Design, synthesis, characterization and in-vivo activity of a novel salmon calcitonin conjugate containing a novel PEG-lipid moiety

Journal of Pharmacy and Pharmacology

Volumn 62, Issue 3, 2010, Pages 296-304

  Cheng, Weiqiang ^a,c   Lim, Lee Yong ^b  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^c UNIVERSITY OF KANSAS   (United States)

Author keywords

Bioconjugation; Calcitonin; Lipidization; PEGylation; Tri block

Indexed keywords

CALCIUM; LIPID; MACROGOL; MALEIMIDE DERIVATIVE; PALMITIC ACID DERIVATIVE; SALCATONIN;

ANIMAL EXPERIMENT; ARTICLE; CALCIUM BLOOD LEVEL; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONJUGATION; DRUG DEGRADATION; DRUG DESIGN; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; EXPERIMENTAL MODEL; FEMALE; NONHUMAN; PARTICLE SIZE; PROTEIN CONFORMATION; RAT; STRUCTURE ANALYSIS;

ANIMALS; CALCITONIN; CALCIUM; CIRCULAR DICHROISM; DIGESTION; DRUG CARRIERS; DRUG DESIGN; FEMALE; GELS; LYSINE; NEPHELOMETRY AND TURBIDIMETRY; OSTEOPOROSIS; PARTICLE SIZE; POLYETHYLENE GLYCOLS; PROTEIN STRUCTURE, SECONDARY; RANDOM ALLOCATION; RATS; RATS, WISTAR; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TIME FACTORS;

EID: 77950255848     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.62.03.0002     Document Type: Article

References (44)

