Site-specific insulin conjugates with enhanced stability and extended action profile

Advanced Drug Delivery Reviews

Volumn 35, Issue 2-3, 1999, Pages 289-306

  Uchio, Takashi ^a   Baudyš, Miroslav ^a   Liu, Feng ^a   Song, Soo Chang ^a   Kim, Sung Wan ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Glycosylated insulin; Insulin immunogenicity; Insulin stability; Parenteral delivery; PEG insulin; Pharmacodynamics; Pharmacokinetics; Poly(ethylene glycol); Polyethylene glycol insulin conjugate

Indexed keywords

GLYCOL; GLYCOSIDE; INSULIN DERIVATIVE;

AMINO TERMINAL SEQUENCE; ANIMAL EXPERIMENT; ANIMAL MODEL; CONJUGATE; CONTROLLED STUDY; DOG; DRUG ABSORPTION; DRUG ACTIVITY; DRUG CLEARANCE; DRUG POTENCY; DRUG STABILITY; HYDROPHILICITY; IMMUNOGENICITY; LECTIN BINDING; MEAN RESIDENCE TIME; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL; RAT; REVIEW; SUBCUTANEOUS DRUG ADMINISTRATION;

EID: 0033008827     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(98)00078-7     Document Type: Review

References (89)

1. Banting F.G., Best C.M. Pancreatic extracts. J. Lab. Clin. Med. 7:1922;464-472.
2. Capaldo B., Home P.D., Massi-Benedetti M., Worth R., Cook D.B., Heaton A., Alberti K.G.M.M. The response of blood intermediary metabolite levels to 24 hours treatment with a blood glucose-controlled insulin infusion system in type 1 diabetes. Diabetes Res. 1:1984;187-193.
3. Skyler J.S. Lessons from studies of insulin pharmacokinetics. Diabetes Care. 9:1986;666-668.
4. Galloway J.A. New directions in drug development: mixtures, analogues, and modeling. Diabetes Care. 16(Suppl. 3):1993;16-23.
5. The Diabetes Control and Complications Trial Group The effect of intensive treatment of diabetes on the development and progression of long-term complications in insulin-dependent diabetes mellitus. New Engl. J. Med. 329:1993;977-986.
6. Malherbe C., de Gasparo M., de Hertogh R., Hoet J.J. Circadian variations of blood sugar and plasma insulin levels in man. Diabetologia. 5:1969;397-404.
7. Ribel U., Hougaard P., Drejer K., Sørensen A.R. Equivalent in vivo biological activity of insulin analogs and human insulin despite different in vitro potencies. Diabetes. 39:1990;1033-1039.
8. The DCCT Research Group Adverse events and their association with treatment regimens in the Diabetes Control and Complications Trial. Diabetes Care. 18:1995;1415-1427.
9. Dimitriadis G., Gerich J. Importance of timing of preprandial subcutaneous insulin administration in the management of diabetes mellitus. Diabetes Care. 6:1983;374-377.
10. Binder C. Absorption of injected insulin. Acta Pharmacol. Toxicol. Suppl. 2:1969;1-87.
11. U. Ribel, K. Jørgensen, J. Brange, U. Henriksen, The pig as a model for subcutaneous insulin absorption in man, in: M. Serrano-Rios, P. Lefèbvre (Eds.), Diabetes 1985, Elsevier, Amsterdam, 1986, pp. 891-896.
12. Blundell T., Dodson G., Hodgkin D., Mercola D. Insulin: the structure in the crystal and its reflection in chemistry and biology. Adv. Protein Chem. 26:1972;279-402.
13. Cunningham L.W., Fischer R.L., Vestling C.S. A study of the binding of zinc and cobalt by insulin. J. Am. Chem. Soc. 77:1955;5703-5707.
14. Brange J., Ribel U., Hansen J.F., Dodson G., Hansen M.T., Havelund S., Melberg S.C., Norris F., Norris K., Snel L., Sørensen A.R., Voigt H.O. Monomeric insulins obtained by protein engineering and their medical implications. Nature. 333:1988;679-682.
