Acylated phospholipid drugs

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

514120, 514121, 514134, 514143, 514148, 554 78, 554 79, 554 80, A61K 31685

Patent

active

058469559

ABSTRACT:
This invention relates to a method for improving the efficiency of a drug containing a free carboxy group, the improvement comprising esterifying said carboxy group to the hydroxy group of the glycerol portion of a glycerolphospholipid ester having the formula: ##STR1## or pharmaceutically acceptable salts thereof wherein one of R.sub.1 and R.sub.2 is hydrogen and the other is hydrogen, a hydrocarbyl fatty acid acyl group having 4-26 carbon atoms or a hydrocarbyl heteroatom fatty acid acyl group having 3-25 carbon atoms, or ##STR2## and R is a naturally occurring polar head group characteristic of a glycerophospholipid isolated from endogenous sources;

REFERENCES:
patent: 4471113 (1984-09-01), MacCoss
patent: 4569794 (1986-02-01), Smith et al.
patent: 4594193 (1986-06-01), Regan
patent: 4814112 (1989-03-01), Paltauf et al.
patent: 4927879 (1990-05-01), Pidgeon
patent: 4931498 (1990-06-01), Pidgeon
patent: 5059591 (1991-10-01), Janoff et al.
patent: 5073571 (1991-12-01), Heuckeroth et al.
patent: 5082967 (1992-01-01), Heuckeroth et al.
patent: 5149527 (1992-09-01), Weesenthal
patent: 5151445 (1992-09-01), Welply et al.
patent: 5158942 (1992-10-01), Herrmann et al.
Pidgeon, et al., Immobilized Artificial Membrane Chromatography, Rapid Purification of Functional Membrane Proteins, Anal. Biochem. 194 pp. 163-173 (1991).
Chae, et al., Modern Phytochemical Methods in Recent Advances in Phytochemistry, eds. N.H. Fischer, et al., 25, pp. 149-174, 1987.
Sandsteam Drugs, vol. 34, pp. 372-390, 1987.
Pidgeon, et al., Photolabile liposomes as carrier, Methods Enzymol. 149, pp. 99-111 (1987).
Markovich, et al., Silica subsurface Amine Effect on the Chemical Stability and Chromatographic Properties of End-Capped Immobilized Artificial Membrane Surfaces, Anal. Chem. 63, pp. 1851-1860 (1991).
Stevens, et al., III. Characterization of Immobilized Artificial Membrane HPLC Columns Using Deoxynucleotides as Model Compounds, Biochromatog. 4, pp. 192-205 (1989).
Pidgeon, Solid phase membrane mimetics, Immobilized artificial membranes, Enz. Microb. Techn. 12, pp. 149-150 (1990).
Pidgeon, et al., U.V. Immobilized artificial membranes, Chromatography supports composed of membrane lipids, Anal. Biochem. 17, pp. 36-47 (1989).
Pidgeon, et al., Immobilized Artificial Membranes Chromatography: Surface Chemistry and Application in Applications of Enzyme Biotechnology, Plenum Press (1991).
Immobilized Artificial Membrane, Regis news, vol. 1, No. 1, pp. 1-4 and vol. 1, No. 2, p. 1-4, 1990.
Markovich, et al., FTIR assay of hydrocarbon ligands immobilized to silica, Leaching and stability of IAM bonded phases, Anal. Biochem., 182, pp. 237-244 (1989).
Lynn, et al., Human Immunodeficiency Virus (HIV-1) Cytotoxicity: Perturbation of the Cell membrane and Depression of Phospholipid Synthesis, Virology 163. pp. 43-51 (1988).
Aloia, et al., Lipid composition and fluidity of the human immunodeficiency virus Proc. Natl. Acad. Sci. USA vol. 85, pp. 900-904 Feb. 1988.
Hostetler, et al., Synthesis and Antiretroviral Activity of Phospholiped Analogs of Azidothymidine and Other Antiviral Nucleosides, J. Biol. Chem., 1990; 265, 6112-6117.
Paige, et al., Metabolic Activation of 2-Substituted Derivates of Myristic Acid to Form Potent Inhibitors of Myristoyl CoA: Protein N-Myristoyltransferase, Bio-chemistry, vol. 29, No. 46, 1990, 10566-10573.
Kishore, et al., The Substrate Specificity of Saccharmyces cerevisiae Myristoyl-CoA: Protein N-Myristoyltransferase, The Journal of Biological Chemistry, vol. 266, No. 14, May 15, 1991, pp. 8835-8855.
Duronio, et al., Myristic Acid Auxotrophy Caused by Mutation of S. cerevisiae Myristoyl-CoA: Protein N-Myristoyltransferase, The Journal of Cell Biology, vol. 113, No. 6, Jun. 1991, pp. 1313-1330.
