Synthesis and chemical modification of degradable polymers to enhance gene delivery

Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemical Engineering, February 2007.

[1]  E. Delain,et al.  Poly[Lys-(AEDTP)]: a cationic polymer that allows dissociation of pDNA/cationic polymer complexes in a reductive medium and enhances polyfection. , 2002, Bioconjugate chemistry.

[2]  Robert Langer,et al.  Degradable Poly(β-amino esters): Synthesis, Characterization, and Self-Assembly with Plasmid DNA , 2000 .

[3]  Daniel W. Pack,et al.  Design and development of polymers for gene delivery , 2005, Nature Reviews Drug Discovery.

[4]  Joel A Swanson,et al.  Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities. , 2003, Advanced drug delivery reviews.

[5]  Y. Lim,et al.  A self-destroying polycationic polymer: Biodegradable poly(4-hydroxy-L- proline ester) , 1999 .

[6]  R. Langer,et al.  Exploring polyethylenimine‐mediated DNA transfection and the proton sponge hypothesis , 2005, The journal of gene medicine.

[7]  D. Lauffenburger,et al.  Vector unpacking as a potential barrier for receptor-mediated polyplex gene delivery. , 2000, Biotechnology and bioengineering.

[8]  C. Pouton,et al.  Polycation-DNA complexes for gene delivery: a comparison of the biopharmaceutical properties of cationic polypeptides and cationic lipids. , 1998, Journal of controlled release : official journal of the Controlled Release Society.

[9]  L. Field,et al.  Organic Disulfides and Related Substances. XVIII. Synthesis and Disproportionation of 2-(Aryldithio)ethylamine Hydrochlorides1a,b , 1966 .

[10]  O. Danos,et al.  Synthesis of linear polyethylenimine derivatives for DNA transfection. , 2003, Bioconjugate chemistry.

[11]  Y. Buechler,et al.  Targeting DNA to Cells with Basic Fibroblast Growth Factor (FGF2)* , 1996, The Journal of Biological Chemistry.

[12]  K. Leong,et al.  Polyphosphoesters in drug and gene delivery. , 2003, Advanced drug delivery reviews.

[13]  K. Ulbrich,et al.  Polyelectrolyte vectors for gene delivery: influence of cationic polymer on biophysical properties of complexes formed with DNA. , 1999, Bioconjugate chemistry.

[14]  D. Cheresh,et al.  Requirement of vascular integrin alpha v beta 3 for angiogenesis. , 1994, Science.

[15]  J. Chung,et al.  Anti-JL1 antibody-conjugated poly (L-lysine) for targeted gene delivery to leukemia T cells. , 2001, Journal of controlled release : official journal of the Controlled Release Society.

[16]  W. Driessen,et al.  Peptide-mediated Gene Transfer of Cationic Lipid/Plasmid DNA Complexes to Endothelial Cells , 2004, Journal of drug targeting.

[17]  Robert Langer,et al.  A polymer library approach to suicide gene therapy for cancer. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[18]  Daniel G. Anderson,et al.  Structure/property studies of polymeric gene delivery using a library of poly(beta-amino esters). , 2005, Molecular therapy : the journal of the American Society of Gene Therapy.

[19]  L. Monaco,et al.  Nanoscopic structure of DNA condensed for gene delivery. , 1997, Nucleic acids research.

[20]  D. Fischer,et al.  Recent advances in rational gene transfer vector design based on poly(ethylene imine) and its derivatives , 2005, The journal of gene medicine.

[21]  E. Wagner,et al.  Different strategies for formation of pegylated EGF-conjugated PEI/DNA complexes for targeted gene delivery. , 2001, Bioconjugate chemistry.

[22]  M. Monsigny,et al.  Glycosylated polylysine/DNA complexes: gene transfer efficiency in relation with the size and the sugar substitution level of glycosylated polylysines and with the plasmid size. , 1995, Bioconjugate chemistry.