15. Anderson J.H., Brunelle R.L., Koivisto V.A., Pfützner A., Trautmann M.E., Vignatti L., DiMarchi R. Reduction of postprandial hyperglycemia and frequency of hypoglycemia in IDDM patients on insulin analog treatment. Diabetes. 46:1997;265-270.
16. Brange J., Owens D.R., Kang S., Vølund A. Monomeric insulins and their experimental and clinical implications. Diabetes Care. 13:1990;923-954.
17. B28) in healthy subjects. Diabetes Care. 14:1991;1057-1065.
18. Howey D.C., Bowsher R.R., Brunelle R.L., Woodworth J.R. [Lys(B28), Pro(B29)]-human insulin: a rapidly absorbed analogue of human insulin. Diabetes. 43:1994;396-402.
19. Lauritzen T., Pramming S., Gale E.A.M., Deckert T., Binder C. Absorption of isophane (NPH) insulin and its clinical implications. Br. Med. J. 285:1982;159-162.
20. Freeman S.L., O'Brien P.C., Rizza R.A. Use of human ultralente as the basal insulin component in treatment of patients with IDDM. Diabetes Res. Clin. Pract. 12:1991;187-192.
21. Galloway J.A., Chance R.E. Improving insulin therapy: achievements and challenges. Horm. Metab. Res. 26:1994;591-598.
22. J. Brange, Galenics of insulin, The Physico-Chemical and Pharmaceutical Aspects of Insulin and Insulin Preparations, Springer, Berlin Heidelberg, 1987.
23. Markussen J., Havelund S., Kurtzhals P., Andersen A.S., Halstrøm J., Larsen U.D., Ribel U., Schäffer K., Vad K., Jonassen I. Soluble, fatty acid acylated insulins bind to albumin and show protracted action in pigs. Diabetologia. 39:1996;281-288.
24. Frid A., Östman J., Linde B. Hypoglycemia risk during exercise after intramuscular injection of insulin in thigh in IDDM. Diabetes Care. 13:1990;473-477.
25. Thow J.C., Johnson A.B., Antsiferov M., Home P.D. Effect of raising injection-site skin temperature on isophane (NPH) insulin crystal dissolution. Diabetes Care. 12:1989;432-434.
26. Markussen J., Diers I., Hougaard P., Langkjaer L., Norris K., Snel N., Sørensen A.R., Sørensen E., Voigt H.O. Soluble, prolonged-acting insulin derivatives. III. Degree of protraction, crystallizability and chemical stability of insulins substituted in positions A21, B13, B23, B27 and B30. Protein Eng. 2:1988;157-166.
27. Jørgensen S., Vaag A., Langkjaer L., Hougaard P., Markussen J. NovoSol Basal: pharmacokinetics of a novel soluble long acting insulin analogue. Br. Med. J. 299:1989;415-419.
28. R. Geiger, R. Obermeier, V. Teetz, R. Uhmann, H.D. Summ, H. Neubauer, K. Geisen, G. Regitz, Biological activity of insulin analogues substituted at the amino group of B1-phenylalanine, in: D. Brandenburg, A. Wollmer (Eds.), Insulin: Chemistry, Structure and Function of Insulin and Related Hormones, Walter de Gruyter, Berlin, New York, 1980, pp. 409-415.
29. Hashimoto M., Takada K., Kiso Y., Muranishi S. Synthesis of palmitoyl derivatives of insulin and their biological activities. Pharm. Res. 6:1989;171-176.
30. Kurtzhals P., Havelund S., Jonassen I., Kiehr B., Larsen U.D., Ribel U., Markussen J. Albumin binding of insulins acylated with fatty acids: characterization of the ligand-protein interaction and correlation between binding affinity and timing of the insulin effect in vivo. Biochem. J. 312:1995;725-731.
31. Myers S.R., Yakubu-Madus F.E., Johnson W.T., Baker J.E., Cusick T.S., Williams V.K., Tinsley F.C., Kriauciunas A., Manetta J., Chen V.J. Acylation of human insulin with palmitic acid extends the time of action of human insulin in diabetic dogs. Diabetes. 46:1997;637-642.
