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Volumn 81, Issue 8, 2011, Pages 1043-1053

A comprehensive understanding of thioTEPA metabolism in the mouse using UPLC-ESI-QTOFMS-based metabolomics

Author keywords

Metabolomics; Tandem mass spectrometry; ThioTEPA; Time of flight mass spectrometry; Ultraperformance liquid chromatography

Indexed keywords

1,2 DICHLOROTEPA; 1,2,3 TRICHLOROTEPA; CARBOCISTEINE; CHLOROACETALDEHYDE; DECHLOROETHYLTRICHLOROTEPA; DRUG METABOLITE; MONOCHLOROTEPA; TEPA; THIODIACETIC ACID; THIOTEPA; THIOTEPA CYSTEINATE; THIOTEPA MERCAPTURATE; UNCLASSIFIED DRUG;

EID: 79952992201     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2011.01.024     Document Type: Article
Times cited : (28)

References (45)
  • 1
    • 78651115683 scopus 로고
    • Breast cancer: A new approach to therapy
    • G.W. Watson, and R.L. Turner Breast cancer: a new approach to therapy Br Med J 1 1959 1315 1320
    • (1959) Br Med J , vol.1 , pp. 1315-1320
    • Watson, G.W.1    Turner, R.L.2
  • 2
    • 0008387762 scopus 로고
    • Thiotepa in the treatment of advanced breast cancer
    • A.R. Lyons, and G.A. Edelstyn Thiotepa in the treatment of advanced breast cancer Br J Cancer 19 1965 490 495
    • (1965) Br J Cancer , vol.19 , pp. 490-495
    • Lyons, A.R.1    Edelstyn, G.A.2
  • 4
    • 0024472575 scopus 로고
    • Liquid chromatrography-thermospray mass spectrometry of DNA adducts formed with mitomycin C, porfiromycin and thiotepa
    • DOI 10.1016/S0021-9673(01)93915-9
    • S.M. Musser, S.S. Pan, and P.S. Callery Liquid chromatography-thermospray mass spectrometry of DNA adducts formed with mitomycin C, porfiromycin and thiotepa J Chromatogr 474 1989 197 207 (Pubitemid 19179104)
    • (1989) Journal of Chromatography , vol.474 , Issue.1 , pp. 197-207
    • Musser, S.M.1    Pan, S.S.2    Callery, P.S.3
  • 6
    • 0026058575 scopus 로고
    • Interaction of N,N′,N″-triethylenethiophosphoramide and N,N′,N″-triethylenephosphoramide with cellular DNA
    • N.A. Cohen, M.J. Egorin, S.W. Snyder, B. Ashar, B.E. Wietharn, and S.S. Pan Interaction of N,N′,N″-triethylenethiophosphoramide and N,N′,N″-triethylenephosphoramide with cellular DNA Cancer Res 51 1991 4360 4366
    • (1991) Cancer Res , vol.51 , pp. 4360-4366
    • Cohen, N.A.1    Egorin, M.J.2    Snyder, S.W.3    Ashar, B.4    Wietharn, B.E.5    Pan, S.S.6
  • 7
    • 0026532588 scopus 로고
    • Alkylation of DNA with aziridine produced during the hydrolysis of N,N′,N″-triethylenethiophosphoramide
    • S.M. Musser, S.S. Pan, M.J. Egorin, D.J. Kyle, and P.S. Callery Alkylation of DNA with aziridine produced during the hydrolysis of N,N′,N″-triethylenethiophosphoramide Chem Res Toxicol 5 1992 95 99
    • (1992) Chem Res Toxicol , vol.5 , pp. 95-99
    • Musser, S.M.1    Pan, S.S.2    Egorin, M.J.3    Kyle, D.J.4    Callery, P.S.5
  • 9
    • 0028910538 scopus 로고
    • The role of human glutathione S-transferase isoenzymes in the formation of glutathione conjugates of the alkylating cytostatic drug thiotepa
    • H.A. Dirven, E.L. Dictus, N.L. Broeders, B. van Ommen, and P.J. van Bladeren The role of human glutathione S-transferase isoenzymes in the formation of glutathione conjugates of the alkylating cytostatic drug thiotepa Cancer Res 55 1995 1701 1706
