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Volumn 27, Issue 6, 1999, Pages 655-666

Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEMENTARY DNA; CYCLOPHOSPHAMIDE; CYTOCHROME P450; IFOSFAMIDE; PRODRUG;

EID: 0033051029     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (295)

References (48)
  • 1
    • 0025196013 scopus 로고
    • Cytochrome b5 potentiation of cytochrome P-450 catalytic activity demonstrated by a vaccinia virus-mediated in situ reconstitution system
    • Aoyama T, Nagata K, Yamazoe Y, Kato R, Matsunaga E, Gelboin HV and Gonzalez FJ (1990) Cytochrome b5 potentiation of cytochrome P-450 catalytic activity demonstrated by a vaccinia virus-mediated in situ reconstitution system. Proc Natl Acad Sci USA 87:5425-5429.
    • (1990) Proc Natl Acad Sci USA , vol.87 , pp. 5425-5429
    • Aoyama, T.1    Nagata, K.2    Yamazoe, Y.3    Kato, R.4    Matsunaga, E.5    Gelboin, H.V.6    Gonzalez, F.J.7
  • 2
    • 0024412071 scopus 로고
    • Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver. CDNA and deduced amino acid sequence and distinct specificities of cDNA-expressed hPCN1 and hPCN3 for the metabolism of steroid hormones and cyclosporine
    • Aoyama T, Yamano S, Waxman DJ, Lapenson DP, Meyer UA, Fischer V, Tyndale R, Inaba T, Kalow W, Gelboin HV and Gonzalez FJ (1989) Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver. cDNA and deduced amino acid sequence and distinct specificities of cDNA-expressed hPCN1 and hPCN3 for the metabolism of steroid hormones and cyclosporine. J Biol Chem 264:10388-10395.
    • (1989) J Biol Chem , vol.264 , pp. 10388-10395
    • Aoyama, T.1    Yamano, S.2    Waxman, D.J.3    Lapenson, D.P.4    Meyer, U.A.5    Fischer, V.6    Tyndale, R.7    Inaba, T.8    Kalow, W.9    Gelboin, H.V.10    Gonzalez, F.J.11
  • 5
    • 0030000708 scopus 로고    scopus 로고
    • Intrasubject variation in children of ifosfamide pharmacokinetics and metabolism during repeated administration
    • Boddy AV, Yule SM, Wyllie R, Price L, Pearson AD and Idle JR (1996) Intrasubject variation in children of ifosfamide pharmacokinetics and metabolism during repeated administration. Cancer Chemother Pharmacol 38:147-154.
    • (1996) Cancer Chemother Pharmacol , vol.38 , pp. 147-154
    • Boddy, A.V.1    Yule, S.M.2    Wyllie, R.3    Price, L.4    Pearson, A.D.5    Idle, J.R.6
  • 6
    • 0031779382 scopus 로고    scopus 로고
    • Modulation of P450-dependent ifosfamide pharmacokinetics: A better understanding of drug activation in vivo
    • Brain EG, Yu LJ, Gustafsson K, Drewes P and Waxman DJ (1998) Modulation of P450-dependent ifosfamide pharmacokinetics: A better understanding of drug activation in vivo. Br J Cancer 77:1768-1776.
    • (1998) Br J Cancer , vol.77 , pp. 1768-1776
    • Brain, E.G.1    Yu, L.J.2    Gustafsson, K.3    Drewes, P.4    Waxman, D.J.5
  • 7
    • 0029936167 scopus 로고    scopus 로고
    • Protection by transfected rat or human class 3 aldehyde dehydrogenase against the cytotoxic effects of oxazaphosphorine alkylating agents in hamster V79 cell lines. Demonstration of aldophosphamide metabolism by the human cytosolic class 3 isozyme
    • Bunting KD and Townsend AJ (1996) Protection by transfected rat or human class 3 aldehyde dehydrogenase against the cytotoxic effects of oxazaphosphorine alkylating agents in hamster V79 cell lines. Demonstration of aldophosphamide metabolism by the human cytosolic class 3 isozyme. J Biol Chem 271:11891-11896.
