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Volumn 36, Issue 2, 2008, Pages 353-360

Influence of mustard group structure on pathways of in vitro metabolism of anticancer N-(2-hydroxyethyl)-3,5-dinitrobenzamide 2-mustard prodrugs

Author keywords

[No Author keywords available]

Indexed keywords

2 (DIETHYLAMINO) N (2 HYDROXYETHYL) 3,5 DINITROBENZAMIDE; 2 [[2 BROMOETHYL] 2 [[(2 HYDROXYETHYL)AMINO]CARBONYL] 4,6 DINITROANILINO]ETHYL METHANETHIOSULFONATE; 2 [BIS(2 BROMOETHYL)AMINO] N (2 HYDROXYETHYL) 3,5 DINITROBENZAMIDE; ANTINEOPLASTIC AGENT; BENZAMIDE DERIVATIVE; BISCHLOROETHYL 2,4 DINITROBENZAMIDE; N (2 HYDROXYETHYL) 3,5 DINITROBENZAMIDE 2 MUSTARD DERIVATIVE; SN 27686; SN 27858; SN 29546; SN 29893; UNCLASSIFIED DRUG;

EID: 38749131554     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.018739     Document Type: Article
Times cited : (7)

References (26)
  • 2
    • 33947669761 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy
    • Atwell GJ, Yang S, Pruijn FB, Pullen SM, Hogg A, Patterson AV, Wilson WR, and Denny WA (2007) Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy. J Med Chem 50:1197-1212.
    • (2007) J Med Chem , vol.50 , pp. 1197-1212
    • Atwell, G.J.1    Yang, S.2    Pruijn, F.B.3    Pullen, S.M.4    Hogg, A.5    Patterson, A.V.6    Wilson, W.R.7    Denny, W.A.8
  • 3
    • 0022535929 scopus 로고
    • Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic tumor cells
    • Denny WA and Wilson WR (1986) Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic tumor cells. J Med Chem 29:879-887.
    • (1986) J Med Chem , vol.29 , pp. 879-887
    • Denny, W.A.1    Wilson, W.R.2
  • 4
    • 34547653834 scopus 로고    scopus 로고
    • Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: A role for cytochrome P450 reductase under hypoxia
    • Guise CP, Wang AT, Theil A, Bridewell DJ, Wilson WR, and Patterson, A.V (2007). Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: a role for cytochrome P450 reductase under hypoxia. Biochem Pharmacol 74, 810-820.
    • (2007) Biochem Pharmacol , vol.74 , pp. 810-820
    • Guise, C.P.1    Wang, A.T.2    Theil, A.3    Bridewell, D.J.4    Wilson, W.R.5    Patterson, A.V.6
  • 5
    • 1942424798 scopus 로고    scopus 로고
    • 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT
    • Helsby NA, Ferry DM, Patterson AV, Pullen SM, and Wilson WR (2004) 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT. Br J Cancer 90:1084-1092.
    • (2004) Br J Cancer , vol.90 , pp. 1084-1092
    • Helsby, N.A.1    Ferry, D.M.2    Patterson, A.V.3    Pullen, S.M.4    Wilson, W.R.5
  • 6
    • 0037399470 scopus 로고    scopus 로고
    • Effect of nitroreduction on the alkylating reactivity and cytotoxicity of the 2,4-dinitrobenzamide-5-aziridine CB 1954 and the corresponding nitrogen mustard SN 23862: Distinct mechanisms of bioreductive activation
    • Helsby NA, Wheeler SJ, Pruijn FB, Palmer BD, Yang S, Denny WA, and Wilson WR (2003) Effect of nitroreduction on the alkylating reactivity and cytotoxicity of the 2,4-dinitrobenzamide-5-aziridine CB 1954 and the corresponding nitrogen mustard SN 23862: distinct mechanisms of bioreductive activation. Chem Res Toxicol 16:469-478.
    • (2003) Chem Res Toxicol , vol.16 , pp. 469-478
    • Helsby, N.A.1    Wheeler, S.J.2    Pruijn, F.B.3    Palmer, B.D.4    Yang, S.5    Denny, W.A.6    Wilson, W.R.7
  • 7
    • 0141790765 scopus 로고    scopus 로고
    • Studies on the nitroreductase prodrug-activating system: Crystal structures of complexes with the inhibitor dicoumarol and dinitrobenzamide prodrugs and of the enzyme active form
