Conjugation of salmon calcitonin to a combed-shaped end functionalized poly(poly(ethylene glycol) methyl ether methacrylate) yields a bioactive stable conjugate

Journal of Controlled Release

Volumn 135, Issue 1, 2009, Pages 51-59

  Ryan, Sinéad M ^a   Wang, Xuexuan ^a   Mantovani, Guiseppe ^b   Sayers, Claire T ^b   Haddleton, David M ^b   Brayden, David J ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

Calcitonin delivery; Conjugated peptides; Osteoporosis; Pegylation; Peptide stability; Polymer conjugates

Indexed keywords

AMINO ACIDS; BODY FLUIDS; CALCIUM; CONJUGATED POLYMERS; ETHERS; ETHYLENE GLYCOL; MOLECULAR WEIGHT; PEPTIDES; POLYACRYLATES; POLYOLS;

CALCITONIN DELIVERY; INTRAVENOUS INJECTIONS; LACTATE DEHYDROGENASE ASSAYS; OSTEOPOROSIS; PEGYLATION; PHARMACOKINETIC PROFILES; POLY(ETHYLENE GLYCOL) METHYL ETHER METHACRYLATE (PEG-MMA); POLYMER CONJUGATE;

POLYETHYLENE GLYCOLS;

CALCITONIN; CALCIUM; CYCLIC AMP; CYSTEINE; LACTATE DEHYDROGENASE; MACROGOL; MACROGOL DERIVATIVE; METHACRYLIC ACID; POLY(POLY ETHYLENE GLYCOL)METHYLETHER METHACRYLATE; SALCATONIN; SERINE PROTEINASE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; BIOLOGICAL ACTIVITY; CALCITONIN BLOOD LEVEL; CALCIUM BLOOD LEVEL; CONTROLLED STUDY; CYTOTOXICITY; DRUG BLOOD LEVEL; DRUG CONJUGATION; DRUG HALF LIFE; DRUG METABOLISM; DRUG PURITY; DRUG STABILITY; ERYTHROCYTE; FEMALE; HEMOLYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; INTESTINE; LIVER; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR WEIGHT; NONHUMAN; PREDICTIVE VALIDITY; PRIORITY JOURNAL; RAT; SERUM;

EID: 61649092532     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2008.12.014     Document Type: Article

References (43)