[23]  G. L. Willingham,et al.  Synthesis and membrane interactions of spin-label bifunctional reagents. , 1983, Biochemistry.

[24]  E. Rajnavölgyi,et al.  Carrier design: cytotoxicity and immunogenicity of synthetic branched polypeptides with poly(L-lysine) backbone , 1992 .

[25]  M. Rots,et al.  Protein transduction domains and their utility in gene therapy. , 2003, Current gene therapy.

[26]  J. Behr,et al.  Intraperitoneal linear polyethylenimine (L-PEI)-mediated gene delivery to ovarian carcinoma nodes in mice , 2006, Cancer Gene Therapy.

[27]  D. Jans,et al.  Using nuclear targeting signals to enhance non‐viral gene transfer , 2002, Immunology and cell biology.

[28]  Daniel G. Anderson,et al.  Biodegradable polymeric vectors for gene delivery to human endothelial cells. , 2006, Bioconjugate chemistry.

[29]  V. Labhasetwar,et al.  Size-dependency of nanoparticle-mediated gene transfection: studies with fractionated nanoparticles. , 2002, International journal of pharmaceutics.

[30]  H. Paik,et al.  Ionization of Poly(ethylenimine) and Poly(allylamine) at Various pH′s , 1994 .

[31]  Daniel G. Anderson,et al.  Semi-automated synthesis and screening of a large library of degradable cationic polymers for gene delivery. , 2003, Angewandte Chemie.

[32]  Giffin D. Jones,et al.  THE POLYMERIZATION OF ETHYLENIMINE , 1944 .

[33]  W. Jiskoot,et al.  Tumor cell and tumor vasculature targeted liposomes for neutron capture therapy , 2005 .

[34]  K. De Yao,et al.  Chitosan and its derivatives--a promising non-viral vector for gene transfection. , 2002, Journal of controlled release : official journal of the Controlled Release Society.

[35]  J. Kopeček,et al.  PEGylation of poly(ethylene imine) affects stability of complexes with plasmid DNA under in vivo conditions in a dose-dependent manner after intravenous injection into mice. , 2005, Bioconjugate chemistry.

[36]  Jindrich Kopecek,et al.  Prospects for cationic polymers in gene and oligonucleotide therapy against cancer. , 2002, Advanced drug delivery reviews.

[37]  M. O'Neill,et al.  Receptor-mediated gene delivery to human peripheral blood mononuclear cells using anti-CD3 antibody coupled to polyethylenimine , 2001, Gene Therapy.

[38]  Freya Q. Schafer,et al.  Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple. , 2001, Free radical biology & medicine.

[39]  D W Pack,et al.  Polymer-based gene delivery with low cytotoxicity by a unique balance of side-chain termini. , 2001, Proceedings of the National Academy of Sciences of the United States of America.

[40]  T. Baldwin,et al.  Use of bacterial and firefly luciferases as reporter genes in DEAE-dextran-mediated transfection of mammalian cells. , 1992, Analytical biochemistry.

[41]  R. Ebright,et al.  Incorporation of an EDTA-metal complex at a rationally selected site within a protein: application to EDTA-iron DNA affinity cleaving with catabolite gene activator protein (CAP) and Cro. , 1992, Biochemistry.

[42]  M. Buchberger,et al.  Coupling of cell-binding ligands to polyethylenimine for targeted gene delivery , 1997, Gene Therapy.

[43]  Daniel G. Anderson,et al.  Synthesis of poly(beta-amino ester)s with thiol-reactive side chains for DNA delivery. , 2006, Journal of the American Chemical Society.

[44]  K. Zatloukal,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. , 1992, Proceedings of the National Academy of Sciences of the United States of America.

[45]  L G Griffith,et al.  Quantitative comparison of polyethylenimine formulations and adenoviral vectors in terms of intracellular gene delivery processes , 2005, Gene Therapy.

