Mechanisms of glucagon degradation at alkaline pH

Peptides

Volumn 45, Issue , 2013, Pages 40-47

  Caputo, Nicholas ^a   Castle, Jessica R ^a   Bergstrom, Colin P ^a   Carroll, Julie M ^b   Bakhtiani, Parkash A ^a   Jackson, Melanie A ^a   Roberts, Charles T ^a,b   David, Larry L ^a   Ward, W Kenneth ^a  

^a OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

^b OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

Author keywords

Alkaline; Deamidation; Degradation; Diabetes mellitus; Glucagon; Oxidation

Indexed keywords

CYCLIC AMP DEPENDENT PROTEIN KINASE; GLUCAGON; PEPTIDE; SOLUTION AND SOLUBILITY;

ALKALINITY; ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DEAMINATION; ISOMERIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; OXIDATION; PH; PRIORITY JOURNAL; PROTEIN DEGRADATION; REGULATORY MECHANISM; ANALOGS AND DERIVATIVES; CHEMISTRY; ENZYME ASSAY; HUMAN; PRECIPITATION; PROTEIN STABILITY; SOLUTION AND SOLUBILITY;

CHEMICAL PRECIPITATION; CHROMATOGRAPHY, LIQUID; CYCLIC AMP-DEPENDENT PROTEIN KINASES; ENZYME ASSAYS; GLUCAGON; HUMANS; HYDROGEN-ION CONCENTRATION; MASS SPECTROMETRY; PEPTIDES; PROTEIN STABILITY; PROTEOLYSIS; SOLUTIONS;

EID: 84878963672     PISSN: 01969781     EISSN: 18735169     Source Type: Journal    
DOI: 10.1016/j.peptides.2013.04.005     Document Type: Article

References (35)