    • (1996) J Biol Chem , vol.271 , pp. 11891-11896
    • Bunting, K.D.1    Townsend, A.J.2
  • 9
    • 0030951908 scopus 로고    scopus 로고
    • Enhanced cyclophosphamide and ifosfamide activation in primary human hepatocyte cultures: Response to cytochrome P-450 inducers and autoinduction by oxazaphosphorines
    • Chang TK, Yu L, Maurel P and Waxman DJ (1997b) Enhanced cyclophosphamide and ifosfamide activation in primary human hepatocyte cultures: Response to cytochrome P-450 inducers and autoinduction by oxazaphosphorines. Cancer Res 57:1946-1954.
    • (1997) Cancer Res , vol.57 , pp. 1946-1954
    • Chang, T.K.1    Yu, L.2    Maurel, P.3    Waxman, D.J.4
  • 10
    • 0028174881 scopus 로고
    • Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450
    • Chang TKH, Gonzalez FJ and Waxman DJ (1994) Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Arch Biochem Biophy 311:437-442.
    • (1994) Arch Biochem Biophy , vol.311 , pp. 437-442
    • Chang, T.K.H.1    Gonzalez, F.J.2    Waxman, D.J.3
  • 11
    • 0027369366 scopus 로고
    • Differential activation of cyclophosphamide and ifosphamide by cytochromes P450 2B and 3A in human liver microsomes
    • Chang TKH, Weber GF, Crespi CL and Waxman DJ (1993) Differential activation of cyclophosphamide and ifosphamide by cytochromes P450 2B and 3A in human liver microsomes. Cancer Res 53:5629-5637.
    • (1993) Cancer Res , vol.53 , pp. 5629-5637
    • Chang, T.K.H.1    Weber, G.F.2    Crespi, C.L.3    Waxman, D.J.4
  • 12
    • 0028936342 scopus 로고
    • Intratumoral activation and enhanced chemotherapeutic effect of oxazaphosphorines following cytochrome P450 gene transfer: Development of a combined chemotherapy/cancer gene therapy strategy
    • Chen L and Waxman DJ (1995) Intratumoral activation and enhanced chemotherapeutic effect of oxazaphosphorines following cytochrome P450 gene transfer: Development of a combined chemotherapy/cancer gene therapy strategy. Cancer Res 55:581-589.
    • (1995) Cancer Res , vol.55 , pp. 581-589
    • Chen, L.1    Waxman, D.J.2
  • 13
    • 0028801467 scopus 로고
    • Nonlinear pharmacokinetics of cyclophosphamide in patients with metastatic breast cancer receiving high-dose chemotherapy followed by autologous bone marrow transplantation
    • Chen TL, Passos-Coelho JL, Noe DA, Kennedy MJ, Black KC, Colvin OM and Grochow LB (1995) Nonlinear pharmacokinetics of cyclophosphamide in patients with metastatic breast cancer receiving high-dose chemotherapy followed by autologous bone marrow transplantation. Cancer Res 55:810-816.
    • (1995) Cancer Res , vol.55 , pp. 810-816
    • Chen, T.L.1    Passos-Coelho, J.L.2    Noe, D.A.3    Kennedy, M.J.4    Black, K.C.5    Colvin, O.M.6    Grochow, L.B.7
  • 14
    • 0024533623 scopus 로고
    • Oxidative metabolism of cyclophosphamide: Identification of the hepatic monooxygenase catalysts of drug activation
    • Clarke L and Waxman DJ (1989) Oxidative metabolism of cyclophosphamide: Identification of the hepatic monooxygenase catalysts of drug activation. Cancer Res 49:2344-2350.
    • (1989) Cancer Res , vol.49 , pp. 2344-2350
    • Clarke, L.1    Waxman, D.J.2
  • 15
    • 0030739223 scopus 로고    scopus 로고
    • Human cytochrome P4502B6: Interindividual hepatic expression, substrate specificity, and role in procarcinogen activation
    • Code EL, Crespi CL, Penman BW, Gonzalez FJ, Chang TK and Waxman DJ (1997) Human cytochrome P4502B6: Interindividual hepatic expression, substrate specificity, and role in procarcinogen activation. Drug Metab Dispos 25:985-993.
    • (1997) Drug Metab Dispos , vol.25 , pp. 985-993
    • Code, E.L.1    Crespi, C.L.2    Penman, B.W.3    Gonzalez, F.J.4    Chang, T.K.5    Waxman, D.J.6
  • 16
    • 0028674392 scopus 로고
    • Xenobiotic-metabolizing human cells as tools for pharmacological and toxicological research
    • Crespi CL (1995) Xenobiotic-metabolizing human cells as tools for pharmacological and toxicological research. Adv Drug Res 26:179-235.
