Patent 5399331 Issued on March 21, 1995. Estimated Expiration Date: September 17, 2012. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
This invention relates to a method for synthesizing a substantially pure reactive lipid including, for example, N-[4-(p-maleimidophenyl)-butyryl]phosphatidylethanolamine (MPB-PE) and related compositions. The compositions of the present invention are useful as coupling agents and may be incorporated into liposomes and subsequently coupled to proteins, cofactors and a number of other molecules. A preferred coupling method is also disclosed as are protein conjugates.
Other References
Allison, et al., "Liposomes as immunological adjuvants",: 1974, Nature, vol. 252, p.252
Bangham, et al.; "Diffusion of Univalent Ions Across the Lamellae of Swollen Phospholipids", 1965; J. Mol. Biol., 13:238-252
Barbet, et al., "Monoclonal antibody Covalently Coupled to Liposomes: Specific Targeting to Cells," J. Supramol. Struct. Cell Biochem., 16:243-258
Bayer, et al., "Affinity Cytochemistry: The Localization of Lectin and Antibody Receptors on Erythrocytes via the Avidin-Biotin Complex," 1976, FEBS Letters, 68, pp. 240-244
Boyum, "Isolation of Leucocytes from Human Blood," 1968, Scand. J. Clin. Lab, Invest., 21, Supp. 97,9
Bragman, et al., "Cytotoxicity of Antibody-Directed Liposomeds that Recognize Two Receptors on K562 cells", 1984, JNCI vol. 73(1):127-131
Bredehorst, et al., "Effect of covalent Attachment of Immunoglobulin Fragements on Liposomal Integrity," 1986, J. Natl. Cancer Inst., 73:5693-5698
Carlsson, et al., "Protein Thiolation and Reversible Protein-Protein Conjugation",: 1978, Biochem. J. 173: 723-737
Deamer, et al., "Liposome Preparation: Methods and Mechanisms," 1983, Chapter 1, pp. 27-51
Fiske, et al., "The Colorimetric Determination of Phosphourus", 1925, J. Biol. Chem., 66:375-400
Forssen, et al., "Improved Therapeutic Benefits of Doxorubicin by Entrapment in Anionic Liposomes", 1983, Cancer Res., 43:546
Gabizon, et al., "Liposomes as in Vivo Carriers of Adriamycin:Reduced Cardiac Uptake and Preserved Antitumor Activity in Mice", 1982, Cancer Res. 42-4734
Goundalker et al., "Covalent binding of antibodies to liposomes using a novel lipid drivative," 1984, J. Pharm. Pharmacol., 36:465-466
Gregoriadis, "Targeting of drugs with molecules, cells and liposomes," 1983, Trends Pharmacol Sci., 4:304-307
Health, et al., "Antibody-targeted liposomes: Increase in specific toxicity of methotrexate-aspartate", 1983, Proc. Natl. Acad. Sci, SA, 80:1377-1381
Heath, et al., "Covalent Attachment of Immunoglobulins to Lipsomes via Glycosphingolipids", 1981, BBA 640:66-81
Ho, et al., "Interactions of Antigen-Sensitized Liposomes with Immobilized Antibody: A Homogeneous Solid-Phase Immunoliposome Assay", 1985, J. Immunol. vol. 134, No. 6.:4035-4040
Howard, et al., "A Human T Lymphocyte Differentiation Market Defined by Monoclonal antibodies that Block E-Rosette Formation", 1981, J. Immunol. vol. 126, No. 6:2117-2122
Huang, et al., "Characterization of Antibody Covalently Coupled to Liposomes", 1982, BBA, 716:140-150
Huang, et al., "Interations of Immunoliposomes with Target Cells". 1983, J. Biol. Chem, vol. 258, No. 22,pp. 14034-14040
Ishimori, et al., "Liposome Immune Lysis Assay (LILA):a Simple Method to Measure Anti-Protein Antibody using Protein Antigen-Bearing Liposomes", 1984, J. Immunol. Methods, 75:351-360
Leserman, et al. "Targeting to cells of fluorescent liposomes covalently coupled with monoclonal antibody or protein A," 1980, Nature, 288:602-604
Leserman, et al., "Covalent coupling of Monoclonal Antibodies and Protein A to Liposomes: Specific Interaction with Cells in Vitro and in Vivo",: Liposome Technology, III, 1984, CRC Press, Inc., CA., pp. 29-40
Loughrey, et al., "A non-covalent method of attaching antibodies to liposomes", 1987, BBA, 901:157-160
Martin, et al., "Irreversible Coupling of Immunoglobulin Freagments to Preformed Vesciles," 1982, J. Biol. Chem., 257, pp. 286-288
Martin et al., "immunospecific Targeting of Liposomes to Cells: A Novel and Efficient Method for Covalent Attachement of Fab' Gragments via Disulfide Bonds", 1981, Biochemistry, 20 4220-4238
Martin, et al., "Binding characteristics of Antibody-Bearing Liposomes", 1985, Ann. NY Acad. Sci. Col 446;443-456
Papahadjopoulos, et al., "Phospholipid Model Membranes", 1967: Biochim. Biophys. Acta., 1345:624-638
Rahman, et al., "Doxorubicin-induced Chronic Cardiotoxicity and its Protection by Liposomal Administration", 1982; Cancer Res. 42:1817
Rahman, et al., "In Vivo Cell Targeting by Liposomes Containing Glycolipids," 1979, J. Cell Biol., MF1509
Sedlack, et al., "Estimation of Total, Protein-Bound, and Nonprotein Sulfhydryl Groups in Tissue with Ellman's Reagent", 1968, Anal. Biochem. 25:192-205
Sharkey, et al., "Targeting of Antibody Coated Liposomes to Tumor Cells producing carcinoembyonic antigen", 1979, Immunotherapy #4557
Stashenko, et al., "Characterization of a huyman B Lymphocyte-Specific Antigen1 " 1980, J. Immunol., vol. 125 No. 4:1678-1685
Urdal et al., "Tumor-associated Ganglio-N-triosylceramide", 1984 J. Biol Chem., 255:10509-10516
Wolff, et al., "The Use of Monocloanl Anti-Thy, IgG,1 for the Targeting of Liposomes to AKR-A cells in vitro and in vivo," 1984, BBA 802:259-273
Bayer, et al., "Methodology Involved in Biotin-Conjugated Phospholipids, Glycolipids, and Gangliosides," Liposome Technology, vol. III, Targeted Drug Delivery and Biological Interaction, 1986, Gregory Gregoriadis, ed., Cp 9, p. 12713
September 17, 2012. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
