메뉴 건너뛰기




Volumn 22, Issue 6, 1999, Pages 533-541

Metabolism-based anticancer drug design

Author keywords

Bioreduction; Cyclophosphamide; Prodrugs; Sulfoxide; Tirapazamine

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOPHOSPHAMIDE; PRODRUG;

EID: 0033254605     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02975322     Document Type: Article
Times cited : (8)

References (90)
  • 2
    • 0343591988 scopus 로고
    • Nitrogen mustard N-oxide and its effects on the Yoshida sarcoma
    • Japan
    • Aiko, I., Owari, S and Torigoe, M., Nitrogen mustard N-oxide and its effects on the Yoshida sarcoma. J. Pharm. Soc. (Japan), 72, 1297-1300 (1952).
    • (1952) J. Pharm. Soc. , vol.72 , pp. 1297-1300
    • Aiko, I.1    Owari, S.2    Torigoe, M.3
  • 3
    • 0021187591 scopus 로고
    • Comparative in vitro cytotoxicity of cyclophosphamide, its major active metabolites and the new oxazaphosphorine ASTA Z 7557 (INN mafosfamide)
    • Alberts, D. S., Einspahr, J. G., Struck, R. F., Bignami, G., Young, L., Surwit, E. A. and Salmon, S. E., Comparative in vitro cytotoxicity of cyclophosphamide, its major active metabolites and the new oxazaphosphorine ASTA Z 7557 (INN mafosfamide). Inv. New Drugs, 2, 141-148 (1984).
    • (1984) Inv. New Drugs , vol.2 , pp. 141-148
    • Alberts, D.S.1    Einspahr, J.G.2    Struck, R.F.3    Bignami, G.4    Young, L.5    Surwit, E.A.6    Salmon, S.E.7
  • 5
    • 0009725395 scopus 로고
    • Enzymatic reduction of methionine sulfoxide. In vitro experiments with rat liver and kidney
    • Aymard, C., Seyer, L. and Cheftel, J., Enzymatic reduction of methionine sulfoxide. In vitro experiments with rat liver and kidney. Agric. Biol. Chem., 43, 1869-1872 (1979).
    • (1979) Agric. Biol. Chem. , vol.43 , pp. 1869-1872
    • Aymard, C.1    Seyer, L.2    Cheftel, J.3
  • 6
    • 0025931950 scopus 로고
    • Synthesis and Antitumor Properties of Activated Cyclophosphamide Analogues
    • Borch, R. F. and Canute, G. W., Synthesis and Antitumor Properties of Activated Cyclophosphamide Analogues. J. Med. Chem., 34, 3044-3052 (1991).
    • (1991) J. Med. Chem. , vol.34 , pp. 3044-3052
    • Borch, R.F.1    Canute, G.W.2
  • 7
    • 0025930682 scopus 로고
    • Synthesis, activation and cytotoxicity of aldophosphamide analogues
    • Borch, R.F. and Valente R.R., Synthesis, activation and cytotoxicity of aldophosphamide analogues. J. Med. Chem., 34, 3052-3058 (1991).
    • (1991) J. Med. Chem. , vol.34 , pp. 3052-3058
    • Borch, R.F.1    Valente, R.R.2
  • 8
    • 0018897309 scopus 로고
    • Synthesis and Antitumor Activity of Cyclophosphamide Analogues. 3. Preparation, Molecular Structure Determination, and Anticancer Screening of Racemic cis- and trans-4-Phenylcyclophosphamide
    • Boyd, V. L., Zon, G., Himes, V. L., Stalick, J. K., Mighell, A. D. and Secor, H. V., Synthesis and Antitumor Activity of Cyclophosphamide Analogues. 3. Preparation, Molecular Structure Determination, and Anticancer Screening of Racemic cis- and trans-4-Phenylcyclophosphamide. J. Med. Chem., 23, 372-375 (1980).
    • (1980) J. Med. Chem. , vol.23 , pp. 372-375
    • Boyd, V.L.1    Zon, G.2    Himes, V.L.3    Stalick, J.K.4    Mighell, A.D.5    Secor, H.V.6
  • 9
    • 0017140119 scopus 로고
    • Comparative pharmacologic study in vitro and in vivo with cyclophosphamide (NSC-26271), cyclophosphamide metabolites, and plain nitrogen mustard compounds
    • Brock, N., Comparative pharmacologic study in vitro and in vivo with cyclophosphamide (NSC-26271), cyclophosphamide metabolites, and plain nitrogen mustard compounds. Cancer Treat. Rep., 60, 301-307 (1976).
    • (1976) Cancer Treat. Rep. , vol.60 , pp. 301-307
    • Brock, N.1
  • 10
    • 0017346430 scopus 로고
    • The problem of specificity and selectivity of alkylating cytostaticis: Studies on N-2-chloroethylamido-oxazaphosphorines
    • Brock, N. and Hohorst, H. J., The problem of specificity and selectivity of alkylating cytostaticis: Studies on N-2-chloroethylamido-oxazaphosphorines. Zeitschr. Krebsforsch. Klin. Onkol., 88, 185-215 (1977).