    • (1995) Adv Drug Res , vol.26 , pp. 179-235
    • Crespi, C.L.1
  • 17
    • 0030858832 scopus 로고    scopus 로고
    • The R144C change in the CYP2C9*2 allele alters interaction of the cytochrome P450 with NADPH:Cytochrome P450 oxidoreductase
    • Crespi CL and Miller VP (1997) The R144C change in the CYP2C9*2 allele alters interaction of the cytochrome P450 with NADPH:cytochrome P450 oxidoreductase. Pharmacogenetics 7:203-210.
    • (1997) Pharmacogenetics , vol.7 , pp. 203-210
    • Crespi, C.L.1    Miller, V.P.2
  • 18
    • 0030627339 scopus 로고    scopus 로고
    • Use of cDNA-expressed human cytochrome P450 enzymes to study potential drug-drug interactions
    • Crespi CL and Penman BW (1997) Use of cDNA-expressed human cytochrome P450 enzymes to study potential drug-drug interactions. Adv Pharmacol 43:171-188.
    • (1997) Adv Pharmacol , vol.43 , pp. 171-188
    • Crespi, C.L.1    Penman, B.W.2
  • 20
    • 0016806456 scopus 로고
    • The effect of chloramphenicol and sulphaphenazole on the biotransformation of cyclophosphamide in man
    • Faber OK, Mouridsen HT and Skovsted L (1975) The effect of chloramphenicol and sulphaphenazole on the biotransformation of cyclophosphamide in man. Br J Clin Pharmacol 2:281-285.
    • (1975) Br J Clin Pharmacol , vol.2 , pp. 281-285
    • Faber, O.K.1    Mouridsen, H.T.2    Skovsted, L.3
  • 21
    • 0030765658 scopus 로고    scopus 로고
    • An overview of cyclophosphamide and ifosfamide pharmacology
    • Fleming RA (1997) An overview of cyclophosphamide and ifosfamide pharmacology. Pharmacotherapy 17:146S-154S.
    • (1997) Pharmacotherapy , vol.17
    • Fleming, R.A.1
  • 22
    • 0028590127 scopus 로고
    • Biochemistry and molecular biology of the human CYP2C subfamily
    • Goldstein JA and de Morais SM (1994) Biochemistry and molecular biology of the human CYP2C subfamily. Pharmacogenetics 4:285-299.
    • (1994) Pharmacogenetics , vol.4 , pp. 285-299
    • Goldstein, J.A.1    De Morais, S.M.2
  • 24
    • 0031921010 scopus 로고    scopus 로고
    • Evaluation of the selectivity of in vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities
    • Hickman D, Wang JP, Wang Y and Unadkat JD (1998) Evaluation of the selectivity of in vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities. Drug Metab Dispos 26:207-215.
    • (1998) Drug Metab Dispos , vol.26 , pp. 207-215
    • Hickman, D.1    Wang, J.P.2    Wang, Y.3    Unadkat, J.D.4
  • 25
    • 0028858960 scopus 로고
    • Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes
    • Newton DJ, Wang RW and Lu AY (1995) Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab Dispos 23:154-158.
    • (1995) Drug Metab Dispos , vol.23 , pp. 154-158
    • Newton, D.J.1    Wang, R.W.2    Lu, A.Y.3
  • 27
    • 0030799414 scopus 로고    scopus 로고
    • Oxidation of cyclophosphamide to 4-hydroxycyclophosphamide and deschloroethylcyclophosphamide in human liver microsomes
    • Ren S, Yang JS, Kalhorn TF and Slattery JT (1997) Oxidation of cyclophosphamide to 4-hydroxycyclophosphamide and deschloroethylcyclophosphamide in human liver microsomes. Cancer Res 57:4229-4235.
    • (1997) Cancer Res , vol.57 , pp. 4229-4235
    • Ren, S.1    Yang, J.S.2    Kalhorn, T.F.3    Slattery, J.T.4
  • 29
    • 0025763625 scopus 로고
    • Cloning and expression of complementary DNAs for multiple members of the human cytochrome P450IIC subfamily
    • published erratum appears in Biochemistry 1993 Feb 9;32(5):1390.
    • Romkes M, Faletto MB, Blaisdell JA, Raucy JL and Goldstein JA (1991) Cloning and expression of complementary DNAs for multiple members of the human cytochrome P450IIC subfamily [published erratum appears in Biochemistry 1993 Feb 9;32(5):1390]. Biochemistry 30:3247-3255.
