MDMA and its phase I and II metabolites in human urine. J Mass Spectrom 46:603-614.
    • (2011) J Mass Spectrom , vol.46 , pp. 603-614
    • Schwaninger, A.E.1    Meyer, M.R.2    Huestis, M.A.3    Maurer, H.H.4
  • 23
    • 70350333887 scopus 로고    scopus 로고
    • The role of human UDP-glucuronyltransferases on the formation of the methylenedioxymethamphetamine (ecstasy) phase II metabolites R- And S-3-methoxymethamphetamine 4-O-glucuronides
    • Schwaninger AE, Meyer MR, Zapp J, and Maurer HH (2009) The role of human UDP-glucuronyltransferases on the formation of the methylenedioxymethamphetamine (ecstasy) phase II metabolites R- and S-3-methoxymethamphetamine 4-O-glucuronides. Drug Metab Dispos 37:2212-2220.
    • (2009) Drug Metab Dispos , vol.37 , pp. 2212-2220
    • Schwaninger, A.E.1    Meyer, M.R.2    Zapp, J.3    Maurer, H.H.4
  • 24
    • 79952616759 scopus 로고    scopus 로고
    • Sulfation of the 3,4- Methylenedioxymethamphetamine (MDMA) metabolites 3,4-dihydroxymethamphetamine (DHMA) and 4-hydroxy-3-methoxymethamphentamine (HMMA) and their capability to inhibit human sulfotransferases
    • Schwaninger AE, Meyer MR, Zapp J, and Maurer HH (2011b) Sulfation of the 3,4- methylenedioxymethamphetamine (MDMA) metabolites 3,4- dihydroxymethamphetamine (DHMA) and 4-hydroxy-3-methoxymethamphentamine (HMMA) and their capability to inhibit human sulfotransferases. Toxicol Lett 202:120-128.
    • (2011) Toxicol Lett , vol.202 , pp. 120-128
    • Schwaninger, A.E.1    Meyer, M.R.2    Zapp, J.3    Maurer, H.H.4
  • 25
    • 39349110177 scopus 로고    scopus 로고
    • Urinary excretion of the main metabolites of 3,4- methylenedioxymethamphetamine (MDMA), including the sulfate and glucuronide of 4-hydroxy-3-methoxymethamphetamine (HMMA), in humans and rats
    • DOI 10.1080/00498250701802506, PII 789872407
    • Shima N, Katagi M, Kamata H, Zaitsu K, Kamata T, Nishikawa M, Miki A, Tsuchihashi H, Sakuma T, and Nemoto N (2008) Urinary excretion of the main metabolites of 3,4- methylenedioxymethamphetamine (MDMA), including the sulfate and glucuronide of 4-hydroxy- 3-methoxymethamphetamine (HMMA), in humans and rats. Xenobiotica 38:314-324. (Pubitemid 351264448)
    • (2008) Xenobiotica , vol.38 , Issue.3 , pp. 314-324
    • Shima, N.1    Katagi, M.2    Kamata, H.3    Zaitsu, K.4    Kamata, T.5    Nishikawa, M.6    Miki, A.7    Tsuchihashi, H.8    Sakuma, T.9    Nemoto, N.10
  • 26
    • 0033674502 scopus 로고    scopus 로고
    • Comparison between cytochrome P450 (CYP) content and relative activity approaches to scaling from cDNA-expressed CYPs to human liver microsomes: Ratios of accessory proteins as sources of discrepancies between the approaches
    • Venkatakrishnan K, von Moltke LL, Court MH, Harmatz JS, Crespi CL, and Greenblatt DJ (2000) Comparison between cytochrome P450 (CYP) content and relative activity approaches to scaling from cDNA-expressed CYPs to human liver microsomes: ratios of accessory proteins as sources of discrepancies between the approaches. Drug Metab Dispos 28:1493-1504.
    • (2000) Drug Metab Dispos , vol.28 , pp. 1493-1504
    • Venkatakrishnan, K.1    Von Moltke, L.L.2    Court, M.H.3    Harmatz, J.S.4    Crespi, C.L.5    Greenblatt, D.J.6
  • 27
    • 25644456179 scopus 로고    scopus 로고
    • Sulfotransferase 2A1 forms estradiol-17-sulfate and celecoxib switches the dominant product from estradiol-3-sulfate to estradiol-17-sulfate
    • Wang LQ and James MO (2005) Sulfotransferase 2A1 forms estradiol-17-sulfate and celecoxib switches the dominant product from estradiol-3-sulfate to estradiol-17-sulfate. J Steroid Biochem Mol Biol 96:367-374.
    • (2005) J Steroid Biochem Mol Biol , vol.96 , pp. 367-374
    • Wang, L.Q.1    James, M.O.2
  • 28
    • 77949445009 scopus 로고    scopus 로고
    • Comparison between recombinant P450s and human liver microsomes in the determination of cytochrome P450 Michaelis-Menten constants
    • Youdim K and Dodia R (2010) Comparison between recombinant P450s and human liver microsomes in the determination of cytochrome P450 Michaelis-Menten constants. Xenobiotica 40:235-244.
    • (2010) Xenobiotica , vol.40 , pp. 235-244
    • Youdim, K.1    Dodia, R.2
  • 29
    • 0032080151 scopus 로고    scopus 로고
    • Sulfuryl transfer: The catalytic mechanism of human estrogen sulfotransferase
    • DOI 10.1074/jbc.273.18.10888
    • Zhang H, Varlamova O, Vargas FM, Falany CN, Leyh TS, and Varmalova O (1998) Sulfuryl transfer: the catalytic mechanism of human estrogen sulfotransferase. J Biol Chem 273: 10888-10892. (Pubitemid 28204925)
    • (1998) Journal of Biological Chemistry , vol.273 , Issue.18 , pp. 10888-10892
    • Zhang, H.1    Varmalova, O.2    Vargas, F.M.3    Falany, C.N.4    Leyh, T.S.5


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