Characterization of peptide-amphiphiles possessing cellular activation sequences

Biomacromolecules

Volumn 4, Issue 3, 2003, Pages 518-528

  Malkar, Navdeep B ^a,b   Lauer Fields, Janelle L ^a   Juska, Darius ^a   Fields, Gregg B ^a  

^a FLORIDA ATLANTIC UNIVERSITY   (United States)

^b Nobex Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; CELLS; HYDROCARBONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMODYNAMIC STABILITY;

PEPTIDES;

PROTEINS;

AMPHOPHILE; BETA1 INTEGRIN; BIOMATERIAL; COLLAGEN TYPE 1; HYDROCARBON; INTEGRIN; LIPID; OSTEONECTIN; PEPTIDE DERIVATIVE;

ACYLATION; ALPHA HELIX; AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ANGIOGENESIS; ANIMAL CELL; ARTICLE; BINDING SITE; CELL ACTIVATION; CELL ADHESION; CELL INTERACTION; CELL KINETICS; CELL SPREADING; CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONTROLLED STUDY; COVALENT BOND; ENDOTHELIUM CELL; EXTRACELLULAR MATRIX; MOLECULAR STABILITY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN STRUCTURE; SIGNAL TRANSDUCTION; THERMOSTABILITY;

AMINO ACID SEQUENCE; ANIMALS; CATTLE; CELL ADHESION; CELL MOVEMENT; CELL SIZE; ENDOTHELIAL CELLS; HUMANS; MOLECULAR SEQUENCE DATA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES; SOLUTIONS; SURFACE-ACTIVE AGENTS;

ANIMALIA;

EID: 0037841389     PISSN: 15257797     EISSN: None     Source Type: Journal    
DOI: 10.1021/bm0256597     Document Type: Article

References (71)

