Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1996-06-27
2000-07-25
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
436136, 5142382, 514357, 514399, 514400, 530350, 5366231, 544143, 544168, 546336, 5483121, 5483144, 5483341, 5483381, C07D41302, C07D26530, C07D29518, A61K 31535, A61K 377115
Patent
active
060938161
ABSTRACT:
The present invention is directed to new cationic lipids and intermediates in their synthesis that are useful for transfecting nucleic acids or peptides into prokaryotic or eukaryotic cells. The lipids comprise one or two substituted histidine residues, or similar compounds, linked to a lipophilic moiety. The lipids form a complex when mixed with polyanions such as nucleic acids or peptides. The complexes permit efficient transfer of polyanions into cells, usually without significant toxicity to the cells.
REFERENCES:
patent: 2426891 (1947-09-01), Lynch
patent: 3190917 (1965-06-01), Johnson et al.
patent: 3387031 (1968-06-01), Johnson et al.
patent: 4229360 (1980-10-01), Schneider et al.
patent: 4388466 (1983-06-01), Beyet et al.
patent: 4548955 (1985-10-01), Okahata et al.
patent: 4857319 (1989-08-01), Crowe et al.
patent: 4863905 (1989-09-01), Hudspeth et al.
patent: 4880635 (1989-11-01), Janoff et al.
patent: 5171678 (1992-12-01), Behr et al.
patent: 5252559 (1993-10-01), Kronholm et al.
patent: 5283185 (1994-02-01), Epand et al.
patent: 5459127 (1995-10-01), Felgner et al.
patent: 5543423 (1996-08-01), Zelle et al.
patent: 5571792 (1996-11-01), Bolton et al.
patent: 5583020 (1996-12-01), Sullivan
patent: 5614503 (1997-03-01), Chaudhary et al.
patent: 5759827 (1998-06-01), Legendre et al.
Koo et al., "A study on the hydrolysis of p-nitrophenyl carboxylates by micellar surfactants catalysts containing histidyl residue", 111(17):149399e, Chem AB, 10/23/89.
Korakas et al., "Structure-retention relationships of diastereopmeric mixtures of lipidic amino acid conjugates on reversed-phase stationary phases", 659:307-315, Journal of Chromatography, 1994.
Murakami et al., "General-Base Catalysis of the Hydrolysis of p-Nitropheny Carboxlates by Micellar Surfactants Involving a Histidyl Residue", 103:2750-2756, J am Chem Soc, 1981.
Murakami et al., "Catalytic Efficiency of Functionalized Vesicles in the Transamination of Pyridoxal-5'-phosphate with a Hydrophobic Amino Acid", 55:3004-3012, Bull Chem Soc Jpn, 1982.
Shinozuka et al., "Enantiomeric Bleomycin Model Compounds Bearing Long Alkyl-Chain", 32(47):6869-6872, Tet Lett, 1991.
Ciccarone et al., "Cationic Liposome-Mediated Transfection: Effect of Serum on Expression and Efficiency," Focus 15(3):80-83 ( ).
Felgner et al, "Enhanced Gene Delivery and Mechanism Studies with a Novel Series of Cationic Lipid Formulations," J Biol Chem 269(4):2550-2561 (1994).
Firestone et al., "Lysosomotropic Agents II. Synthesis and Cytotoxic Action of Lysosomotropic Detergents," Lysosomotropic Detergents pp. 1455-1464 ( ).
Firestone et al., "Lysosomotropic Agents. 1. Synthesis and Cytotoxic Action of Lysosomotropic Detergents," J Med Chem 22(9):1130-1133 (1979).
Firestone et al., "Lysosomotropic Agents. 7. Broad-Spectrum Antifungal Activity of Lysosomotropic Detergents," J Med Chem 30:1519-1521 (1987).
Firestone et al., "Selective Delivery of Cytotoxic Compounds to Cells by the LDL Pathway," J Med Chem 27:1037-1043 (1984).
Forster et al., "The effect of lysosomotropic detergents on the permeability properties of the lysosome membrane," Biochem Biophys Acta 924:452-457 (1987).
Hawley-Nelson et al., "LipofectAMINE Reagent: A New, Higher Efficiency Polycationic Liposome Transfection Reagent," Focus 15(3):73-79 ( ).
Hussain et al., "Killing of Saccharomyces cerevisiae by the Lysosomotropic Detergent N-Dodecylimidazole," Antimicro AG & Chemo 31(4):512-517 (1987).
Jaaskelainen et al., "Oligonucleotide-Cationic Liposome Interations. A Physicochemical Study," Biochem Biophys Acta 1195:115-123 (1994).
Leserman et al., "Immunoliposome-Mediated Delivery of Nucleic Acids: A Review Of Our Laboratory's Experience, " Journal Liposome Research 4(1):107-119 (1994).
Miller et al., "Cell Killing by Lysosomotropic Detergents," J Cell Biol 97:1841-1851 (1983).
