Transformation of oligomers of lipidated peptide induced by change in pH

Molecular Pharmaceutics

Volumn 12, Issue 2, 2015, Pages 411-419

  Wang, Ying ^a   Lomakin, Aleksey ^a   Kanai, Sonoko ^c   Alex, Rainer ^c   Benedek, George B ^a,b  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b Massachusetts Institute of Technology   (United States)

^c F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

incretin; light scattering; micelle; oligomerization; peptide amphiphile; self assembly

Indexed keywords

LIRAGLUTIDE; MONOMER; OLIGOMER; PEPTIDE; GLUCAGON LIKE PEPTIDE 1; INCRETIN; POLYMER;

ARTICLE; CIRCULAR DICHROISM; DESORPTION; HYDRODYNAMICS; KINETICS; LIGHT SCATTERING; OLIGOMERIZATION; PH; PRIORITY JOURNAL; PROTEIN SECONDARY STRUCTURE; AGONISTS; CHEMISTRY;

GLUCAGON-LIKE PEPTIDE 1; HYDROGEN-ION CONCENTRATION; INCRETINS; KINETICS; LIRAGLUTIDE; PEPTIDES; POLYMERS;

EID: 84922189568     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500519s     Document Type: Article

References (29)

1. Craik, D. J.; Fairlie, D. P.; Liras, S.; Price, D. The future of peptide-based drugs Chem. Biol. Drug Des. 2013, 81, 136-147
2. Kaspar, A. A.; Reichert, J. M. Future directions for peptide therapeutics development Drug Discovery Today 2013, 18, 807-817
3. Crunkhorn, S. Anticancer drugs: Stapled peptide reactivates p53 Nat. Rev. Drug Discovery 2013, 12, 741
4. Meier, J. J. GLP-1 receptor agonists for individualized treatment of type 2 diabetes mellitus Nat. Rev. Endocrinol. 2012, 8, 728-742
5. Drucker, D. J.; Nauck, M. A. The incretin system: glucagon-like peptide-1 receptor agonists and dipeptidyl peptidase-4 inhibitors in type 2 diabetes Lancet 2006, 368, 1696-1705
6. Holst, J. J. The physiology of glucagon-like peptide 1 Physiol. Rev. 2007, 87, 1409-1439
7. Willard, F. S.; Sloop, K. W. Physiology and emerging biochemistry of the glucagon-like peptide-1 receptor Exp. Diabetes Res. 2012, 2012, 470851
8. Knudsen, L. B.; Nielsen, P. F.; Huusfeldt, P. O.; Johansen, N. L.; Madsen, K.; Pedersen, F. Z.; Thogersen, H.; Wilken, M.; Agerso, H. Potent derivatives of glucagon-like peptide-1 with pharmacokinetic properties suitable for once daily administration J. Med. Chem. 2000, 43, 1664-1669
9. Clodfelter, D.; Pekar, A.; Rebhun, D.; Destrampe, K.; Havel, H.; Myers, S.; Brader, M. Effects of non-covalent self-association on the subcutaneous absorption of a therapeutic peptide Pharm. Res. 1998, 15, 254-262
10. Zhang, L.; Bulaj, G. Converting peptides into drug leads by lipidation Curr. Med. Chem. 2012, 19, 1602-1618
11. Havelund, S.; Plum, A.; Ribel, U.; Jonassen, I.; Vølund, A.; Markussen, J.; Kurtzhals, P. The mechanism of protraction of insulin detemir, a long-acting, acylated analog of human insulin Pharm. Res. 2004, 21, 1498-1504
12. Li, Y.; Shao, M.; Zheng, X.; Kong, W.; Zhang, J.; Gong, M. Self-assembling peptides improve the stability of glucagon-like peptide-1 by forming a stable and sustained complex Mol. Pharmaceutics 2013, 10, 3356-3365
13. Khan, S.; Sur, S.; Newcomb, C. J.; Appelt, E. A.; Stupp, S. I. Self-assembling glucagon-like peptide 1-mimetic peptide amphiphiles for enhanced activity and proliferation of insulin-secreting cells Acta Biomater. 2012, 8, 1685-1692
