Synthesis and purification of mono-PEGylated insulin

Chemical Biology and Drug Design

Volumn 69, Issue 2, 2007, Pages 132-138

  Dou, Huaizhi ^a   Zhang, Min ^a   Zhang, Yu ^a   Yin, Chunhua ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Chemical structure; Insulin; mPEG aldehyde; PEGylation; Peptide

Indexed keywords

ALDEHYDE; INSULIN; MACROGOL; MONOMETHOXYPOLY(ETHYLENE GLYCOL) 2000; MONOMETHOXYPOLY(ETHYLENE GLYCOL) 5000; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; HORMONE SYNTHESIS; ION EXCHANGE CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PH; PRIORITY JOURNAL; PURIFICATION; REACTION TIME; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ANIMALS; INSULIN; MICE; POLYETHYLENE GLYCOLS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 33947419377     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2007.00479.x     Document Type: Article

References (22)

1. Liu F., Song S.C., Mix D., Baudyš M., Kim S.W. (1997) Glucose-induced release of glycosylpoly(ethylene glycol) insulin bound to a soluble conjugate of concanavalin A. Bioconjug Chem;8:664-672.
2. Uchio T., Baudyš M., Liu F., Song S.C., Kim S.W. (1999) Site-specific insulin conjugates with enhanced stability and extended action profile. Adv Drug Deliv Rev;35:289-360.
3. Myers S.R., Yakubu-Madus F.E., Johnson W.T., Baker J.E., Cusick T.S., Williams V.K., Tinsley F.C., Kriauciunas A., Manetta J., Chen V.J. (1997) Acylation of human insulin with palmitic acid extends the time action of human insulin in diabetic dogs. Diabetes;46:637.
4. Calceti P., Salmaso S., Walker G., Bernkop-Schnürch A. (2004) Development and in vivo evaluation of an oral insulin-PEG delivery system. Eur J Pharm Sci;22:315-323.
5. Hashimoto M., Takada K., Kiso Y., Muranishi S. (1989) Synthesis of palmitoyl derivatives of insulin and their biological activities. Pharm Res;6:171-176.
6. Hinds K., Koh J.J., Joss L., Liu F., Baudyš M., Kim S.W. (2000) Synthesis and characterization of poly (ethylene glycol)-insulin conjugates. Bioconjug Chem;11:195-201.
7. Veronese F.M., Harris J.M. (2002) Introduction and overview of peptide and protein pegylation. Adv Drug Deliv Rev;54:453-456.
8. Bailon P., Berthold W. (1998) Polyethylene glycol-conjugated pharmaceutical proteins. Pharm Sci Technol Today;1:352-353.
9. Hinds K.D., Kim S.W. (2002) Effects of PEG conjugation on insulin properties. Adv Drug Deliv Rev;54:505-530.
10. Harris J.M., Struck E.C., Case M.G., Paley M.S. (1984) Synthesis and characterization of poly (ethylene glycol) derivatives. J Polym Sci;22:341-352.
11. Kinstler O.B., Brems D.N., Lauren S.L. (1996) Characterization and stability of N-terminally PEGylated rhG-CSF. Pharm Res;13:996-1002.
12. Kinstler O., Molineux G., Treuheit M., Ladd D., Gegg C. (2002) Mono-N-terminal poly (ethylene glycol)-protein conjugates. Adv Drug Deliv Rev;54:477-485.
13. Kinstler O.B., Gabriel N.E., Farrar C.E., DePrince R.B. (1999) N-terminally Chemically Modified Protein Compositions and Methods. US Patent 5,985,265.
14. Baker D.P., Lin E.Y., Lin K.C., Pellegrini M., Petter R.C., Chen L.L., Arduini R.M. et al. (2006) N-terminally PEGylated human interferon-β-1a with improved pharmacokinetic properties and in vivo efficacy in a melanoma angiogenesis model. Bioconjug Chem;17:179-188.
15. Roberts M.J., Bentley M.D., Harris J.M. (2002) Chemistry for peptide and protein PEGylation. Adv Drug Deliv Rev;54:459-476.
16. Sherman M.R., Williams D., Saifer M.G.P., French J.A., Kwak L.W., Oppenheim J.J. (1997) Conjugation of high-molecular weight poly (ethylene glycol) to cytokines: granulocayte-macrophage colony-stimulating factors as model substrates. In: Harris J.M., Zalipsky S., editors. Poly (ethylene glycol) Chemistry and Biological Applications. Washington, USA: American Chemical Society;p. 155-169.
17. Bentley M.D., Harris J.M. (1999) Poly (ethylene glycol) Aldehyde Hydrates and Related Polymers and Application in Modifying. US Patent 5,990,237.
18. Vogel A.I. (1978) Vogel's Textbook of Practice Chemistry. New York: Longman;p. 1071.
19. Snyder S.L., Sobocinski P.Z. (1975) An improved 2,4,6-trinitroben- zenesulfonic acid method for the determination of amines. Anal Biochem;64:284-288.
20. Kurfurst M.K. (1992) Detection and molecular weight determination of polyethylene glycol-modified hirudin by staining after sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Anal Biochem;200:244-248.
21. Nelson D.L., Cox M.M. (2000) Lehninger Principles of Biochemistry. New York: Worth Publishers;p. 118.
22. Brange J., Andersen L., Laurensen E.D., Meyn G., Rasmussen E. (1997) Toward understanding insulin fibrillation. J Pharm Sci;86:517-525.