A new pH-responsive and glutathione-reactive, endosomal membrane-disruptive polymeric carrier for intracellular delivery of biomolecular drugs

Journal of Controlled Release

Volumn 93, Issue 2, 2003, Pages 105-120

  Bulmus, Volga ^a   Woodward, Monica ^a   Lin, Lianne ^a   Murthy, Niren ^a   Stayton, Patrick ^a   Hoffman, Allan ^a  

^a University of Washington   (United States)

Author keywords

Cytoplasmic delivery; Endosomal membrane disruption; Glutathione; pH sensitive polymer; Polymer conjugates

Indexed keywords

CELLS; COMPLEXATION; DRUG PRODUCTS; ENZYMES; PH EFFECTS; POLYMERS; SYNTHESIS (CHEMICAL);

FIBROBLASTS; FUNCTIONAL GROUPS;

BIOLOGICAL MEMBRANES;

ACRYLIC ACID BUTYL ESTER; ACRYLIC ACID DERIVATIVE; AMPHOPHILE; ANTISENSE OLIGODEOXYNUCLEOTIDE; DRUG CARRIER; GLUTATHIONE; METHACRYLIC ACID; POLY(METHACRYLIC ACID CO BUTYL ACRYLIC ACID CO PYRIDYL DISULFIDE ACRYLIC ACID); POLYMER; PYRIDYL DISULFIDE ACRYLATE; TERPOLYMER; THIOL GROUP; UNCLASSIFIED DRUG;

ANIMAL CELL; CELL MEMBRANE TRANSPORT; CELL STRAIN 3T3; CONFERENCE PAPER; CONTROLLED STUDY; CYTOPLASM; DNA DRUG COMPLEX; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SYNTHESIS; DRUG UPTAKE; EMBRYO; ERYTHROCYTE; ERYTHROCYTE MEMBRANE; FIBROBLAST; HEMOLYSIS; HUMAN; HUMAN CELL; ISOTOPE LABELING; MOUSE; NONHUMAN; PH MEASUREMENT; PRIORITY JOURNAL;

EID: 0242662545     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2003.06.001     Document Type: Conference Paper

References (29)