    • Johansson E, Parkinson GN, Denny WA, and Neidle S (2003) Studies on the nitroreductase prodrug-activating system: crystal structures of complexes with the inhibitor dicoumarol and dinitrobenzamide prodrugs and of the enzyme active form. J Med Chem 46:4009-4020.
    • (2003) J Med Chem , vol.46 , pp. 4009-4020
    • Johansson, E.1    Parkinson, G.N.2    Denny, W.A.3    Neidle, S.4
  • 8
    • 0033729429 scopus 로고    scopus 로고
    • Pharmacokinetics and metabolism of the nitrogen mustard bioreductive drug 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (SN 23862) and the corresponding aziridine (CB 1954) in KHT tumourbearing mice
    • Kestell P, Pruijn FB, Siim BG, Palmer BD, and Wilson WR (2000) Pharmacokinetics and metabolism of the nitrogen mustard bioreductive drug 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (SN 23862) and the corresponding aziridine (CB 1954) in KHT tumourbearing mice. Cancer Chemother Pharmacol 46:365-374.
    • (2000) Cancer Chemother Pharmacol , vol.46 , pp. 365-374
    • Kestell, P.1    Pruijn, F.B.2    Siim, B.G.3    Palmer, B.D.4    Wilson, W.R.5
  • 9
    • 0029929547 scopus 로고    scopus 로고
    • The involvement of cytochrome P4502E1 in 2-bromoethanol-induced hepatocyte cytotoxicity
    • Khan S, Sood C, and O'Brien PJ (1996) The involvement of cytochrome P4502E1 in 2-bromoethanol-induced hepatocyte cytotoxicity. Pharmacol Toxicol 78:241-248.
    • (1996) Pharmacol Toxicol , vol.78 , pp. 241-248
    • Khan, S.1    Sood, C.2    O'Brien, P.J.3
  • 11
    • 0028916689 scopus 로고
    • Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino] -2,4-dinitrobenzamide
    • Palmer BD, van Zijl P, Denny WA, and Wilson WR (1995) Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino] -2,4-dinitrobenzamide. J Med Chem 38:1229-1241.
    • (1995) J Med Chem , vol.38 , pp. 1229-1241
    • Palmer, B.D.1    van Zijl, P.2    Denny, W.A.3    Wilson, W.R.4
  • 12
    • 0026665360 scopus 로고
    • Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells
    • Palmer BD, Wilson WR, Cliffe S, and Denny WA (1992) Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells. J Med Chem 35:3214-3222.
    • (1992) J Med Chem , vol.35 , pp. 3214-3222
    • Palmer, B.D.1    Wilson, W.R.2    Cliffe, S.3    Denny, W.A.4
  • 13
    • 0025021102 scopus 로고
    • Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines
    • Palmer BD, Wilson WR, Pullen SM, and Denny WA (1990) Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines. J Med Chem 33:112-121.
    • (1990) J Med Chem , vol.33 , pp. 112-121
    • Palmer, B.D.1    Wilson, W.R.2    Pullen, S.M.3    Denny, W.A.4
  • 14
    • 34548140058 scopus 로고    scopus 로고
    • Analysis of the hypoxia-activated dinitrobenzamide mustard phosphate pre-preprodrug PR-104 and its alcohol metabolite PR-104A in plasma and tissues by liquid chromatography-mass spectrometry
    • Patel, K, Lewiston D, Gu Y, Hicks KO, and Wilson WR (2007) Analysis of the hypoxia-activated dinitrobenzamide mustard phosphate pre-preprodrug PR-104 and its alcohol metabolite PR-104A in plasma and tissues by liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 856:302-311.
    • (2007) J Chromatogr B Analyt Technol Biomed Life Sci , vol.856 , pp. 302-311
    • Patel, K.1    Lewiston, D.2    Gu, Y.3    Hicks, K.O.4    Wilson, W.R.5
  • 16
    • 0031306972 scopus 로고    scopus 로고
    • Nitro reduction as an electronic switch for bioreductive drug activation
    • Siim BG, Denny WA, and Wilson WR (1997) Nitro reduction as an electronic switch for bioreductive drug activation. Oncol Res 9:357-369.
    • (1997) Oncol Res , vol.9 , pp. 357-369
    • Siim, B.G.1    Denny, W.A.2    Wilson, W.R.3
  • 18
    • 0027431867 scopus 로고
    • Molecular mechanisms of chloroacetaldehyde- induced cytotoxicity in isolated rat hepatocytes