14. Ward, B. P.; Ottaway, N. L.; Perez-Tilve, D.; Ma, D.; Gelfanov, V. M.; Tschop, M. H.; Dimarchi, R. D. Peptide lipidation stabilizes structure to enhance biological function Mol. metab. 2013, 2, 468-479
15. Trent, A.; Marullo, R.; Lin, B.; Black, M.; Tirrell, M. Structural properties of soluble peptide amphiphile micelles Soft Matter 2011, 7, 9572-9582
16. Missirlis, D.; Krogstad, D. V.; Tirrell, M. Internalization of p53(14-29) peptide amphiphiles and subsequent endosomal disruption results in SJSA-1 cell death Mol. Pharmaceutics 2010, 7, 2173-2184
17. Kastantin, M.; Missirlis, D.; Black, M.; Ananthanarayanan, B.; Peters, D.; Tirrell, M. Thermodynamic and kinetic stability of DSPE-PEG(2000) micelles in the presence of bovine serum albumin J. Phys. Chem. B 2010, 114, 12632-12640
18. Dong, H.; Dube, N.; Shu, J. Y.; Seo, J. W.; Mahakian, L. M.; Ferrara, K. W.; Xu, T. Long-circulating 15 nm micelles based on amphiphilic 3-helix peptide-PEG conjugates ACS Nano 2012, 6, 5320-5329
19. Yu, Y. C.; Pakalns, T.; Dori, Y.; McCarthy, J. B.; Tirrell, M.; Fields, G. B. Construction of biologically active protein molecular architecture using self-assembling peptide-amphiphiles Methods Enzymol. 1997, 289, 571-587
20. Yu, Y.-C.; Berndt, P.; Tirrell, M.; Fields, G. B. Self-assembling amphiphiles for construction of protein molecular architecture J. Am. Chem. Soc. 1996, 118, 12515-12520
21. Steensgaard, D. B.; Thomsen, J. K.; Olsen, H. B.; Knudsen, L. B. The molecular basis for the delayed absorption of the once-daily human GLP-1 analogue, liraglutide. (Abstract 552-P) Diabetes 2008, 57, A164
22. Nauck, M. A. Liraglutide, a once-daily human GLP-1 analogue Br. J. Diabetes Vasc. Dis. 2008, 8, S26-S33
23. Pike, E. R.; Pomeroy, W. R. M.; Vaughan, J. M. Measurement of Rayleigh ratio for several pure liquids using a laser and monitored photon counting J. Chem. Phys. 1975, 62, 3188-3192
24. Wang, Y.; Lomakin, A.; McManus, J. J.; Ogun, O.; Benedek, G. B. Phase behavior of mixtures of human lens proteins Gamma D and Beta B1 Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 13282-13287
25. Slifkin, M. A.; Ali, S. M. Measurements of protonation reaction kinetics of histidine using a chemical relaxation technique J. Mol. Liq. 1984, 28, 165-174
26. Armstrong, K. M.; Baldwin, R. L. Charged histidine affects alpha-helix stability at all positions in the helix by interacting with the backbone charges Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11337-11340
27. Callahan, D. J.; Liu, W.; Li, X.; Dreher, M. R.; Hassouneh, W.; Kim, M.; Marszalek, P.; Chilkoti, A. Triple stimulus-responsive polypeptide nanoparticles that enhance intratumoral spatial distribution Nano Lett. 2012, 12, 2165-2170
28. Tu, Z.; Volk, M.; Shah, K.; Clerkin, K.; Liang, J. F. Constructing bioactive peptides with pH-dependent activities Peptides 2009, 30, 1523-1528
29. Greenfield, N. J. Using circular dichroism spectra to estimate protein secondary structure Nat. Protoc. 2006, 1, 2876-2890