Native protein-initiated ATRP: A viable and potentially superior alternative to PEGylation for stabilizing biologics

Acta Biomaterialia

Volumn 5, Issue 2, 2009, Pages 560-569

  Depp, Virginia ^a   Alikhani, Azadeh ^a   Grammer, Victoria ^a   Lele, Bhalchandra S ^a  

^a ICx Technologies   (United States)

Author keywords

ATRP; PEGylation; Polymer conjugate; Protein; Stability

Indexed keywords

BIOCOMPATIBILITY; BIOSYNTHESIS; BODY FLUIDS; CATALYST ACTIVITY; CONJUGATED POLYMERS; ENZYME ACTIVITY; GRAFTING (CHEMICAL);

ATOM-TRANSFER RADICAL POLYMERIZATION; IN-VITRO; NATIVE PROTEINS; PEGYLATED; PEGYLATION; POLYMER CONJUGATE; POLYMER GRAFTS; POLYMERIZATION INITIATORS; SYNTHESISED; VINYL POLYMER;

ATOM TRANSFER RADICAL POLYMERIZATION;

2 BROMOISOBUTYRIC ACID; CHYMOTRYPSIN; ISOBUTYRIC ACID; MACROGOL; POLY(2 METHACRYLOYLOXYETHYLPHOSPHORYLCHOLINE); POLY(N 2 HYDROXYPROPYLMETHACRYLAMIDE); POLYMER; UNCLASSIFIED DRUG;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; BIOCOMPATIBILITY; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; ENZYME INACTIVATION; ENZYME MODIFICATION; ENZYME STABILITY; ENZYME SYNTHESIS; HUMAN; IN VITRO STUDY; INTERMETHOD COMPARISON; MOUSE; NONHUMAN; PRIORITY JOURNAL;

EID: 57949093539     PISSN: 17427061     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.actbio.2008.08.010     Document Type: Article

References (31)

