High-yield production of biologically active mono-PEGylated salmon calcitonin by site-specific PEGylation

Journal of Controlled Release

Volumn 117, Issue 3, 2007, Pages 371-379

  Youn, Yu Seok ^a   Na, Dong Hee ^b   Lee, Kang Choon ^a  

^a Sungkyunkwan University   (South Korea)

^b Kyungsung University   (South Korea)

Author keywords

Biological activity; Peptide delivery; Salmon calcitonin; Site specific PEGylation; Stability

Indexed keywords

AMINES; OPTIMIZATION;

BIOLOGICAL ACTIVITIES; PEPTIDE DELIVERY; SALMON CALCITONIN; SITE-SPECIFIC PEGYLATION;

DRUG PRODUCTS;

MACROGOL; SALCATONIN;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DEPROTECTION REACTION; DRUG CONJUGATION; DRUG MANUFACTURE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN STABILITY; RAT;

AMINO ACID SEQUENCE; ANIMALS; CALCITONIN; CALCIUM; CHEMISTRY, PHYSICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIC AMP; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG STABILITY; EXCIPIENTS; FLUORENES; HALF-LIFE; KIDNEY; LIVER; MALE; MOLECULAR SEQUENCE DATA; POLYETHYLENE GLYCOLS; RATS; RATS, SPRAGUE-DAWLEY; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 33846874991     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2006.11.013     Document Type: Article

References (31)