    • Sood C and O'Brien PJ (1993) Molecular mechanisms of chloroacetaldehyde- induced cytotoxicity in isolated rat hepatocytes. Biochem Pharmacol 46:1621-1626.
    • (1993) Biochem Pharmacol , vol.46 , pp. 1621-1626
    • Sood, C.1    O'Brien, P.J.2
  • 19
    • 0031041912 scopus 로고    scopus 로고
    • Ifosfamide metabolite chloroacetaldehyde causes renal dysfunction in vivo
    • Springate JE (1997) Ifosfamide metabolite chloroacetaldehyde causes renal dysfunction in vivo. J Appl Toxicol 17:75-79.
    • (1997) J Appl Toxicol , vol.17 , pp. 75-79
    • Springate, J.E.1
  • 20
    • 28244460232 scopus 로고    scopus 로고
    • Aerobic 2- and 4-nitroreduction of CB 1954 by human liver
    • Tang MHY, Helsby NA, Wilson WR, and Tingle MD (2005) Aerobic 2- and 4-nitroreduction of CB 1954 by human liver. Toxicology 216:129-139.
    • (2005) Toxicology , vol.216 , pp. 129-139
    • Tang, M.H.Y.1    Helsby, N.A.2    Wilson, W.R.3    Tingle, M.D.4
  • 21
    • 0028943138 scopus 로고
    • Hypoxia-selective antitumor agents. 11. Chlorambucil N-oxide: A reappraisal of its synthesis, stability, and selective toxicity for hypoxic cells
    • Tercel M, Wilson WR, and Denny WA (1995) Hypoxia-selective antitumor agents. 11. Chlorambucil N-oxide: a reappraisal of its synthesis, stability, and selective toxicity for hypoxic cells. J Med Chem 38:1247-1252.
    • (1995) J Med Chem , vol.38 , pp. 1247-1252
    • Tercel, M.1    Wilson, W.R.2    Denny, W.A.3
  • 22
    • 33847375101 scopus 로고    scopus 로고
    • Glucuronidation of anti-HIV drug candidate bevirimat: Identification of human UDP-glucuronosyltransferases and species differences
    • Wen Z, Martin DE, Bullock P, Lee, K-H, and Smith PC (2007) Glucuronidation of anti-HIV drug candidate bevirimat: identification of human UDP-glucuronosyltransferases and species differences. Drug Metab Dispos 35:440-448.
    • (2007) Drug Metab Dispos , vol.35 , pp. 440-448
    • Wen, Z.1    Martin, D.E.2    Bullock, P.3    Lee, K.-H.4    Smith, P.C.5
  • 24
    • 33947621321 scopus 로고    scopus 로고
    • Bystander effects of bioreductive drugs: Potential for exploiting pathological tumor hypoxia with dinitrobenzamide mustards
    • Wilson WR, Hicks KO, Pullen SM, Ferry DM, Helsby NA, and Patterson AV (2007) Bystander effects of bioreductive drugs: potential for exploiting pathological tumor hypoxia with dinitrobenzamide mustards. Radiat Res 167:625-636.
    • (2007) Radiat Res , vol.167 , pp. 625-636
    • Wilson, W.R.1    Hicks, K.O.2    Pullen, S.M.3    Ferry, D.M.4    Helsby, N.A.5    Patterson, A.V.6
  • 25
    • 0036494169 scopus 로고    scopus 로고
    • Quantitation of bystander effects in nitroreductase suicide gene therapy using three-dimensional cell cultures
    • Wilson WR, Pullen SM, Hogg A, Helsby NA, Hicks KO, and Denny WA (2002) Quantitation of bystander effects in nitroreductase suicide gene therapy using three-dimensional cell cultures. Cancer Res 62:1425-1432.
    • (2002) Cancer Res , vol.62 , pp. 1425-1432
    • Wilson, W.R.1    Pullen, S.M.2    Hogg, A.3    Helsby, N.A.4    Hicks, K.O.5    Denny, W.A.6
  • 26
    • 0033673590 scopus 로고    scopus 로고
    • Identification of the human liver cytochrome P450 isoenzyme responsible for the 6-methylhydroxylation of the novel anticancer drug 5,6-dimethylxanthenone-4-acetic acid
    • Zhou S, Paxton JW, Tingle MD, and Kestell P (2000) Identification of the human liver cytochrome P450 isoenzyme responsible for the 6-methylhydroxylation of the novel anticancer drug 5,6-dimethylxanthenone-4-acetic acid. Drug Metab Dispos 28:1449 -1456.
    • (2000) Drug Metab Dispos , vol.28 , pp. 1449-1456
    • Zhou, S.1    Paxton, J.W.2    Tingle, M.D.3    Kestell, P.4


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