    • (1977) Zeitschr. Krebsforsch. Klin. Onkol. , vol.88 , pp. 185-215
    • Brock, N.1    Hohorst, H.J.2
  • 11
    • 0000349218 scopus 로고    scopus 로고
    • Tumor hypoxia: Problems and opportunities
    • Bertino, J. R. Ed.; Academic Press: San Diego, Lontoa
    • Brown, J. M., Tumor hypoxia: problems and opportunities. In Encyclopedia of Cancer, Volume III; Bertino, J. R. Ed.; Academic Press: San Diego, Lontoa; pp 1883-1898, 1997.
    • (1997) Encyclopedia of Cancer , vol.3 , pp. 1883-1898
    • Brown, J.M.1
  • 12
    • 0021805337 scopus 로고
    • Phase-l Study of Mafosfamide-Cyclohexylamine (ASTA-Z-7557, NSC 345842) and Limited Phase-l Data on Mafosfamide-Lysine
    • Bruntsch, U., Groos, G., Hiller, T. A., Wandt, H., Tigges, F.-J. and Gallmeier, W. M., Phase-l Study of Mafosfamide-Cyclohexylamine (ASTA-Z-7557, NSC 345842) and Limited Phase-l Data on Mafosfamide-Lysine. Invest. New Drugs, 3, 293-296 (1985).
    • (1985) Invest. New Drugs , vol.3 , pp. 293-296
    • Bruntsch, U.1    Groos, G.2    Hiller, T.A.3    Wandt, H.4    Tigges, F.-J.5    Gallmeier, W.M.6
  • 14
    • 0014024073 scopus 로고
    • Cure of mice bearing advanced plasma cell tumors with aniline mustard: The relationship between glucurinidase activity and tumor sensitivity
    • Connors, T. A. and Whisson, M.E., Cure of mice bearing advanced plasma cell tumors with aniline mustard: The relationship between glucurinidase activity and tumor sensitivity. Nature, 210, 866-867 (1966).
    • (1966) Nature , vol.210 , pp. 866-867
    • Connors, T.A.1    Whisson, M.E.2
  • 16
    • 0015968586 scopus 로고
    • Some studies of the active intermediates formed in the microsomal metabolism of cyclophosphamide and isophosphamide
    • Connors, T. A., Cox, P. J., Farmer, P. B., Foster, A. B.and Jarman, M., Some studies of the active intermediates formed in the microsomal metabolism of cyclophosphamide and isophosphamide. Biochem. Pharmacol., 23, 115-129 (1974).
    • (1974) Biochem. Pharmacol. , vol.23 , pp. 115-129
    • Connors, T.A.1    Cox, P.J.2    Farmer, P.B.3    Foster, A.B.4    Jarman, M.5
  • 17
    • 21044439834 scopus 로고
    • Reinhoudt, D. N.; Connors, T. A.; Pinedo, H. M.; van den Poll, K. W., Eds.; The Hague: Martinus Nijhoff
    • Connors, T. A., In "Structure-activity Relationships of Anti-tumour Agents"; Reinhoudt, D. N.; Connors, T. A.; Pinedo, H. M.; van den Poll, K. W., Eds.; The Hague: Martinus Nijhoff,; pp 47-57 (1983).
    • (1983) Structure-activity Relationships of Anti-tumour Agents , pp. 47-57
    • Connors, T.A.1
  • 18
    • 0026539267 scopus 로고
    • Mechanistic studies of enhanced in vitro radiosensitization and hypoxic cell cytotoxicity by targeting radiosensitizers to DNA via intercalation
    • Cowan, D. S. M., Kanagasabapathy, V. M., McClelland, R. A. and Rauth, A. M., Mechanistic studies of enhanced in vitro radiosensitization and hypoxic cell cytotoxicity by targeting radiosensitizers to DNA via intercalation. Int. J. Radiation Oncology Biol. Phys., 22, 541-544 (1992).
    • (1992) Int. J. Radiation Oncology Biol. Phys. , vol.22 , pp. 541-544
    • Cowan, D.S.M.1    Kanagasabapathy, V.M.2    McClelland, R.A.3    Rauth, A.M.4
  • 19
    • 0018749594 scopus 로고
    • Cyclophosphamide cystitis-identification of acrolein as the causative agent
    • Cox, P. J., Cyclophosphamide cystitis-identification of acrolein as the causative agent. Biochem. Pharmacol., 28, 2045-2049 (1979).
    • (1979) Biochem. Pharmacol. , vol.28 , pp. 2045-2049
    • Cox, P.J.1
  • 20
    • 0022349983 scopus 로고
    • Sulindac oxidation/ reduction by microbial cultures; microbial models for mammalian metabolism
    • Davis, P. J. and Guenthner, L. E., Sulindac oxidation/ reduction by microbial cultures; microbial models for mammalian metabolism. Xenobiotica, 15, 845-857 (1985).