1. Welsh, E. R.; Tirrell, D. A. Engineering the extracellular matrix: A novel approach to polymeric materials I: Control of the physical properties of artificial protein matrixes designed to support adhesion of vascular endothelial cells. Biomacromolecules 2000, 1, 23-30.
2. Pierschbacher, M. D.; Ruoslahti, E. Cell attachment activity of fibronectin can be duplicated by small synthetic fragments of the molecule. Nature 1984, 309, 30-33.
3. Hubbell, J. L. Bioactive biomaterials. Curr. Opin. Biotech. 1999, 10, 123-129.
4. Shakesheff, K. M.; Cannizzaro, S. M.; Langer, R. Creating biomimetic micro-environments with synthetic polymer-peptide hybrid molecules. J. Biomater. Sci. Polym. Ed. 1998, 9, 507-518.
5. Dillow, A. K.; Tirrell, M. Targeted cellular adhesion at biomaterial interfaces. Curr. Opin. Solid State Mater. Sci. 1998, 3, 252-259.
6. Ruoslahti, E. Integrins as receptors for extracellular matrix. Cell Biology of the Extracellular Matrix; Plenum Press: New York, 1991; pp 343-363.
7. Chelberg, M. K.; McCarthy, J. B.; Skubitz, A. P. N.; Furcht, L. T.; Tsilibary, E. C. Characterization of a synthetic peptide from type IV collagen that promotes melanoma cell adhesion, spreading, and motility. J. Cell Biol. 1990, 111, 261-270.
8. Mayo, K. H.; Parra-Diaz, D.; McCarthy, J. B.; Chelberg, M. Cell adhesion promoting peptide GVKGDKGNPGWPGAP from the collagen type IV triple helix. Biochemistry 1991, 30, 8251-8267.
9. Fields, C. G.; Mickelson, D. J.; Drake, S. L.; McCarthy, J. B.; Fields, G. B. Melanoma cell adhesion and spreading activities of a synthetic 124-residue triple-helical "mini-collagen". J. Biol. Chem. 1993, 268, 14153-14160.
10. Miles, A. J.; Skubitz, A. P. N.; Furcht, L. T.; Fields, G. B. Promotion of cell adhesion by single-stranded and triple-helical peptide models of basement membrane collagen α1(IV)531-543: Evidence for conformationally dependent and corformationally independent type IV collagen cell adhesion sites. J. Biol. Chem. 1994, 269, 30939-30945.
11. Miles, A. J.; Knutson, J. R.; Skubitz, A. P. N.; Furcht, L. T.; McCarthy, J. B.; Fields, G. B. A peptide model of basement membrane collagen (IV)531-543 binds the α3β1 integrin. J. Biol. Chem. 1995, 270, 29047-29050.
12. Maldonado, B. A.; Furcht, L. T. Involvement of integrins with adhesion promoting, heparin-binding peptides of type IV collagen in cultured human corneal epithelial cells. Invest. Ophthalmol. Vision Sci. 1995, 36, 364-372.
13. Morton, L. F.; Peachey, A. R.; Knight, C. G.; Farndale, R. W.; Barnes, M. J. The platelet reactivity of synthetic peptides based on the collagen III fragment α1(III)CB4. J. Biol. Chem. 1997, 272, 11044-11048.
14. Li, C.; McCarthy, J. B.; Furcht, L. T.; Fields, G. B. An all-D amino acid peptide model of α1(IV)531-543 from type IV collagen binds the α3β1 integrin and mediates tumor cell adhesion, spreading, and motility. Biochemistry 1997, 36, 15404-15410.
15. Yu, Y.-C.; Pakalns, T.; Dori, Y.; McCarthy, J. B.; Tiffell, M.; Fields, G. B. Construction of biologically active protein molecular architecture using self-assembling peptide-amphiphiles. Methods Enzymol. 1997, 289, 571-587.
16. Lauer, J. L.; Gendron, C. M.; Fields, G. B. Effect of ligand conformation on melanoma cell α3β1 integrin-mediated signal transduction events: Implications for a collagen structural modulation mechanism of tumor cell invasion. Biochemistry 1998, 37, 5279-5287.
17. Knight, C. G.; Morton, L. F.; Onley, D. J.; Peachey, A. R.; Messent, A. J.; Smethurst, P. A.; Tuckwell, D. S.; Farndale, R. W.; Barnes, M. J. Identification in collagen type I of an integrin α2β1-binding site containing an essential GER sequence. J. Biol. Chem. 1998, 273, 33287-33294.
18. Fields, G. B.; Lauer, J. L.; Dori, Y.; Forns, P.: Yu, Y.-C.; Tirrell, M. Proteinlike molecular architecture: Biomaterial applications for inducing cellular receptor binding and signal transduction. Biopolymers 1998, 47, 143-151.
19. Setty, S.; Kim, Y.; Fields, G. B.; Clegg, D. O.; Wayner, E. A.; Tsilibary, E. C. Interactions of Type IV Collagen and Its Domains With Human Mesangial Cells. J. Biol. Chem. 1998, 273, 12244-12249.
20. Knight, C. G.; Morton, L. F.; Peachey, A. R.; Tuckwell, D. S.; Farndale, R. W.; Barnes, M. J. The collagen-binding A-domains of integrin α1β1 and α2β1 recognize the same specific amino acid sequence, GFOGER, in native (triple-helical) collagens. J. Biol. Chem. 2000, 275, 35-40.
