Biodegradable poly(β-amino esters) and uses thereof

Drug – bio-affecting and body treating compositions – Solid synthetic organic polymer as designated organic active... – Monomer contains oxygen

Reexamination Certificate

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C528S288000, C528S362000, C564S078000

Reexamination Certificate

active

07427394

ABSTRACT:
Poly(β-amino esters) prepared from the conjugate addition of bis(secondary amines) or primary amines to a bis(acrylate ester) are described. Methods of preparing these polymers from commercially available starting materials are also provided. These tertiary amine-containing polymers are preferably biodegradable and biocompatible and may be used in a variety of drug delivery systems. Given the poly(amine) nature of these polymers, they are particularly suited for the delivery of polynucleotides. Nanoparticles containing polymer/polynucleotide complexes have been prepared. The inventive polymers may also be used to encapsulate other agents to be delivered. They are particularly useful in delivering labile agents given their ability to buffer the pH of their surroundings. A system for preparing and screening polymers in parallel using semi-automated robotic fluid delivery systems is also provided.

REFERENCES:
patent: 5180424 (1993-01-01), Hutter
patent: 5364634 (1994-11-01), Lew
patent: 5462990 (1995-10-01), Hubbell et al.
patent: 5705188 (1998-01-01), Junichi et al.
patent: 5770637 (1998-06-01), Vanderlaan et al.
patent: 5858746 (1999-01-01), Hubbell et al.
patent: 5904927 (1999-05-01), Amiji
patent: 5962520 (1999-10-01), Smith et al.
patent: 6060582 (2000-05-01), Hubbell et al.
patent: 6998115 (2006-02-01), Langer et al.
Lynn et al. ((“Degradable Poly(b-amino esters): Synthesis, Characterization and self Assembly with Plasmid DNA” in J. Am. Chem. Soc. 2000, 122, 10761-10768).
Angeloni et al., “Liquid crystalline poly(beta-aminoester)s containing different mesogenic groups,” Mahromolekulare Chemie, 1985, 186 (5), 977-997.
Korshak et al., “Water-soluble anion exchange resins based on methacrylic beta-aminoesters,” Vysokomolekulyarnye Soedineniya, Seriya B: Kratkie Soobscheniya (1975), 17 (5), 401-404.
Angeloni, et al., “Liquid Crystalline Poly(β-aminoester)s Containing Different Mesogenic Groups,”Makromol. Chem., 186: 977-997, 1985.
Akinc, et al., Parallel Synthesis and Biophysical Characterization of a Degradable Polymer Library of Gene Delivery,J. Am. Chem. Soc.2003.
Akinc, et al.,“Measuring the pH Environmental of DNA Delivered Using Nonviral Vectors: Implications for Lysosomal Trafficking”Biotechnol. Bioeng., 78(5): 503-508, 2002.
Allison, “The Mode of Action of Immunological Adjuvants”Dev. Biol. Stand.92: 3-11, 1998.
*Anderson, “Humen Gene Therapy”Nature, 392: 25-30, 1996.
*Anderson, et al., “Biodegration and Biocompatibility of PLA and PLGA Microspheres”Adv. Drug Delivery Rev. 28: 5-24, 1997.
*Ando, et al., “PLGA Micospheres Containing Plasmid DNA: Preservation of Supercoiled DNA via Cryopreparation and Carbohydrate Stabilization”J. Pharm. Sci.88: 126-130, 1999.
Barbucci, et al., “Macroinorganics. 7. Property-Structure Relationsips for Polymeric Bases Whose Monomeric Units Behave Independently toward Protonation”Macromolecules, 14:1203-1209, 1981.
Barbucci, et al., “Protonation Studies of Multifunctional Polymers with a Poly(Amido-Amine) Structure”,Polymer, 19: 1329-1334, 1978.
Barbucci, et al., “Thermodynamic and13C n.m.r. Data on the Protonation of Polymeric Bases Whose Repeating Units Behave Independently Towards Protonation”Polymer, 21: 81-85, 1980.
*Barrera, et al., “Synthesis and RGD Peptide Modification of a New Biodegradable Copolymer: Poly (lactic acid-co-lysine)”J. Am. Chem. Soc.115:11010-11011, 1993.
*Behr, “Synthetic Gene-Transfer Vectors”Acc. Chem. Res.26: 274-278, 1993.
*Behr, “The Proton Sponge: a Trick to Enter Cells the Viruses Did Not Expoit”Chimia, 51: 34-36, 1997.
