Tailored Presentation of Carbohydrates on a Coiled Coil-Based Scaffold for Asialoglycoprotein Receptor Targeting

ACS Chemical Biology

Volumn 10, Issue 9, 2015, Pages 2065-2072

  Zacco, Elsa ^a   Hütter, Julia ^a,b,c   Heier, Jason L ^a   Mortier, Jérémie ^a   Seeberger, Peter H ^a,b   Lepenies, Bernd ^a,b,d   Koksch, Beate ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b MAX PLANCK INSTITUTE OF COLLOIDS AND INTERFACES   (Germany)

^c TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^d UNIVERSITY OF VETERINARY MEDICINE HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ASIALOGLYCOPROTEIN RECEPTOR; CARBOHYDRATE; CYTOCHALASIN D; GALACTOSE; GLYCOPEPTIDE; PEPTIDE; LIGAND; PEPTIDE LIBRARY; PROTEIN BINDING;

AMINO ACID SEQUENCE; ARTICLE; BINDING SITE; CONTROLLED STUDY; ENDOCYTOSIS; FLOW CYTOMETRY; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; LIVER CELL; PEPTIDE LIBRARY; PRIORITY JOURNAL; CHEMISTRY; CYTOLOGY; HEPG2 CELL LINE; METABOLISM; MOLECULAR GENETICS; PROTEIN SECONDARY STRUCTURE;

AMINO ACID SEQUENCE; ASIALOGLYCOPROTEIN RECEPTOR; BINDING SITES; GALACTOSE; GLYCOPEPTIDES; HEP G2 CELLS; HEPATOCYTES; HUMANS; LIGANDS; MOLECULAR SEQUENCE DATA; PEPTIDE LIBRARY; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY;

EID: 84942016738     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/acschembio.5b00435     Document Type: Article

References (31)

