Design, synthesis, and biocompatibility of an arginine-based polyester

Biotechnology Progress

Volumn 28, Issue 1, 2012, Pages 257-264

  Chu, Hunghao ^a   Gao, Jin ^a   Wang, Yadong ^a  

^a MCGOWAN INSTITUTE FOR REGENERATIVE MEDICINE   (United States)

Author keywords

Biocompatibility; Polycation; Self assembly

Indexed keywords

ASPARTIC ACIDS; CLINICAL TRANSLATION; CONTROLLED RELEASE; HIGH AFFINITY; HYALURONIC ACIDS; IN-VITRO ASSAYS; MEDICAL DEVICES; POLYANIONS; POLYCATIONS; ZETA POTENTIAL MEASUREMENTS;

ARGININE; BIOSENSORS; CYTOTOXICITY; ETHYLENE; ETHYLENE GLYCOL; GLYCEROL; ORGANIC ACIDS; TISSUE ENGINEERING; ZETA POTENTIAL;

BIOCOMPATIBILITY;

ARGININE; ASPARTIC ACID; DNA; ETHYLENE GLYCOL; GLYCEROL; HYALURONIC ACID; PEPTIDE; POLY(ETHYLENE ARGININYLASPARTATE DIGLYCERIDE); POLYAMINE; POLYANIONS; POLYCATIONS; POLYESTER; POLYETHYLENEIMINE; POLYMER;

ANIMAL; ARTICLE; CHEMISTRY; MALE; MATERIALS TESTING; METABOLISM; METHODOLOGY; RAT; SCANNING ELECTRON MICROSCOPY; SPRAGUE DAWLEY RAT; SYNTHESIS;

ANIMALS; ARGININE; ASPARTIC ACID; DNA; ETHYLENE GLYCOL; GLYCEROL; HYALURONIC ACID; MALE; MATERIALS TESTING; MICROSCOPY, ELECTRON, SCANNING; PEPTIDES; POLYAMINES; POLYESTERS; POLYETHYLENEIMINE; POLYMERS; RATS; RATS, SPRAGUE-DAWLEY; RESEARCH DESIGN;

RATTUS;

EID: 84856570724     PISSN: 87567938     EISSN: 15206033     Source Type: Journal    
DOI: 10.1002/btpr.728     Document Type: Article

References (40)

