Mono-PEGylated dimeric exendin-4 as high receptor binding and long-acting conjugates for type 2 anti-diabetes therapeutics

Bioconjugate Chemistry

Volumn 22, Issue 4, 2011, Pages 625-632

  Kim, Tae Hyung ^a   Jiang, Hai Hua ^a   Lee, Seulki ^b   Youn, Yu Seok ^c   Park, Chan Woong ^a   Byun, Youngro ^d   Chen, Xiaoyuan ^b   Lee, Kang Choon ^a  

^a Sungkyunkwan University   (South Korea)

^b NATIONAL INSTITUTE OF BIOMEDICAL IMAGING AND BIOENGINEERING   (United States)

^c Pusan National University   (South Korea)

^d Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DIMERIZATION; MASS SPECTROMETRY; PROTEINS; SIZE EXCLUSION CHROMATOGRAPHY;

BINDING AFFINITIES; COUPLING REACTION; DIMERIZATIONS; HIGH PURITY; IN-VIVO; LIFESPANS; PEGYLATED; PEGYLATION; RECEPTOR BINDING; SIZE-EXCLUSION CHROMATOGRAPHY;

BINDING ENERGY;

AMINE; CYSTEINE; EXENDIN 4;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CIRCULATION; CONTROLLED STUDY; DIMERIZATION; DRUG EFFICACY; IN VIVO STUDY; MALE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOUSE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; RAT; RECEPTOR BINDING;

MUS;

EID: 79955014687     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100404x     Document Type: Article

References (34)

