Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
2008-03-25
2008-03-25
Aulakh, Charanjit S. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C424S194100, C424S179100, C562S459000, C562S471000
Reexamination Certificate
active
10929707
ABSTRACT:
Described are ortho carboxy phenol derived acetals and compositions containing ortho carboxy phenol derived acetals which are useful for delivering biologically active compounds to cells. The acetals can be used to reversibly link up to three different molecules and have rapid hydrolysis kinetics in conditions which are present in a cell as well as in vivo. Cleavage of the acetal enhances delivery of the biologically active compound.
REFERENCES:
patent: 4946931 (1990-08-01), Heller et al.
patent: 4957998 (1990-09-01), Heller et al.
patent: 6414001 (2002-07-01), Tomiyama et al.
Adami RC et al. “Metabolic stability of glutaraldehyde cross-linked peptide DNA condensates.” J Pharm Sci. 1999 vol. 88 No. 8 pp. 739-746.
Boussif O et al. “A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: polyethylenimine.” Proc Natl Acad Sci U S A. 1995 vol. 92 No. 16 pp. 7297-7301.
Capon B “.Intramolecular Catalysis in Glycoside Hydrolysis” Tetrahedron Letters, 1963 vol. 4 pp. 911-913.
Cheung CY et al. “A pH-sensitive polymer that enhances cationic lipid-mediated gene transfer.” Bioconjug Chem; 2001 vol. 12 No. 6 pp. 906-910.
Danko et al. “High expression of naked plasmid DNA in muscles of young rodents.” Hum. Mol. Genetics 1997 vol. 6 pp. 1435.
Dunn et al. “Steric and electronic effects on the neighboring general acid catalyzed hydrolysis of methyl phenyl acetals of formaldehyde.” JACS 1970 vol. 92 pp. 2410-2416.
Fife et al. “Intramolecular carboxyl group participation in acetal hydrolysis.” JACS 1971 vol. 93 pp. 6610-6614.
Godwin A et al. “New strategies for polymer development in pharmaceutical science—a short review.” J Pharm Pharmacol 2001 vol. 53 No. 9 pp. 1175-1184.
Hu Z et al. “Characterization of norfloxacine release from tablet coated with a new pH-sensitive polymer, P-4135F.” J Drug Target 1999 vol. 7 No. 3 pp. 223-232.
Jain R et al. “Controlled drug delivery by biodegradable poly(ester) devices: different preparative approaches.” Drug Dev Ind Pharm 1998 vol. 24 No. 8 pp. 703-727.
Kamata H et al. “Amphiphilic peptides enhance the efficiency of liposome-mediated DNA transfection.” Nucleic Acids Res. 1994 vol. 22 pp. 536-537.
Lai et al. “Acid-and Calcium-induced structural changed in phosphatidylethanolamine membranes stabilized by cholesteryl hemisuccinate” Biochemistry 1985 vol. 24 p. 1654-1661.
Lowman AM et al. “Oral delivery of insulin using pH-responsive complexation gels.” J Pharm Sci 1999 vol. 88 No. 9 pp. 933-937.
Mechtler K et al “Gene transfer mediated by influenze virus peptides: the role of peptide sequences” New J. Chem. 1997 vol. 21 pp. 105-111.
Metrikin DC et al. “Intravitreal drug administration with depot devices.” Curr Opin Ophthalmol 1994 vol. 5 No. 3 pp. 21-29.
Meyer O et al. “Copolymers of N-isopropylacrylamide can trigger pH sensitivity to stable liposomes.” FEBS Lett 1998 vol. 421 No. 1 pp. 61-64.
Murthy N et al. “The design and synthesis of polymers for eukaryotic membrane disruption.” J Control Release. 1999 vol. 61 No. 1-2 pp. 137-143.
Ohmori N et al. “The enhancing effect of anionic alpha-helical peptide on cationic peptide-mediating transfection systems.” Biochem Biophys Res Commun. 1997 vol. 235 No. 3 pp. 726-729.
Pastan I et al. “Pseudomonas exotoxin: chimeric toxins.” J Biol Chem. 1989 vol. 264 No. 26 pp. 15157-15160.
Plank C et al. “Application of membrane-active peptides for drug and gene delivery across cellular membranes.” Adv Drug Deliv Rev 1998 vol. 34 No. 1 pp. 21-35.
Potineni A et al. “Poly(ethylene oxide)-modified poly(beta-amino ester) nanoparticles as a pH-sensitive biodegradable system for paclitaxel delivery.” J Control Release 2003 vol. 86 No. 2-3 pp. 223-234.
Sezaki H et al. “Soluble macromolecular carriers for the delivery of antitumour drugs.” Adv Drug Deliv Rev 1989 vol. 3 No. 2 pp. 247-266.
Wagner E et al. “Delivery of drugs, proteins and genes into cells using transferrin as a ligand for receptor-mediated endocytosis.” Adv Drug Deliv Rev 1994 vol. 14 pp. 113-135.
Wagner E et al. “Influenza virus hemagglutinin HA-2 N-terminal fusogenic peptides augment gene transfer by transferrin-polylysine-DNA complexes: toward a synthetic virus-like gene-transfer vehicle.” Proc Natl Acad Sci U S A. 1992 vol. 89 No. 17 pp. 7934-7938.
Wolff JA et al. “Direct gene transfer into mouse muscle in vivo.” Science 1990 vol. 247 pp. 1465-1468.
Zuber et al. “Towards synthetic viruses” Adv Drug Deliv Rev. 2001 vol. 52 p. 245-253.
Rozema David B.
Wakefield Darren
Aulakh Charanjit S.
Ekena Kirk
Johnson Mark K.
Mirus Bio Corporation
LandOfFree
Labile linkage for compound delivery to a cell does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Labile linkage for compound delivery to a cell, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Labile linkage for compound delivery to a cell will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3911688