    • (1995) Cancer Res , vol.55 , pp. 1701-1706
    • Dirven, H.A.1    Dictus, E.L.2    Broeders, N.L.3    Van Ommen, B.4    Van Bladeren, P.J.5
  • 10
    • 0025061102 scopus 로고
    • Biotransformation of N,N',N''-triethylenethiophosphoramide: Oxidative desulfuration to yield N,N',-N''-triethylenephosphoramide associated with suicide inactivation of a phenobarbital-inducible hepatic P-450 monooxygenase
    • S.F. Ng, and D.J. Waxman Biotransformation of N,N′,N″- triethylenethiophosphoramide: oxidative desulfuration to yield N,N′,N″-triethylenephosphoramide associated with suicide inactivation of a phenobarbital-inducible hepatic P-450 monooxygenase Cancer Res 50 1990 464 471 (Pubitemid 20054162)
    • (1990) Cancer Research , vol.50 , Issue.3 , pp. 464-471
    • Ng, S.-F.1    Waxman, D.J.2
  • 11
    • 0025810921 scopus 로고
    • N,N′,N″-triethylenethiophosphoramide (thio-TEPA) oxygenation by constitutive hepatic P450 enzymes and modulation of drug metabolism and clearance in vivo by P450-inducing agents
    • S.F. Ng, and D.J. Waxman N,N′,N″-triethylenethiophosphoramide (thio-TEPA) oxygenation by constitutive hepatic P450 enzymes and modulation of drug metabolism and clearance in vivo by P450-inducing agents Cancer Res 51 1991 2340 2345
    • (1991) Cancer Res , vol.51 , pp. 2340-2345
    • Ng, S.F.1    Waxman, D.J.2
  • 12
    • 0036090053 scopus 로고    scopus 로고
    • Cytochrome P450 isozymes 3A4 and 2B6 are involved in the in vitro human metabolism of thiotepa to TEPA
    • DOI 10.1007/s00280-002-0453-3
    • P.A. Jacobson, K. Green, A. Birnbaum, and R.P. Remmel Cytochrome P450 isozymes 3A4 and 2B6 are involved in the in vitro human metabolism of thiotepa to TEPA Cancer Chemother Pharmacol 49 2002 461 467 (Pubitemid 34671281)
    • (2002) Cancer Chemotherapy and Pharmacology , vol.49 , Issue.6 , pp. 461-467
    • Jacobson, P.1    Green, K.2    Birnbaum, A.3    Remmel, R.4
  • 13
    • 0021181405 scopus 로고
    • Effects of pH and temperature on the stability and decomposition of N,N'N''-triethylenethiophosphoramide in urine and buffer
    • B.E. Cohen, M.J. Egorin, M.S. Nayar, and P.L. Gutierrez Effects of pH and temperature on the stability and decomposition of N,N′,N″- triethylenethiophosphoramide in urine and buffer Cancer Res 44 1984 4312 4316 (Pubitemid 14008741)
    • (1984) Cancer Research , vol.44 , Issue.10 , pp. 4312-4316
    • Cohen, B.E.1    Egorin, M.J.2    Nayar, M.S.B.3    Gutierrez, P.L.4
  • 15
    • 0034254283 scopus 로고    scopus 로고
    • Chemistry, pharmacology and pharmacokinetics of N,N',N′- triethylenethiophosphoramide (ThioTEPA)
    • DOI 10.1053/ctrv.2000.0170
    • M.J. Maanen, C.J. Smeets, and J.H. Beijnen Chemistry, pharmacology and pharmacokinetics of N,N′,N″-triethylenethiophosphoramide (ThioTEPA) Cancer Treat Rev 26 2000 257 268 (Pubitemid 30604037)
    • (2000) Cancer Treatment Reviews , vol.26 , Issue.4 , pp. 257-268
    • Maanen, M.J.V.1    Smeets, C.J.M.2    Beijnen, J.H.3
  • 16
    • 0034915905 scopus 로고    scopus 로고