1. Plank C., Oberhauser B., Mechtler K., Koch C., Wagner E. The influence of endosome-disruptive peptides on gene transfer using synthetic virus like gene transfer systems. J. Biol. Chem. 269(17):1994;12918-12924.
2. Murthy N., Robichaud J., Tirrell D., Stayton P., Hoffman A. The design and synthesis of polymers for eukaryotic membrane disruption. J. Control. Release. 61:1999;137-143.
3. Murthy N., Chang I., Stayton P., Hoffman A. pH-sensitive hemolysis by random copolymer of alkyl acrylates and acrylic acid. Macromol. Symp. 172:2001;49-55.
4. Lackey C., Murthy N., Press O., Tirrell D., Hoffman A., Stayton P. Hemolytic activity of pH-responsive polymer-streptavidin bioconjugate. Bioconjug. Chem. 10:1999;401-405.
5. Lackey C., Press O., Hoffman A., Stayton P. A biomimetic pH-responsive polymer directs endosomal release and intracellular delivery of an endocytosed antibody complex. Bioconjug. Chem. 13:2002;996-1001.
6. Murthy N., Campbell J., Fausto N., Hoffman A.S., Stayton P.S. Bioinspired pH-responsive polymers for the intracellular delivery of biomolecular drugs. Bioconjug. Chem. 14:2003;412-419.
7. Haensler J., Szoka F.C. Polyamidoamine cascade polymers mediate efficient transfection of cells in culture. Bioconjug. Chem. 4:1993;372-379.
8. Choi Y.H., Lui F., Choi J.S., Kim S.W., Park J.S. Characterization of a targeted gene carrier, lactose-polyethyleneglycol-grafted poly L-lysine and its complex with plasmid DNA. Hum. Gene Ther. 10:1999;2657-2665.
9. Richardson S., Ferruti S., Duncan R. Poly(amidoamine)s as potential endosomolytic polymers: evaluation in vitro and body distribution in normal and tumour bearing animals. J. Drug Target. 6:1999;391-404.
10. Vinogradov S.V., Bronich T.K., Kabanov A.V. Self-assembly of polyamine-poly(ethylene glycol) copolymers with phosphorothioate oligonucleotides. Bioconjug. Chem. 9:1998;805-812.
11. Lim D.W., Yeom Y.I., Park T.G. Poly(DMAEMA-NVP)-b-PEG-galactose as gene delivery vector for hepatocytes. Bioconjug. Chem. 11:2000;688-695.
12. Lim Y., Kim S., Suh H., Park J. Biodegradable, endosome disruptive and cationic network-type polymer as a highly efficient and nontoxic gene delivery carrier. Bioconjugate Chem. 13:2002;952-957.
13. Godbey W.T., Barry M.A., Saggau P., Wu K.K., Mikos A.G. PEI-mediated transfection: a new paradigm for gene therapy. J. Biomed. Mater. Res. 51:2000;321-328.
14. Nagy I.B., Dancs A., Koczan G., Mezo G., Hudecz F. Conjugation of HS-oligopeptides with polymeric branched chain polypeptides containing multiple amino groups. J. Bioact. Compat. Polym. 15:2000;139-154.
15. Wang L., Kristensen J., Ruffner D.E. Delivery of antisense oligonucleotides using HPMA polymer: synthesis of a thiol polymer and its conjugation to water-soluble molecules. Bioconjug. Chem. 9:1998;749-757.
16. Habeeb A.F.S.A. Determination of free amino groups in proteins by trinitrobenzenesulfonic acid. Anal. Biochem. 14:1966;328-336.
17. Freshney I.R. Culture of Animal Cells. 3rd ed. 1994;296-299 Wiley-Liss, New York, NY.
18. F. Black, P. Stayton, A.S. Hoffman, The effect of molecular weight on the pH-sensitive membrane lytic properties of poly(propylacrylic acid), in preparation.
19. Borden K., Eum K., Langley K., Tirrell D. On the mechanism of polyelectrolyte-induced structural reorganization in thin molecular films. Macromolecules. 20:1987;454-456.
20. Olea A., Thomas J. Fluorescence studies of the conformational changes of poly(methacrylic acid) with pH. Macromolecules. 22:1989;1165-1169.
21. Linhardt J., Tirrell D.A. pH-induced fusion and lysis of phoshatidylcholine vesicles by the hydrophobic polyelectrolyte poly(2-ethylacrylic acid). Langmuir. 16:2000;122-127.
22. Feener E.P., Shen W.C., Ryser H.J. Cleavage of disulfide bonds in endocytosed macromolecules. A processing not associated with lysosomes or endosomes. J. Biol. Chem. 4(5):1990;18780-18785.
23. McIntyre G.D., Scott C.F. Jr., Ritz J., Blattler W.A., Lambert J.M. Preparation and characterization of interleukin-2-gelonin conjugates made using different cross-linking reagents. Bioconjug. Chem. 5(1):1994;88-97.
24. Schafer F.Q., Buettner G.R. Redox environment of the cell as viewed trough the redox state of the glutathione disulfide/glutathione couple. Free Radic. Biol. Med. 30(11):2001;1191-1212.
25. Ravve A. Free-radical chain growth polymerization. Principles of Polymer Chemistry. 1995;35-75 Plenum, New York.
26. Brandrup J., Immergut E. Polymer Handbook. 3rd ed. 1989;II-153 Wiley.
27. Painter P., Coleman M. Reactivity ratios and copolymer composition. Fundamentals of Polymer Science. 1994;Technomic Publishing, Lancaster, PA.
28. Solomons T.W.G. Organic Chemistry. 6th ed. 1996;953 Wiley.
29. Crooke S.T. Progress in Antisense Technology. Methods in Enzymology. vol. 313:1999;3-45 Academic Press, NYC, NY.