1. Pagel, K. and Koksch, B. (2008) Following Polypeptide Folding and Assembly with Conformational Switches Curr. Opin. Chem. Biol. 12, 730-739
2. Cerpa, R., Cohen, F. E., and Kuntz, I. D. (1996) Conformational Switching in Designed Peptides: The Helix/Sheet Transition Fold. Des. 1, 91-101
3. Falenski, J. A., Gerling, U. I. M., and Koksch, B. (2010) Multiple Glycosylation of de Novo Designed α-Helical Coiled Coil Peptides Bioorg. Med. Chem. 18, 3703-3706
4. Deshmukh, R. and Purohit, H. J. (2012) Peptide Scaffolds: Flexible Molecular Structures with Diverse Therapeutic Potentials Int. J. Pept. Res. Ther. 18, 125-143
5. Unverzagt, C., Kelm, S., and Paulson, J. C. (1994) Chemical and Enzymatic Synthesis of Multivalent Sialoglycopeptides Carbohydr. Res. 251, 285-301
6. Liu, S. and Kiick, K. L. (2008) Architecture Effects on the Binding of Cholera Toxin by Helical Glycopolypeptides Macromolecules 41, 764-772
7. Chan, L. Y., Gunasekera, S., Henriques, S. T., Worth, N. F., Le, S. J., Clark, R. J., Campbell, J. H., Craik, D. J., and Daly, N. L. (2011) Engineering Pro-Angiogenic Peptides Using Stable, Disulfide-Rich Cyclic Scaffolds Blood 118, 6709-6717
8. Kroll, C., Mansi, R., Braun, F., Dobitz, S., Maecke, H. R., and Wennemers, H. (2013) Hybrid Bombesin Analogues: Combining an Agonist and an Antagonist in Defined Distances for Optimized Tumor Targeting J. Am. Chem. Soc. 135, 16793-16796
9. Mason, J. M. and Arndt, K. M. (2004) Coiled Coil Domains: Stability, Specificity, and Biological Implications ChemBioChem 5, 170-176
10. Hakoshima, T. (2005) Leucine Zippers in eLS, Wiley, Chichester.
11. Apgar, J. R., Gutwin, K. N., and Keating, A. E. (2008) Predicting Helix Orientation for Coiled-Coil Dimers Proteins 72, 1048-1065
12. Falenski, J. A., Broncel, M., Wagner, S. C., Hackenberger, C., and Koksch, B. (2010) How Post-Translational Modifications Influence Amyloid Formation: A Systematic Study of Phopshorylation and Glycosylation in Model Peptides Chem.-Eur. J. 16, 7881-7888
13. Wagner, S. C., Roskamp, M., Pallerla, M., Araghi, R. R., Schlecht, S., and Koksch, B. (2010) Nanoparticle-Induced Pepide Folding and Aggregation Small 6, 1321-1328
14. Broncel, M., Wagner, S. C., Hackenberger, C., and Koksch, B. (2010) Towards Understanding Secondary Structure Transitions: Phosphorylation and Metal Coordination in Model Peptides Org. Biomol. Chem. 8, 2575-2579
15. Zacco, E., Anish, C., Martin, C. E., v. Berlepsch, H., Brandenburg, E., Seeberger, P. H., and Koksch, B. (2015) A Self-Assembling Peptide Scaffold for the Multivalent Presentation of Antigens Biomacromolecules 10.1021/acs.biomac.5b00572
16. Johnson, A. A. D., Lewis, J., Walter, P., Roberts, K., Raff, M., Hopkin, K., Bray, D., and Alberts, B. (2013) Essential Cell Biology: Protein Structure and Function, Chapter 4, Garland Science, New York, NY.
17. Stockert, R. J. (1995) The Asialoglycoprotein Receptor: Relationships between Structure, Function, and Expression Physiol. Rev. 75, 591-609
18. Park, J. H., Cho, E. W., Shin, S. Y., Lee, Y. J., and Kim, K. L. (1998) Detection of the Asialoglycoprotein Receptor on Cell Lines of Extrahepatic Origin Biochem. Biophys. Res. Commun. 244, 304-311
19. Lepenies, B., Leec, J., and Sonkaria, S. (2013) Targeting C-Type Lectin Receptors with Multivalent Carbohydrate Ligands Adv. Drug Delivery Rev. 65, 1271-1281
20. Ashwell, G. and Morell, A. G. (1974) The role of Carbohydrate in the Hepatic Recognition and Transport of Circulating Glycoprotein Adv. Enzymol. Relat. Areas Mol. Biol. 41, 99-128
21. Kolatkar, A. R., Leung, A. K., Isecke, R., Brossmer, R., Drickamer, K., and Weis, W. I. (1998) Mechanism of N-Acetylgalactosamine Binding to a C-Type Animal Lectin Carbohydrate-Recognition Domain J. Biol. Chem. 273, 19502-19508
22. Rifai, A., Fadden, K., Morrison, S. L., and Chintalacharuvu, K. R. (2000) Asialoglycoprotein Receptor Deficiency in Mice Lacking the Major Receptor Subunit: Its Obligate Requirement for the Stable Expression of Oligomeric Receptor J. Exp. Med. 191, 1171-1181
23. Rotundo, R. F., Rebres, R. A., McKeown-Longo, P. J., Blumenstock, F. A., and Saba, T. M. (1998) Circulating Cellular Fibronectin May Be a Natural Ligand for the Hepatic Asialoglycoprotein Receptor: Possible Pathway for Fibronectin Deposition and Turnover in the Rat Liver Hepatology 28, 475-485
24. Treichel, U., Meyer zum Büschenfelde, K. H., Stockert, R. J., Poralla, T., and Gerken, G. J. (1994) The Asialoglycoprotein Receptor Mediates Hepatic Binding and Uptake of Natural Hepatitis B Virus Particles Derived from Viraemic Carriers Gen. Virol. 75, 3021-3029
25. Halberg, D. F., Wager, R. E., Farrell, D. C., Hildreth, J., Quesenberry, M. S., Loeb, J. A., Holland, E. C., and Drickamer, K. (1987) Major and Minor Forms of the Rat Liver Asialoglycoprotein Receptor are Independent Galactose-Binding Proteins. Primary Structure and Glycosylation Heterogeneity of Minor Receptor Forms J. Biol. Chem. 262, 9828-9838
26. Meier, M., Bider, M. D., Malashkevich, V. N., Spiess, M., and Burkhard, P. (2000) Crystal Structure of the Carbohydrate Recognition Domain of the H1 Subunit of the Asialoglycoprotein Receptor J. Mol. Biol. 300, 857-865
27. Lee, Y. C., Lee, R. T., Ernst, B., Hart, G. W., and Sinaý, P. (2000) Interactions of Oligosaccharides and Glycopeptides with Hepatic Carbohydrate Receptors, in Carbohydrates in Chemistry and Biology, pp 549-561, Wiley-VCH Verlag GmbH, Weinheim.
28. Khorev, O., Stokmaier, D., Schwardt, O., Cutting, B., and Ernst, B. (2008) Trivalent, Gal/GalNAc-Containing Ligands Designed for the Asialoglycoprotein Receptor Bioorg. Med. Chem. 16, 5216-5231
29. Kelly, S. M., Jess, T. J., and Price, N. C. (2005) How To Study Proteins by Circular Dichroism Biochim. Biophys. Acta 1751, 119-139
30. Fujimoto, L. M., Roth, R., Heuser, J. E., and Schmid, S. L. (2000) Actin Assembly Plays a Variable, but not Obligatory Role in Receptor-Mediated Endocytosis in Mammalian Cells Traffic 1, 161-171
31. Li, D. and Elbert, D. L. (2002) The Kinetics of the Removal of the N-Methyltrityl (Mtt) Group during the Synthesis of Branched Peptides J. Pept. Res. 60, 300-303