Deamidation of model β-turn cyclic peptides in the solid state

Journal of Pharmaceutical Sciences

Volumn 94, Issue 12, 2005, Pages 2616-2631

  Krogmeier, Stephanie L ^a   Reddy, D Srinivasa ^a   Velde, David Vander ^a   Lushington, Gerald H ^a   Siahaan, Teruna J ^a   Middaugh, C Russell ^a   Borchardt, Ronald T ^a   Topp, Elizabeth M ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; PEPTIDE; POVIDONE;

ARTICLE; CIRCULAR DICHROISM; DEAMINATION; DRUG FORMULATION; MODEL; MOLECULAR DYNAMICS; PEPTIDE ANALYSIS; PROTEIN DEGRADATION; PROTEIN SECONDARY STRUCTURE; PROTEIN STABILITY; SIMULATION; SOLID STATE; STRUCTURE ANALYSIS;

EID: 33144477193     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.20468     Document Type: Article

References (33)

1. Manning MC, Patel K, Borchardt RT. 1989. Stability of protein pharmaceuticals. Pharm Res 6:903-918.
2. Clarke S. 1987. Propensity for spontaneous succinimide formation from aspartyl and asparaginyl residues in cellular proteins. Int J Pept Protein Res 30:808-821.
3. Kosky AA, Razzaq UO, Treuheit MJ, Brems DN. 1999. The effects of alpha-helix on the stability of Asn residues: Deamidation rates in peptides of varying helicity. Protein Sci 8:2519-2523.
4. Stevenson CL, Friedman AR, Kubiak TM, Donlan ME, Borchardt RT. 1993. Effect of secondary structure on the rate of deamidation of several growth hormone releasing factor analogs. Int J Pept Protein Res 42:497-503.
5. Wearne SJ, Creighton TE. 1989. Effect of protein conformation on rate of deamidation: Ribonuclease A. Proteins 5:8-12.
6. 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.
7. Xie M, Schowen RL. 1999. Secondary structure and protein deamidation. J Pharm Sci 88:8-13.
8. Carpenter JF, Prestrelski SJ, Dong A. 1998. Application of infrared spectroscopy to development of stable lyophilized protein formulations. Eur J Pharm Biopharm 45:231-238.
9. Rose GD, Gierasch LM, Smith JA. 1985. Turns in peptides and proteins. Adv Protein Chem 37:1-109.
10. Greenfield NJ. 1996. Methods to estimate the conformation of proteins and polypeptides from circular dichroism data. Anal Biochem 235:1-10.
11. Haris PI, Chapman D. 1995. The conformational analysis of peptides using Fourier transform IR spectroscopy. Biopolymers 37:251-263.
12. Mantsch HH, Perczel A, Hollosi M, Fasman GD. 1993. Characterization of beta-turns in cyclic hexapeptides in solution by Fourier transform IR spectroscopy. Biopolymers 33:201-207.
13. Tishmack PA, Bugay DE, Byrn SR. 2003. Solid-state nuclear magnetic resonance spectroscopy-pharmaceutical applications. J Pharm Sci 92:441-474.
14. Mahadevan J, Xu C, Siahaan T, Kuczera K. 2002. Molecular dynamics simulations of conformational behavior of linear RGD peptidomimetics and cyclic prodrugs in aqueous and octane solutions. J Biomol Struct Dyn 19:775-788.
15. Karvounis G, Nerukh D, Glen RC. 2004. Water network dynamics at the critical moment of a peptide's beta-turn formation: A molecular dynamics study. J Chem Phys 121:4925-4935.
16. Perczel A, Park K, Fasman GD. 1992. Analysis of the circular dichroism spectrum of proteins using the convex constraint algorithm: A practical guide. Anal Biochem 203:83-93.
17. Song Y, Schowen RL, Borchardt RT, Topp EM. 2001. Effect of 'pH' on the rate of asparagine deamidation in polymeric formulations: 'pH'-rate profile. J Pharm Sci 90:141-156.
18. Strickley RG, Anderson BD. 1996. Solid-state stability of human insulin I. Mechanism and the effect of water on the kinetics of degradation in lyophiles from pH 2-5 solutions. Pharm Res 13: 1142-1153.
19. Lai MC, Hageman MJ, Schowen RL, Borchardt RT, Topp EM. 1999. Chemical stability of peptides in polymers 1. Effect of water on peptide deamidation in poly(vinyl alcohol) and poly(vinyl pyrrolidone) matrixes. J Pharm Sci 88:1073-080.
20. Bell LN, Hageman MJ. 1994. Differentiating between the effects of water activity and glass transition dependent mobility on a solid state chemical reaction: Aspartame degradation. J Agric Food Chem 42:2398-2401.
21. Streefland L, Auffret AD, Franks F. 1998. Bond cleavage reactions in solid aqueous carbohydrate solutions. Pharm Res 15:843-849.
22. Nyqvist H. 1983. Saturated salt solutions for maintaining specified relative humidities. Int J Pharm Tech Prod Mfr 4:47-48.
23. Lai MC, Topp EM. 1999. Solid-state chemical stability of proteins and peptides. J Pharm Sci 88: 489-500.
24. Brooks BR, Bruccoleri RE, Olafson BD, States DJ, Swaminathan S, Karplus M. 1983. CHARMM: A program for macromolecular energy, minization, and dynamics calculations. J Comput Chem 4:187-217.
25. Meyer JD, Jun Bai S, Rani M, Suryanarayanan R, Nayar R, Carpenter JF, Manning MC. 2004. Infrared spectroscopic studies of protein formulations containing glycine. J Pharm Sci 93:1359-1366.
26. Krimm S, Bandekar J. 1980. Vibrational analysis of peptides, polypeptides, and proteins V. Normal vibrations of beta-turns. Biopolymers 19:1-29.
27. Strickley RG, Anderson BD. 1996. Solid-state stability of human insulin I. Mechanism and the effect of water on the kinetics of degradation in lyophiles from pH 2-5 solutions. Pharm Res 13: 1142-1153.
28. Lai MC, Hageman MJ, Schowen RL, Borchardt RT, Topp EM. 1999. Chemical stability of peptides in polymers 1. Effect of water on peptide deamidation in poly(vinyl alcohol) and poly(vinyl pyrrolidone) matrixes. J Pharm Sci 88:1073-1080.
29. Bell LN, Hageman MJ. 1994. Differentiating between the effects of water activity and glass transition dependent mobility on a solid state chemical reaction: Aspartame degradation. J Agric Food Chem 42:2398-2401.
30. Streefland L, Auffret AD, Franks F. 1998. Bond cleavage reactions in solid aqueous carbohydrate solutions. Pharm Res 15:843-849.
31. Nyqvist H. 1983. Saturated salt solutions for maintaining specified relative humidities. Int J Pharm Tech Prod Mfr 4:47-48.
32. Lai MC, Topp EM. 1999. Solid-state chemical stability of proteins and peptides. J Pharm Sci 88: 489-500.
33. Brooks BR, Bruccoleri RE, Olafson BD, States DJ, Swaminathan S, Karplus M. 1983. CHARMM: A program for macromolecular energy, minization, and dynamics calculations. J Comput Chem 4:187-217.