32. Kurtzhals P., Kiehr B., Sørensen A.R. The cobalt(III)-insulin hexamer is a prolonged-acting insulin prodrug. J. Pharm. Sci. 84:1995;1164-1168.
33. Kurtzhals P., Ribel U. Action profile of cobalt(III)-insulin. A novel principle of protraction of potential use for basal insulin delivery. Diabetes. 44:1995;1381-1385.
34. 2+ ions. Biochemistry. 24:1985;1749-1756.
35. Coffman F.D., Dunn M.F. Insulin-metal ion interactions: the binding of divalent cations to insulin hexamers and tetramers and the assembly of insulin hexamers. Biochemistry. 27:1988;6176-6187.
36. J. Brange, Stability of insulin, in: Studies on the Physical and Chemical Stability of Insulin in Pharmaceutical Formulation, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1994.
37. Farrant J.L., Mercer E.H. Electron microscopical observations of fibrous insulin. Biochim. Biophys. Acta. 8:1952;355-359.
38. Baudyš M., Mix D., Kim S.W. Stabilization and intestinal absorption of human calcitonin. J. Control. Release. 39:1996;145-151.
39. Brange J., Andersen L., Laursen E.D., Meyn G., Rasmussen E. Toward understanding insulin fibrillation. J. Pharm. Sci. 86:1997;517-525.
40. Glenner G.G., Eanes E.D., Bladen H.A., Linke R.P., Termine J.D. A comparison of native amyloid with synthetic protein fibrils. J. Histochem. Cytochem. 22:1974;1141-1158.
41. Brange J., Dodson G.G., Edwards D.J., Holden P.H., Whittingham J.L. A model of insulin fibrils derived from the x-ray crystal structure of monomeric insulin (despentapeptide insulin). Proteins Struct. Funct. Genet. 27:1997;507-516.
42. G.R. Bock, J.A. Goode (Eds.), The Nature and Origin of Amyloid Fibrils, John Wiley, New York, 1996.
43. C.C.F. Blake, L.C. Serpell, M. Sunde, O. Sandgren, E. Lundgren, A molecular model of the amyloid fibril, in: G.R. Bock, J.A. Goode (Eds.), The Nature and Origin of Amyloid Fibrils, John Wiley, New York, 1996, pp. 6-21.
44. J. Brange, J.F. Hansen, S. Havelund, S.G. Melberg, Studies of the insulin fibrillation process, in: Brunetti, P., Waldhäusl, W.K. (Eds.), Advanced Models for the Therapy of Insulin-Dependent Diabetes, Raven Press, New York, 1987, pp. 85-90.
45. Sluzky V., Tamada J.A., Klibanov A.M., Langer R. Kinetics of insulin aggregation in aqueous solutions upon agitation in the presence of hydrophobic surfaces. Proc. Natl. Acad. Sci. USA. 88:1991;9377-9381.
46. Lougheed W.D., Albisser A.M., Martindale H.M., Chow J.C., Clement J.R. Physical stability of insulin formulations. Diabetes. 32:1983;424-432.
47. Thurow H., Geisen K. Stabilization of dissolved proteins against denaturation at hydrophobic interfaces. Diabetologia. 27:1984;212-218.
48. Sluzky V., Klibanov A.M., Langer R. Mechanism of insulin aggregation and stabilization in agitated aqueous solutions. Biotechnol. Bioeng. 40:1992;895-903.
49. B29-insulin hexamers: a comparison study. Pharm. Res. 14:1997;25-36.
50. Schernthaner G. Immunogenicity and allergic potential of animal and human insulins. Diabetes Care. 16:1993;155-165.
51. Robbins D.C., Mead P.M. Free covalent aggregates of therapeutic insulin in blood of insulin-dependent diabetics. Diabetes. 36:1987;147-151.
52. Kim S.W., Jacobs H.A. Self-regulated insulin delivery - artificial pancreas. Drug Dev. Ind. Pharm. 20:1994;575-580.
