메뉴 건너뛰기




Volumn 44, Issue 2-3, 1998, Pages 62-69

Synthesis of methotrexate α,γ-bis(amides) and correlation of thermotropic and DPPC biomembrane interaction parameters with their anticancer activity

Author keywords

Anticancer activity; Differential scanning calorimetry; Membrane; Methotrexate; Prodrug

Indexed keywords

DIPALMITOYLPHOSPHATIDYLCHOLINE; METHOTREXATE ALPHA,GAMMA BIS(TETRADECYLAMIDE); METHOTREXATE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0031658065     PISSN: 02724391     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2299(199806/07)44:2/3<62::AID-DDR3>3.0.CO;2-8     Document Type: Article
Times cited : (10)

References (26)
  • 2
    • 0027421528 scopus 로고
    • Characterization by flow cytometry and fluorescein-methotrexate labeling of hydrophilic and lipophilic antifolate resistance in cultured mammalian cells
    • Assaraf YG (1993): Characterization by flow cytometry and fluorescein-methotrexate labeling of hydrophilic and lipophilic antifolate resistance in cultured mammalian cells. Anticancer Drugs 4:535-544.
    • (1993) Anticancer Drugs , vol.4 , pp. 535-544
    • Assaraf, Y.G.1
  • 3
    • 0001989286 scopus 로고
    • Calorimetric studies of model and natural biomembranes
    • Chapman D (ed): London: Macmillan Press
    • Bach D (1984): Calorimetric studies of model and natural biomembranes. In Chapman D (ed): Biomembrane Structure and Function, London: Macmillan Press, pp 1-41.
    • (1984) Biomembrane Structure and Function , pp. 1-41
    • Bach, D.1
  • 5
    • 70449246528 scopus 로고
    • Phosphorous assay in column chromatography
    • Bartlett GR (1959): Phosphorous assay in column chromatography. J Biol Chem 234:466-468.
    • (1959) J Biol Chem , vol.234 , pp. 466-468
    • Bartlett, G.R.1
  • 6
    • 0024308410 scopus 로고
    • Calorimetric studies of the interaction of 4-biphenylacetic acid and its β-cyclodextrin inclusion compound with lipid model membrane
    • Castelli F, Puglisi G, Pignatello R, Gurrieri S (1989): Calorimetric studies of the interaction of 4-biphenylacetic acid and its β-cyclodextrin inclusion compound with lipid model membrane. Int J Pharm 52:115-121.
    • (1989) Int J Pharm , vol.52 , pp. 115-121
    • Castelli, F.1    Puglisi, G.2    Pignatello, R.3    Gurrieri, S.4
  • 7
    • 0002764947 scopus 로고
    • Membrane transport of folate compounds in mammalian cells
    • Sirotnak FM et al. (eds): New York: Academic Press
    • Dembo M, Sirotnak FM (1984): Membrane transport of folate compounds in mammalian cells. In Sirotnak FM et al. (eds): Folate Antagonists as Therapeutic Agents. Vol. 1. New York: Academic Press, pp 173-217.
    • (1984) Folate Antagonists As Therapeutic Agents , vol.1 , pp. 173-217
    • Dembo, M.1    Sirotnak, F.M.2
  • 8
    • 0022358528 scopus 로고
    • Curative cancer chemotherapy
    • Frei E III (1985): Curative cancer chemotherapy. Cancer Res 45:6523-6537.
    • (1985) Cancer Res , vol.45 , pp. 6523-6537
    • Frei III, E.1
  • 9
    • 0027070974 scopus 로고
    • Evaluation and optimization of liposomes as a delivery device for methotrexate
    • Fresta M, Puglisi G, Pignatello R, Giovinazzo C (1992): Evaluation and optimization of liposomes as a delivery device for methotrexate. Pharmazie 47:926-929.
    • (1992) Pharmazie , vol.47 , pp. 926-929
    • Fresta, M.1    Puglisi, G.2    Pignatello, R.3    Giovinazzo, C.4
  • 10
    • 1842478694 scopus 로고
    • Interaction of the fluoroquinolone antimicrobial agent ofloxacin with a biological membrane model
    • Fresta M, Ventura CA, Puglisi G (1995): Interaction of the fluoroquinolone antimicrobial agent ofloxacin with a biological membrane model. Acta Technol Legis Medicam 5:173-188.
    • (1995) Acta Technol Legis Medicam , vol.5 , pp. 173-188
    • Fresta, M.1    Ventura, C.A.2    Puglisi, G.3
  • 12
    • 0016598116 scopus 로고
    • Changes of molecular properties associated with the development of resistance against methotrexate in human lymphoblastoid cells
    • Niethammer D, Jackson RC (1975): Changes of molecular properties associated with the development of resistance against methotrexate in human lymphoblastoid cells. Eur J Cancer 11:845-854.
    • (1975) Eur J Cancer , vol.11 , pp. 845-854
    • Niethammer, D.1    Jackson, R.C.2
  • 14
    • 0020037138 scopus 로고
    • Syntheses of α- And γ-substituted amides, peptides, and esters of methotrexate and their evaluation as inhibitors of folate metabolism
    • Piper JR, Montgomery JA, Sirotnak FM, Chello PL (1982): Syntheses of α- and γ-substituted amides, peptides, and esters of methotrexate and their evaluation as inhibitors of folate metabolism. J Med Chem 25:182-187.
    • (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
  • 15
    • 0026511640 scopus 로고
    • Liposomes as a potential drug carrier for citicoline (CDP-choline) and the effect of formulation conditions on encapsulation efficiency
