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Volumn 10, Issue 3, 2000, Pages 237-245

Lipophilic methotrexate conjugates with antitumor activity

Author keywords

Antitumor agents; CCRF CEM cells; CEM MTX cells; Lipoamino acids; Lipophilicity; Methotrexate conjugates

Indexed keywords

DIHYDROFOLATE REDUCTASE; LIPOAMINO ACID CONJUGATE; LIVER ENZYME; METHOTREXATE; METHOTREXATE DERIVATIVE; METHOTREXATE GAMMA ETHYL ESTER; UNCLASSIFIED DRUG;

EID: 0034126277     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0928-0987(00)00062-2     Document Type: Article
Times cited : (40)

References (26)
  • 1
    • 37049099338 scopus 로고
    • Synthesis of monoamides of methotrexate from L-glutamic acid monoamide t.-butyl esters
    • Antonjuk D.J., Boadle D.K., Cheung H.T.A., Tran T.Q. Synthesis of monoamides of methotrexate from L-glutamic acid monoamide t.-butyl esters. J. Chem. Soc. Perkin Trans. 1:1984;1989-2003.
    • (1984) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 1989-2003
    • Antonjuk, D.J.1    Boadle, D.K.2    Cheung, H.T.A.3    Tran, T.Q.4
  • 4
    • 0002327694 scopus 로고
    • Design of prodrugs: Bioreversible derivatives for various functional groups and chemical entities
    • H. Bundgaard. Amsterdam-New York-Oxford: Elsevier
    • Bundgaard H. Design of prodrugs: bioreversible derivatives for various functional groups and chemical entities. Bundgaard H. Design of Prodrugs. 1985;1-92 Elsevier, Amsterdam-New York-Oxford.
    • (1985) Design of Prodrugs , pp. 1-92
    • Bundgaard, H.1
  • 5
    • 0001206491 scopus 로고
    • Continuous culture of lymphoblasts from peripheral blood of a child with acute leukemia
    • Foley G.F., Lazarus H., Farber S., Uzman B.G., Boone B.A., McCarthy R.E. Continuous culture of lymphoblasts from peripheral blood of a child with acute leukemia. Cancer. 18:1965;522-529.
    • (1965) Cancer , vol.18 , pp. 522-529
    • Foley, G.F.1    Lazarus, H.2    Farber, S.3    Uzman, B.G.4    Boone, B.A.5    McCarthy, R.E.6
  • 8
    • 0032498638 scopus 로고    scopus 로고
    • Synthesis and in vitro evaluation of lipoamino acid and carbohydrate modified enkephalins as potential antinociceptive agents
    • Kellam B., Drouillat B., Dekany G., Starr M.S., Toth I. Synthesis and in vitro evaluation of lipoamino acid and carbohydrate modified enkephalins as potential antinociceptive agents. Int. J. Pharm. 161:1998;55-64.
    • (1998) Int. J. Pharm. , vol.161 , pp. 55-64
    • Kellam, B.1    Drouillat, B.2    Dekany, G.3    Starr, M.S.4    Toth, I.5
  • 9
    • 0023273951 scopus 로고
    • Circumvention of the methotrexate transport system by methotrexate-phosphatidylethanolamine derivatives: Effect of fatty acid chain length
    • Kinsky S.C., Loader J.E. Circumvention of the methotrexate transport system by methotrexate-phosphatidylethanolamine derivatives: effect of fatty acid chain length. Bioch. Biophys. Acta. 921:1987;96-103.
    • (1987) Bioch. Biophys. Acta , vol.921 , pp. 96-103
    • Kinsky, S.C.1    Loader, J.E.2
  • 10
    • 0025817134 scopus 로고
    • Decreased folylpolyglutamate synthetase activity as a mechanism of methotrexate resistance in CCRF-CEM human leukemia sublines
    • McCloskey D.E., McGuire J.J., Russell C.A., Rowan B.G., Bertino J.R., Pizzorno G., et al. Decreased folylpolyglutamate synthetase activity as a mechanism of methotrexate resistance in CCRF-CEM human leukemia sublines. J. Biol. Chem. 266:1991;6181-6187.