    • Urinary excretion of thioTEPA and its metabolites in patients treated with high-dose cyclophosphamide, thioTEPA and carboplatin
    • DOI 10.1097/00001813-200107000-00005
    • M.J. van Maanen, A.D. Huitema, S. Rodenhuis, and J.H. Beijnen Urinary excretion of thioTEPA and its metabolites in patients treated with high-dose cyclophosphamide, thioTEPA and carboplatin Anticancer Drugs 12 2001 519 524 (Pubitemid 32692596)
    • (2001) Anti-Cancer Drugs , vol.12 , Issue.6 , pp. 519-524
    • Van Maanen, M.J.1    Huitema, A.D.R.2    Rodenhuis, S.3    Beijnen, J.H.4
  • 17
    • 0022525143 scopus 로고
    • Human plasma pharmacokinetics and urinary excretion of thiotepa and its metabolites
    • B.E. Cohen, M.J. Egorin, E.A. Kohlhepp, J. Aisner, and P.L. Gutierrez Human plasma pharmacokinetics and urinary excretion of thiotepa and its metabolites Cancer Treat Rep 70 1986 859 864 (Pubitemid 16058549)
    • (1986) Cancer Treatment Reports , vol.70 , Issue.7 , pp. 859-864
    • Cohen, B.E.1    Egorin, M.J.2    Kohlhepp, E.A.3
  • 18
    • 0025020494 scopus 로고
    • Long-term pharmacokinetics of thio-TEPA, TEPA and total alkylating activity following i.v. bolus administration of thio-TEPA in ovarian cancer patients
    • DOI 10.1007/BF00684882
    • B. Hagen, G. Neverdal, R.A. Walstad, and O.G. Nilsen Long-term pharmacokinetics of thio-TEPA, TEPA and total alkylating activity following i. v. bolus administration of thio-TEPA in ovarian cancer patients Cancer Chemother Pharmacol 25 1990 257 262 (Pubitemid 20014968)
    • (1990) Cancer Chemotherapy and Pharmacology , vol.25 , Issue.4 , pp. 257-262
    • Hagen, B.1    Neverdal, G.2    Walstad, R.A.3    Nilsen, O.G.4
  • 20
    • 0028840208 scopus 로고
    • Rapidly cycled courses of high-dose alkylating agents supported by filgrastim and peripheral blood progenitor cells in patients with metastatic breast cancer
    • L. Vahdat, G. Raptis, D. Fennelly, N. Hamilton, L. Reich, and A. Tiersten Rapidly cycled courses of high-dose alkylating agents supported by filgrastim and peripheral blood progenitor cells in patients with metastatic breast cancer Clin Cancer Res 1 1995 1267 1273
    • (1995) Clin Cancer Res , vol.1 , pp. 1267-1273
    • Vahdat, L.1    Raptis, G.2    Fennelly, D.3    Hamilton, N.4    Reich, L.5    Tiersten, A.6
  • 22
    • 0344074048 scopus 로고    scopus 로고
    • Thiodiglycolic acid is excreted by humans receiving ifosfamide and inhibits mitochondrial function in rats
    • T.M. Visarius, H. Bahler, A. Küpfer, T. Cerny, and B.H. Lauterburg Thiodiglycolic acid is excreted by humans receiving ifosfamide and inhibits mitochondrial function in rats Drug Metab Dispos 26 1998 193 196 (Pubitemid 28182392)
    • (1998) Drug Metabolism and Disposition , vol.26 , Issue.3 , pp. 193-196
    • Visarius, T.M.1    Bahler, H.2    Kupfer, A.3    Cerny, T.4    Lauterburg, B.H.5
  • 23
    • 0035201805 scopus 로고    scopus 로고
    • Insights into the mechanisms of ifosfamide encephalopathy: Drug metabolites have agonistic effects on α-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid (AMPA)/kainate receptors and induce cellular acidification in mouse cortical neurons