1. Harris, JM. Chess, RB. Effect of pegylation on pharmaceuticals. Nat Rev Drug Discov 2003 2 : 214 221.
2. Harris, JM, et al. Pegylation: a novel process for modifying pharmacokinetics. Clin Pharmacokinet 2001 40 : 539 551.
3. Wang, J, et al. Preparation, purification, and characterization of a reversibly lipidized desmopressin with potentiated anti-diuretic activity. Pharm Res 1999 16 : 1674 1679.
4. Wang, J, et al. Reversible lipidization for the oral delivery of salmon calcitonin. J Control Release 2003 88 : 369 380.
5. Kabanov, AV, et al. Fatty acid acylated antibodies against virus suppress its reproduction in cells. FEBS Lett 1989 250 : 238 240.
6. Lockwood, NA, et al. Acylation of SC4 dodecapeptide increases bactericidal potency against Gram-positive bacteria, including drug-resistant strains. Biochem J 2004 378 : 93 103.
7. Ekrami, HM, et al. Water-soluble fatty acid derivatives as acylating agents for reversible lipidization of polypeptides. FEBS Lett 1995 371 : 283 286.
8. Slepnev, VI, et al. Fatty acid acylated peroxidase as a model for the study of interactions of hydrophobically-modified proteins with mammalian cells. Bioconjug Chem 1995 6 : 608 615.
9. Klibanov, AL, et al. Amphipathic polyethyleneglycols effectively prolong the circulation time of liposomes. FEBS Lett 1990 268 : 235 237.
10. Klibanov, AL, et al. Activity of amphipathic poly(ethylene glycol) 5000 to prolong the circulation time of liposomes depends on the liposome size and is unfavorable for immunoliposome binding to target. Biochim Biophys Acta 1991 1062 : 142 148.
11. Ashok, B, et al. In vitro characterization of PEGylated phospholipid micelles for improved drug solubilization: effects of PEG chain length and PC incorporation. J Pharm Sci 2004 93 : 2476 2487.
12. Dabholkar, RD, et al. Polyethylene glycol-phosphatidylethanolamine conjugate (PEG-PE)-based mixed micelles: some properties, loading with paclitaxel, and modulation of P-glycoprotein-mediated efflux. Int J Pharm 2006 315 : 148 157.
13. Torchilin, VP, et al. Immunomicelles: targeted pharmaceutical carriers for poorly soluble drugs. Proc Natl Acad Sci U S A 2003 100 : 6039 6044.
14. Huwyler, J, et al. Brain drug delivery of small molecules using immunoliposomes. Proc Natl Acad Sci U S A 1996 93 : 14164 14169.
15. Kipnes, M, et al. Control of postprandial plasma glucose by an oral insulin product (HIM2) in patients with type 2 diabetes. Diabetes Care 2003 26 : 421 426.
16. Clement, S, et al. Oral modified insulin (HIM2) in patients with type 1 diabetes mellitus: results from a phase I/II clinical trial. Metabolism 2004 53 : 54 58.
17. Cataliotti, A, et al. Oral human brain natriuretic peptide activates cyclic guanosine 3′,5′-monophosphate and decreases mean arterial pressure. Circulation 2005 112 : 836 840.
18. Miller, MA, et al. Amphiphilic conjugates of human brain natriuretic peptide designed for oral delivery: in vitro activity screening. Bioconjug Chem 2006 17 : 267 274.
19. Chin, CM, et al. Pharmacokinetics of modified oral calcitonin product in healthy volunteers. Pharmacotherapy 2004 24 : 994 1001.
20. Cheng, W, et al. Aqueous-soluble, non-reversible lipid conjugate of salmon calcitonin: synthesis, characterization and in vivo activity. Pharm Res 2007 24 : 99 110.
21. Cheng, W. Lim, LY. Comparison of reversible and nonreversible aqueous-soluble lipidized conjugates of salmon calcitonin. Mol Pharm 2008 5 : 610 621.
22. Cheng, W. Lim, LY. Lipeo-sCT: a novel reversible lipidized salmon calcitonin derivative, its biophysical properties and hypocalcemic activity. Eur J Pharm Sci 2009 37 : 151 159.
23. Cheng, W. Lim, LY. Synthesis, characterization and in vivo activity of salmon calcitonin coconjugated with lipid and polyethylene glycol. J Pharm Sci 2009 98 : 1438 1451.
24. Cheng, TL, et al. Poly(ethylene glycol) modification of beta-glucuronidase-antibody conjugates for solid-tumor therapy by targeted activation of glucuronide prodrugs. Cancer Immunol Immunother 1997 44 : 305 315.
25. Lee, KC, et al. Intranasal delivery of PEGylated salmon calcitonins: hypocalcemic effects in rats. Calcif Tissue Int 2003 73 : 545 549.
26. Manjula, BN, et al. Conjugation of multiple copies of polyethylene glycol to hemoglobin facilitated through thiolation: influence on hemoglobin structure and function. Protein J 2005 24 : 133 146.
27. Schagger, H. von Jagow, G. Tricine-sodium dodecyl sulfate-polyacrylamide gel electrophoresis for the separation of proteins in the range from 1 to 100 kDa. Anal Biochem 1987 166 : 368 379.
28. Sinko, PJ, et al. Utility of pharmacodynamic measures for assessing the oral bioavailability of peptides. 1. Administration of recombinant salmon calcitonin in rats. J Pharm Sci 1995 84 : 1374 1378.
29. Van Loon JC. Analytical atomic absorption spectroscopy: selected methods. New York : Academic Press, 1980.
30. Bailon, P, et al. 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 2001 12 : 195 202.
31. Youn, YS, et al. Improved intestinal delivery of salmon calcitonin by Lys18-amine specific PEGylation: stability, permeability, pharmacokinetic behavior and in vivo hypocalcemic efficacy. J Control Release 2006 114 : 334 342.
32. Gesell, J, et al. Two-dimensional 1H NMR experiments show that the 23-residue magainin antibiotic peptide is an alpha-helix in dodecylphosphocholine micelles, sodium dodecylsulfate micelles, and trifluoroethanol/water solution. J Biomol NMR 1997 9 : 127 135.
33. Meadows, RP, et al. Two-dimensional NMR and structure determination of salmon calcitonin in methanol. Biochemistry 1991 30 : 1247 1254.
34. Vajda, T. Szabo, T. Specificity of trypsin and alpha-chymotrypsin towards neutral substrates. Acta Biochim Biophys Acad Sci Hung 1976 11 : 287 294.
35. Orlowski, RC, et al. Biologically potent analogues of salmon calcitonin which do not contain an N-terminal disulfide-bridged ring structure. Eur J Biochem 1987 162 : 399 402.
36. Yates, AJ, et al. A noncyclical analog of salmon calcitonin (N alpha-propionyl Di-Ala1,7,des-Leu19 sCT) retains full potency without inducing anorexia in rats. Endocrinology 1990 126 : 2845 2849.
37. Wang, Y, et al. Solution structure and biological activity of recombinant salmon calcitonin S-sulfonated analog. Biochem Biophys Res Commun 2003 306 : 582 589.
38. Moe, GR, et al. Design of a peptide-hormone - synthesis and characterization of a model peptide with calcitonin-like activity. J Am Chem Soc 1983 105 : 4100 4102.
39. Epand, RM, et al. Conformational flexibility and biological activity of salmon calcitonin. Biochemistry 1986 25 : 1964 1968.
40. Houssami, S, et al. Divergent structural requirements exist for calcitonin receptor binding specificity and adenylate cyclase activation. Mol Pharmacol 1995 47 : 798 809.
41. Mayer, JP, et al. Insulin structure and function. Biopolymers 2007 88 : 687 713.
42. Rajan, RS, et al. Modulation of protein aggregation by polyethylene glycol conjugation: GCSF as a case study. Protein Sci 2006 15 : 1063 1075.
43. Leamon, CP, et al. Folate-liposome-mediated antisense oligodeoxynucleotide targeting to cancer cells: evaluation in vitro and in vivo. Bioconjug Chem 2003 14 : 738 747.
44. Savic, R, et al. Micellar nanocontainers distribute to defined cytoplasmic organelles. Science 2003 300 : 615 618.