    • (1985) Xenobiotica , vol.15 , pp. 845-857
    • Davis, P.J.1    Guenthner, L.E.2
  • 21
    • 0022535929 scopus 로고
    • Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic tumor cells
    • Denny, W. A. and Wilson, W. R., Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic tumor cells. J. Med. Chem., 29 (6), 879-887 (1986).
    • (1986) J. Med. Chem. , vol.29 , Issue.6 , pp. 879-887
    • Denny, W.A.1    Wilson, W.R.2
  • 22
    • 0025274372 scopus 로고
    • Hypoxia-selective antitumor agents: 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: the "lminoacridan Hypothesis."
    • Denny, W. A., Atwell, G. J., Anderson, R. F. and Wilson, W. R., Hypoxia-selective antitumor agents: 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: The "lminoacridan Hypothesis." J. Med. Chem., 33, 1288-1295 (1990).
    • (1990) J. Med. Chem. , vol.33 , pp. 1288-1295
    • Denny, W.A.1    Atwell, G.J.2    Anderson, R.F.3    Wilson, W.R.4
  • 24
    • 0018843531 scopus 로고
    • Kinetics of Cyclophosphamide biotransformation in vivo
    • Domeyer, B. E. and Sladek, N. E., Kinetics of Cyclophosphamide biotransformation in vivo. Cancer Res., 40, 174-180 (1980).
    • (1980) Cancer Res. , vol.40 , pp. 174-180
    • Domeyer, B.E.1    Sladek, N.E.2
  • 25
    • 0017063480 scopus 로고
    • Deactivation of cyclophosphamide (NSC-26271) metabolites by sulfhydryl compounds
    • Draeger, U., Peter, G. and Hohorst, H. J., Deactivation of cyclophosphamide (NSC-26271) metabolites by sulfhydryl compounds. Cancer Treat. Rep., 60, 355-359 (1976).
    • (1976) Cancer Treat. Rep. , vol.60 , pp. 355-359
    • Draeger, U.1    Peter, G.2    Hohorst, H.J.3
  • 27
    • 0020333289 scopus 로고
    • 31P NMR kinetic studies of the intra- and intermolecular alkylation chemistry of phosphoramide mustard and cognate N-phosphorylated derivatives of N,N-bis(2-chloroethyl) amine
    • 31P NMR kinetic studies of the intra- and intermolecular alkylation chemistry of phosphoramide mustard and cognate N-phosphorylated derivatives of N,N-bis(2-chloroethyl) amine. J. Med. Chem., 25, 1347-1357 (1982).
    • (1982) J. Med. Chem. , vol.25 , pp. 1347-1357
    • Engel, T.W.1    Zon, G.2    Egan, W.3
  • 29
    • 0025951037 scopus 로고
    • Nitroheterocycle reduction as a paradigm for intramolecular catalysis of drug delivery to hypoxic cells
    • Firestone, A., Mulcahy, R. T. and Borch, R. F., Nitroheterocycle reduction as a paradigm for intramolecular catalysis of drug delivery to hypoxic cells. J. Med. Chem., 34, 2933-2935 (1991).
    • (1991) J. Med. Chem. , vol.34 , pp. 2933-2935
    • Firestone, A.1    Mulcahy, R.T.2    Borch, R.F.3
  • 30
    • 0017115559 scopus 로고
    • Cyclophosphamide (NSC-26271)-related phosphoramide mustards-recent advances and historical perspective
    • Friedman, O. M., Wodinsky, I. and Myles, A., Cyclophosphamide (NSC-26271)-related phosphoramide mustards-recent advances and historical perspective. Cancer Treat. Rep., 60, 337-346 (1976).
    • (1976) Cancer Treat. Rep. , vol.60 , pp. 337-346
    • Friedman, O.M.1    Wodinsky, I.2    Myles, A.3
  • 31
    • 0345670711 scopus 로고
    • Histochemical demonstration of sites of phosphoramidase activity
    • Gomori, G., Histochemical demonstration of sites of phosphoramidase activity. Proc Soc Exp Biol Med, 69, 407-409 (1948).
    • (1948) Proc Soc Exp Biol Med , vol.69 , pp. 407-409
    • Gomori, G.1
  • 32
    • 0022358539 scopus 로고
    • Binding of metabolites of cyclophosphamide to DNA in a rat liver microsomal system and in vivo in mice
    • Hemminki, K., Binding of metabolites of cyclophosphamide to DNA in a rat liver microsomal system and in vivo in mice. Cancer Res., 45, 4237-4243 (1985).
    • (1985) Cancer Res. , vol.45 , pp. 4237-4243
    • Hemminki, K.1
  • 33
    • 0021722034 scopus 로고
    • Role of aldehyde dehydrogenase in cyclophosphamide-resistant L1210 leukemia
    • Hilton, J., Role of aldehyde dehydrogenase in cyclophosphamide-resistant L1210 leukemia. Cancer Res., 44, 5156-5160 (1984).
