Highly selective cyclic peptide ligands for neutravidin and avidin identified by phage display

Chemical Biology and Drug Design

Volumn 68, Issue 1, 2006, Pages 3-10

  Meyer, Scott C ^a   Gaj, Thomas ^a   Ghosh, Indraneel ^a  

^a University of Arizona   (United States)

Author keywords

4 hydroxyazobenzene 2 carboxylic acid; Avidin; In vitro selection; NeutrAvidin; Peptide; Phage display; Streptavidin

Indexed keywords

ASPARTYLARGINYLLEUCYLALANYLSERYLTHREONYLPROLYLTYROSYLTRYPTOPHANAMIDE; AVIDIN; AVIDIN DERIVATIVE; CYCLOPEPTIDE; GLYCINAMIDE; HISTIDYLPROLYLGLYCINAMIDE; LIGAND; NEUTRAVIDIN; STREPTAVIDIN; UNCLASSIFIED DRUG;

ARTICLE; BIOTINYLATION; COMBINATORIAL LIBRARY; CONSENSUS SEQUENCE; DEGLYCOSYLATION; DISSOCIATION CONSTANT; MACROMOLECULE; PEPTIDE ANALYSIS; PHAGE DISPLAY; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN IMMOBILIZATION; PROTEIN MOTIF; PROTEIN PROTEIN INTERACTION; PROTEIN PURIFICATION; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION;

AMINO ACID MOTIFS; AMINO ACID SEQUENCE; AVIDIN; AZO COMPOUNDS; BACTERIOPHAGE M13; BINDING SITES; DRUG DESIGN; LIGANDS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PEPTIDE LIBRARY; PEPTIDES, CYCLIC; PROTEIN CONFORMATION; STREPTAVIDIN;

EID: 33747655831     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2006.00401.x     Document Type: Article

References (49)