    • (1991) J. Biol. Chem. , vol.266 , pp. 6181-6187
    • McCloskey, D.E.1    McGuire, J.J.2    Russell, C.A.3    Rowan, B.G.4    Bertino, J.R.5    Pizzorno, G.6
  • 11
    • 0001733531 scopus 로고    scopus 로고
    • Antifolate polyglutamylation in preclinical and clinical antifolate resistance
    • A.L. Jackman. Totowa: Humana Press
    • McGuire J.J. Antifolate polyglutamylation in preclinical and clinical antifolate resistance. Jackman A.L. Anticancer Drug Development Guide: Antifolate Drugs in Cancer Therapy. 1998;339-363 Humana Press, Totowa.
    • (1998) Anticancer Drug Development Guide: Antifolate Drugs in Cancer Therapy , pp. 339-363
    • McGuire, J.J.1
  • 12
    • 20744456789 scopus 로고
    • Solid phase synthesis of a tetrapeptide
    • Merrifield R.B. Solid phase synthesis of a tetrapeptide. J. Am. Chem. Soc. 85:1963;2149-2154.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2149-2154
    • Merrifield, R.B.1
  • 13
    • 0029977393 scopus 로고    scopus 로고
    • Synthesis and preliminary in vitro screening of lipophilic α,γ-bis(amides) as potential prodrugs of methotrexate
    • Pignatello R., Sorrenti V., Spampinato G., Pecora T., Panico A., Di Giacomo C., et al. Synthesis and preliminary in vitro screening of lipophilic α,γ-bis(amides) as potential prodrugs of methotrexate. Anti-Cancer Drug Design. 11:1996;253-264.
    • (1996) Anti-Cancer Drug Design , vol.11 , pp. 253-264
    • Pignatello, R.1    Sorrenti, V.2    Spampinato, G.3    Pecora, T.4    Panico, A.5    Di Giacomo, C.6
  • 14
    • 0032988957 scopus 로고    scopus 로고
    • Aliphatic α,γ-bis(amides) of methotrexate. Influence of chain length on in vitro activity against sensitive and resistant tumor cells.
    • Pignatello R., Spampinato G., Sorrenti V., Vicari L., Di Giacomo C., Vanella A., et al. Aliphatic α,γ-bis(amides) of methotrexate. Influence of chain length on in vitro activity against sensitive and resistant tumor cells. Pharm. Pharmacol. Commun. 5:1999;299-305.
    • (1999) Pharm. Pharmacol. Commun. , vol.5 , pp. 299-305
    • Pignatello, R.1    Spampinato, G.2    Sorrenti, V.3    Vicari, L.4    Di Giacomo, C.5    Vanella, A.6
  • 16
    • 0020037138 scopus 로고
    • Syntheses of α- And γ-substituted amides, peptides, and esters of methotrexate and their evaluation as inhibitors of folate metabolism
    • Piper J.R., Montgomery J.A., Sirotnak F.M., Chello P.L. Syntheses of α- and γ-substituted amides, peptides, and esters of methotrexate and their evaluation as inhibitors of folate metabolism. J. Med. Chem. 25:1982;182-187.
    • (1982) J. Med. Chem. , vol.25 , pp. 182-187
    • Piper, J.R.1    Montgomery, J.A.2    Sirotnak, F.M.3    Chello, P.L.4
  • 17
    • 0023857756 scopus 로고
    • The chemistry of methotrexate and its analogues
    • Rahman L.K.A., Cchabra S.R. The chemistry of methotrexate and its analogues. Med. Res. Rev. 8:1988;95-156.
    • (1988) Med. Res. Rev. , vol.8 , pp. 95-156
    • Rahman, L.K.A.1    Cchabra, S.R.2
  • 18
    • 0015901102 scopus 로고
    • Methotrexate analogs. 2. A facile method of preparation of lipophilic derivatives of methotrexate and 3′,5′-dichloromethotrexate by direct esterification
    • Rosowsky A. Methotrexate analogs. 2. A facile method of preparation of lipophilic derivatives of methotrexate and 3′,5′-dichloromethotrexate by direct esterification. J. Med. Chem. 16:1973;1190-1193.
