Synthesis and characterization of methotrexate-dimyristoylphosphatidylethanolamine derivatives and the glycerophosphorylethanolamine analogs
作者： Keiichiro Hashimoto , Joan E. Loader , Stephen C. Kinsky
DOI: 10.1016/0005-2736(85)90404-3
关键词:
摘要: Research in this laboratory is currently focused on the biochemical and pharmacological properties of liposomes which an otherwise water-soluble drug anchored to lipid bilayers via appropriate non-polar residue. To end, we have synthesized three (I-III) methotrexate (MTX) derivatives dimyristoylphosphatidylethanolamine (DMPE) by conjugation alpha and/or gamma glutamyl carboxyl groups with amino function phospholipid. These been characterized analytically chromatographically as MTX-gamma-DMPE (I), MTX-alpha-DMPE (II), MTX-alpha, gamma-diDMPE (III). The corresponding glycerophosphorylethanolamine analogs also prepared identified. biological activity these compounds (as inhibitors vitro cell proliferation dihydrofolate reductase) described following paper.
elsevier.com
sci-hub.se 参考文章(9)
John N. Weinstein, William D. Terry, Lee D. Leserman, John J. Moore, Specific Interaction of Myeloma Tumor Cells with Hapten-bearing Liposomes Containing Methotrexate and Carboxyfluorescein Cancer Research. ,vol. 40, pp. 4768- 4774 ,(1980)
A Huang, S J Kennel, L Huang, Interactions of immunoliposomes with target cells. Journal of Biological Chemistry. ,vol. 258, pp. 14034- 14040 ,(1983) , 10.1016/S0021-9258(17)44020-8
Lee D. Leserman, Patrick Machy, Jacques Barbet, Cell-specific drug transfer from liposomes bearing monoclonal antibodies Nature. ,vol. 293, pp. 226- 228 ,(1981) , 10.1038/293226A0
Keiichi Uemura, Stephen C. Kinsky, Active vs. passive sensitization of liposomes toward antibody and complement by dinitrophenylated derivatives of phosphatidylethanolamine. Biochemistry. ,vol. 11, pp. 4085- 4094 ,(1972) , 10.1021/BI00772A010
A. Rosowsky, R. Forsch, Methotrexate analogues. 16. Importance of the side-chain amide carbonyl group as a structural determinant of biological activity. Journal of Medicinal Chemistry. ,vol. 25, pp. 1454- 1459 ,(1982) , 10.1021/JM00354A013
J. R. Piper, J. A. Montgomery, F. M. Sirotnak, P. L. Chello, Syntheses of .alpha.- and .gamma.-substituted amides, peptides, and esters of methotrexate and their evaluation as inhibitors of folate metabolism Journal of Medicinal Chemistry. ,vol. 25, pp. 182- 187 ,(1982) , 10.1021/JM00344A018
Andre Rosowsky, Cheng-Sein Yu, Methotrexate analogs. 10. Direct coupling of methotrexate and diethyl L-glutamate in the presence of peptide bond-forming reagents Journal of Medicinal Chemistry. ,vol. 21, pp. 170- 175 ,(1978) , 10.1021/JM00200A005
Keiichiro Hashimoto, Joan E. Loader, Marcia S. Knight, Stephen C. Kinsky, Inhibition of cell proliferation and dihydrofolate reductase by liposomes containing methotrexate-dimyristoylphosphatidylethanolamine derivatives and by the glycerophosphorylethanolamine analogs. Biochimica et Biophysica Acta. ,vol. 816, pp. 169- 178 ,(1985) , 10.1016/0005-2736(85)90405-5
R. M. C. Dawson, A hydrolytic procedure for the identification and estimation of individual phospholipids in biological samples Biochemical Journal. ,vol. 75, pp. 45- 53 ,(1960) , 10.1042/BJ0750045