1. Gante J. (1994) Peptidomimetics - tailored enzyme inhibitors. Angew Chem Int Ed Engl;33:1699-1720.
2. Giannis A., Kolter T. (1993) Peptidomimetics for receptor ligands - discovery, development, and medical perspectives. Angew Chem Int Ed Engl;32:1244-1267.
3. Hruby V.J., Balse P.M. (2000) Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads. Curr Med Chem;7:945-970.
4. Haskell-Luevano C., Hendrata S., North C., Sawyer T.K., Hadley M.E., Hruby V.J., Dickinson C., Gantz I. (1997) Discovery of prototype peptidomimetic agonists at the human melanocortin receptors MC1R and MC4R. J Med Chem;40:2133-2139.
5. Pavia M., Sawyer T., Moos W. (1993) The generation of molecular diversity. Bioorg Med Chem Lett;3:387-396.
6. Adermann K., John H., Standker L., Forssmann W.G. (2004) Exploiting natural peptide diversity: novel research tools and drug leads. Curr Opin Biotechnol;15:599-606.
7. Lam K.S., Salmon S.E., Hersh E.M., Hruby V.J., Kazmierski W.M., Knapp R.J. (1991) A new type of synthetic peptide library for identifying ligand-binding activity. Nature;354:82-84.
8. Smith G.P. (1985) Filamentous fusion phage: novel expression vectors that display cloned antigens on the virion surface. Science;228:1315-1317.
9. Smith G.P., Petrenko V.A. (1997) Phage display. Chem Rev;97:391-410.
10. Clackson T., Hoogenboom H.R., Griffiths A.D., Winter G. (1991) Making antibody fragments using phage display libraries. Nature;352:624-628.
11. Hanes J., Pluckthun A. (1997) In vitro selection and evolution of functional proteins by using ribosome display. Proc Natl Acad Sci U S A;94:4937-4942.
12. Roberts R.W., Szostak J.W. (1997) RNA-peptide fusions for the in vitro selection of peptides and proteins. Proc Natl Acad Sci U S A;94:12297-12302.
13. Green N.M. (1990) Avidin and streptavidin. Methods Enzymol;184:51-67.
14. Lin H., Cornish V.W. (2002) Screening and selection methods for large-scale analysis of protein function. Angew Chem Int Ed Engl;41:4402-4425.
15. Finn F.M., Hofmann K. (1990) Isolation and characterization of hormone receptors. Methods Enzymol;184:244-274.
16. Barbas C.F., Burton D.R., Scott J.K., Silverman G.J. (2001) Phage Display: A Laboratory Manual. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press.
17. Devlin J.J., Panganiban L.C., Devlin P.E. (1990) Random peptide libraries: a source of specific protein binding molecules. Science;249:404-406.
18. Kay B.K., Adey N.B., He Y.S., Manfredi J.P., Mataragnon A.H., Fowlkes D.M. (1993) An M13 phage library displaying random 38-amino-acid peptides as a source of novel sequences with affinity to selected targets. Gene;128:59-65.
19. McLafferty M.A., Kent R.B., Ladner R.C., Markland W. (1993) M13 bacteriophage displaying disulfide-constrained microproteins. Gene;128:29-36.
20. Petrenko V.A., Smith G.P. (2000) Phages from landscape libraries as substitute antibodies. Protein Eng;13:589-592.
21. Wilson D.S., Keefe A.D., Szostak J.W. (2001) The use of mRNA display to select high-affinity protein-binding peptides. Proc Natl Acad Sci U S A;98:3750-3755.
22. Lamla T., Erdmann V.A. (2003) Searching sequence space for high-affinity binding peptides using ribosome display. J Mol Biol;329:381-388.
23. Adey N.B., Mataragnon A.H., Rider J.E., Carter J.M., Kay B.K. (1995) Characterization of phage that bind plastic from phage-displayed random peptide libraries. Gene;156:27-31.
24. Weber P.C., Pantoliano M.W., Thompson L.D. (1992) Crystal structure and ligand-binding studies of a screened peptide complexed with streptavidin. Biochemistry;31:9350-9354.
25. Green N.M. (1970) Spectrophotometric determination of avidin and biotin. Methods Enzymol;18:418-424.
26. Parang K., Cole P.A. (2002) Designing bisubstrate analog inhibitors for protein kinases. Pharmacol Ther;93:145-157.
27. Melamed M.D., Green N.M. (1963) Avidin. 2. Purification and composition. Biochem J;89:591-599.
28. Duhamel R.C., Whitehead J.S. (1990) Prevention of nonspecific binding of avidin. Methods Enzymol;184:201-207.
29. Alon R., Bayer E.A., Wilchek M. (1990) Streptavidin contains an RYD sequence which mimics the RGD receptor domain of fibronectin. Biochem Biophys Res Commun;170:1236-1241.
30. Hiller Y., Bayer E.A., Wilchek M. (1990) Nonglycosylated avidin. Methods Enzymol;184:68-70.
31. Hiller Y., Gershoni J.M., Bayer E.A., Wilchek M. (1987) Biotin binding to avidin. Oligosaccharide side chain not required for ligand association. Biochem J;248:167-171.
32. Skerra A., Schmidt T.G. (1999) Applications of a peptide ligand for streptavidin: the Strep-tag. Biomol Eng;16:79-86.
33. Schmidt T.G., Koepke J., Frank R., Skerra A. (1996) Molecular interaction between the Strep-tag affinity peptide and its cognate target, streptavidin. J Mol Biol;255:753-766.
34. Meyer S.C., Huerta C., Ghosh I. (2005) Single-site mutations in a hyperthermophilic variant of the B1 domain of protein G result in self-assembled oligomers. Biochemistry;44:2360-2368.
35. Rajagopal S., Meza-Romero R., Ghosh I. (2004) Dual surface selection methodology for the identification of thrombin binding epitopes from hotspot biased phage-display libraries. Bioorg Med Chem Lett;14:1389-1393.
36. Zhou M., Bentley D., Ghosh I. (2004) Helical supramolecules and fibers utilizing leucine zipper-displaying dendrimers. J Am Chem Soc;126:734-735.
37. Zhou M., Ghosh I. (2004) Noncovalent multivalent assembly of jun peptides on a leucine zipper dendrimer displaying fos peptides. Org Lett;6:3561-3564.
38. Hill H. (1910) The possible effects of the aggregation of the molecules of haemoglobin on its dissociation curves. J Physiol;40:4-8.
39. Cheng Y., Prusoff W.H. (1973) Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol;22:3099-3108.
40. Giebel L.B., Cass R.T., Milligan D.L., Young D.C., Arze R., Johnson C.R. (1995) Screening of cyclic peptide phage libraries identifies ligands that bind streptavidin with high affinities. Biochemistry;34:15430-15435.
41. Zang X., Yu Z., Chu Y.H. (1998) Tight-binding streptavidin ligands from a cyclic peptide library. Bioorg Med Chem Lett;8:2327-2332.
42. Schmidt T.G., Skerra A. (1993) The random peptide library-assisted engineering of a C-terminal affinity peptide, useful for the detection and purification of a functional Ig Fv fragment. Protein Eng;6:109-122.
43. Menendez A., Scott J.K. (2005) The nature of target-unrelated peptides recovered in the screening of phage-displayed random peptide libraries with antibodies. Anal Biochem;336:145-157.
44. Lam K.S., Lebl M. (1992) Streptavidin and avidin recognize peptide ligands with different motifs. Immunomethods;1:11-15.
45. Green N.M. (1965) A spectrophotometric assay for avidin and biotin based on binding of dyes by avidin. Biochem J;94:23C-24C.
46. Katz B.A., Cass R.T. (1997) In crystals of complexes of streptavidin with peptide ligands containing the HPQ sequence the pKa of the peptide histidine is less than 3.0. J Biol Chem;272:13220-13228.
47. Weber P.C., Wendoloski J.J., Pantoliano M.W., Salemme F.R. (1992) Crystallographic and thermodynamic comparison of natural and synthetic ligands bound to streptavidin. J Am Chem Soc;114:3197-3200.
48. Pugliese L., Coda A., Malcovati M., Bolognesi M. (1993) Three-dimensional structure of the tetragonal crystal form of eggwhite avidin in its functional complex with biotin at 2.7 A resolution. J Mol Biol;231:698-710.
49. Weber P.C., Ohlendorf D.H., Wendoloski J.J., Salemme F.R. (1989) Structural origins of high-affinity biotin binding to streptavidin. Science;243:85-88.