1. Meier, J. J. and Nauck, M. A. (2005) Glucagon-like peptide 1(GLP-1) in biology and pathology Diabetes Metab. Res. Rev. 21, 91-117 (Pubitemid 40467658)
2. Eng, J., Kleinman, W. A., Singh, L., Singh, G., and Raufman, J. P. (1992) Isolation and characterization of exendin-4, an exendin-3 analogue, from Heloderma suspectum venom J. Biol. Chem. 267, 7402-7405
3. Davidson, M. B., Bat, G., and Kirkpatrick, P. (2005) Exenatide Nat. Rev. Drug Discovery 4, 713-714
4. Kolterman, O. G., Buse, J. B., Fineman, M. S., Gaines, E., Heintz, S., Bicsak, T. A., Taylor, K., Kim, D., Aisporna, M., Wang, Y., and Baron, A. D. (2003) Synthetic exendin-4 (exenatide) significantly reduces postprandial and fasting plasma glucose in subjects with type 2 diabetes J. Clin. Endocrinol. Metab. 88, 3082-3089 (Pubitemid 36877476)
5. Szayna, M., Doyle, M. E., Betkey, J. A., Holloway, H. W., Spencer, R. G., Greig, N. H., and Egan, J. M. (2000) Exendin-4 decelerates food intake, weight gain, and fat deposition in Zucker rats Endocrinology 141, 1936-1941 (Pubitemid 32274340)
6. Nielsen, L. L., Young, A. A., and Parkes, D. G. (2004) Pharmacology of exenatide (synthetic exendin-4): a potential therapeutic for improved glycemic control of type 2 diabetes Regul. Pept. 117, 77-88 (Pubitemid 38045329)
7. Drucker, D. J. and Nauck, M. A. (2006) The incretin system: glucagon-like peptide-1 receptor agonists and dipeptidyl peptidase-4 inhibitors in type 2 diabetes Lancet 368, 1696-1705 (Pubitemid 46048557)
8. Simonsen, L., Holst, J. J., and Deacon, C. F. (2006) Exendin-4, but not glucagon-like peptide-1, is cleared exclusively by glomerular filtration in anaesthetised pigs Diabetologia 49, 706-712 (Pubitemid 43357544)
9. Lee, S., Youn, Y. S., Lee, S. H., Byun, Y., and Lee, K. C. (2006) PEGylated glucagon-like peptide-1 displays preserved effects on insulin release in isolated pancreatic islets and improved biological activity in db/db mice Diabetologia 49, 1608-1611 (Pubitemid 43848097)
10. Tsubery, H., Mironchik, M., Fridkin, M., and Shechter, Y. (2004) Prolonging the action of protein and peptide drugs by a novel approach of reversible polyethylene glycol modification J. Biol. Chem. 279, 38118-38124 (Pubitemid 39295957)
11. Kim, D., MacConell, L., Zhuang, D., Kothare, P. A., Trautmann, M., Fineman, M., and Taylor, K. (2007) Effects of once-weekly dosing of a long-acting release formulation of exenatide on glucose control and body weight in subjects with type 2 diabetes Diabetes Care 30, 1487-1493 (Pubitemid 46871159)
12. Kim, J. G., Baggio, L. L., Bridon, D. P., Castaigne, J. P., Robitaille, M. F., Jetté, L., Benquet, C., and Drucker, D. J. (2003) Development and characterization of a glucagon-like peptide 1-albumin conjugate: the ability to activate the glucagon-like peptide 1 receptor in vivo Diabetes 52, 751-759 (Pubitemid 36323583)
13. Jin, C. H., Chae, S. Y., Son, S., Kim, T. H., Um, K. A., Youn, Y. S., Lee, S., and Lee, K. C. (2009) A new orally available glucagon-like peptide-1 receptor agonist, biotinylated exendin-4, displays improved hypoglycemic effects in db/db mice J. Controlled Release 133, 172-177
14. Chae, S. Y., Jin, C. H., Shin, J. H., Son, S., Kim, T. H., Lee, S., Youn, Y. S., Byun, Y., Lee, M. S, and Lee, K. C. (2010) Biochemical, pharmaceutical and therapeutic properties of long-acting lithocholic acid derivatized exendin-4 analogs J. Controlled Release 142, 206-213
15. Son, S., Chae, S. Y., Kim, C. W., Choi, Y. G., Jung, S. Y., Lee, S., and Lee, K. C. (2009) Preparation and structural, biochemical, and pharmaceutical characterizations of bile acid-modified long-acting exendin-4 derivatives J. Med. Chem. 52, 6889-6896
16. Chae, S. Y., Choi, Y. G., Son, S., Jung, S. Y., Lee, D. S., and Lee, K. C. (2010) The fatty acid conjugated exendin-4 analogs for type 2 antidiabetic therapeutics J. Controlled Release 144, 10-16
17. Johansson, S. M., Arnberg, N., Elofsson, M., Wadell, G., and Kihlberg, J. (2005) Multivalent HSA conjugates of 3-sialyllactose are potent inhibitors of adenoviral cell attachment and infection ChemBioChem 6, 358-364 (Pubitemid 40879749)