1. M. Amblard, J.A. Fehrentz, J. Martinez, and G. Subra Methods and protocols of modern solid phase peptide synthesis Mol Biotechnol 33 2006 239 254 (Pubitemid 44337228)
2. G.H. Beaven, W.B. Gratzer, and H.G. Davies Formation and structure of gels and fibrils from glucagon Eur J Biochem 11 1969 37 42
3. W.W. Bromer Chemical characteristics of glucagon 1983 Springer-Verlag New York, NY
4. J.R. Castle, J.M. Engle, J. El Youssef, R.G. Massoud, and W.K. Ward Factors influencing the effectiveness of glucagon for preventing hypoglycemia J Diabetes Sci Technol 4 2010 1305 1310
5. J.R. Castle, J.M. Engle, J. El Youssef, R.G. Massoud, K.C. Yuen, and R. Kagan Novel use of glucagon in a closed-loop system for prevention of hypoglycemia in type 1 diabetes Diabetes Care 33 2010 1282 1287
6. J.R. Chabenne, M.A. DiMarchi, V.M. Gelfanov, and R.D. DiMarchi Optimization of the native glucagon sequence for medicinal purposes J Diabetes Sci Technol 4 2010 1322 1331
7. A.D. Cherrington, J.L. Chiasson, J.E. Liljenquist, A.S. Jennings, U. Keller, and W.W. Lacy The role of insulin and glucagon in the regulation of basal glucose production in the postabsorptive dog J Clin Invest 58 1976 1407 1418
8. P.A. Christensen, J.S. Pedersen, G. Christiansen, and D.E. Otzen Spectroscopic evidence for the existence of an obligate pre-fibrillar oligomer during glucagon fibrillation FEBS Lett 582 2008 1341 1345
9. F.H. El-Khatib, J. Jiang, R.G. Gerrity, and E.R. Damiano Pharmacodynamics and stability of subcutaneously infused glucagon in a type 1 diabetic Swine model in vivo Diabetes Technol Ther 9 2007 135 144 (Pubitemid 46652547)
10. F.H. El-Khatib, S.J. Russell, D.M. Nathan, R.G. Sutherlin, and E.R. Damiano A bihormonal closed-loop artificial pancreas for type 1 diabetes Sci Trans Med 2 2010 27ra
11. A. Haidar, L. Legault, M. Dallaire, A. Alkhateeb, A. Coriati, and V. Messier Glucose-responsive insulin and glucagon delivery (dual-hormone artificial pancreas) in adults with type 1 diabetes: a randomized crossover controlled trial CMAJ 185 2013 297 305
12. H. Ichiba, T. Ogawa, T. Yajima, and T. Fukushima Analysis of hydroxyl radical-induced oxidation process of glucagon by reversed-phase HPLC and ESI-MS/MS Biomed Chromatogr 23 2009 1051 1058
13. A. Ichihara, T. Nakamura, and K. Tanaka Use of hepatocytes in primary culture for biochemical studies on liver functions Mol Cell Biochem 43 1982 145 160 (Pubitemid 12078395)
14. M.A. Jackson, N. Caputo, J.R. Castle, L.L. David, C.T. Roberts Jr., and W.K. Ward Stable liquid glucagon formulations for rescue treatment and bi-hormonal closed-loop pancreas Curr Diab Rep 12 2012 705 710
15. B.A. Johnson, J.M. Shirokawa, and D.W. Aswad Deamidation of calmodulin at neutral and alkaline pH: quantitative relationships between ammonia loss and the susceptibility of calmodulin to modification by protein carboxyl methyltransferase Arch Biochem Biophys 268 1989 276 286 (Pubitemid 19038260)
16. A.B. Joshi, and L.E. Kirsch The estimation of glutaminyl deamidation and aspartyl cleavage rates in glucagon Int J Pharm 273 2004 213 219 (Pubitemid 38317054)
17. A.B. Joshi, and L.E. Kirsch The relative rates of glutamine and asparagine deamidation in glucagon fragment 22-29 under acidic conditions J Pharm Sci 91 2002 2331 2345
18. A.B. Joshi, E. Rus, and L.E. Kirsch The degradation pathways of glucagon in acidic solutions Int J Pharm 203 2000 115 125 (Pubitemid 30627632)
19. A.B. Joshi, M. Sawai, W.R. Kearney, and L.E. Kirsch Studies on the mechanism of aspartic acid cleavage and glutamine deamidation in the acidic degradation of glucagon J Pharm Sci 94 2005 1912 1927 (Pubitemid 41551476)
20. N. Kedia Treatment of severe diabetic hypoglycemia with glucagon: an underutilized therapeutic approach Diabetes Metab Syndr Obes 4 2011 337 346
21. L. Matilainen, S.L. Maunu, J. Pajander, S. Auriola, I. Jaaskelainen, and K.L. Larsen The stability and dissolution properties of solid glucagon/gamma-cyclodextrin powder Eur J Pharm Sci 36 2008 412 420
22. Y.C. Meinwald, E.R. Stimson, and H.A. Scheraga Deamidation of the asparaginyl-glycyl sequence Int J Pept Protein Res 28 1986 79 84
23. W.J. Nooijen, and H.J. Kempen Immunogenicity and bioactivity of glucagon, modified at methionine-27 Horm Metab Res 11 1979 459 463 (Pubitemid 10221155)
24. S. Onoue, K. Ohshima, K. Debari, K. Koh, S. Shioda, and S. Iwasa Mishandling of the therapeutic peptide glucagon generates cytotoxic amyloidogenic fibrils Pharm Res 21 2004 1274 1283 (Pubitemid 38954214)
25. J.S. Pedersen, D. Dikov, J.L. Flink, H.A. Hjuler, G. Christiansen, and D.E. Otzen The changing face of glucagon fibrillation: structural polymorphism and conformational imprinting J Mol Biol 355 2005 501 523 (Pubitemid 41785753)
26. J.S. Pedersen, D. Dikov, and D.E. Otzen N- and C-terminal hydrophobic patches are involved in fibrillation of glucagon Biochemistry 45 2006 14503 14512 (Pubitemid 44865205)
27. N.E. Robinson Protein deamidation Proc Natl Acad Sci U S A 99 2002 5283 5288 (Pubitemid 34411540)
28. N.E. Robinson, V. Zabrouskov, J. Zhang, K.J. Lampi, and A.B. Robinson Measurement of deamidation of intact proteins by isotopic envelope and mass defect with ion cyclotron resonance Fourier transform mass spectrometry Rapid Commun Mass Spectrom 20 2006 3535 3541 (Pubitemid 44871309)
29. S.J. Russell, F.H. El-Khatib, D.M. Nathan, and E.R. Damiano Efficacy determinants of subcutaneous microdose glucagon during closed-loop control J Diabetes Sci Technol 4 2010 1288 1304
30. S.S. Steiner, M. Li, R. Hauser, and R. Pohl Stabilized glucagon formulation for bihormonal pump use J Diabetes Sci Technol 4 2010 1332 1337
31. A.K. Verma, J.H. da Silva, and D.R. Kuhl Diuretic effects of subcutaneous furosemide in human volunteers: a randomized pilot study Ann Pharmacother 38 2004 544 549 (Pubitemid 38404274)
32. W.K. Ward, J.R. Castle, D.L. Branigan, R.G. Massoud, and J. El Youssef Discomfort from an alkaline formulation delivered subcutaneously in humans: albumin at pH 7 versus pH 10 Clin Drug Investig 32 2012 433 438
33. W.K. Ward, R.G. Massoud, C.J. Szybala, J.M. Engle, J. El Youssef, and J.M. Carroll In vitro and in vivo evaluation of native glucagon and glucagon analog (MAR-D28) during aging: lack of cytotoxicity and preservation of hyperglycemic effect J Diabetes Sci Technol 4 2010 1311 1321
34. H. Yang, and R.A. Zubarev Mass spectrometric analysis of asparagine deamidation and aspartate isomerization in polypeptides Electrophoresis 31 2010 1764 1772
35. M. Zaccolo, F. De Giorgi, C.Y. Cho, L. Feng, T. Knapp, and P.A. Negulescu A genetically encoded, fluorescent indicator for cyclic AMP in living cells Nat Cell Biol 2 2000 25 29