    • (1984) Cancer Res. , vol.44 , pp. 5156-5160
    • Hilton, J.1
  • 34
    • 0019442713 scopus 로고
    • Role of aldehyde dehydrogenase in the metabolism-dependent biological activity of cyclophosphamide
    • Hipkens, J. H., Struck, R. F. and Gurtoo, H. L., Role of aldehyde dehydrogenase in the metabolism-dependent biological activity of cyclophosphamide. Cancer Res., 41, 3571-3583 (1981).
    • (1981) Cancer Res. , vol.41 , pp. 3571-3583
    • Hipkens, J.H.1    Struck, R.F.2    Gurtoo, H.L.3
  • 35
    • 0018143999 scopus 로고
    • Quantitation by gas chromatography-chemical ionization mass spectrometry of cyclophosphamide, phosphoramide mustard, and nornitrogen mustard in the plasma and urine of patients receiving cyclophosphamide therapy
    • Jardine, I., Fenselau, C., Appler, M., Kan, M. -N., Brundrett, R. B. and Colvin, M., Quantitation by gas chromatography-chemical ionization mass spectrometry of cyclophosphamide, phosphoramide mustard, and nornitrogen mustard in the plasma and urine of patients receiving cyclophosphamide therapy. Cancer Res., 38, 408-415 (1978).
    • (1978) Cancer Res. , vol.38 , pp. 408-415
    • Jardine, I.1    Fenselau, C.2    Appler, M.3    Kan, M.N.4    Brundrett, R.B.5    Colvin, M.6
  • 37
    • 0020713095 scopus 로고
    • A sulfoxide-reducing enzyme system consisting of aldehyde oxidase and xanthine oxidase - A new electron transfer system
    • Kitamura, S. and Tatsumi, K., A sulfoxide-reducing enzyme system consisting of aldehyde oxidase and xanthine oxidase - a new electron transfer system. Chem. Pharm. Bull. (Japan), 31(2), 760-763 (1983).
    • (1983) Chem. Pharm. Bull. (Japan) , vol.31 , Issue.2 , pp. 760-763
    • Kitamura, S.1    Tatsumi, K.2
  • 38
    • 0023094045 scopus 로고
    • Activation Mechanisms of Mafosfamide and the Role of Thiols in Cyclophosphamide Metabolism
    • won, C.-H., Borch, R. F., Engel, J. and Niemeyer, U., Activation Mechanisms of Mafosfamide and the Role of Thiols in Cyclophosphamide Metabolism. J. Med. Chem., 30, 395-399 (1987).
    • (1987) J. Med. Chem. , vol.30 , pp. 395-399
    • Won, C.-H.1    Borch, R.F.2    Engel, J.3    Niemeyer, U.4
  • 39
    • 0025981529 scopus 로고
    • Chemically stable, lipophilic prodrugs of phosphoramide mustard as potential anticancer agents
    • Kwon, C.-H., Moon, K.-Y., Baturay, N. and Shirota, F. N., Chemically stable, lipophilic prodrugs of phosphoramide mustard as potential anticancer agents. J. Med. Chem., 34, 588-592 (1991).
    • (1991) J. Med. Chem. , vol.34 , pp. 588-592
    • Kwon, C.-H.1    Moon, K.-Y.2    Baturay, N.3    Shirota, F.N.4
  • 40
    • 0026721021 scopus 로고
    • p-(Methyl-sulfinyl)phenyl nitrogen mustard as a novel bioreductive prodrug selective against hypoxic tumors
    • Kwon, C. -H., Blanco, D. R. and Baturay, N., p-(Methyl-sulfinyl)phenyl nitrogen mustard as a novel bioreductive prodrug selective against hypoxic tumors. J. Med. Chem., 35, 2137-2139 (1992).
    • (1992) J. Med. Chem. , vol.35 , pp. 2137-2139
    • Kwon, C.H.1    Blanco, D.R.2    Baturay, N.3
  • 41
    • 21044439069 scopus 로고    scopus 로고
    • Manuscripts in preparation 1999b
    • Kwon, C. -H. Manuscripts in preparation (1999a and 1999b).
    • (1999)
    • Kwon, C.H.1
  • 42
    • 0030018650 scopus 로고    scopus 로고
    • The effect of tirapazamine (SR-4233) alone or combined with chemotherapeutic agents on xenografted human tumours
    • Lartigau, E. and Guichard, M., The effect of tirapazamine (SR-4233) alone or combined with chemotherapeutic agents on xenografted human tumours. British Journal of Cancer, 73, 1480-1485 (1996).
    • (1996) British Journal of Cancer , vol.73 , pp. 1480-1485
    • Lartigau, E.1    Guichard, M.2
  • 43
    • 0029049802 scopus 로고
    • Sulphoxide reduction by rat and rabbit tissues in vitro
    • Lee, S. C. and Renwick, A. G., Sulphoxide reduction by rat and rabbit tissues in vitro. Biochem. Pharmacol., 49, 1557-1565 (1995).