18. Mammen, M., Choi, S. K., and Whitesides, G. M. (1998) Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors Angew. Chem. Int. Ed. 37, 2754-2794 (Pubitemid 29008561)
19. Joosten, J. A., Loimaranta, V., Appeldoorn, C. C., Haataja, S., El Maate, F. A., Liskamp, R. M., Finne, J., and Pieters, R. J. (2004) Inhibition of Streptococcus suis adhesion by dendritic galabiose compounds at low nanomolar concentration J. Med. Chem. 47, 6499-6508 (Pubitemid 39657312)
20. Goel, A., Baranowska-Kortylewicz, J., Hinrichs, S. H., Wisecarver, J., Pavlinkova, G., Augustine, S., Colcher, D., Booth, B. J., and Batra, S. K. (2001) 99mTc-labeled divalent and tetravalent CC49 single-chain Fvs: novel imaging agents for rapid in vivo localization of human colon carcinoma J. Nucl. Med. 42, 1519-1527 (Pubitemid 32953132)
21. Chang, C. H., Rossi, E. A., Cardillo, T. M., Nordstrom, D. L., McBride, W. J., and Goldenberg, D. M. (2009) A new method to produce monoPEGylated dimeric cytokines shown with human interferon-alpha2b Bioconjugate Chem. 20, 1899-1907
22. Kubetzko, S., Balic, E., Waibel, R., Zangemeister-Wittke, U., and Plückthun, A. (2006) PEGylation and multimerization of the anti-p185HER-2 single chain Fv fragment 4D5: effects on tumor targeting J. Biol. Chem. 281, 35186-35201 (Pubitemid 46043248)
23. Harris, J. M. and Chess, R. B. (2003) Effect of pegylation on pharmaceuticals Nat. Rev. Drug Discovery 2, 214-221 (Pubitemid 37361666)
24. Veronese, F. M. and Pasut, G. (2005) PEGylation, successful approach to drug delivery Drug Discovery Today 10, 1451-1458 (Pubitemid 41483874)
25. Kang, J. S., Deluca, P. P., and Lee, K. C. (2009) Emerging PEGylated drugs Expert Opin. Emerg. Drugs 14, 363-380
26. Chae, S. Y., Chun, Y. G., Lee, S., Jin, C. H., Lee, E. S., Lee, K. C., and Youn, Y. S. (2009) Pharmacokinetic and pharmacodynamic evaluation of site-specific PEGylated glucagon-like peptide-1 analogs as flexible postprandial-glucose controllers J. Pharm. Sci. 98, 1556-1567
27. Uchio, T., Baudys, M., Liu, F., Song, S. C., and Kim, S. W. (1999) Site-specific insulin conjugates with enhanced stability and extended action profile Adv. Drug Delivery Rev. 35, 289-306 (Pubitemid 29073620)
28. Lee, S. H., Lee, S., Youn, Y. S., Na, D. H., Chae, S. Y., Byun, Y., and Lee, K. C. (2005) Synthesis, characterization, and pharmacokinetic studies of PEGylated glucagon-like peptide-1 Bioconjugate Chem. 16, 377-382 (Pubitemid 40388214)
29. Shin, B. S., Kim, C. H., Lee, M. N., Hur, M. W., Lee, K. C., Youn, Y. S., and Yoo, S. D. (2006) Pharmacokinetics of 125I-GST-TatdMt, a recombinant fusion protein possessing potent anti-obesity activity, after intravenous, nasal, oral, and subcutaneous administration Regul. Pept. 140, 74-80
30. Youn, Y. S., Na, D. H., Yoo, S. D., Song, S. C., and Lee, K. C. (2005) Carbohydrate-specifically polyethylene glycol-modified ricin A-chain with improved therapeutic potential Int. J. Biochem. Cell Biol. 37, 1525-1533
31. Kendall, D. M., Riddle, M. C., Rosenstock, J., Zhuang, D., Kim, D. D., Fineman, M. S., and Baron, A. D. (2005) Effects of exenatide (exendin-4) on glycemic control over 30 weeks in patients with type 2 diabetes treated with metformin and a sulfonylurea Diabetes Care 28, 1083-1091 (Pubitemid 40616617)
32. Drucker, D. J., Buse, J. B., Taylor, K., Kendall, D. M., Trautmann, M., Zhuang, D., and Porter, L for the DURATION-1 Study Group. (2008) Exenatide once weekly versus twice daily for the treatment of type 2 diabetes: a randomised, open-label, non-inferiority study. Lancet 372, 1240 - 1250.
33. Göke, R., Fehmann, H. C., Linn, T., Schmidt, H., Krause, M., Eng, J., and Göke, B. (1993) Exendin-4 is a high potency agonist and truncated exendin-(9-39)-amide an antagonist at the glucagon-like peptide 1-(7-36)-amide receptor of insulin-secreting beta-cells J. Biol. Chem. 268, 19650-19655 (Pubitemid 23270754)
34. Al-Sabah, S. and Donnelly, D. (2003) A model for receptor-peptide binding at the glucagon-like peptide-1 (GLP-1) receptor through the analysis of truncated ligands and receptors Br. J. Pharmacol. 140, 339-346 (Pubitemid 37249194)