    • (1991) Biochemistry , vol.30 , pp. 3247-3255
    • Romkes, M.1    Faletto, M.B.2    Blaisdell, J.A.3    Raucy, J.L.4    Goldstein, J.A.5
  • 31
    • 0028175687 scopus 로고
    • Selective expression of cytochrome P450 CYP3A mRNAs in embryonic and adult human liver
    • Schuetz JD, Beach DL and Guzelian PS (1994) Selective expression of cytochrome P450 CYP3A mRNAs in embryonic and adult human liver. Pharmacogenetics 4:11-20.
    • (1994) Pharmacogenetics , vol.4 , pp. 11-20
    • Schuetz, J.D.1    Beach, D.L.2    Guzelian, P.S.3
  • 32
    • 0030959377 scopus 로고    scopus 로고
    • Cytochrome P450-dependent drug oxidation activities in liver microsomes of various animal species including rats, guinea pigs, dogs, monkeys, and humans
    • Shimada T, Mimura M, Inoue K, Nakamura S, Oda H, Ohmori S and Yamazaki H (1997) Cytochrome P450-dependent drug oxidation activities in liver microsomes of various animal species including rats, guinea pigs, dogs, monkeys, and humans. Arch Toxicol 71:401-408.
    • (1997) Arch Toxicol , vol.71 , pp. 401-408
    • Shimada, T.1    Mimura, M.2    Inoue, K.3    Nakamura, S.4    Oda, H.5    Ohmori, S.6    Yamazaki, H.7
  • 33
    • 0028237729 scopus 로고
    • Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians
    • Shimada T, Yamazaki H, Mimura M, Inui Y and Guengerich FP (1994) Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 270:414-423.
    • (1994) J Pharmacol Exp Ther , vol.270 , pp. 414-423
    • Shimada, T.1    Yamazaki, H.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 34
    • 0023945947 scopus 로고
    • Metabolism of oxazaphosphorines
    • Sladek NE (1988) Metabolism of oxazaphosphorines. Pharmacol Ther 37:301-355.
    • (1988) Pharmacol Ther , vol.37 , pp. 301-355
    • Sladek, N.E.1
  • 35
    • 0001358252 scopus 로고
    • Oxazaphosphorine-specific acquired cellular resistance
    • Teicher BA, ed. Marcel Dekker, New York
    • Sladek NE (1993) Oxazaphosphorine-specific acquired cellular resistance, in Drug Resistance in Oncology (Teicher BA, ed.) pp 375-411, Marcel Dekker, New York.
    • (1993) Drug Resistance in Oncology , pp. 375-411
    • Sladek, N.E.1
  • 38
    • 0023929834 scopus 로고
    • Human liver microsomal steroid metabolism: Identification of the major microsomal steroid hormone 6 beta-hydroxylase cytochrome P-450 enzyme
    • Waxman DJ, Attisano C, Guengerich FP and Lapenson DP (1988) Human liver microsomal steroid metabolism: Identification of the major microsomal steroid hormone 6 beta-hydroxylase cytochrome P-450 enzyme. Arch Biochem Biophys 263:424-436.
    • (1988) Arch Biochem Biophys , vol.263 , pp. 424-436
    • Waxman, D.J.1    Attisano, C.2    Guengerich, F.P.3    Lapenson, D.P.4
  • 39
    • 0032901285 scopus 로고    scopus 로고
    • Cytochrome P450-based cancer gene therapy: Recent advances and future prospects
    • Waxman DJ, Chen L, Hecht JED and Jounaidi Y (1999) Cytochrome P450-based cancer gene therapy: Recent advances and future prospects. Drug Metab Rev 31:503-522.
    • (1999) Drug Metab Rev , vol.31 , pp. 503-522
    • Waxman, D.J.1    Chen, L.2    Hecht, J.E.D.3    Jounaidi, Y.4
  • 40
    • 0020530615 scopus 로고
    • Cytochrome P-450 isozyme 1 from phenobarbital-induced rat liver: Purification, characterization, and interactions with metyrapone and cytochrome b5
    • Waxman DJ and Walsh C (1983) Cytochrome P-450 isozyme 1 from phenobarbital-induced rat liver: Purification, characterization, and interactions with metyrapone and cytochrome b5. Biochemistry 22:4846-4855.
