Problems and solutions in pegylation of protein and peptide drugs

Yaoxue Xuebao

Volumn 37, Issue 5, 2002, Pages 396-400

  Jiang, Zhong Yi ^a   Gao, Rong ^a   Wang, Yan Qiang ^a   Sun, Yan ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

PEGylation; Peptides; Proteins

Indexed keywords

MACROGOL DERIVATIVE; PEPTIDE; PROTEIN;

ARTICLE; CHEMISTRY;

PEPTIDES; POLYETHYLENE GLYCOLS; PROTEINS;

EID: 0042884035     PISSN: 05134870     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. Abuchowski A, Van ET, Palczuk NC, et al. Alteration of immunological properties of bovine serum albumin by covalent attachment of poly (ethylene glycol) [J]. J Biol Chem, 1977,252(11) :3578-3581.
2. Kodera Y, Matsushima A, Hiroto M, et al. Pegylation of proteins and bioactive substances for medical and technical applications [J]. Prog Polymer Sci, 1998, 23 (7) : 1233-1271.
3. Inada Y, Furukawa M, Sasaki H, et al. Biomedical and biotechnological applications of PEG-modified proteins [J]. Trends Biotechnol, 1995,13(3) :86-91.
4. Veronese FM, Morpurgo M. Bioconjugation in pharmaceutical chemistry [J]. IL Farmaco, 1999,54:497-516.
5. Yin CQ, Zhang M. PEG conjugates of protein and peptide drugs - a new type drug delivery system [J]. Chin Pharm J, 2001,36(5) :292-296.
6. Bailon P, Berthold W. Polyethlyene glycol-conjugated pharmaceutical proteins [J]. PSTT, 1998,1(8) :352-256.
7. Veronese FM. Peptide and protein PEGyllation: a review of problems and solutions [J]. Biomaterials, 2001,22:405-417.
8. Harris J, Zalipsky S. Poly (ethyleneglycol ) Chemistry and Biological Applications [M]. Washington DC: ACS Books, 1997.347-381.
9. Kozlowski A, Harris JM. Improvements in protein PEGylation: pegylated interferons for treatment of Hepatitis C [J]. J Controlled Release, 2001,72(3) :217-224.
10. Harris J. Polyethylene Glycol Chemistry: Biotechnological and Biomedical Applications [M]. New York: Plenum, 1992.171-192.
11. Palaparthy R, Wang H, Gulati A. Current aspects in pharmacology of modified hemoglobins [J]. Adv Drug Deliv Rev, 2000,40(2): 185-198.
12. He XH, Shaw PC, Xu LH, et al. Site-directed polyethylene glycol modification of trichosanthin: effects on its biological activities, pharmacokinetics and activity [J]. Life Sci, 1999,64(14): 1163-1175.
13. Zalipsky S, Seltzer R, Meron-Rudolph S. Evaluation of a new reagent for covalent attachment of polyethylene glycol to proteins [J]. Biotechnol Appl Biochem, 1992,15 : 100-114.
14. Zalipsky S. Alkyl succinimidyl carbonates undergo Lossen rearrangement in basic buffers [J]. Chem Commun, 1998,1 (1) :69-70.
15. Kinstler OB, Brems DN, Lauren SL, et al. Characterization and stability of N-terminally PEGylated rhG-CSF [J]. Pharm Res, 1996,13(7) :996-1002.
16. Morpurgo M, Veronese FM, Kachensky D, et al. Preparation and characterization of poly (ethyleneglycol) vinylsulfone [J]. Bioconjugate Chem, 1996,7(3): 363-368.
17. Monfardini C, Schiavon O, Caliceti P et al. A branched monomethoxypoly (ethyleneglycol) for protein modification [J]. Bioconjugate Chem, 1995,6(1) :62-69.
18. Harris J, Kozlowski A. Polyethyleneglycol and related polymers monosubstituted with propionic or butanoic acids and functional derivatives thereof for biotechnical applications [P]. US Pat: 5672662, 1997-09-30.
19. Bentley MD, Harris J, Kozlowski A. Heterobifunctional poly (ethyleneglycol) derivatives and methods for their preparation [P]. P.C.T. US 99/23536, 1999-10-08.
20. Schiavon O, Caliceti P, Veronese FM. Therapeutic proteins: a comparison of chemical and biological properties of uricase conjugated to linear or branched poly (ethylene glycol) and poly(N-acryloylmorpholine) [J]. IL Farmaco, 2000,50: 264-269.
21. Elsner C, Crahn S, Bauer S, et al. Effects of chemical modification of lysine residues in trypsin [J]. J Mol Cata B: Enzymatic , 2000,8:193-200.
22. Lee KC, Tak KK, Park MO, et al. Preparation and characterization of polyethylene glycol modified salmon calcitonins [J]. Pharm Dev Technol, 1999, 4 (4) : 269-275.
23. Caliceti P, Veronese FM. Improvement of the physicochemical and biopharmaceutical properties of insulin by poly(ethyleneglycol) conjugation [J]. STP Pharm Sci, 1999,9(2) : 107-113.
24. Uchio T, Baudys M, Liu F, et al. Site-specific insulin conjugates with enhanced stability and extended action profile [J]. Adv Drug Deliv Rev , 1999,35(4) :289-306.
25. Hinds K, Koh JJ, Joss L, et al. Synthesis and characterization of poly (ethylene glycol)-insulin conjugates [J]. Bioconjugate Chem, 2000,11(3) : 195-201.
26. Campbell RM, Heimer EP, Ahmad M, et al. PEGylated peptides [J]. J Peptide Res, 1997,49(6) :527-537.
27. Carrion C, Domingo JC, Madariaga MA. Preparation of long-circulating immonoliposomes using PEG-cholesterol conjugates: effect of the spacer arm between PEG and cholesterol on liposomal characteristics [J]. Chem Phys Lipids, 2001,113:97-110.
28. Veronese FM, Sacca B, Polverino de Laureto P, et al. New PEGs for peptide and protein modification, suitable for identification of the PEGylation site [J]. Bioconjugate Chem, 2001,12(1):62-67.
29. Li WJ. Protein modification with polyethylene glycol and related analytical and separation techniques [A]. Dissertation for Doctor degree [D]. Beijing: Institute of Chemical Metallurgy, 2001.1-146.
30. Li WJ, Lin BC, Su ZG. Analytical methods of polyethylene glycol-modified proteins [J]. Chin J Anal Chem, 2001,29(2) :228-231.
31. Habeeb AFSA. Determination of free amino groups in proteins by trinitrobenzenesulfonic acid [J]. Anal Biochem, 1966, 14:328-336.
32. Guermant C, Brygier BB, Looze Y, et al. Quantitative determination of polyethylene glycol based upon its salting out and partitioning of a dye into the resulting aqueous two -phase system [J]. Anal Biochem, 1995,230:254-260.
33. Wang CX, Yang SC. The development of electrospray ionization mass spectrometry (ESI-MS) in studies of non-covalent protein complexes [J]. Acta Pharm Sin, 2001,36(4) :315-320.
34. Jiang ZY, Gao R, Xu SW, et al. Progress in chemical modification of protein [J]. Mod Chem Ind (91K ft -T. ), 2001,21(8) :25-28.
35. Jiang ZY, Gao R, Xu SW, et al. Chemical modification of protein side chains [J/OL]. Chem Online ( it ¥ilffi 1*3 $ JK), 2001,64(6) :W062 1-4.
36. Bradley D. EU approval for pegylated hepatitics C drug [J]. PSTT, 2000,3(9) :299-299.