Heuckeroth, et al., Heteroatom-substituted fatty acid analogs as substrates for N-myristoyltransferase: An approach for studying both the enzymology and function of protein acylation, Proc. Natl. Acad. Sci. USA, vol. 85,pp. 8795-8799, Dec. 1988.
Bryant, et al., Peplication of human immunodeficiency virus 1 and Maloney murine leukemia virus is inhibited by different heteroatom-containing analogs of myristic acid, Proc. Natl. Acad. Sci USA, vol. 86, pp. 8655-8659, Nov. 1989.
Towler, et al., Protein fatty acid acylation: Enzymatic synthesis of an N-myristoylglycyl peptide, Proc. Natl. Acad. Sci. USA vol. 83, pp. 2812-2816, May 1986.
Towler, et al., The Biology and Enzymology of Eukaryotic Protein Acylation, Ann. Rev. Biochem. 1988, 57 pp. 69-99.
Towler, et al., Amino-terminal Processing of Proteins by N-Myristoylation, The Journal of Biological chemistry, vol. 262, No. 3, Jan. 25, 1987 pp. 1030-1036.
Heuckeroth, et al., Altered membrane association of p60.sup.v-src and a murine 63-kDa N-myristoyl protein after incorporation of an oxygen-substituted analog of myristic acid, Proc. Natl. Acad. Sci. USA vol. 86, pp. 5262-5266, Jul. 1989.
Towler, et al., Purification and characterization of yeast myristoyl CoA: protein N-myristoyltransferase, Proc. Natl. Acad. Sci. USA vol. 84, pp. 2708-2712, 1987.
Duronio, et al., Analyzing the Substrate Specificity of Saccharomyces cerevisiae Myristoyl-CoA: Protein N-Myristoyltransferase by Co-expressing It The Journal of Biological chemistry, vol. 266, No. 16, pp. 10498-10504, 1991.
Duronio, et al., Protein N-myristoylation in Escherichia coli: REconstitution of a eukaryotic protein modification in bacteria, Proc. Natl. Acad. Sci USA vol. 87, pp. 1506-1510, Feb. 1990.
Johnson, et al., Functional analysis of protein N-myristoylation: Metabolic labeling studies using three oxygen-substituted analogs of myristic acid and cultured mammalian cells provide evidence for protein-sequence-specific incorporation and analog-specific redistribution, Proc. Natl. Acad. Sci. USA vol. 87, pp. 8511-8515, Nov. 1990.
Rudnick, et al., Kinetic and Structural Evidence for a Sequential Ordered Bi Mechanism of Catalysis by Saccharomyces cerevisiae Myristoyl-CoA: Protein N-Myristoyltransferase, The Journal of Biol. Chem., vol. 266,No.15 pp. 9732-9739, 1991.
Gordon, et al., Protein N-Myristoylation, The Journal of Biological Chemistry, vol. 266, No. 14. pp. 8647-8650, 1991.
Schultz, et al., Fatty Acylation of proteins, Ann. Rev. Cell Biol. 1988, 4: pp. 611-647.
Alvarez, et al., Pancreatic Lipase-Caralyzed Hydrolysis of Esters of Hydroxymethy-Phenytoin Dissolved in Various Metabolizable Vehicles, Dispersed in Micellar Systems, and in Aqueous suspension, Pharmaceutical Research, vol. 6, No. 7, 1989. pp. 555-563.
Huber, et al., Dietary Egg Yolk-Derived Phospholipids: Rationale for Their Benefits in Syndromes of Senescence, Drug Withdrawal. and AIDS, Phospholipids, 1990, pp. 241-255.
James, et al., Fatty Acylated Proteins as Components of Intracellular Signaling Pathways, Biochemistry, vol. 29, No. 11, Mar. 20, 1990, pp. 2623-2634.
Hostetler, et al., Phosphatidylazidothymidine, Mechanism of Antiretroviral Action In CEM Cells, J. Biol. Chem., 266, 1991; 266, 11714-11717.
Heuckeroth, et al., 11-(Ethylthio) undecanoic Acid A Myristic Acid Analogue of Altered Hydrophobicity Which is Functional for Peptide N-Myristoylation with Wheat Germ and Yeast Acyltransferase, The Journal of Biological Chemistry, vol. 263, No. 5, Feb. 15, 1988, pp. 2127-2133.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Acylated phospholipid drugs does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Acylated phospholipid drugs, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Acylated phospholipid drugs will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-177391

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.