    • J.Y. Chatton, J.R. Idle, C.B. Vgbø, and P.J. Magistretti Insights into the mechanisms of ifosfamide encephalopathy: drug metabolites have agonistic effects on alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)/kainate receptors and induce cellular acidification in mouse cortical neurons J Pharmacol Exp Ther 299 2001 1161 1168 (Pubitemid 33104990)
    • (2001) Journal of Pharmacology and Experimental Therapeutics , vol.299 , Issue.3 , pp. 1161-1168
    • Chatton, J.-Y.1    Idle, J.R.2    Vagbo, C.B.3    Magistretti, P.J.4
  • 24
    • 31344450220 scopus 로고    scopus 로고
    • Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: A further clue to the mechanism of ifosfamide encephalopathy
    • DOI 10.1016/j.toxlet.2005.09.002, PII S0378427405002705
    • S. Lerch, A. Küpfer, J.R. Idle, and B.H. Lauterburg Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy Toxicol Lett 161 2006 188 194 (Pubitemid 43138858)
    • (2006) Toxicology Letters , vol.161 , Issue.3 , pp. 188-194
    • Lerch, S.1    Kupfer, A.2    Idle, J.R.3    Lauterburg, B.H.4
  • 27
    • 0043069547 scopus 로고    scopus 로고
    • Understanding 'global' systems biology: Metabonomics and the continuum of metabolism
    • J.K. Nicholson, and I.D. Wilson Opinion: understanding 'global' systems biology: metabonomics and the continuum of metabolism Nat Rev Drug Discov 2 2003 668 676 (Pubitemid 37361770)
    • (2003) Nature Reviews Drug Discovery , vol.2 , Issue.8 , pp. 668-676
    • Nicholson, J.K.1    Wilson, I.D.2
  • 28
    • 35548938974 scopus 로고    scopus 로고
    • Metabolomics
    • DOI 10.1016/j.cmet.2007.10.005, PII S1550413107002987
    • J.R. Idle, and F.J. Gonzalez Metabolomics Cell Metab 6 2007 348 351 (Pubitemid 350012005)
    • (2007) Cell Metabolism , vol.6 , Issue.5 , pp. 348-351
    • Idle, J.R.1    Gonzalez, F.J.2
  • 29
    • 77952337695 scopus 로고    scopus 로고
    • Xenobiotic metabolism: A view through the metabolometer
    • A.D. Patterson, F.J. Gonzalez, and J.R. Idle Xenobiotic metabolism: a view through the metabolometer Chem Res Toxicol 23 2010 851 860
    • (2010) Chem Res Toxicol , vol.23 , pp. 851-860
    • Patterson, A.D.1    Gonzalez, F.J.2    Idle, J.R.3
  • 30
    • 41949134860 scopus 로고    scopus 로고
    • Identification of novel toxicity-associated metabolites by metabolomics and mass isotopomer analysis of acetaminophen metabolism in wild-type and Cyp2e1-null mice
    • C. Chen, K.W. Krausz, J.R. Idle, and F.J. Gonzalez Identification of novel toxicity-associated metabolites by metabolomics and mass isotopomer analysis of acetaminophen metabolism in wild-type and Cyp2e1-null mice J Biol Chem 283 2008 4543 4559
    • (2008) J Biol Chem , vol.283 , pp. 4543-4559
    • Chen, C.1    Krausz, K.W.2    Idle, J.R.3    Gonzalez, F.J.4
  • 31
    • 41549100628 scopus 로고    scopus 로고
    • A metabolomic perspective of melatonin metabolism in the mouse
    • DOI 10.1210/en.2007-1412
    • X. Ma, C. Chen, K.W. Krausz, J.R. Idle, and F.J. Gonzalez A metabolomic perspective of melatonin metabolism in the mouse Endocrinology 149 2008 1869 1879 (Pubitemid 351468324)
    • (2008) Endocrinology , vol.149 , Issue.4 , pp. 1869-1879
    • Ma, X.1    Chen, C.2    Krausz, K.W.3    Idle, J.R.4    Gonzalez, F.J.5
