Effects of sucrose and mannitol on asparagine deamidation rates of model peptides in solution and in the solid state

Journal of Pharmaceutical Sciences

Volumn 94, Issue 8, 2005, Pages 1723-1735

  Li, Bei ^a   O'Meara, Matthew H ^b   Lubach, Joseph W ^a   Schowen, Richard L ^a   Topp, Elizabeth M ^a   Munson, Eric J ^a   Borchardt, Ronald T ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b ST JOHN'S UNIVERSITY   (United States)

Author keywords

Deamidation; Mannitol; Peptides; Solid state stability; Sucrose

Indexed keywords

ASPARAGINE; GLYCYLGLUTAMINYLASPARAGINYLGLYCYLGLYCINE; MANNITOL; RECOMBINANT PROTEIN; SUCROSE; UNCLASSIFIED DRUG; VALYLTYROSYLPROLYLASPARAGINYLGLYCYLALAMINE;

AMINO ACID SEQUENCE; ARTICLE; DEAMINATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DEGRADATION; DRUG FORMULATION; FREEZE DRYING; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; PH; PHYSICAL CHEMISTRY; PROTEIN STRUCTURE; SOLID STATE; THERMOGRAVIMETRY; TITRIMETRY;

EID: 25444524564     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.20372     Document Type: Article

References (52)