53. Liu F., Song S.C., Mix D., Baudyš M., Kim S.W. Glucose-induced release of glycosylpoly(ethylene glycol) insulin bound to a soluble conjugate of concanavalin A. Bioconjugate Chem. 8:1997;664-672.
54. Jeong S.Y., Kim S.W., Eenink M.J.D., Feijen J. Self-regulating insulin delivery systems: I. Synthesis and characterization of glycosylated insulin. J. Control. Release. 1:1984;57-66.
55. Baudyš M., Uchio T., Mix D., Wilson D., Kim S.W. Physical stabilization of human insulin by glycosylation. J. Pharm. Sci. 84:1995;28-33.
56. Říhová B., Baudyš M., Tlaskalová H., Říhová H., Kim S.W. Immunogenicity of glycosylated derivatives of insulin. I. Antibodies to gliadin detected after immunization with insulin and its glycosylated derivatives. J. Clin. Lab. Immunol. 44:1994;191-214.
57. Uchio T., Baudyš M., Mix D., Kim S.W. Pharmacodynamic and pharmacokinetic study of glycosylated insulin derivatives in dog. Proc. Control. Release Bioact. Mat. 23:1996;883-884.
58. J.M. Harris, Introduction to biotechnical and biomedical applications of poly(ethylene glycol), in: J.M. Harris (Ed.), Poly(ethylene Glycol) Chemistry: Biotechnical and Biomedical Applications, Plenum Press, New York, 1992, pp. 1-14.
59. Abuchowski A., McCoy J.R., Palczuk N.C., van Es T., Davis F.F. Effect of covalent attachment of polyethylene glycol on immunogenicity and circulating life of bovine liver catalase. J. Biol. Chem. 252:1977;3582-3586.
60. Dreborg S., Akerblom E. Immunotherapy with monomethoxypolyethylene glycol modified allergens. Crit. Rev. Ther. Drug Carrier Syst. 6:1990;315-365.
61. Baudyš M., Uchio T., Hovgaard L., Zhu E.F., Avramoglou T., Jozefowicz M., Říhová B., Park J.Y., Lee H.K., Kim S.W. Glycosylated insulins. J. Control. Release. 36:1995;151-157.
62. A. Abuchowski, F.F. Davis, Soluble polymer-enzyme adducts, in: J.S. Holcenberg, J. Roberts (Eds.), Enzymes as Drugs, John Wiley, New York, 1981, pp. 367-395.
63. S. Nagaoka, Y. Mori, H. Takiuchi, K. Yokota, H. Tanzawa, S. Nishium, Polymers as biomaterials, in: S.W. Shalaby, A.S. Hoffman, B.D. Ratner, T.A. Horbett (Eds.), Plenum Press, New York, 1985, pp. 361-370.
64. F.F. Davis, G.M. Kazo, G.M.L. Nucciand, A. Abuchowski, Reduction of immunogenicity and extension of circulating half-life of peptides and proteins. In: V.H. Lee (Ed.), Peptide and Protein Drug Delivery, Marcel Dekker, New York, 1991, pp. 831-865.
65. Abuchowski A., Van Es T., Palczuk N.C., Davis F.F. Alteration of immunological properties of bovine serum albumin by covalent attachment of polyethylene glycol. J. Biol. Chem. 252:1977;3578-3581.
66. Sehon A.H. Suppression of antibody responses by chemically modified antigens. Int. Arch. Allergy Appl. Immunol. 94:1991;11-20.
67. Baudyš M., Song S.C., Uchio T., Mix D., Kim S.W. Chemical modification of insulin to enhance its physical stability. Proc. Control. Release Bioact. Mat. 22:1995;538-539.
68. Liu F., Baudyš M., Mix D., Hinds K., Kim S.W. Bioactive polyethylene glycol-insulin conjugates with enhanced stability. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.). 38:1997;595-596.
69. Ehrat M., Luisi P.L. Synthesis and spectroscopic characterization of insulin derivatives containing one or two poly(ethylene oxide) chains at specific positions. Biopolymers. 22:1983;569-573.
70. Baudyš M., Uchio T., Song S.C., Liu F., Mix D., Říhová B., Kim S.W. Design of stable and bioactive insulin conjugates. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.). 37:1996;117-118.