    • (1983) Biochemistry , vol.22 , pp. 4846-4855
    • Waxman, D.J.1    Walsh, C.2
  • 41
    • 0027174822 scopus 로고
    • Activation of the anti-cancer drug ifosphamide by rat liver microsomal P450 enzymes
    • Weber GF and Waxman DJ (1993) Activation of the anti-cancer drug ifosphamide by rat liver microsomal P450 enzymes. Biochem Pharmacol 45:1685-1694.
    • (1993) Biochem Pharmacol , vol.45 , pp. 1685-1694
    • Weber, G.F.1    Waxman, D.J.2
  • 42
    • 0029156695 scopus 로고
    • The use of in vitro metabolism techniques in the planning and interpretation of drug safety studies
    • Wrighton SA, Ring BJ and VandenBranden M (1995) The use of in vitro metabolism techniques in the planning and interpretation of drug safety studies. Toxicol Pathol 23:199-208.
    • (1995) Toxicol Pathol , vol.23 , pp. 199-208
    • Wrighton, S.A.1    Ring, B.J.2    VandenBranden, M.3
  • 43
    • 0024464027 scopus 로고
    • cDNA cloning and sequence and cDNA-directed expression of human P450 IIB1: Identification of a normal and two variant cDNAs derived from the CYP2B locus on chromosome 19 and differential expression of the IIB mRNAs in human liver
    • Yamano S, Nhamburo PT, Aoyama T, Meyer UA, Inaba T, Kalow W, Gelboin HV, McBride OW and Gonzalez FJ (1989) cDNA cloning and sequence and cDNA-directed expression of human P450 IIB1: Identification of a normal and two variant cDNAs derived from the CYP2B locus on chromosome 19 and differential expression of the IIB mRNAs in human liver. Biochemistry 28:7340-7348.
    • (1989) Biochemistry , vol.28 , pp. 7340-7348
    • Yamano, S.1    Nhamburo, P.T.2    Aoyama, T.3    Meyer, U.A.4    Inaba, T.5    Kalow, W.6    Gelboin, H.V.7    McBride, O.W.8    Gonzalez, F.J.9
  • 44
    • 0029926494 scopus 로고    scopus 로고
    • Lack of electron transfer from cytochrome b5 in stimulation of catalytic activities of cytochrome P450 3A4. Characterization of a reconstituted cytochrome P450 3A4/NADPH-cytochrome P450 reductase system and studies with apo-cytochrome b5
    • Yamazaki H, Johnson WW, Ueng YF, Shimada T and Guengerich FP (1996) Lack of electron transfer from cytochrome b5 in stimulation of catalytic activities of cytochrome P450 3A4. Characterization of a reconstituted cytochrome P450 3A4/NADPH-cytochrome P450 reductase system and studies with apo-cytochrome b5. J Biol Chem 271:27438-27444.
    • (1996) J Biol Chem , vol.271 , pp. 27438-27444
    • Yamazaki, H.1    Johnson, W.W.2    Ueng, Y.F.3    Shimada, T.4    Guengerich, F.P.5
  • 46
    • 0033055342 scopus 로고    scopus 로고
    • In vivo modulation of alternative pathways of P450-catalyzed cyclophosphamide metabolism: Impact on pharmacokinetics and antitumor activity
    • Yu LJ, Drewes P, Gustafsson K, Brain EGC, Hecht JED and Waxman DJ (1999) In vivo modulation of alternative pathways of P450-catalyzed cyclophosphamide metabolism: Impact on pharmacokinetics and antitumor activity. J Pharmacol Exp Ther 288:928-937.
    • (1999) J Pharmacol Exp Ther , vol.288 , pp. 928-937
    • Yu, L.J.1    Drewes, P.2    Gustafsson, K.3    Brain, E.G.C.4    Hecht, J.E.D.5    Waxman, D.J.6
  • 47
    • 0030476592 scopus 로고    scopus 로고
    • Role of cytochrome P450 in oxazaphosphorine metabolism. Deactivation via N-dechloroethylation and activation via 4-hydroxylation catalyzed by distinct subsets of rat liver cytochromes P450
    • Yu L and Waxman DJ (1996) Role of cytochrome P450 in oxazaphosphorine metabolism. Deactivation via N-dechloroethylation and activation via 4-hydroxylation catalyzed by distinct subsets of rat liver cytochromes P450. Drug Metab Dispos 24:1254-1262.
    • (1996) Drug Metab Dispos , vol.24 , pp. 1254-1262
    • Yu, L.1    Waxman, D.J.2


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