    • (1995) Biochem. Pharmacol. , vol.49 , pp. 1557-1565
    • Lee, S.C.1    Renwick, A.G.2
  • 44
    • 0020070463 scopus 로고
    • Conversion of 4-hydroperoxycyclophosphamide and 4-hydroxycyclophosphamide to phosphoramide mustard and acrolein mediated by bifunctional catalysts
    • Low, J. E., Borch, R. F. and Sladek, N. E., Conversion of 4-hydroperoxycyclophosphamide and 4-hydroxycyclophosphamide to phosphoramide mustard and acrolein mediated by bifunctional catalysts. Cancer Res., 42, 830-837 (1982).
    • (1982) Cancer Res. , vol.42 , pp. 830-837
    • Low, J.E.1    Borch, R.F.2    Sladek, N.E.3
  • 45
    • 0022474778 scopus 로고
    • Synthesis and Antitumor Activity of Cyclophosphamide Analogues. 4. Preparation, Kinetics Studies, and Anticancer Screening of "Phenylketophosphamide" and Similar Compounds Related to the Cyclophosphamide Metabolite Aldophosphamide
    • Ludeman, S. M., Boyd, V. L., Regan, J. B., Gallo, K. A., Zon, G. and Ishii, K., Synthesis and Antitumor Activity of Cyclophosphamide Analogues. 4. Preparation, Kinetics Studies, and Anticancer Screening of "Phenylketophosphamide" and Similar Compounds Related to the Cyclophosphamide Metabolite Aldophosphamide. J. Med. Chem., 29, 716-727 (1986).
    • (1986) J. Med. Chem. , vol.29 , pp. 716-727
    • Ludeman, S.M.1    Boyd, V.L.2    Regan, J.B.3    Gallo, K.A.4    Zon, G.5    Ishii, K.6
  • 49
    • 0028935417 scopus 로고
    • Chemically Stable N-Methyl-4-(alkylthio) cyclophosphamide Derivatives as Prodrugs of 4-Hydroxycyclophosphamide
    • Moon, K. -Y., Shirota, F. N., Baturay, N. and Kwon, C. -H., Chemically Stable N-Methyl-4-(alkylthio) cyclophosphamide Derivatives as Prodrugs of 4-Hydroxycyclophosphamide J. Med. Chem., 38, 848-851 (1995).
    • (1995) J. Med. Chem. , vol.38 , pp. 848-851
    • Moon, K.Y.1    Shirota, F.N.2    Baturay, N.3    Kwon, C.H.4
  • 50
    • 0032493193 scopus 로고    scopus 로고
    • 3-Methyl-Mafosfamide as a Chemically Stable, Alternative Prodrug of Mafosfamide
    • 3-Methyl-Mafosfamide as a Chemically Stable, Alternative Prodrug of Mafosfamide. Bioorg Med. Chem. Letters, 8: 1673-1678, (1998).
    • (1998) Bioorg Med. Chem. Letters , vol.8 , pp. 1673-1678
    • Moon, K.Y.1    Kwon, C.H.2
  • 51
    • 0023104247 scopus 로고
    • Mitomycin analogues, I. Indoloquinones as (potential) bisalkylating agents
    • Oostveen, E. A. and Speckamp, W. N., Mitomycin analogues, I. Indoloquinones as (potential) bisalkylating agents. Tetrahedron, 43, 255-262 (1987).
    • (1987) Tetrahedron , vol.43 , pp. 255-262
    • Oostveen, E.A.1    Speckamp, W.N.2
  • 52
    • 0025606616 scopus 로고
    • Nitro analogues of chlorambucil as potential hypoxia-selective anti-tumor drugs
    • Palmer, B. D., Wilson, W. R. and Denny, W. A., Nitro analogues of chlorambucil as potential hypoxia-selective anti-tumor drugs. Anti-cancer Drug Design, 5, 337-349 (1990a).
    • (1990) Anti-cancer Drug Design , vol.5 , pp. 337-349
    • Palmer, B.D.1    Wilson, W.R.2    Denny, W.A.3
  • 53
    • 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, B. D., Wilson, W. R., Pullen, S. M. and Denny, W. A., 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 (1990b).
    • (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
  • 54
    • 0026665360 scopus 로고
    • Hypoxia-slective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells
    • Palmer, B. D., Wilson, W. R., Cliffe, S. and Denny, W. A., Hypoxia-slective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells. J. Med. Chem., 35, 3214-3222 (1992).
    • (1992) J. Med. Chem. , vol.35 , pp. 3214-3222
    • Palmer, B.D.1    Wilson, W.R.2    Cliffe, S.3    Denny, W.A.4
  • 56
    • 0021227885 scopus 로고
    • Experimental Toxicology of ASTA Z 7557 (INN mafosfamide)
    • Pohl, J., Hilgard, P., Jahn, W. and Zechel, H. J., Experimental Toxicology of ASTA Z 7557 (INN mafosfamide). Invest. New Drugs, 2, 201-206 (1984).
    • (1984) Invest. New Drugs , vol.2 , pp. 201-206
    • Pohl, J.1    Hilgard, P.2    Jahn, W.3    Zechel, H.J.4
  • 57
    • 0022572076 scopus 로고
    • Pathogenesis of metastatic disease. Implications for current therapy and for the development of new therapeutic strategies
    • Poste, G., Pathogenesis of metastatic disease. Implications for current therapy and for the development of new therapeutic strategies. Cancer Treat. Rep., 70, 183-199 (1986).
