Synthesis and chemical stability of a disulfide bond in a model cyclic pentapeptide: Cyclo(1,4)-Cys-Gly-Phe-Cys-Gly-OH

Journal of Pharmaceutical Sciences

Volumn 95, Issue 10, 2006, Pages 2222-2234

  He, Henry T ^a,b   Gürsoy, R Neslihan ^a,c   Kupczyk Subotkowska, Lidia ^a   Tian, Jiaher ^a,d   Williams, Todd ^a   Siahaan, Teruna J ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b Pharmaceutical Product Development   (United States)

^c HACETTEPE UNIVERSITY   (Turkey)

^d WYETH RESEARCH   (United States)

Author keywords

Conformational restriction; Cyclic peptide; Disulfide degradation; Peptide formulation

Indexed keywords

AMINE; CYCLOPEPTIDE; DEHYDROALANINE; PENTAPEPTIDE; SULFIDE;

ARTICLE; CONFORMATIONAL TRANSITION; DEGRADATION KINETICS; DISULFIDE BOND; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STABILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; IONIC STRENGTH; PEPTIDE SYNTHESIS;

EID: 33749996172     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.20701     Document Type: Article

References (30)

1. Falciani C, Lozzi L, Fini A, Bracci L. 2005. Bioactive peptides from libraries. Chem Biol 12:417-426.
2. Hruby VJ. 2002. Designing peptide receptor agonists and antagonists. Nat Rev Drug Discov 1:847-858.
3. Yusuf-Makagiansar H, Anderson ME, Yakovleva TV, Murray JS, Siahaan TJ. 2002. Inhibition of LFA-1/ICAM-1 and VLA-4/VCAM-1 as a therapeutic approach to inflammation and autoimmune diseases. Med Res Rev 22:146-167.
4. Ruoslahti E. 2004. Vascular zip codes in angiogenesis and metastasis. Biochem Soc Trans 32:397-402.
5. Devanathan S, Salamon Z, Nagar A, Narang S, Schleich D, Darman P, Hruby V, Tollin G. 2005. Subpicomolar sensing of delta-opioid receptor ligands by molecular-imprinted polymers using plasmon-waveguide resonance spectroscopy. Anal Chem 77:2569-2574.
6. Gu X, Ying J, Min B, Cain JP, Davis P, Willey P, Navratilova E, Yamamura HI, Porreca F, Hruby VJ. 2005. Parallel synthesis and biological evaluation of different sizes of bicyclo[2,3]Leu-enkephalin analogues. Biopolymers 80:151-163.
7. Rizo J, Gierasch LM. 1992. Constrained peptides: Models of bioactive peptides and protein substructures. Annu Rev Biochem 61:387-418.
8. Kessler H. 1982. Conformation and biological activity of cyclic peptides. Angew Chem Int Ed Engl 21:512-523.
9. Hruby VJ. 1982. Conformational restrictions of biologically active peptides via amino acid side chain groups. Life Sciences 31:189-199.
10. van der Hoek J, Hofland LJ, Lamberts SW. 2005. Novel subtype specific and universal somatostatin analogues: Clinical potential and pitfalls. Curr Pharm Des 11:1573-1592.
11. Reissmann S, Imhof D. 2004. Development of conformationally restricted analogues of bradykinin and somatostatin using constrained amino acids and different types of cyclization. Curr Med Chem 11:2823-2844.
12. Quartara L, Pavone V, Pedone C, Lombardi A, Renzetti AR, Maggi CA. 1996. A review of the design, synthesis and biological activity of the bicyclic hexapeptide tachykinin NK2 antagonist MEN 10627. Regul Pept 65:55-59.
13. Malicka J, Czaplewski C, Groth M, Wiczk W, Oldziej S, Lankiewicz L, Ciarkowski J, Liwo A. 2004. Use of NMR and fluorescence spectroscopy as well as theoretical conformational analysis in conformation-activity studies of cyclic enkephalin analogues. Curr Top Med Chem 4:123-133.
14. Fung S, Hruby VJ. 2005. Design of cyclic and other templates for potent and selective peptide alpha-MSH analogues. Curr Opin Chem Biol 9:352-358.
15. Schiller PW. 1991. Rational design of peptidomimetics: Structural and pharmacological Aspects. In: Wermuth CG, editor. Medicinal Chemistry for the 21st Century, edition. Oxford: IUPAC/Blackwell. p 215-232.
16. Veber DF, Freidinger RM. 1985. The design of metabolically-stable peptide analogs. Trends Neurosci 8:392-396.
17. Ploux O, Lavielle S, Chassaing G, Julien S, Marquet A, d'Orleans-Juste P, Dion S, Regoli D, Beaujouan JC, Bergstrom L, Torrens Y, Glowinski J. 1987. Interaction of tachykinins with their receptors studied with cyclic analogues of substance P and neurokinin B. Proc Natl Acad Sci USA 84:8095-8099.
18. Hruby VJ, Al-Obeidi F, Kazmierski W. 1990. Emerging approaches in the molecular design of receptor-selective peptide ligands: Conformational, topographical and dynamic considerations. Biochem J 268:249-262.
19. Wright HT. 1991. Nonenzymatic deamidation of asparaginyl and glutaminyl residues in proteins. Crit Rev Biochem Mol Biol 26:1-52.
20. Xie M, Aube J, Borchardt RT, Morton M, Topp EM, Vander Velde D, Schowen RL. 2000. Reactivity toward deamidation of asparagine residues in beta-turn structures. J Pept Res 56:165-171.
21. Bogdanowich-Knipp SJ, Chakrabarti S, Williams TD, Dillman RK, Siahaan TJ. 1999. Solution stability of linear vs. cyclic RGD peptides. J Pept Res 53:530-541.
22. Krogmeier SL, Reddy DS, Vander Velde D, Lushington GH, Siahaan TJ, Middaugh CR, Borchardt RT, Topp EM. 2005. Deamidation of model beta-turn cyclic peptides in the solid state. J Pharm Sci 94:2616-2631.
23. Ortiz-Acevedo A, Dieckmann GR. 2004. Synthesis of reversible cyclic peptides. Tetrahedron Lett 45:6795-6798.
24. Villafranca JE, Howell EE, Oatley SJ, Xuong NH, Kraut J. 1987. An engineered disulfide bond in dihydrofolate reductase. Biochemistry 26:2182-2189.
25. Manning MC, Patel K, Borchardt RT. 1989. Stability of protein pharmaceuticals. Pharm Res 6:903-918.
26. Patel K, Borchardt RT. 1990. Chemical pathways of peptide degradation. II. Kinetics of deamidation of an asparaginyl residue in a model hexapeptide. Pharm Res 7:703-711.
27. Yoshioka S, Stella V. 2000. Stability of Drug and Dosage Forms, edition. New York: Kluwer Academic. p 1-162.
28. Florence TM. 1980. Degradation of protein disulphide bonds in dilute alkali. Biochem J 189:507-520.
29. Whitaker JR, Feeney RE. 1983. Chemical and physical modification of proteins by the hydroxide ion. Crit Rev Food Sci Nutrition 19:173-212.
30. Kice JL. 1973. Sulfur-centered radicals. Free Radicals 2:711-740.