1. Decher G. Fuzzy nanoassemblies: toward layered polymeric multicomposites. Science. 1997; 277: 1232-1237.
2. Picart C, Mutterer J, Richert L, Luo Y, Prestwich GD, Schaaf P, Voegel JC, Lavalle P. Molecular basis for the explanation of the exponential growth of polyelectrolyte multilayers. Proc Natl Acad Sci USA. 2002; 99: 12531-12535.
3. Capito RM, Azevedo HS, Velichko YS, Mata A, Stupp SI. Self-sssembly of large and small molecules into hierarchically ordered sacs and membranes. Science. 2008; 319: 1812-1816.
4. Pack DW, Hoffman AS, Pun S, Stayton PS. Design and development of polymers for gene delivery. Nat Rev Drug Discov. 2005; 4: 581-593.
5. Nguyen DN, Green JJ, Chan JM, Langer R, Anderson DG. Polymeric materials for gene delivery and DNA vaccination. Adv Mater. 2009; 21: 847-867.
6. Jessel N, Oulad-Abdelghani M, Meyer F, Lavalle P, Haîkel Y, Schaaf P, Voegel J-C. Multiple and time-scheduled in situ DNA delivery mediated by β-cyclodextrin embedded in a polyelectrolyte multilayer. Proc Natl Acad Sci USA. 2006; 103: 8618-8621.
7. Wood KC, Chuang HF, Batten RD, Lynn DM, Hammond PT. Controlling interlayer diffusion to achieve sustained, multiagent delivery from layer-by-layer thin films. Proc Natl Acad Sci USA. 2006; 103: 10207-10212.
8. Ono SS, Decher G. Preparation of ultrathin self-standing polyelectrolyte multilayer membranes at physiological conditions using pH-responsive film segments as sacrificial layers. Nano Lett. 2006; 6: 592-598.
9. Dimitrova M, Affolter C, Meyer F, Nguyen I, Richard DG, Schuster C, Bartenschlager R, Voegel J-C, Ogier J, Baumert TF. Sustained delivery of siRNAs targeting viral infection by cell-degradable multilayered polyelectrolyte films. Proc Natl Acad Sci USA. 2008; 105: 16320-16325.
10. Mazia D, Schatten G, Sale W. Adhesion of cells to surfaces coated with polylysine. Applications to electron microscopy. J Cell Biol. 1975; 66: 198-200.
11. Jacobson BS, Branton D. Plasma membrane: rapid isolation and exposure of the cytoplasmic surface by use of positively charged beads. Science. 1977; 195: 302-304.
12. Kinoshita T, Nachman RL, Minick R. Isolation of human platelet plasma membranes with polylysine beads. J Cell Biol. 1979; 82: 688-896.
13. Yazynina EV, Zherdev AV, Dzantiev BB, Izumrudov VA, Gee SJ, Hammock BD. Immunoassay techniques for detection of the herbicide simazine based on use of oppositely charged water-soluble polyelectrolytes. Anal Chem. 1999; 71: 3538-3543.
14. Zeya HI, Spitznagel JK. Arginine-rich proteins of polymorphonuclear leukocyte lysosomes: antimicrobial specificity and biochemical heterogeneity. J Exp Med. 1968; 127: 927-941.
15. Peterson PK, Gekker G, Shapiro R, Freiberg M, Keane WF. Polyamino acid enhancement of bacterial phagocytosis by human polymorphonuclear leukocytes and peritoneal macrophages. Infect Immun. 1984; 43: 561-566.
16. Helander IM, Alakomi HL, LatvaKala K, Koski P. Polyethyleneimine is an effective permeabilizer of Gram-negative bacteria. Microbiology. 1997; 143: 3193-3199.
17. Elferink JGR. Cytolytic effect of polylysine on rabbit polymorphonuclear leukocytes. Inflammation. 1985; 9: 321-331.
18. Elferink J, Deierkauf M. Permeabilization and calcium-dependent activation of rabbit polymorphonuclear leukocytes by poly-L-arginine. Inflammation. 1989; 13: 285-294.
19. Moghimi SM, Symonds P, Murray JC, Hunter AC, Debska G, Szewczyk A. A two-stage poly(ethylenimine)-mediated cytotoxicity: implications for gene transfer/therapy. Mol Ther. 2005; 11: 990-995.
20. Hunter AC. Molecular hurdles in polyfectin design and mechanistic background to polycation induced cytotoxicity. Adv Drug Deliv Rev. 2006; 58: 1523-1531.
21. Choksakulnimitr S, Masuda S, Tokuda H, Takakura Y, Hashida M. In vitro cytotoxicity of macromolecules in different cell culture systems. J Control Release. 1995; 34: 233-241.
22. Moreau E, Domurado M, Chapon P, Vert M, Domurado D. Biocompatibility of polycations: in vitro agglutination and lysis of red blood cells and in vivo toxicity. J Drug Target. 2002; 10: 161-173.
23. Fischer D, Li YX, Ahlemeyer B, Krieglstein J, Kissel T. In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis. Biomaterials. 2003; 24: 1121-1131.
24. Breunig M, Lungwitz U, Liebl R, Goepferich A. Breaking up the correlation between efficacy and toxicity for nonviral gene delivery. Proc Natl Acad Sci USA. 2007; 104: 14454-14459.
25. De Koker S, De Geest BG, Cuvelier C, Ferdinande L, Deckers W, Hennink WE, De Smedt S, Mertens N. In vivo cellular uptake, degradation, and biocompatibility of polyelectrolyte microcapsules. Adv Funct Mater. 2007; 17: 3754-3763.
26. Xiong MP, Bae Y, Fukushima S, Forrest ML, Nishiyama N, Kataoka K, Kwon GS. pH-Responsive multi-PEGylated dual cationic nanoparticles enable charge modulations for safe gene delivery. ChemMedChem. 2007; 2: 1321-1327.
27. Xiong MP, Laird Forrest M, Ton G, Zhao A, Davies NM, Kwon GS. Poly(aspartate-g-PEI800), a polyethylenimine analogue of low toxicity and high transfection efficiency for gene delivery. Biomaterials. 2007; 28: 4889-4900.
28. Zern BJ, Chu H, Osunkoya A, Gao J, Wang Y. A biocompatible arginine-based polycation. Adv Funct Mater. 2011; 21: 434-440.
29. Zern BJ, Chu H, Wang Y. Control growth factor release using a self-assembled [polycation:heparin] complex. PLoS One. 2010; 5: e11017.
30. Rick DL, Davis JW, Kram SL, Mang MN, Lickly TD. Biodegradation of an epoxy-based thermoplastic polyester, poly(hydroxy ester ether) in a laboratory-scale compost system. J Environ Polym Degrad. 1998; 6: 143-157.
31. Ito N, Tonosaki S, Kudo H, Kameyama A, Nishikubo T. Synthesis and characterization of fluoropolymers by the polyaddition of bis(epoxide)s with dicarboxylic acids and diols. J Polym Sci Part A: Polym Chem. 2002; 40: 1395-1404.
32. You Z, Cao H, Gao J, Shin PH, Day BW, Wang Y. A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties. Biomaterials. 2010; 31: 3129-3138.
33. Gao J, Kim YM, Coe H, Zern B, Sheppard B, Wang Y. A neuroinductive biomaterial based on dopamine. Proc Natl Acad Sci USA. 2006; 103: 16681-16686.
34. Boussif O, Lezoualc'h F, Zanta MA, Mergny MD, Scherman D, Demeneix B, Behr, JP. A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: polyethylenimine. Proc Natl Acad Sci USA. 1995; 92: 7297-7301.
35. Morgan D, Clover J, Pearson J. Effects of synthetic polycations on leucine incorporation, lactate dehydrogenase release, and morphology of human umbilical vein endothelial cells. J Cell Sci. 1988; 91: 231-238.
36. Boussif O, Lezoualch F, Zanta MA, Mergny MD, Scherman D, Demeneix B, Behr JP. A versatile vector for gene and oligonucleotide transfer into cells in culture and in-vivo: polyethylenimine. Proc Natl Acad Sci USA. 1995; 92: 7297-7301.
37. Chu H, Gao J, Chen CW, Huard J, Wang Y. Injectable fibroblast growth factor-2 coacervate for persistent angiogenesis. Proc Natl Acad Sci USA. 2011; 108: 13444-13449
38. Chu H, Johnson NR, Mason NS, Wang Y. A [polycation:heparin] complex releases growth factors with enhanced bioactivity. J Control Release. 2011; 150: 157-163
39. Kim T-I, Baek J-u, Yoon JK, Choi JS, Kim K, Park J-s. Synthesis and characterization of a novel arginine-grafted dendritic block copolymer for gene delivery and study of its cellular uptake pathway leading to transfection. Bioconjug Chem. 2007; 18: 309-317
40. Yamanouchi D, Wu J, Lazar AN, Kent KC, Chu CC, Liu B. Biodegradable arginine-based poly(ester-amide)s as non-viral gene delivery reagents. Biomaterials. 2008; 29: 3269-3277