  • 32
    • 33745320763 scopus 로고    scopus 로고
    • A metabolomic approach to the metabolism of the areca nut alkaloids arecoline and arecaidine in the mouse
    • DOI 10.1021/tx0600402
    • S. Giri, J.R. Idle, C. Chen, T.M. Zabriskie, K.W. Krausz, and F.J. Gonzalez A metabolomic approach to the metabolism of the areca nut alkaloids arecoline and arecaidine in the mouse Chem Res Toxicol 19 2006 818 827 (Pubitemid 43939061)
    • (2006) Chemical Research in Toxicology , vol.19 , Issue.6 , pp. 818-827
    • Giri, S.1    Idle, J.R.2    Chen, C.3    Zabriskie, T.M.4    Krausz, K.W.5    Gonzalez, F.J.6
  • 33
    • 77955660756 scopus 로고    scopus 로고
    • Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC-ESI-QTOFMS-based metabolomics
    • F. Li, A.D. Patterson, C.C. Höfer, K.W. Krausz, F.J. Gonzalez, and J.R. Idle Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC-ESI-QTOFMS-based metabolomics Biochem Pharmacol 80 2010 1063 1074
    • (2010) Biochem Pharmacol , vol.80 , pp. 1063-1074
    • Li, F.1    Patterson, A.D.2    Höfer, C.C.3    Krausz, K.W.4    Gonzalez, F.J.5    Idle, J.R.6
  • 34
    • 0037342251 scopus 로고    scopus 로고
    • Regeneration of serotonin from 5-methoxytryptamine by polymorphic human CYP2D6
    • DOI 10.1097/00008571-200303000-00007
    • A.M. Yu, J.R. Idle, L.G. Byrd, K.W. Krausz, A. Küpfer, and F.J. Gonzalez Regeneration of serotonin from 5-methoxytryptamine by polymorphic human CYP2D6 Pharmacogenetics 13 2003 173 181 (Pubitemid 36324247)
    • (2003) Pharmacogenetics , vol.13 , Issue.3 , pp. 173-181
    • Yu, A.-M.1    Idle, J.R.2    Byrd, L.G.3    Krausz, K.W.4    Kupfer, A.5    Gonzalez, F.J.6
  • 35
    • 0033975570 scopus 로고    scopus 로고
    • The degradation of N,N',N''-triethylenephosphoramide in aqueous solutions: A qualitative and kinetic study
    • DOI 10.1016/S0378-5173(99)00444-5, PII S0378517399004445
    • R.J. van Maanen, I.M. Tijhof, J.M. Damen, J.W. Zwikker, and J.H. Beijnen The degradation of N,N′,N″-triethylenephosphoramide in aqueous solutions: a qualitative and kinetic study Int J Pharm 196 2000 85 94 (Pubitemid 30089517)
    • (2000) International Journal of Pharmaceutics , vol.196 , Issue.1 , pp. 85-94
    • Van Maanen, R.J.1    Tijhof, I.M.2    Damen, J.M.A.3    Zwikker, J.W.4    Beijnen, J.H.5
  • 36
    • 0026033602 scopus 로고
    • Identification of thiodiglycolic acid, thiodiglycolic acid sulfoxide, and (3-carboxymethylthio)lactic acid as major human biotransformation products of S-carboxymethyl-l-cysteine
    • U. Hofmann, M. Eichelbaum, S. Seefried, and C.O. Meese Identification of thiodiglycolic acid, thiodiglycolic acid sulfoxide, and (3-carboxymethylthio) lactic acid as major human biotransformation products of S-carboxymethyl-l- cysteine Drug Metab Dispos 19 1991 222 226
    • (1991) Drug Metab Dispos , vol.19 , pp. 222-226
    • Hofmann, U.1    Eichelbaum, M.2    Seefried, S.3    Meese, C.O.4
  • 38
    • 32144445103 scopus 로고    scopus 로고
    • Severe encephalopathy after high-dose chemotherapy with autologous stem cell support for brain tumours