21. Xu, Y.; Gurusiddappa, S.; Rich, R. L.; Owens, R. T.; Keene, D. R.; Mayne, R.; Höök, A.; Höök, M. Multiple binding sites in collagen type I for the integrins α1β1 and α2β1. J. Biol. Chem. 2000, 275, 38981-38989.
22. Dori, Y.; Bianco-Peled, H.; Satija, S. K.; Fields, G. B.; McCarthy, J. B.; Tirrell, M. Ligand accessibility as a means to control cell response to bioactive bilayer membranes. J. Biomed. Mater. Res. 2000, 50, 75-81.
23. Malkar, N. B.; Lauer-Fields, J. L.; Borgia, J. A.; Fields, G. B. Modulation of triple-helical stability and subsequent melanoma cellular responses by single-site substitution of fluoroproline derivatives. Biochemistry 2002, 41, 6054-6064.
24. Qian, J. J.; Bhatnagar, R. S. Enhanced cell attachment to anorganic bone mineral in the presence of a synthetic peptide related to collagen. J. Biomed. Mater. Res. 1996, 31, 545-554.
25. Yan, Q.; Sage, E. H. SPARC, a matricellular glycoprotein with important biological functions. J. Histochem. Cytochem. 1999, 47, 1495-1505.
26. Brekken, R. A.; Sage, E. H. SPARC, a matricellular protein: At the crossroads of cell-matrix. Matrix Biol. 2000, 19, 569-580.
27. Funk, S. E.; Sage, E. H. Differential effects of SPARC and cationic SPARC peptides on DNA synthesis by endothelial cells and fibroblasts. J. Cell Physiol. 1993, 154, 53-63.
28. Lane, T. F.; Iruela-Arispe, M. L.; Johnson, R. S.; Sage, E. H. SPARC is a source of copper-binding peptides that stimulate angiogenesis. J. Cell Biol. 1994, 125, 929-943.
29. Sanders, J. E.; Baker, A. B.; Golledge, S. L. Control of in vivo microvessel ingrowth by modulation of biomaterial local architecture and chemistry. J. Biomed. Mater. Res. 2002, 60, 36-43.
30. Pierschbacher, M. D.; Ruoslahti, E. Influence of stereochemistry of the sequence Arg-Gly-Asp-Xaa on binding specificity in cell adhesion. J. Biol. Chem. 1987, 262, 17297-17298.
31. 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.
32. Yu, Y.-C.; Tirrell, M.; Fields, G. B. Minimal lipidation stabilizes protein-like molecular architecture. J. Am. Chem. Soc. 1998, 120, 9979-9987.
33. Pakalns, T.; Haverstick, K. L.; Fields, G. B.; McCarthy, J. B.; Mooradian, D. L.; Tirrell, M. Cellular recognition of synthetic peptide amphiphiles in self-assembled monolayer films. Biomaterials 1999, 20, 2265-2279.
34. Forns, P.; Lauer-Fields, J. L.; Gao, S.; Fields, G. B. Induction of Protein-Like Molecular Architecture by Monoalkyl Hydrocarbon Chains. Biopolymers 2000, 54, 531-546.
35. Mammen, M.; Choi, S.-K.; Whitesides, G. M. Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors. Angew. Chem., Int. Ed. 1998, 37, 2754-2794.
36. Dillow, A. K.; Ochsenhirt, S. E.; McCarthy, J. B.; Fields, G. B.; Tirrell, M. Adhesion of α5β1 receptors to biomimetic substrates constructed from peptide amphiphiles. Biomaterials 2001, 22, 1493-1505.
37. Huo, Q.; Sui, G.; Kele, P.; Leblanc, R. M. Combinatorial surface chemistry - is it possible? Angew. Chem., Int. Ed. 2000, 39, 1854-1857.
38. Hartgerink, J. D.; Beniash, E.; Stupp, S. I. Peptide-amphiphile nanofibers: A versatile scaffold for the preparation of self-assembling materials. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5133-5138.
39. Fields, C. G.; VanDrisse, V. L.; Fields, G. B. Edman degradation sequence analysis of resin-bound peptides synthesized by 9-fluorenyl-methoxycarbonyl chemistry. Pept. Res. 1993, 6, 39-47.
40. Jorgensen, W. L.; Chandrasekhas, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. Comparison of simple potential functions for simulation of liquid water. J. Chem. Phys. 1983, 79, 926-935.
41. Su, J. Y.; Hodges, R. S.; Hay, C. M. Effect of chain length on the formation of stability of synthetic α-helical coiled coils. Biochemistry 1994, 33, 15501-15510.
42. Woody, R. W. Circular dichroism of peptides. The Peptides; Academic Press: New York, 1985; Vol. 7, pp 15-114.
43. Forns, P.; Fields, G. B. Peptide-amphiphile induction of α-helical structures. Polym. Prepr. 2000, 41, 1152-1153.
44. Houston, M. E., Jr.; Campbell, A. P.; Lix, B.; Kay, C. M.; Sykes, B. D.; Hodges, R. S. Lactam bridge stabilization of α-helices: The role of hydrophobicity in controlling dimeric versus monomeric α-helices. Biochemistry 1996, 35, 10041-10050.
45. Wishart, D. S.; Sykes, B. D.; Richards, F. M. Relationship between nuclear magnetic resonance chemical shift and protein secondary structure. J. Mol. Biol. 1991, 222, 311-333.
46. Zhou, N. E.; Zhu, B.-Y.; Sykes, B. D.; Hodges, R. S. Relationship between amide proton chemical shifts and hydrogen bonding in amphipathic α-helical peptides. J. Am. Chem. Soc. 1992, 114, 4320-4326.