    • Puglisi G, Fresta M, La Rosa C, Ventura CA, Panico AM, Mazzone G (1992): Liposomes as a potential drug carrier for citicoline (CDP-choline) and the effect of formulation conditions on encapsulation efficiency. Pharmazie 47:211-215.
    • (1992) Pharmazie , vol.47 , pp. 211-215
    • Puglisi, G.1    Fresta, M.2    La Rosa, C.3    Ventura, C.A.4    Panico, A.M.5    Mazzone, G.6
  • 16
    • 51649143260 scopus 로고
    • The interaction occurring between methotrexate and a lipid model membrane of DPPC
    • Puglisi G, Fresta M, Ventura CA, Mazzone G, Vandelli MA (1995): The interaction occurring between methotrexate and a lipid model membrane of DPPC. J Thermal Anal 44:1287-1299.
    • (1995) J Thermal Anal , vol.44 , pp. 1287-1299
    • Puglisi, G.1    Fresta, M.2    Ventura, C.A.3    Mazzone, G.4    Vandelli, M.A.5
  • 17
    • 0023857756 scopus 로고
    • The chemistry of methotrexate and its analogues
    • Rahman LKA, Chhabra SR (1988): The chemistry of methotrexate and its analogues. Med Res Rev 8:95-156.
    • (1988) Med Res Rev , vol.8 , pp. 95-156
    • Rahman, L.K.A.1    Chhabra, 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 (1973): Methotrexate analogs. 2. A facile method of preparation of lipophilic derivatives of methotrexate and 3′,5′-dichloromethotrexate by direct esterification. J Med Chem 16:1190-1193.
    • (1973) J Med Chem , vol.16 , pp. 1190-1193
    • Rosowsky, A.1
  • 19
    • 0019839154 scopus 로고
    • Methotrexate analogues. 14. Synthesis of new γ-substituted derivatives as dihydrofolate reductase inhibitors and potential anticancer agents
    • Rosowsky A, Forsch R, Uren J, Wick M (1981a): Methotrexate analogues. 14. Synthesis of new γ-substituted derivatives as dihydrofolate reductase inhibitors and potential anticancer agents. J Med Chem 24:1450-1455.
    • (1981) J Med Chem , vol.24 , pp. 1450-1455
    • Rosowsky, A.1    Forsch, R.2    Uren, J.3    Wick, M.4
  • 20
    • 0019860179 scopus 로고
    • Methotrexate analogues. 13. Chemical and pharmacological studies on amide, hydrazide and hydroxamic acid derivatives of the glutamate side chain
    • Rosowsky A, Yu CS, Uren J, Lazarus H, Wick M (1981b): Methotrexate analogues. 13. Chemical and pharmacological studies on amide, hydrazide and hydroxamic acid derivatives of the glutamate side chain. J Med Chem 24:559-567.
    • (1981) J Med Chem , vol.24 , pp. 559-567
    • Rosowsky, A.1    Yu, C.S.2    Uren, J.3    Lazarus, H.4    Wick, M.5
  • 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 RA, Yu CS, Lazarus H, Beardsley GP (1984): Methotrexate analogues. 21. Divergent influence of alkyl chain length on the dihydrofolate reductase affinity and cytotoxicity of methotrexate monoesters. J Med Chem 27:605-609.
    • (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
    • 0022922474 scopus 로고
    • Methotrexate analogues. 28. Synthesis and biological evaluation of newγ-monoamides of aminopterin and methotrexate
    • Rosowsky A, Bader H, Radike-Smith M, Cucchi CA, Wick MM, Freisheim JH (1986): Methotrexate analogues. 28. Synthesis and biological evaluation of newγ-monoamides of aminopterin and methotrexate. J Med Chem 29:1703-1709.
    • (1986) J Med Chem , vol.29 , pp. 1703-1709
    • Rosowsky, A.1    Bader, H.2    Radike-Smith, M.3    Cucchi, C.A.4    Wick, M.M.5    Freisheim, J.H.6
  • 23
    • 0011118654 scopus 로고
    • Structural specificity of folate analog transport and binding to dihydropholate reductase in murine tumor and normal cells: Relevance to therapeutic efficacy
    • Kislink RL, Brown GM (eds): New York: Elsevier
    • Sirotnak FM, Chello PL, Piper JR, Montgomery JA, DeGraw JI (1979): Structural specificity of folate analog transport and binding to dihydropholate reductase in murine tumor and normal cells: Relevance to therapeutic efficacy. In Kislink RL, Brown GM (eds): Chemistry and Biology of Pteridines, New York: Elsevier, pp 597-608.
    • (1979) Chemistry and Biology of Pteridines , pp. 597-608
    • Sirotnak, F.M.1    Chello, P.L.2    Piper, J.R.3    Montgomery, J.A.4    DeGraw, J.I.5
  • 24
    • 0019848289 scopus 로고
    • Relative frequency and kinetic properties of transport defective phenotypes among methotrexate-resistant L1210 clonal cell lines derived in vivo
    • Sirotnak FM, Moccio DM, Kelleher LE, Goutas LJ (1981): Relative frequency and kinetic properties of transport defective phenotypes among methotrexate-resistant L1210 clonal cell lines derived in vivo. Cancer Res 41:4447-4452.
    • (1981) Cancer Res , vol.41 , pp. 4447-4452
    • Sirotnak, F.M.1    Moccio, D.M.2    Kelleher, L.E.3    Goutas, L.J.4
  • 25
    • 0014981957 scopus 로고
    • Methotrexate for psoriasis. A new therapeutic schedule
    • Weinstein GD, Frost P (1971): Methotrexate for psoriasis. A new therapeutic schedule. Arch Dermatol 103:33-38.
    • (1971) Arch Dermatol , vol.103 , pp. 33-38
    • Weinstein, G.D.1    Frost, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.