1. Cadarette S.M., Katz J.N., Brookhart M.A., Sturmer T., Stedman M.R., and Solomon D.H. Relative effectiveness of osteoporosis drugs for preventing non-vertebral fracture. Ann. Intern. Med. 148 (2008) 637-646
2. Karsdal M.A., Henriksen K., Arnold M., and Christiansen C. Calcitonin - a drug of the past or for the future? Physiologic inhibition of bone resorption while sustaining osteoclast numbers improves bone quality. BioDrugs 22 (2008) 137-144
3. Chestnut III C.H., Silverman S., Andriano K., Gennant H., Gimona A., Harris S., Kiel D., LeBoff M., Maricic M., Miller P., Moniz C., Peacock M., Richardson P., Watts N., and Baylink D. A randomized trial of nasal spray salmon calcitonin in postmenopausal women with established osteoporosis: the prevent recurrence of osteoporotic fractures study. PROOF Study Group. Am. J. Med. 109 (2000) 267-276
4. Lee V.H.L., and Yamamoto A. Penetration and enzymatic barriers to peptide and protein absorption. Adv. Drug Deliv. Rev. 4 (1990) 171-207
5. Shah R.B., and Khan M.A. Regional permeability of salmon calcitonin in isolated rat gastrointestinal tracts: transport mechanism using Caco-2 cell monolayer. AAPS J 6 (2004) e31
6. Sinko P.J., Lee Y.H., Makhey V., Leesman G.D., Sutyak J.P., Yu H., Perry B., Smith C.L., Hu P., Wagner E.J., Falzone L.M., McWhorter L.T., Gilligan J.P., and Stern W. Biopharmaceutical approaches for developing and assessing oral peptide delivery strategies and systems: in vitro permeability and in vivo oral absorption of salmon calcitonin (sCT). Pharm. Res. 16 (1999) 527-533
7. McHorney C.A., Schousboe J.T., Cline R.R., and Weiss T.W. The impact of osteoporosis medication beliefs and side-effect experiences on non-adherence to oral bisphosphonates. Curr. Med. Res. Opin. 23 (2007) 3137-3152
8. Strampel W., Emkey R., and Civitelli R. Safety considerations with bisphosphonates for the treatment of osteoporosis. Drug Safety 30 (2007) 755-763
9. Hamidi M., Azadi A., and Rafiei P. Pharmacokinetic consequences of PEGylation. Drug Deliv. 13 (2006) 399-409
10. Werle M., and Bernkop-Schnurch A. Strategies to improve plasma half life time of peptide and protein drugs. Amino Acids 30 (2006) 351-367
11. Veronese F.M., and Pasut G. PEGylation, successful approach to drug delivery. Drug Discov. Today 10 (2005) 1451-1458
12. Gaberc-Porekar V., Zore I., Podobnik B., and Menart V. Obstacles and pitfalls in the PEGylation of therapeutic proteins. Curr. Opin. Drug Discov. Devel. 11 (2008) 242-250
13. Ryan S.M., Mantovani G., Wang X., Haddleton D.M., and Brayden D.J. Advances in PEGylation of important biotech molecules: delivery aspects. Expert Opin. Drug Deliv. 5 4 (2008) 371-383
14. Kamigaito M., Ando T., and Sawamoto M. Metal-catalyzed living radical polymerization. Chem. Rev. 101 (2001) 3689-3746
15. Nicolas J., Mantovani G., and Haddleton D.M. Living radical polymerization as a tool for the synthesis of polymer-protein/peptide bioconjugates. Macromol. Rap. Commun. 28 (2007) 1083-1111
16. Lecolley F., Tao L., Mantovani G., Durkin I., Lautru S., and Haddleton D.M. A new approach to bioconjugates for proteins and peptides ("PEGylation") utilizing living radical polymerisation. Chem. Commun. 18 (2004) 2026-2027
17. Tao L., Mantovani G., Lecolley F., and Haddleton D.M. Alpha-aldehyde terminally functional methacrylic polymers from living radical polymerization: application in protein conjugation "pegylation". J. Amer. Chem. Soc. 126 (2004) 13220-13221
18. Mantovani G., Lecolley F., Tao L., Haddleton D.M., Clerx J., Cornelissen J.J.L.M., and Velonia K. Design and synthesis of N-maleimido-functionalized hydrophilic polymers via copper-mediated living radical polymerization: a suitable alternative to pegylation chemistry. J. Amer. Chem. Soc. 127 (2005) 2966-2973
19. Asayama S., Maruyama A., Cho C.S., and Akaike T. Design of comb-type polyamine copolymers for a novel pH-sensitive DNA carrier. Bioconjug. Chem. 8 (1997) 833-838
20. Srividhya M., Preethi S., Gnanamani A., and Reddy B.S. Sustained release of protein from poly(ethylene glycol) incorporated amphiphilic comb like polymers. Int. J. Pharm. 326 (2006) 119-127