71. Baker E.N., Blundell T.L., Cutfield J.F., Cutfield S.M., Dodson E.J., Dodson G.G., Hodgkin D.C., Hubbard R.E., Isaacs N.W., Reynolds C.D., Sakabe K., Sakabe N., Vijayan N.M. The structure of 2Zn pig insulin crystals at 1.5 Å resolution. Phil. Trans. R. Soc. London. 319:1988;369-456.
72. Derewenda U., Derewenda Z., Dodson E.J., Dodson G.G., Reynolds C.D., Smith G.D., Sparks C., Swenson D. Phenol stabilizes more helix in a new symmetrical zinc insulin hexamer. Nature. 338:1989;594-596.
73. Wollmer A., Rannefeld B., Johansen B.R., Hejnaes K.R., Baldschmidt P., Hansen F.B. Phenol-promoted structural transformation of insulin in solution. Biol. Chem. Hoppe-Seyler. 368:1987;903-911.
74. Rahuel-Clermont S., French C.A., Kaarsholm N.C., Dunn M.F. Mechanisms of stabilization of insulin hexamer through allosteric ligand interactions. Biochemistry. 36:1997;5837-5845.
75. Pocker Y., Biswas S.B. Conformational dynamics of insulin in solution. Circular dichroic studies. Biochemistry. 19:1980;5043-5049.
76. Murray-Rust J., McLeod A.N., Blundell T.L., Wood S.P. Structure and evolution of insulins: implications for receptor binding. BioEssays. 14:1992;325-330.
77. Neubauer H.P., Obermeier R., Schöne H.H. Influence of polyethylene glycol insulin on lipid tissues of experimental animals. Diabetes. 32:1983;953-958.
78. H. Thurow, Studies on the denaturation of dissolved insulin, in: D. Brandenburg, A. Wollmer (Eds.), Insulin: Chemistry, Structure and Function of Insulin and Related Hormones, Walter de Gruyter, Berlin, 1980, pp. 216-221.
79. Van Haeften T.W., Heiling V.J., Gerich J.E. Adverse effects of insulin antibodies on postprandial plasma glucose and insulin profiles in diabetic patients without immune insulin resistance: implications for intensive insulin regimens. Diabetes. 36:1987;305-309.
80. W.G. Reewes, The immune response to insulin: characterization and clinical consequences, in: K.G.M.M. Alberti, L.P. Krall (Eds.), The Diabetes Annual/2, Elsevier, Amsterdam, 1986, pp. 81-93.
81. Bolli G.B., Dimitriades G.D., Pehling G.B., Baker B.A., Haymond M.W., Cryer P.E., Gerich J.E. Abnormal glucose counterregulation after subcutaneous insulin in insulin-dependent diabetes. New Engl. J. Med. 310:1984;1706-1711.
82. Van Haeften T.W. Clinical significance of insulin antibodies in insulin-treated diabetic patients. Diabetic Care. 12:1989;641-648.
83. S.H. Barondes, Vertebrate lectins: properties and functions. In: I.E. Liener, N. Sharon, I.J. Goldstein (Eds.), The Lectins, Academic Press, Orlando, FL, 1986, pp. 437-466.
84. Lee Y.C. Biochemistry of carbohydrate-protein interaction. FASEB J. 6:1992;3193-3200.
85. Drejer K. The bioactivity of insulin analogs from in vitro receptor binding to in vivo glucose uptake. Diabetes/Metab. Rev. 8:1992;259-286.
86. King G.L., Johnson S. Receptor mediated transport of insulin across the endothelial cells. Science. 229:1985;1583-1586.
87. Ferrannini E., Wahren J., Faber O.K., Felig P., Binder C., DeFronzo R.A. Splanchnic and renal metabolism of insulin in human subjects: a dose-response study. Am. J. Physiol. 244:1983;E517-E527.
88. DeFronzo R.A. Lilly lecture 1987: the triumvirate: β-cell, muscle, liver: a collusion responsible for NIDDM. Diabetes. 37:1988;667-687.
89. 29. Diabetologia. 20:1981;94-101.