    • (1986) Cancer Treat. Rep. , vol.70 , pp. 183-199
    • Poste, G.1
  • 58
    • 0020663027 scopus 로고
    • Cytotoxic activity relative to 4-hydroxycyclophosphamide and phosphoramide mustard concentrations in the plasma of cyclophosphamide-treated rats
    • Powers, J. F. and Sladek, N. E., Cytotoxic activity relative to 4-hydroxycyclophosphamide and phosphoramide mustard concentrations in the plasma of cyclophosphamide-treated rats. Cancer Res., 43, 1101-1106 (1983).
    • (1983) Cancer Res. , vol.43 , pp. 1101-1106
    • Powers, J.F.1    Sladek, N.E.2
  • 60
    • 0023902264 scopus 로고
    • Therapeutic attack of hypoxic cells of solid tumors: Presidential Address
    • Sartorelli, A. C., Therapeutic attack of hypoxic cells of solid tumors: Presidential Address. Cancer Res., 48, 775-778 (1988).
    • (1988) Cancer Res. , vol.48 , pp. 775-778
    • Sartorelli, A.C.1
  • 61
    • 0030066696 scopus 로고    scopus 로고
    • Comparison of in vivo efficacy of hypoxic cytotoxin tirapazamine and hypoxic cell radiosensitizer KU-2285 in combination with single and fractinated irradiation
    • Shibata, T., Shibamoto, Y, Sasai, K., Oya, N., Murata, R., Takagi, T., Hiraoka, M. and Abe, M., Comparison of in vivo efficacy of hypoxic cytotoxin tirapazamine and hypoxic cell radiosensitizer KU-2285 in combination with single and fractinated irradiation Jpn. J. Cancer Res., 87, 98-104 (1996).
    • (1996) Jpn. J. Cancer Res. , vol.87 , pp. 98-104
    • Shibata, T.1    Shibamoto, Y.2    Sasai, K.3    Oya, N.4    Murata, R.5    Takagi, T.6    Hiraoka, M.7    Abe, M.8
  • 62
    • 0021864126 scopus 로고
    • Restoration of sensitivity to oxazaphosphorines by inhibitors of aldehyde dehydrogenase activity in cultured oxazaphosphorine-resistant L1210 and cross-linking agent-resistant P388 cell lines
    • Sladek, N. E. and Landkamer, G. J., Restoration of sensitivity to oxazaphosphorines by inhibitors of aldehyde dehydrogenase activity in cultured oxazaphosphorine-resistant L1210 and cross-linking agent-resistant P388 cell lines. Cancer Res., 45, 1549-1555 (1985).
    • (1985) Cancer Res. , vol.45 , pp. 1549-1555
    • Sladek, N.E.1    Landkamer, G.J.2
  • 63
    • 0021922114 scopus 로고
    • Collateral sensitivity to cross-linking agents exhibited by cultured L1210 cells resistant to oxazaphosphorines
    • Sladek, N. E., Low, J. E. and Landkamer, G. J., Collateral sensitivity to cross-linking agents exhibited by cultured L1210 cells resistant to oxazaphosphorines. Cancer Res., 45, 625-629 (1985).
    • (1985) Cancer Res. , vol.45 , pp. 625-629
    • Sladek, N.E.1    Low, J.E.2    Landkamer, G.J.3
  • 64
    • 0023945947 scopus 로고
    • Metabolism of oxazaphosphorines
    • Sladek, N. E., Metabolism of oxazaphosphorines. Pharmacol. Ther., 37, 301-355 (1988).
    • (1988) Pharmacol. Ther. , vol.37 , pp. 301-355
    • Sladek, N.E.1
  • 66
    • 0001358252 scopus 로고
    • Oxazaphosphorine-specific acquired cellular resistance
    • Teicher B.A., ed. New York: Marcel Dekker
    • Sladek, N. E., Oxazaphosphorine-specific acquired cellular resistance. In: Teicher B.A., ed. Drug Resistance in Oncology. New York: Marcel Dekker., pp. 375-410, 1993.
    • (1993) Drug Resistance in Oncology , pp. 375-410
    • Sladek, N.E.1
  • 67
    • 0021205291 scopus 로고
    • Mechanisms of DNA strand breakage and interstrand cross-linking by diaziridinylbenzoquinone (diaziquone) in isolated nuclei
    • Smigiero, L. and Kohn, K. W., Mechanisms of DNA strand breakage and interstrand cross-linking by diaziridinylbenzoquinone (diaziquone) in isolated nuclei. Cancer Res., 44, 4453-4457 (1984).
    • (1984) Cancer Res. , vol.44 , pp. 4453-4457
    • Smigiero, L.1    Kohn, K.W.2
  • 68
    • 21044443164 scopus 로고
    • Reduction of methionine sulfoxides by Escherichia coli
    • Sourkes, T. L. and Tano, Y., Reduction of methionine sulfoxides by Escherichia coli. Arch. Biochem. Biophys., 42, 321-326 (1953).