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. Youn Y.S., Kwon M.J., Na D.H., Chae S.Y., Lee S., and Lee K.C. Improved intrapulmonary delivery of site-specific PEGylated salmon calcitonin: optimization by PEG size selection. J. Control. Release 125 (2008) 68-75
23. Wang J., Chow D., Heiati H., and Shen W.C. Reversible lipidization for the oral delivery of salmon calcitonin. J. Control. Release 88 (2003) 369-380
24. Bentley M.D., Roberts M.J., and Harris J.M. Reductive amination using poly(ethylene glycol) acetaldehyde hydrate generated in situ: applications to chitosan and lysozyme. J. Pharm. Sci. 87 (1998) 1446-1449
25. 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
26. Keely S., Rullay A., Wilson C., Carmichael A., Carrington S., Corfield A., Haddleton D.M., and Brayden D.J. In vitro and ex vivo intestinal tissue models to measure mucoadhesion of poly (methacrylate) and N-trimethylated chitosan polymers. Pharm. Res. 22 (2005) 38-49
27. Shin S.Y., Lee S.H., Yang S.T., Park E.J., Lee D.G., Lee M.K., Eom S.H., Song W.K., Kim Y., Hahm K.S., and Kim J.I. Antibacterial, antitumor and hemolytic activities of alpha-helical antibiotic peptide, P18 and its analogs. J. Pept. Res. 58 (2001) 504-514
28. Fowler S.B., Poon S., Muff R., Chiti F., Dobson C.M., and Zurdo J. Rational design of aggregation-resistant bioactive peptides: re-engineering human calcitonin. Proc. Natl. Acad. Sci. U. S. A. 102 (2005) 10105-10110
29. Team R.D.C. R: A Language and Environment for Statistical Computing, R Foundation for Statistical Computing, Vienna, Austria (2008). http://www.r-project.org http://www.r-project.org. Accessed September, 2008
30. Harris J.M., and Chess R.B. Effect of PEGylation on pharmaceuticals. Nat. Rev. Drug Discov. 2 (2003) 214-221
31. 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
32. Mansoor S., Youn Y.S., and Lee K.C. Oral delivery of mono-PEGylated sCT (Lys18) in rats: regional difference in stability and hypocalcemic effect. Pharm Dev. Technol. 10 (2005) 389-396
33. Bendele A., Seely J., Richey C., Sennello G., and Shopp G. Short communication: renal tubular vacuolation in animals treated with polyethylene-glycol-conjugated proteins. Toxicol. Sci. 42 (1998) 152-157
34. Greenwald R.B., Choe Y.H., Conover C.D., Shum K., Wu D., and Royen M. Poly(ethylene glycol) conjugated drugs and prodrugs: a comprehensive review. Crit. Rev. Ther. Drug Carrier Syst. 17 (2000) 101-161
35. Siegel E.G., Gallwitz B., Scharf G., Mentlein R., Morys-Wortmann C., Folsch U.R., Schrezenmeir J., Drescher K., and Schmidt W.E. Biological activity of GLP-1-analogues with N-terminal modifications. Regul. Pept. 79 (1999) 93-102
36. Fee C.J. Size comparison between proteins PEGylated with branched and linear poly(ethylene glycol) molecules. Biotech. Bioeng. 98 (2007) 725-731
37. 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
38. Lee K.C., Tak K.K., Park M.O., Lee J.T., Woo B.H., Lee H.S., and Deluca P.P. Preparation and characterization of polyethylene-glycol-modified salmon calcitonins. Pharm. Dev. Technol. 4 (1999) 269-275
39. Chae S.Y., Chun Y.G., Lee S., Jin C.-H., Lee E.S., Lee K.C., and Youn Y.S. Pharmacokinetic and pharmacodynamic evaluation of site-specific PEGylated glucagon-like peptide-1 analogues as flexible postprandial glucose controllers. J. Pharm. Sci. (2008) Aug. 14 Electronic publication ahead of print. PMID: 18704955
40. Youn Y.S., Na D.H., and Lee K.C. High-yield production of biologically active mono-PEGylated salmon calcitonin by site-specific PEGylation. J. Control. Release. 117 (2007) 371-379
41. Buclin T., Randin J.P., Jacquet A.F., Azria M., Attinger M., Gomez F., and Burckhardt P. The effect of rectal and nasal administration of salmon calcitonin in normal subjects. Calcif. Tissue Intern. 41 (1987) 252-258
42. Mochizuki K., and Inoue T. Effect of salmon calcitonin on experimental osteoporosis induced by ovariectomy and low-calcium diet in the rat. J. Bone Miner. Metab. 18 (2000) 194-207
43. Goodman H.M. Basic Medical Endocrinology. 4th Ed. (1989-2009), Academic Press, New York 197-218