1. Reissner KJ, Aswad DW. 2003. Deamidation and isoaspartate formation in proteins: Unwanted alterations or surreptitious signals? Cell Mol Life Sci 60:1281-1295.
2. Wright HT. 1991. Nonenzymatic deamidation of asparaginyl and glutaminyl residues in proteins. Crit Rev Biochem Mol Biol 26:1-52.
3. Gotte G, Libonati M, Laurents DV. 2003. Glycosylation and specific deamidation of ribonuclease B affect the formation of three-dimensional domain-swapped oligomers. J Biol Chem 278:46241-46251.
4. Li C, Thompson CB. 2002. DNA damage, deamidation, and death. Science (Washington, DC, United States) 298:1346-1347.
5. Johnstone RW. 2002. Deamidation of Bcl-XL: A new twist in a genotoxic murder mystery. Molecular Cell 10:695-697.
6. Harding JJ, Beswick HT, Ajiboye R, Huby R, Blakytny R, Rixon KC. 1989. Non-enzymic posttranslational modification of proteins in aging. A review. Mech Ageing Dev 50:7-16.
7. McAdam SN, Fleckenstein B, Rasmussen IB, Schmid DG, Sandlie I, Bogen B, Viner NJ, Sollid LM. 2001. T cell recognition of the dominant I-A(k)-restricted hen egg lysozyme epitope: critical role for asparagine deamidation. J Exp Med 193:1239-1246.
8. Orru S, Vitagliano L, Esposito L, Mazzarella L, Marino G, Ruoppolo M. 2000. Effect of deamidation on folding of ribonuclease A. Protein Sci 9:2577-2582.
9. Patel K, Borchardt RT. 1990. Deamidation of asparaginyl residues in proteins: A potential pathway for chemical degradation of proteins in lyophilized dosage forms. J Parenter Sci Technol 44:300-301.
10. Liu DT. 1992. Deamidation: A source of microheterogeneity in pharmaceutical proteins. Trends Biotechnol 10:364-369.
11. Cleland JL, Powell MF, Shire SJ. 1993. The development of stable protein formulations: A close look at protein aggregation, deamidation, and oxidation. Crit Rev Ther Drug Carrier Syst 10: 307-377.
12. Brange J, Langkjoer L. 1993. Insulin structure and stability. Pharm Biotechnol 5:315-350.
13. Chang BS, Reeder G, Carpenter JF. 1996. Development of a stable freeze-dried formulation of recombinant human interleukin-1 receptor antagonist. Pharm Res 13:243-249.
14. Cleland JL, Mac A, Boyd B, Yang J, Duenas ET, Yeung D, Brooks D, Hsu C, Chu H, Mukku V, Jones AJ. 1997. The stability of recombinant human growth hormone in poly(lactic-co-glycolic acid) (PLGA) microspheres. Pharm Res 14:420-425.
15. Pikal MJ, Dellerman KM, Roy ML, Riggin RM. 1991. The effects of formulation variables on the stability of freeze-dried human growth hormone. Pharm Res 8:427-436.
16. Geiger T, Clarke S. 1987. Deamidation, isomerization, and racemization at asparaginyl and aspartyl residues in peptides. Succinimide-linked reactions that contribute to protein degradation. J Biol Chem 262:785-794.
17. Stephenson RC, Clarke S. 1989. Succinimide formation from aspartyl and asparaginyl peptides as a model for the spontaneous degradation of proteins. J Biol Chem 264:6164-6170.
18. Li B, Borchardt RT, Topp EM, VanderVelde D, Schowen RL. 2003. Racemization of an asparagine residue during peptide deamidation. J Am Chem Soc 125:11486-11487.
19. Capasso S. 2000. Estimation of the deamidation rate of asparagine side chains. J Pept Res 55:224-229.
20. Robinson NE, Robinson AB. 2001. Prediction of protein deamidation rates from primary and three-dimensional structure. Proc Natl Acad Sci USA 98: 4367-4372.
21. Robinson NE. 2002. Protein deamidation. Proc Natl Acad Sci USA 99:5283-5288.
22. Robinson NE, Robinson AB. 2001. Deamidation of human proteins. Proc Natl Acad Sci USA 98:12409-12413.
23. Brennan TV, Clarke S. 1994. Deamidation and isoaspartate formation in model synthetic peptides: The effects of sequence and solution environment. In: Aswad DW, editor. Deamidation and isoaspartate formation in peptides and Proteins, edition. Boca Raton: CRC Press, Inc. pp 65-90.
24. Carpenter JF, Chang BS, Garzon-Rodriguez W, TW R. 2002. Rational design of stable protein formulations: Theory and practice. In: Carpenter JF, Manning MC, editors. Rational design of stable protein formulations: Theory and practice [In: Pharm Biotechnol, 2002; 13], edition. New York: Kluwer Academic/Plenum Publishers, pp 109-135.
25. Wang W. 2000. Lyophilization and development of solid protein pharmaceuticals. Int J Pharmaceutics 203:1-60.
26. Cleland JL, Lam X, Kendrick B, Yang J, Yang TH, Overcashier D, Brooks D, Hsu C, Carpenter JF. 2001. A specific molar ratio of stabilizer to protein is required for storage stability of a lyophilized monoclonal antibody. J Pharm Sci 90:310-321.