    • (1953) Arch. Biochem. Biophys. , vol.42 , pp. 321-326
    • Sourkes, T.L.1    Tano, Y.2
  • 69
    • 0000916698 scopus 로고
    • Cyclophosphamide and Its Congeners
    • Stec, W. J., Cyclophosphamide and Its Congeners. J. Organophosphorous Chem., 13, 145-174 (1982).
    • (1982) J. Organophosphorous Chem. , vol.13 , pp. 145-174
    • Stec, W.J.1
  • 71
    • 0016466370 scopus 로고
    • Isolation and mass spectral identification of blood metabolites of cyclophosphamide: Evidence for phosphoramide mustard as the biologically active metabolite
    • Struck, R. F., Kirk, M. C., Witt, M. H. and Laster, W. R. Jr., Isolation and mass spectral identification of blood metabolites of cyclophosphamide: Evidence for phosphoramide mustard as the biologically active metabolite. Biomed. Mass Specfrom., 2, 46-52 (1975).
    • (1975) Biomed. Mass Specfrom. , vol.2 , pp. 46-52
    • Struck, R.F.1    Kirk, M.C.2    Witt, M.H.3    Laster Jr., W.R.4
  • 72
    • 0020675066 scopus 로고
    • Isophosphoramide mustard, a metabolite of ifosfamide with activity against murine tumours comparable to cyclophosphamide
    • Struck, R. F., Dykes, D. J., Corbett, T. H., Suling, W. J. and Trader, M. W., Isophosphoramide mustard, a metabolite of ifosfamide with activity against murine tumours comparable to cyclophosphamide. Br. J. Cancer, 47, 15-26 (1983).
    • (1983) Br. J. Cancer , vol.47 , pp. 15-26
    • Struck, R.F.1    Dykes, D.J.2    Corbett, T.H.3    Suling, W.J.4    Trader, M.W.5
  • 74
    • 0020467177 scopus 로고
    • Involvement of liver aldehyde oxidase in sulfoxide reduction
    • Tatsumi, K., Kitamura, S. and Yamada, H., Involvement of liver aldehyde oxidase in sulfoxide reduction. Chem. Pharm. Bull. (Japan), 30(12), 4585-4588 (1982).
    • (1982) Chem. Pharm. Bull. (Japan) , vol.30 , Issue.12 , pp. 4585-4588
    • Tatsumi, K.1    Kitamura, S.2    Yamada, H.3
  • 75
    • 0003164090 scopus 로고
    • Glutathione-S-transferase and anticancer drug resistance
    • Wooley, P. V., Tew, K. D., Eds.; Academic Press: Orlando, FL
    • Tew, K. D. and Clapper, M. L., Glutathione-S-transferase and anticancer drug resistance. In Mechanism of Drug resistance in Neoplastic Cells; Wooley, P. V., Tew, K. D., Eds.; Academic Press: Orlando, FL; pp 141-159, 1987.
    • (1987) Mechanism of Drug Resistance in Neoplastic Cells , pp. 141-159
    • Tew, K.D.1    Clapper, M.L.2
  • 76
    • 0023123806 scopus 로고
    • Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA
    • Tomasz, M., Lipman, R., Chowdary, D., Pawlak, J., Verdine, G. L. and Nakanish, K., Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA. Science, 235, 1204-1208 (1987).
    • (1987) Science , vol.235 , pp. 1204-1208
    • Tomasz, M.1    Lipman, R.2    Chowdary, D.3    Pawlak, J.4    Verdine, G.L.5    Nakanish, K.6
  • 77
    • 0019769657 scopus 로고
    • Identification of three alkylated nucleotide adducts from the reaction of guanosine 5′-monophosphate with phosphoramide mustard
    • Vu, V. T., Fenselau, C. C. and Colvin, M. Identification of three alkylated nucleotide adducts from the reaction of guanosine 5′-monophosphate with phosphoramide mustard. J. Am. Chem. Soc., 103, 7362-7364 (1981).
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 7362-7364
    • Vu, V.T.1    Fenselau, C.C.2    Colvin, M.3
  • 78
    • 0024324086 scopus 로고
    • Molecular enzymology of the bioactivation of hypoxic cell cytotoxins
    • Walton, M. I., Wolf, C. R. and Workman, P., Molecular enzymology of the bioactivation of hypoxic cell cytotoxins. Int. J. Radiat. Oncol. Biol. Phys., 16, 983-986 (1989).
    • (1989) Int. J. Radiat. Oncol. Biol. Phys. , vol.16 , pp. 983-986
    • Walton, M.I.1    Wolf, C.R.2    Workman, P.3
  • 79
    • 0025284525 scopus 로고
    • Enzymology of the reductive bioactivation of SR 4233. A novel benzotriazine di-N-oxide hypoxic cell cytotoxin
    • Walton, M. I. and Workman, P., Enzymology of the reductive bioactivation of SR 4233. A novel benzotriazine di-N-oxide hypoxic cell cytotoxin. Biochem. Pharmacol., 39, 1735-1742 (1990).