1. Harris J.M., and Chess R.B. Effect of pegylation on pharmaceuticals. Nature 2 (2003) 214-221
2. Vicent M.J., and Duncan R. Polymer conjugates: nanosized medicines for treating cancer. Trends Biotechnol 24 (2006) 39-47
3. Duncan R. The dawning of polymer therapeutics. Nat Rev Drug Discov 2 (2003) 347-360
4. ] Sheffield W.P. Modification of clearance of therapeutic and potentially therapeutic proteins. Curr Drug Targets Cardiovas Hemat Dis 1 (2001) 1-22
5. Veronese F.M., and Pasut G. PEGylation successful approach to drug delivery. Drug Deliv Today 10 (2005) 1451-1458
6. Mehvar R. Modulation of pharmacokinetics and pharmacodynamics of proteins by polyethylene glycol conjugation. J Pharm Pharm Sci 3 (2000) 125-136
7. Kozlowski A., and Harris J.M. Improvements in protein PEGylation: PEGylated intereferons for treatment of hepatitis C. J Control Release 72 (2001) 217-224
8. Monkarsh S.P., et al. Positional isomers of monopegylated interferon α-2a: isolation, characterization, and biological activity. Anal Biochem 247 (1997) 434-440
9. Wang Y.-S., Youngster S., Bausch J., Zhang R., McNemar C., and Wyss D.F. Identification of major positional isomer of pegylated interferon alpha-2b. Biochemistry 39 (2000) 10634-10640
10. Bailon P., et al. Rational design of a potent, long-lasting form of interferon: a 40 kDa branched polyethylene glycol-conjugated interferon α-2a for the treatment of hepatitis C. Bioconjug Chem 12 (2001) 195-202
11. Kondera Y., Tanaka H., Matsushima A., and Inada Y. Chemical modification of l-asparaginase with a comb-shaped copolymer of polyethylene glycol derivative and maleic anhydride. Biochem Biophys Res Commun 184 (1992) 144-148
12. Davis F.F. PEG-adenosine deaminase and PEG-asparaginase. In: Maeda, et al. (Ed). Drugs in the clinical stage (2003), Kluwar Academic/Plenum Publishers, New York
13. Seely J.E., et al. Issues encountered in the production of site-specific monopegylated therapeutic proteins. Polym Preprints 38 (1997) 572-573
14. Seely J.E., and Richey C.W. Use of ion-exchange chromatography and hydrophobic interaction chromatography in the preparation and recovery of polyethylene glycol-linked proteins. J Chromatogr A 908 (2001) 235-241
15. Seely JE, Buckel SD, Green PD, Richey CW. Making site specific pegylation work. BioPharm International 2005 (www.biopharminternational.com).
16. Yamamoto Y., et al. Site-specific pegylation of a lysine-deficient TNF-α with full bioactivity. Nat Biotechnol 21 (2003) 546-552
17. Tsutsumi Y., Onda M., Nagata S., Lee B., Kreitman R.J., and Pastan I. Site-specific chemical modification with polyethylene glycol of recombinant immunotoxin anti-Tac(Fv)-PE38 (LMB-2) improves antitumor activity and reduces animal toxicity and immunogenicity. Proc Natl Acad Sci USA 97 (2000) 8548-8553
18. Benhar I., Wang Q.C., Fitzgerald D.J., and Pastan I. Pseudomonas exotoxin A mutants. Replacement of surface-exposed residues in domain III with cysteine residues that can be modified with polyethylene glycol in a site-specific manner. J Biol Chem 269 (1994) 13398-133404
19. Kaun C.T., Wang Q.C., and Pastan I. Pseudomonas exotoxin A mutants. Replacement of surface exposed residues in domain II with cysteine residues that can be modified with polyethylene glycol in a site-specific manner. J Biol Chem 269 (1994) 7610-7616
20. Deiters A., Cropp T.A., Summerer D., Mukherji M., and Schultz P.G. Site specific pegylation of proteins containing unnatural amino acids. Bioorg Med Chem Lett 14 (2004) 5743-5745
21. Bontempo D., and Maynard H.D. Streptavidin as a macroinitiator for polymerization: in situ protein-polymer conjugate formation. J Am Chem Soc 127 (2005) 6508-6509
22. Heredia K.L., Bontempo D., Ly T., Byers J.T., Halstenberg S., and Maynard H.D. In-situ preparation of protein-smart polymer conjugates with retention of bioactivity. J Am Chem Soc 127 (2005) 16955-16960
23. Lele B.S., Murata H., Matyjaszewski K., and Russell A.J. Synthesis of uniform polymer-protein conjugates. Biomacromolecules 5 (2005) 1947-1955
24. Boyer C., Bulmus V., Liu J., Davis T.P., Stenzel M.H., and Barner-Kowollik C. Well-defined protein-polymer conjugates via in situ RAFT polymerization. J Am Chem Soc 129 (2007) 7145-7154
25. Broyer R.M., Quaker G.M., and Maynard H.D. Designed amino acid ATRP initiators for the synthesis of biohybrid materials. J Am Chem Soc 130 (2008) 1041-1047
26. Kodera Y., Tanaka H., Matsushima A., and Inada Y. Chemical modification of l-asparaginase with a comb-shaped copolymer of polyethylene glycol derivative and maleic anhydride. Biochem Biophys Res Commun 184 (1992) 144-148
27. Miyamoto D., Watanabe J., and Ishihara K. Effect of water soluble phospholipid polymers conjugated with papain on the enzymatic stability. Biomaterials 25 (2004) 71-76
28. Oupick D., Ulbrich K., and Rihova B. Conjugates of semitelechelic poly[N-(2-hydroxypropyl)methacrylamide] with enzymes for protein delivery. J Bioactive Compat Polym 14 (1999) 213-231
29. Wang X.-S., Lascelles S.F., Jackson R.A., and Armes S.P. Facile synthesis of well-defined water-soluble polymers via atom transfer radical polymerization in aqueous media at ambient temperature. Chem Commun (1999) 1817-1818
30. Lobb E.J., Ma I., Billingham N.C., Armes S.P., and Lewis A.L. Facile synthesis of well-defined, biocompatible phosphorylcholine-based methacrylate copolymers via atom transfer radical polymerization at 20 °C. J Am Chem Soc 123 (2001) 7913-7914
31. Teodorescu M., and Matyjaszewski K. Atom transfer radical polymerization of (meth)acrylamides. Macromolecules 32 (1999) 4826-4831