    • (1973) J. Med. Chem. , vol.16 , pp. 1190-1193
    • Rosowsky, A.1
  • 19
    • 0017799711 scopus 로고
    • Methotrexate Analogues. 11. Unambiguous chemical synthesis and in vitro biological evaluation of α- And γ-monoesters as potential prodrugs
    • Rosowsky A., Beardsley G.P., Ensminger W.D., Lazarus H., Yu C.-S. Methotrexate Analogues. 11. Unambiguous chemical synthesis and in vitro biological evaluation of α- and γ-monoesters as potential prodrugs. J. Med. Chem. 21:1978;380-386.
    • (1978) J. Med. Chem. , vol.21 , pp. 380-386
    • Rosowsky, A.1    Beardsley, G.P.2    Ensminger, W.D.3    Lazarus, H.4    Yu, C.-S.5
  • 20
    • 0018912764 scopus 로고
    • III. Effects of methotrexate esters and other lipophilic antifolates on methotrexate-resistant human leukemia lymphoblasts
    • Rosowsky A., Lazarus H., Yuan G.C., Beltz W.R., Mangini L., Abelson H.T., et al. III. Effects of methotrexate esters and other lipophilic antifolates on methotrexate-resistant human leukemia lymphoblasts. Biochem. Pharmacol. 29:1980;648-652.
    • (1980) Biochem. Pharmacol. , vol.29 , pp. 648-652
    • Rosowsky, A.1    Lazarus, H.2    Yuan, G.C.3    Beltz, W.R.4    Mangini, L.5    Abelson, H.T.6
  • 21
    • 0021354218 scopus 로고
    • Methotrexate Analogues. 21. Divergent influence of alkyl chain length on the dihydrofolate reductase affinity and cytotoxicity of methotrexate monoesters.
    • Rosowsky A., Forsch R.A., Yu C.S., Lazarus H., Beardsley G.P. Methotrexate Analogues. 21. Divergent influence of alkyl chain length on the dihydrofolate reductase affinity and cytotoxicity of methotrexate monoesters. J. Med. Chem. 27:1984;605-609.
    • (1984) J. Med. Chem. , vol.27 , pp. 605-609
    • Rosowsky, A.1    Forsch, R.A.2    Yu, C.S.3    Lazarus, H.4    Beardsley, G.P.5
  • 22
    • 0018860563 scopus 로고
    • Correlates of folate analog transport, pharmacokinetics and selective antitumor action
    • Sirotnak F.M. Correlates of folate analog transport, pharmacokinetics and selective antitumor action. Pharmacol. Ther. 8:1980;71-103.
    • (1980) Pharmacol. Ther. , vol.8 , pp. 71-103
    • Sirotnak, F.M.1
  • 25
    • 0029118446 scopus 로고
    • Carrier and receptor-mediated transport of folate antagonists targeting folate-dependent enzymes, correlates of molecular-structure and biological activity
    • Westerhof G.R., Schornagel J.H., Kathmann I., Jackman A.L., Rosowsky A., Forsch R.A., et al. Carrier and receptor-mediated transport of folate antagonists targeting folate-dependent enzymes, correlates of molecular-structure and biological activity. Molec. Pharmacol. 48:1995;459-471.
    • (1995) Molec. Pharmacol. , vol.48 , pp. 459-471
    • Westerhof, G.R.1    Schornagel, J.H.2    Kathmann, I.3    Jackman, A.L.4    Rosowsky, A.5    Forsch, R.A.6
  • 26
    • 0026564126 scopus 로고
    • Lipidic peptides. XIII: Synthesis, structure elucidation and in vitro toxicity assessment of chlorambucil conjugates with lipidic acids, lipidic amino acids and their oligomers
    • Wood I.P., Toth I., Holley J.L., Gibbons W.A. Lipidic peptides. XIII: synthesis, structure elucidation and in vitro toxicity assessment of chlorambucil conjugates with lipidic acids, lipidic amino acids and their oligomers. Int. J. Pharm. 87:1992;141-147.
    • (1992) Int. J. Pharm. , vol.87 , pp. 141-147
    • Wood, I.P.1    Toth, I.2    Holley, J.L.3    Gibbons, W.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.