    • F. van den Berkmortel, C. Gidding, M. De Kanter, and C.J. Punt Severe encephalopathy after high-dose chemotherapy with autologous stem cell support for brain tumours Anticancer Res 26 2006 729 733 (Pubitemid 43206041)
    • (2006) Anticancer Research , vol.26 , Issue.1 , pp. 729-733
    • Van Den Berkmortel, F.1    Gidding, C.2    De Kanter, M.3    Punt, C.J.A.4
  • 39
    • 33748617860 scopus 로고    scopus 로고
    • Pancreatic encephalopathy and Wernicke encephalopathy in association with acute pancreatitis: A clinical study
    • G.H. Sun, Y.S. Yang, Q.S. Liu, L.F. Cheng, and X.S. Huang Pancreatic encephalopathy and Wernicke encephalopathy in association with acute pancreatitis: a clinical study World J Gastroenterol 12 2006 4224 4227
    • (2006) World J Gastroenterol , vol.12 , pp. 4224-4227
    • Sun, G.H.1    Yang, Y.S.2    Liu, Q.S.3    Cheng, L.F.4    Huang, X.S.5
  • 40
    • 68049123295 scopus 로고    scopus 로고
    • Wernicke's encephalopathy and pancreatic encephalopathy after necrotic-hemorrhagic pancreatitis. A case report
    • E. Zangheri, A. Pigna, E. Amanti, R. D'Alessandro, F. Bova, and R.M. Melotti Wernicke's encephalopathy and pancreatic encephalopathy after necrotic-hemorrhagic pancreatitis. A case report Minerva Anestesiol 75 2009 401 404
    • (2009) Minerva Anestesiol , vol.75 , pp. 401-404
    • Zangheri, E.1    Pigna, A.2    Amanti, E.3    D'Alessandro, R.4    Bova, F.5    Melotti, R.M.6
  • 41
    • 48549096882 scopus 로고    scopus 로고
    • Effects of thiamine and benfotiamine on intracellular glucose metabolism and relevance in the prevention of diabetic complications
    • E. Beltramo, E. Berrone, S. Tarallo, and M. Porta Effects of thiamine and benfotiamine on intracellular glucose metabolism and relevance in the prevention of diabetic complications Acta Diabetol 45 2008 131 141
    • (2008) Acta Diabetol , vol.45 , pp. 131-141
    • Beltramo, E.1    Berrone, E.2    Tarallo, S.3    Porta, M.4
  • 43
    • 0014341180 scopus 로고
    • Encephalopathy of thiamine deficieny: Studies of intracerebral mechanisms
    • D.W. McCandless, S. Schenker, and M. Cook Encephalopathy of thiamine deficieny: studies of intracerebral mechanisms J Clin Invest 47 1968 2268 2280
    • (1968) J Clin Invest , vol.47 , pp. 2268-2280
    • McCandless, D.W.1    Schenker, S.2    Cook, M.3
  • 44
    • 0038797080 scopus 로고    scopus 로고
    • Acute encephalopathy due to thiamine deficiency with hyperammonemia in a chronic hemodialysis patient: A case report
    • S. Ookawara, M. Suzuki, and M. Saitou Acute encephalopathy due to thiamine deficiency with hyperammonemia in a chronic hemodialysis patient: a case report Nippon Jinzo Gakkai Shi 45 2003 393 397 (Pubitemid 36702127)
    • (2003) Japanese Journal of Nephrology , vol.45 , Issue.4 , pp. 393-397
    • Ookawara, S.1    Suzuki, M.2    Saitou, M.3
  • 45
    • 33846208731 scopus 로고    scopus 로고
    • Role of thiamine in managing ifosfamide-induced encephalopathy
    • M. Hamadani, and F. Awan Role of thiamine in managing ifosfamide-induced encephalopathy J Oncol Pharm Pract 12 2006 237 239
    • (2006) J Oncol Pharm Pract , vol.12 , pp. 237-239
    • Hamadani, M.1    Awan, F.2


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