Benns, et al., “pH-Sensitive Cationic Polymer Gene Delivery Vehicle: N-Ac-Poly (L-Histidine)-Graft-Poly (L-Lysine) Comb Shaped Polymer”,Bioconjugate Chem,. 11: 637-645, 2000.
*Boussif, et al., “A Versatile Vector for Gene and Oligonucleotide Transfer into Cells in Culture and In Vivo: Polyethylenimine”Proc. Natl. Acad. Sci. USA, 92: 7297-7301, 1995.
*Brazeau, et al., “In Vitro Myotoxicity of Selected Cationic Macromolecules Used in Non-Viral Gene Delivery”Pharm. Res. 15: 680-684, 1998.
Brocchini,“Combinatorial Chemistry and Biomedical Polymer Development”Advanced Drug Delivery Reviews, 53: 123-130, 2001.
Brocchini, et al., “A Combinatorial Approach for Polymer Design”J. Am. Soc. 119: 4553-4554, 1997.
Chan, et al., “Triplex DNA: Fundamentals, Advances, and Potential Applications for Gene Therapy”J. Mol. Med. 75(4): 267-282, 1997.
*Choksakulnimitr et al., “In Vitro Cytotoxicity of Macromolcules in Different Cell Culture Systems”Controlled Release, 34: 233-241, 1995.
*Cotten, et al., “Receptor-Mediated Transport of DNA into Eukaryotic Cells”Methods Enzym. 217: 618, 1993.
Crooke, “Molecular Mechanisms of Action of Antisense Drugs”Biochim. Biophys. Acta, 1489(1): 31-44, 1999.
Crooke, “Evaluating the Mechanism of Action of Antiproliferative Antisense Drugs”Antisense Nucleic Acid Drug Dev. 10(2): 123-126, 2000.
*Crystal, “Transfer of Genes to Humans: Early Lessons and Obstacles to Success”Science, 270: 404-410, 1995.
*Danusso, et al., “Synthesis of Tertiary Amine Polymers”Polymer, 11:88-113, 1970.
*Demeneix, et al., InArtifical Self-Assembling Systems for Gene Delivery(Felgner, et al., Eds). American Chemical Society, Washington, D.C., 1996, 146-151.
*Deshmukh, et al., “Liposome and Polylysine Mediated Gene Transfer”New J. Chem. 21: 113-124, 1997.
De Smedt, et al., Cationic Polymer Based Gene Delivery Systems,Pharmaceutical Research, 17(2): 113-126, 2000.
*Ferruti, et al., “Linear Amino Polymers: Synthesis, Protonation and Complex Formation”Advances in Polymer Science, 58: 55-92, 1984.
*Ferrutti, et al., “Recent Results on Functional Polymers and Macromonomers of Interest as Biomaterials or for Biomaterial Modification”Biomaterials, 15: 1235-1241, 1994.
*Ferruti, et al., “Synthesis, Characterisation and Antitumor Activity of Platinum (II) Complexes of Novel Functionalised Poly (Amido Amine)s”Macromol. Chem. Phys. 200: 1644-1654, 1999.
*Ferruti, et al., “Synthesis, Physico-Chemical Properties and Biomedical Applications of Poly(amino-amine)s”Polymer, 26: 1336, 1985.
*Fire, et al., “Potent and Specific Genetic Interference by Double-Stranded RNA in Caenorhabditis Elegans”Nature, 391: 806-811, 1998.
Fominaya, et al., “Target Cell-Specific DNA Transfer Mediated by a Chimeric Multidomain Protein”,Journal of Biological Chemistry, 271(18): 10560-1996.
*Friedman, “Human Gene Therapy—An Immature Genie,k But Certainly out of the Bottle”Nature Med, 2: 144-147, 1996.
Fritz, et al., “Gene Transfer into Mammalian Cells Using Histone-Condensed Plasmid DNA”Hum. Gene Ther, 7(12):1395-1404,1996.
Gebhart, et al., “Evaluation of Polyplexes as Gene Transfer Agents”Journal of Controlled Release, 73: 401-416, 2001.
*Gerasimov, et al., “Cytosolic Drug Delivery Using pH- and Light-Sensitive Liposomes”Adv. Drug Delivery Rev. 38: 317-338, 1999.
*Gonzalez, et al., “New Class of Polymers for the Delivery of Macromolecular Therapeutics”Bioconjugate Chem. 10: 1068-1074, 1999.
*Haensler, et al., “Polyamidoamine Cascade Polymers Mediate Efficient Transfection of Cells In Culture”Bioconjugate Chem. 4:372-379, 1993.
*Hanes, et al., “New Advances in Microsphere-Based Single-Dose Vaccines”Adv. Drug Delivery Rev. 28: 97-119, 1997.
*Hanson, et al., “Re-Examination and Further Development of a Precise and Rapid Dye Method for Measuring Cell Growth/Cell Kill”Immunol. Methods, 119:203-210, 1989.
*Hill, et al., “In Vitro Cytotoxicity of Poly(amidoamine)s: Relevance to DNA Delivery”Biochim. Biophys. Acta, 1427: 161-174, 1999.
*Hope, e

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