[46]  J F Murray,et al.  Determination of sulfhydryl groups with 2,2'- or 4,4'-dithiodipyridine. , 1967, Archives of biochemistry and biophysics.

[47]  J. Behr,et al.  Gene transfer with synthetic virus-like particles via the integrin-mediated endocytosis pathway , 1999, Gene Therapy.

[48]  J. Hughes,et al.  In Vitro Myotoxicity of Selected Cationic Macromolecules Used in Non-Viral Gene Delivery , 1998, Pharmaceutical Research.

[49]  C. van Nostrum,et al.  Water-soluble biodegradable cationic polyphosphazenes for gene delivery. , 2003, Journal of controlled release : official journal of the Controlled Release Society.

[50]  A. Fahr,et al.  SPECTROSCOPIC METHODS FOR CHARACTERIZATION OF NONVIRAL GENE DELIVERY SYSTEMS FROM A PHARMACEUTICAL POINT OF VIEW , 2001 .

[51]  Allan Hoffman,et al.  A new pH-responsive and glutathione-reactive, endosomal membrane-disruptive polymeric carrier for intracellular delivery of biomolecular drugs. , 2003, Journal of controlled release : official journal of the Controlled Release Society.

[52]  E. Wagner.  Strategies to Improve DNA Polyplexes for in Vivo Gene Transfer: Will “Artificial Viruses” Be the Answer? , 2004, Pharmaceutical Research.

[53]  R. Cartier,et al.  Utilization of synthetic peptides containing nuclear localization signals for nonviral gene transfer systems , 2002, Gene Therapy.

[54]  F. Eckstein,et al.  Site specific labelling of sugar residues in oligoribonucleotides: reactions of aliphatic isocyanates with 2' amino groups. , 1996, Nucleic acids research.

[55]  A. Parker,et al.  The Scission Of The Sulfur-Sulfur Bond , 1959 .

[56]  E. Joly,et al.  A simple procedure to increase efficiency of DEAE-dextran transfection of COS cells. , 1995, Trends in genetics : TIG.

[57]  E Ruoslahti,et al.  RGD and other recognition sequences for integrins. , 1996, Annual review of cell and developmental biology.

[58]  Akin Akinc,et al.  Synthesis of poly (β-amino ester)s optimized for highly effective gene delivery , 2003 .

[59]  C. Plank,et al.  Application of membrane-active peptides for drug and gene delivery across cellular membranes. , 1998, Advanced drug delivery reviews.

[60]  Y. Mély,et al.  Monitoring of the formation and dissociation of polyethylenimine/DNA complexes by two photon fluorescence correlation spectroscopy. , 2003, Biophysical journal.

[61]  Y. Lim,et al.  Biodegradable polyester, poly[alpha-(4-aminobutyl)-L-glycolic acid], as a non-toxic gene carrier. , 2000, Pharmaceutical research.

[62]  Stefaan C. De Smedt,et al.  Cationic Polymer Based Gene Delivery Systems , 2000, Pharmaceutical Research.

[63]  C Russell Middaugh,et al.  Barriers to nonviral gene delivery. , 2003, Journal of pharmaceutical sciences.

[64]  Thomas Kissel,et al.  In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis. , 2003, Biomaterials.

[65]  R. Langer,et al.  Accelerated discovery of synthetic transfection vectors: parallel synthesis and screening of a degradable polymer library. , 2001, Journal of the American Chemical Society.

[66]  A. Miller,et al.  Gene delivery and expression mediated by an integrin-binding peptide. , 1995, Gene therapy.

[67]  M. Davies,et al.  Star-shaped poly(ethylene glycol)-block-polyethylenimine copolymers enhance DNA condensation of low molecular weight polyethylenimines. , 2002, Biomacromolecules.

[68]  D. Pei,et al.  5-(2-Aminoethyl)dithio-2-nitrobenzoate as a more base-stable alternative to Ellman's reagent. , 2004, Organic letters.