47. Wüthrich, K.; Billeter, M.; Braun, W. Polypeptide secondary structure determination by nuclear magnetic resonance observation of short proton-proton distances. J. Mol. Biol. 1984, 180, 715-740.
48. 10-helix secondary structure in rabbit liver metallothionein-2. J. Mol. Biol. 1986, 187, 131-135.
49. Dyson, H. J.; Wright, P. E. Defining solution conformations of small linear peptides. Annu. Rev. Biophys. Chem. 1991, 20, 519-538.
50. Nelson, D. L.; Cox, M. M. Lehninger Principles of Biochemistry, 3rd ed.; Worth: New York, 2000.
51. Klevens, H. B. Structure and aggregation in dilute solutions of surface active agents. J. Am. Oil Chem. Soc. 1953, 30, 74-80.
52. Shinoda, K.; Nakagawa, T.; Tamamushi, B.-I.; Isemura, T. Colloidal Surfactants: Some Physicochemical Properties; Academic Press: New York, 1963.
53. Myers, D. Surfactants in solution: Micellization and related association phenomena. Surfactant Science and Technology; VCH Publishers: 1988; pp 81-121.
54. Israelachvili, J. N. Intermolecular and Surface Forces, 2nd ed.; Academic Press Limited: London, 1992; pp 366-394.
55. Mutter, M. Nature's rules and chemist's tools: A way for creating novel proteins. Trends Biochem. Sci. 1988, 13, 260-265.
56. Wattenbarger, M. R.; Chan, H. S.; Evans, D. F.; Bloomfield, V. A.; Dill, K. A. Surface-induced enhancement of internal structure in polymers and proteins. J. Chem. Phys. 1990, 93, 8343-8351.
57. Chan, H. S.; Wattenbarger, M. R.; Evans, D. J.; Bloomfield, V. A.; Dill, K. A. Enhanced structure in polymers at interfaces. J. Chem. Phys. 1991, 94, 8542-8556.
58. DeGrado, W. F.; Lear, J. D. Induction of peptide conformation at apolar/water interfaces: A study with model peptides of defined hydrophobic periodicity. J. Am. Chem. Soc. 1985, 107, 7684-7689.
59. Ösapay, G.; Taylor, J. W. Multicyclic polypeptide model compounds 1: Synthesis of a tricyclic amphiphilic α-helical peptide using an oxime resin, segment-condensation approach. J. Am. Chem. Soc. 1990, 112, 6046-6051.
60. Ösapay, G.; Taylor, J. W. Multicyclic polypeptide model compounds 2: Synthesis and conformational properties of a highly α-helical uncosapeptide constrained by three side-chain to side-chain lactam bridges. J. Am. Chem. Soc. 1992, 114, 6966-6973.
61. Mutter, M.; Tuchscherer, G. G.; Miller, C.; Altmann, K. H.; Carey, R. I.; Wyss, D. F.; Labhardt, A. M.; Rivier, J. E. Template-assembled synthetic proteins with four-helix-bundle topology. J. Am. Chem. Soc. 1992, 114, 1463-1470.
62. Dawson, P. E.; Kent, S. B. H. Convenient total synthesis of a 4-helix TASP molecule by chemoselective ligation. J. Am. Chem. Soc. 1993, 115, 7263-7266.
63. Vuilleumer, S.; Mutter, M. Synthetic peptide and template-assembled synthetic protein models of the hen egg white lysozyme 87-97 helix. Biopolymers 1993, 33, 389-400.
64. Berndt, P.; Fields, G. B.; Tirrell, M. Synthetic lipidation of peptides and amino acids: Monolayer structure and properties, J. Am. Chem. Soc. 1995, 117, 9515-9522.
65. Bianco-Peled, H.; Dori, Y.; Schneider, J.; Sung, L.-P.; Satija, S.; Tirrell, M. Structural study of langmuir monolayers containing lipidated poly(ethylene glycol) and peptides. Langmuir 2001, 17, 6931-6937.
66. Emsley, J.; Knight, C. G.; Farndale, R. W.; Barnes, M. J.; Liddington, R. C. Structural basis of collagen recognition by integrin α2β1. Cell 2000, 101, 47-56.
67. Grab, B.; Miles, A. J.; Furcht, L. T.; Fields, G. B. Promotion of fibroblast adhesion by triple-helical peptide models of type I collagen-derived sequences. J. Biol. Chem. 1996, 271, 12234-12240.
68. Creighton, T. E. Proteins: Structures and Molecular Properties, 2nd ed.; W. H. Freeman and Company: New York, 1993.
69. Motamed, K.; Funk, S. E.; Koyama, H.; Ross, R.; Raines, E. W.; Sage, E. H. Inhibition of PDGF-stimulated and matrix-mediated proliferation of human vascular smooth muscle cells by SPARC is independent of changes in cell shape or cyclin-dependent kinase inhibitors. J. Cell. Biochem. 2002, 84, 759-771.
70. Mrksich, M.; Chen, C. S.; Xia, Y.; Dike, L. E.; Ingber, D. E.; Whitesides, G. M. Controlling cell attachment on contoured surfaces with self-assembled monolayers of alkanethiolates on gold. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10775-10778.
71. Winger, T. M.; Ludovice, P. J.; Chaikof, E. L. Lipopeptide conjugates: Biomolecular building blocks for receptor activating membrane-mimetic structures. Biomaterials 1996, 17, 437-440.