27. Byrn SR, Xu W, Newman AW. 2001. Chemical reactivity in solid-state pharmaceuticals: Formulation implications. Adv Drug Deliv Rev 48:115-136.
28. 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.
29. Lai MC, Schowen RL, Borchardt RT, Topp EM. 2000. Deamidation of a model hexapeptide in poly(vinyl alcohol) hydrogels and xerogels. J Pept Res 55:93-101.
30. 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.
31. Lai MC, Hageman MJ, Schowen RL, Borchardt RT, Laird BB, Topp EM. 1999. Chemical stability of peptides in polymers. 2. Discriminating between solvent and plasticizing effects of water on peptide deamidation in poly(vinylpyrrolidone). J Pharm Sci 88:1081-1089.
32. Pikal MJ, Dellerman K, Roy ML. 1992. Formulation and stability of freeze-dried proteins: Effects of moisture and oxygen on the stability of freeze-dried formulations of human growth hormone. Dev Biol Stand 74:21-37.
33. Johnson RE, Kirchhoff CF, Gaud HT. 2002. Mannitol-sucrose mixtures-versatile formulations for protein lyophilization. J Pharm Sci 91:914-922.
34. 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.
35. Goolcharran C, Stauffer LL, Cleland JL, Borchardt RT. 2000. The effects of a histidine residue on the C-terminal side of an asparaginyl residue on the rate of deamidation using model pentapeptides. J Pharm Sci 89:818-825.
36. Peersen OB, Wu X, Smith SO. 1994. Enhancement of CP-MAS signals by variable-amplitude cross polarization. Compensation for inhomogeneous B1 fields. J Magn Reson Ser A 106:127-131.
37. Stejskal EO, Schaefer J, Waugh JS. 1977. Magic-angle spinning and polarization transfer in proton-enhanced NMR. J Magn Reson (1969-1992) 28:105-112.
38. Bennett AE, Rienstra CM, Auger M, Lakshmi KV, Griffin RG. 1995. Heteronuclear decoupling in rotating solids. J Chem Phys 103:6951-6958.
39. Dixon WT, Schaefer J, Sefcik MD, Stejskal EO, McKay RA. 1982. Total suppression of sidebands in CPMAS carbon-13 NMR. J Magn Reson (1969-1992) 49:341-345.
40. Pines A, Gibby MG, Waugh JS. 1973. Proton-enhanced NMR of dilute spins in solids. J Chem Phys 59:569-590.
41. Stratton LP, Kelly RM, Rowe J, Shively JE, Smith DD, Carpenter JF, Manning MC. 2001. Controlling deamidation rates in a model peptide: effects of temperature, peptide concentration, and additives. J Pharm Sci 90:2141-2148.
42. Tyler-Cross R, Schirch V. 1991. Effects of amino acid sequence, buffers, and ionic strength on the rate and mechanism of deamidation of asparagine residues in small peptides. J Biol Chem 266:22549-22556.
43. Kreilgaard L, Frokjaer S, Flink JM, Randolph TW, Carpenter JF. 1998. Effects of additives on the stability of recombinant human factor XIII during freeze-drying and storage in the dried solid. Arch Biochem Biophys 360:121-134.
44. Kreilgaard L, Frokjaer S, Flink JM, Randolph TW, Carpenter JF. 1999. Effects of additives on the stability of humicola lanuginosa lipase during freeze-drying and storage in the dried solid. J Pharm Sci 88:281-290.
45. Oliyai C, Patel JP, Carr L, Borchardt RT. 1994. Chemical pathways of peptide degradation. VII. Solid state chemical instability of an aspartyl residue in a model hexapeptide. Pharm Res 11: 901-908.
46. Kacurakova M, Wilson RH. 2001. Developments in mid-infrared FT-IR spectroscopy of selected carbohydrates. Carbohydr Polymers 44:291-303.
47. Ottenhof M-A, MacNaughtan W, Farhat IA. 2003. FTIR study of state and phase transitions of low moisture sucrose and lactose. Carbohydr Res 338: 2195-2202.
48. Costantino HR, Curley JG, Wu S, Hsu CC. 1998. Water sorption behavior of lyophilized protein-sugar systems and implications for solid-state interactions. Int J Pharm 166:211-221.
49. Walter-Levy L. 1968. Crystalline forms of D-mannitol. Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques 267:1779-1782.
50. Grindley TB, McKinnon MS, Wasylishen RE. 1990. Towards understanding carbon-13 NMR chemical shifts of carbohydrates in the solid state. The spectra of D-mannitol polymorphe and of DL-mannitol. Carbohydr Res 197:41-52.
51. Yoshinari T, Forbes RT, York P, Kawashima Y. 2002. Moisture induced polymorphic transition of mannitol and its morphological transformation. Int J Pharm 247:69-77.
52. Carpenter JF, Izutsu K, Randolph T. 1999. Freezing- and drying-induced pertubations of protein structure and mechanisms of protein protection by stabilizing additives. In: Ray L, May J, editors. Freeze-drying/lyophilization of pharmaceutical and biological products, edition. New York: Marcel Dekker. pp 123-161.