1. Katre N.V. The conjugation of proteins with polyethylene glycol and other polymers: altering properties of proteins to enhance their therapeutic potential. Adv. Drug Deliv. Rev. 10 (1993) 91-114
2. Veronese F.M., Monfardini C., Caliceti P., Schiavon O., Scrawen M.D., and Beer D. Improvement of pharmacokinetic, immunological and stability properties of asparaginase by conjugation to linear and branched monomethoxy poly(ethylene glycol). J. Control. Release 40 (1996) 199-209
3. Bailon P., Palleroni A., Schaffer C.A., Spence C.L., Fung W.-J., Porter J.E., Ehrlich G.K., Pan W., Xu Z.-X., Modi M.W., Farid A., Berthold W., and Graves M. Rational design of a potent, long-lasting form of interferon: a 40 kDa branched polyethylene glycol-conjugated interferon-alpha 2a for the treatment of hepatitis. C. Bioconjug. Chem. 12 (2001) 195-202
4. Parkinson C., Scarlett J.A., and Trainer P.J. Pegvisomant in the treatment of acromegaly. Adv. Drug Deliv. Rev. 55 (2003) 1303-1314
5. Edwards III C.K., Martin S.W., Seely J., Kinstler O., Buckel S., Bendele A.M., D.V.M., Cosenza M.E., Feige U., and Kohno T. Design of PEGylated soluble tumor necrosis factor receptor type I (PEG sTNF-RI) for chronic inflammatory diseases. Adv. Drug Deliv. Rev. 55 (2003) 1315-1336
6. Whelan J. Beyond PEGylation. Drug Discov. Today 10 (2005) 301
7. Yoshioka Y., Tsutsumi Y., Ikemizu S., Yamamoto Y., Shibata H., Nishibata T., Mukai Y., Okamoto T., Taniai M., Kawamura M., Abe Y., Nakagawa S., Nagata S., Yamagata Y., and Mayumi T. Optimal site-specific PEGylation of mutant TNF-α improves its antitumor potency. Biochem. Biophys. Res. Commun. 315 (2004) 808-814
8. Cazalis C.S., Haller C.A., Sease-Cargo L., and Chaikof E.L. C-terminal site-specific PEGylation of a truncated thrombomodulin mutant with retention of full bioactivity. Bioconjug. Chem. 15 (2004) 1005-1009
9. Youn Y.S., Na D.H., Yoo S.D., Song S.-C., and Lee K.C. Carbohydrate-specifically polyethylene glycol-modified ricin A-chain with improved therapeutic potential. Int. J. Biochem. Cell Biol. 37 (2005) 1525-1533
10. Kinstler O., Molineux G., Treuheit M., Ladd D., and Gegg C. Mono-N-terminal poly(ethylene glycol)-protein conjugates. Adv. Drug Deliv. Rev. 54 (2002) 477-485
11. Yamamoto Y., Tsutsumi Y., Yoshioka Y., Nishibata T., Kobahashi K., Okamoto T., Mukai Y., Shimizu T., Nakagawa S., Nagata S., and Mayumi T. Site-specific PEGylation of a lysine-deficient TNF-α with full bioactivity. Nat. biotechnol. 21 (2003) 546-552
12. Moreadith R.W., and Collen D. Clinical development of PEGylated recombinant staphylokinase (PEG-Sak) for bolus thrombolytic treatment of patients with acute myocardial infarction. Adv. Drug Deliv. Rev. 55 (2003) 1337-1345
13. Rosendahl M.S., Doherty D.H., Smith D.J., Carlson S.J., Chlipala E.A., and Cox S.J. A long-acting, highly potent interferon α-2 conjugate created using site-specific PEGylation. Bioconjug. Chem. 16 (2005) 200-207
14. Natarajan A., Xiong C.Y., Albrecht H., DeNardo G.L., and DeNardo S.J. Characterization of site-specific scFv PEGylation for tumor-targeting pharmaceuticals. Bioconjug. Chem. 16 (2005) 113-121
15. Youn Y.S., Na D.H., Yoo S.D., Song S.-C., and Lee K.C. Chromatographic separation and mass spectrometric identification of positional isomers of polyethylene glycol-modified growth hormone-releasing factor (1-29). J. Chromatogr., A 1061 (2004) 45-49
16. Na D.H., Youn Y.S., Park E.J., Lee J.M., Lee K.R., Lee S.D., Yoo S.D., DeLuca P.P., and Lee K.C. Stability of PEGylated salmon calcitonin in nasal mucosa. J. Pharm. Sci. 93 (2004) 256-261
17. Lu Y.-A., and Felix A.M. Pegylated peptides II: solid-phase synthesis of amino-, carboxy- and side-chain pegylated peptides. Int. J. Protein Res. 43 (1994) 127-138
18. F. Liu, S.W. Kim, M. Baudys, Synthesis of insulin derivatives, US Patent 6,323,311, 2001.
19. 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
20. Lee K.C., Moon S.C., Park M.O., Lee J.T., Na D.H., Yoo S.D., Lee H.S., and DeLuca P.P. Isolation, characterization, and stability of positional isomers of mono-PEGylated salmon calcitonins. Pharm. Res. 16 (1999) 813-818
21. Youn Y.S., Jung J.Y., Oh S.H., Yoo S.D., and Lee K.C. Improved intestinal delivery of salmon calcitonin by Lys18-amine specific PEGylation: stability, permeability, pharmacokinetic behavior and in vivo hypocalcemic efficacy. J. Control. Release 114 (2006) 334-342
22. Lee K.C., Tak K.K., Park M.O., Lee J.T., Woo B.H., Yoo S.D., Lee H.S., and DeLuca P.P. Preparation and characterization of polyethylene glycol modified salmon calcitonins. Pharm. Dev. Technol. 4 (1999) 269-275
23. Lee K.C., Park M.-O., Na D.H., Youn Y.S., Lee S.D., Yoo S.D., Lee H.S., and DeLuca P.P. Intranasal delivery of PEGylated salmon calcitonins: hypocalcemic effects in rats. Calcif. Tissue Int. 73 (2003) 545-549
24. Na D.H., Park M.O., Choi S.Y., Kim Y.S., Lee S.S., Yoo S.D., Lee H.S., and Lee K.C. Identification of the modifying sites of mono-PEGylated salmon calcitonins by capillary electrophoresis and MALDI-TOF mass spectrometry. J. Chromatogr., B. 754 (2001) 259-263
25. Lee S.H., Lee S., Youn Y.S., Na D.H., Chae S.Y., Byun Y., and Lee K.C. Synthesis, characterization, and pharmacokinetic studies of PEGylated glucagon-like peptide-1. Bioconjug. Chem. 16 (2005) 377-382
26. Katayama T., Furuya M., Yamaichi K., Konishi K., Sugiura N., Murafuji H., Magota K., Saito M., Tanaka S., and Oikawa S. Discovery of a non-peptide small molecule that selectively mimics the biological actions of calcitonin. Biochim. Biophys. Acta 1526 (2001) 183-190
27. 18) in rats: regional difference in stability and hypocalcemic effect. Pharm. Dev. Technol. 10 (2005) 389-396
28. 18-mono-PEGylated salmon calcitonin. AAPS J. 6 S1 (2004) T2162
29. Wylie D.C., Voloch M., Lee S., Liu Y.-H., Cannon-Carlson S., Cutler C., and Pramanik B. Carboxyalkylated histidine is a pH-dependent product of PEGylation with SC-PEG. Pharm. Res. 18 (2001) 1354-1360
30. Azria M. The Calcitonins: Physiology and Pharmacology (1989), Karger, Basel
31. Lang S.R., Staudenmann W., James P., Manz H., Kessler R., Galli B., Moser H., Rummelt A., and Merkle H.P. Proteolysis of human calcitonin in excised bovine nasal mucosa: elucidation of the metabolic pathway by liquid secondary ionization mass spectrometry (LSIMS) and matrix assisted laser desorption ionization mass spectrometry (MALDI). Pharm. Res. 13 (1996) 1679-1685