    • (1990) Biochem. Pharmacol. , vol.39 , pp. 1735-1742
    • Walton, M.I.1    Workman, P.2
  • 80
    • 0026092707 scopus 로고
    • Aldophosphamide acetal diacetate and structural analogues: Synthesis and cytotoxicity studies
    • Wang, Y. and Farquhar, D., Aldophosphamide acetal diacetate and structural analogues: synthesis and cytotoxicity studies. J. Med. Chem., 34, 197-203 (1991).
    • (1991) J. Med. Chem. , vol.34 , pp. 197-203
    • Wang, Y.1    Farquhar, D.2
  • 82
    • 0024427760 scopus 로고
    • Reduction of nitromin to nitrogen mustard: Unsceduled DNA synthesis in aerobic or anaerobic rat hepatocytes, JB1, BL8 and Walker carcinoma cell lines
    • White I. N. H., Suzanger, M., Mattocks, A. R., Bailey, E., Farmer, P. B. and Conners, T. A., Reduction of nitromin to nitrogen mustard: unsceduled DNA synthesis in aerobic or anaerobic rat hepatocytes, JB1, BL8 and Walker carcinoma cell lines. Carcinogenesis, 10, 2113 (1989).
    • (1989) Carcinogenesis , vol.10 , pp. 2113
    • White, I.N.H.1    Suzanger, M.2    Mattocks, A.R.3    Bailey, E.4    Farmer, P.B.5    Conners, T.A.6
  • 83
    • 0024491246 scopus 로고
    • Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine
    • Wilson, W. R., Anderson, R. F. and Denny, W. A., Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine. J. Med. Chem., 32, 23-30 (1989a).
    • (1989) J. Med. Chem. , vol.32 , pp. 23-30
    • Wilson, W.R.1    Anderson, R.F.2    Denny, W.A.3
  • 84
    • 0024529829 scopus 로고
    • Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicty and metabolic stability of nitracrine derivatives
    • Wilson, W. R., Thompson, L. H., Anderson, R. F. and Denny, W. A., Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicty and metabolic stability of nitracrine derivatives. J. Med. Chem., 32, 31-38 (1989b).
    • (1989) J. Med. Chem. , vol.32 , pp. 31-38
    • Wilson, W.R.1    Thompson, L.H.2    Anderson, R.F.3    Denny, W.A.4
  • 85
    • 0002563124 scopus 로고
    • Enzyme-directed bioreductive drug development
    • Adams, G. E.; Breccia, A.; Fielden, E. M.; Wardman, R eds., New York, NY, Plenum
    • Workman, P. and Walton, M. I., Enzyme-directed bioreductive drug development In "Selective activation of drugs by redox process", Adams, G. E.; Breccia, A.; Fielden, E. M.; Wardman, R eds., New York, NY, Plenum; pp. 173-191, 1991.
    • (1991) Selective Activation of Drugs by Redox Process , pp. 173-191
    • Workman, P.1    Walton, M.I.2
  • 87
    • 0019180231 scopus 로고
    • Does acrolein contribute to the cytotoxicity of cyclophosphamide?
    • Wrabetz, E., Peter, G. and Hohorst, H. -J., Does acrolein contribute to the cytotoxicity of cyclophosphamide? Cancer Res. Clin. Oncol., 98, 119-126 (1980).
    • (1980) Cancer Res. Clin. Oncol. , vol.98 , pp. 119-126
    • Wrabetz, E.1    Peter, G.2    Hohorst, H.J.3
  • 88
    • 0017167325 scopus 로고
    • Therapeutic trial of aniline mustard in patients with advanced cancer. Comparison of the therapeutic response with cytochemical assessment of tumor cell β-glucuronidase activity
    • Young, C. W., Yogoda, A., Bitlar, E. S., Smith, S. W., Gradstald, H. and Whitmore, W., Therapeutic trial of aniline mustard in patients with advanced cancer. Comparison of the therapeutic response with cytochemical assessment of tumor cell β-glucuronidase activity Cancer, 38, 1887-1895 (1976).
    • (1976) Cancer , vol.38 , pp. 1887-1895
    • Young, C.W.1    Yogoda, A.2    Bitlar, E.S.3    Smith, S.W.4    Gradstald, H.5    Whitmore, W.6
  • 89
    • 0022344589 scopus 로고
    • Guinea pig liver aldehyde oxidase as a sulfoxide reductase: Its purification and characterization
    • Yoshihara, S. and Tatusumi, K., Guinea pig liver aldehyde oxidase as a sulfoxide reductase: its purification and characterization. Arch. Biochim. Biophys., 242, 213-224 (1985).
    • (1985) Arch. Biochim. Biophys. , vol.242 , pp. 213-224
    • Yoshihara, S.1    Tatusumi, K.2
  • 90
    • 0020437503 scopus 로고
    • Cyclophosphamide Analogues
    • Zon, G., Cyclophosphamide Analogues. Prog. Med. Chem., 19, 205-246 (1982).
    • (1982) Prog. Med. Chem. , vol.19 , pp. 205-246
    • Zon, G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.