Murakami et al, "Aggregate Morphology and Intermembrane Interaction of Synthetic Peptide Lipids Bearing Various Head Group," J Am Chem Soc 107(7):2161-2167 (1985).
Murakami et al, "Preparation of Stable Single-Compartment Vesicles with Cationic and Zwitterionic Amphiphiles Involving Amino Acid Residues," J Org Chem 47(11):2137-2144 (1982).
Murakami et al., "Synthetic Peptide Lipids Having Axial Chirality. Preparation and Aggregate Morphology.," Chemistry Letters, Tokyo JP 7:1481-1484 (1987).
Perrin et al., "pKa Prediction for Organic Acids and Bases," Chapman and Hall Ltd. pp. 1-65 (1981).
Puyal et al.,a "A new cationic liposome encapsulating genetic material," Eur J Biochem 228:697-703 (1995).
Remy et al., "Gene Transfer with a Series of Lipophilic DNA-Binding Molecules," Bioconj Chem 5(6):647-654 (1994).
Ropert et al., "Oligonucleotides Encapsulated in pH Sensitive Liposomes are Efficient Toward Friend Retrovirus," Biochem Biophys Res Comm 183(2):879-885 (1992).
Singhal et al, "Direct Gene Transfer by Liposomes," Journal Liposome Research 4(1):289-299 (1994).
Smart et al., "Surface Titration: A Continuum Electrostatics Model," J Am Chem Soc 118:2283-2284 (1996).
Wilson et al., "The Role of Lysosomal Enzymes in Killing of Mammalian Cells by the Lysomotropic Detergent N-Dodecylimidazole," J Cell Biol 104:1223-1229 (1987).
Xu et al., "Mechanism of DNA Release from Cationic Liposome/DNA Complexes Used in Cell Transfection," Biochem 35:5616-5623 (1996).
Zalipsky et al., "Long circulating, cationic liposomes containing amino-PEG-phosphatidylethanolamine," FEBS 353:71-74 (1994).
Zulauf et al, "[29] Critical Micellar Concentrations of Detergents," Methods in Enzymology 172:528-538 (1989).
Boussif et al., "A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: Polyethylenimine," Proc Natl Acad Sci 92:7297-7301(Aug. 1995).
Chu et al. "Efficiency of Cytoplasmic Delivery by pH-Sensitive Liposomes to Cells in Culture," Pharm Res 7(8):824-834 (1990).
Dijkstra et al., "Interaction of Liposomes with Kupffer Cells in Vitro," Experimental Cell Research 150:161-176 (1984).
Kuppermann et al., "Liposome-Encapsulated (S)-1-(3-Hydroxy-2-Phosphonylmethoxypropyl)cytosine for Long-Acting Therapy of Viral Retinitis," The Journal of Infectious Diseases 173:18-23 (1996).
Murakami et al., "Aggregation Behavior of Amphiphiles Functionalized with Dipeptide Segments an Enantioselective Ester Hydrolysis in Their Bilayer Membranes," Bull Chem Soc Jpn 58(1):172-180 (1985).
Tycko et al., "Rapid Acidification of Endocytic Vesicles Containing alpha2-Macroglobulin," Cell 28:643-651 (Mar. 1982).
Wang et al., "Highly Efficient DNA Delivery Mediated by pH-Sensitive Immunoliposomes,"Biochem 28:9508-9514 (1989).
Behr, Jean-Paul, "DNA Strongly Binds to Micelles and Vesicles Containing Lipopolyamines or Lipointercalants, " Tet Lett 27(48):5861-5864 (1986).
Behr, Jean-Paul, "Synthetic Gene-Transfer Vectors, " ACC Chem Res 26:274-278 (1993).
Felgner, Philip L., "Particulate systems and polymers for in vitro and in vivo delivery of polynucleotides," Advanced Drug Delivery Reviews 5:163-187 (1990).
Kato et al., "Synthetic Cationic Amphiphile for Limposome-Mediated DNA Transfection with Less Cytotoxicity," Biol Pharm Bull 19(6):860-863 (1996).
Legendre et al., "Delivery of Plasmid DNA into Mammalian Cell Lines Using pH-Sensitive Liposomes: Comparison with Cationic Liposomes," Pharm Res 9(10):1235-1242 (1992).
Reimer et al., "Formation of Novel Hydrophobic Complexes between Cationic Lipids and Plasmid DNA," Biochem 34:12877-12883 (1995).
Solodin et al., "A Novel Series of Amphiphilic Imidazolinium Compounds for in Vitro and in Vivo Gene Delivery", Biochemistry 34:13537-13544 (1995).
Lin Kuei-Ying
Mattuecci Mark D.
Higel Floyd D.
ISIS Pharmaceuticals Inc.
LandOfFree
Cationic lipids does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Cationic lipids, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cationic lipids will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1337509