Decoration of silk fibroin by click chemistry for biomedical application

Journal of Structural Biology

Volumn 186, Issue 3, 2014, Pages 420-430

  Zhao, Hongshi ^a   Heusler, Eva ^a   Jones, Gabriel ^a   Li, Linhao ^a,b   Werner, Vera ^a   Germershaus, Oliver ^a   Ritzer, Jennifer ^a   Luehmann, Tessa ^a   Meinel, Lorenz ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b CHONGQING UNIVERSITY   (China)

Author keywords

Click chemistry; Decoration; Fibroblast growth factor 2; Silk fibroin

Indexed keywords

CARBOXYL GROUP; DIAZONIUM COMPOUND; FIBROBLAST GROWTH FACTOR 2; SILK FIBROIN; AZIDE; COPPER; FIBROIN; MACROGOL DERIVATIVE;

ARTICLE; CLICK CHEMISTRY; CONJUGATE; CONTROLLED STUDY; CROSS LINKING; CYCLOADDITION; FOURIER TRANSFORMATION; INFRARED SPECTROSCOPY; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; CHEMISTRY; GENETICS; METABOLISM; PROCEDURES;

AZIDES; CLICK CHEMISTRY; COPPER; DIAZONIUM COMPOUNDS; FIBROBLAST GROWTH FACTOR 2; FIBROINS; POLYETHYLENE GLYCOLS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84901604555     PISSN: 10478477     EISSN: 10958657     Source Type: Journal    
DOI: 10.1016/j.jsb.2014.02.009     Document Type: Article

References (54)

1. Altman G.H., et al. Silk matrix for tissue engineered anterior cruciate ligaments. Biomaterials 2002, 23(20):4131-4141.
2. Bai L.Q., et al. Surface modification and properties of Bombyx mori silk fibroin films by antimicrobial peptide. Appl. Surf. Sci. 2008, 254(10):2988-2995.
3. Bikfalvi A., et al. Biological roles of fibroblast growth factor-2. Endocrine Rev. 1997, 18(1):26-45.
4. Burgess W.H., Maciag T. The heparin-binding (fibroblast) growth-factor family of proteins. Annu. Rev. Biochem. 1989, 58:575-606.
5. Cunniff P.M., et al. Mechanical properties of major ampullate gland silk fibers extracted from Nephila clavipes spiders. ACS Symp. Ser. 1994, 544:234-251. (Silk Polymers).
6. Dabbagh H.A., Teimouri A., Chermahini A.N. Green and efficient diazotization and diazo coupling reactions on clays. Dyes Pigm. 2007, 73(2):239-244.
7. Das S., et al. Synthesis of silk fibroin-glycopolypeptide conjugates and their recognition with lectin. Biomacromolecules 2012, 13(11):3695-3702.
8. Doherty D.H., et al. Site-specific PEGylation of engineered cysteine analogues of recombinant human granulocyte-macrophage colony-stimulating factor. Bioconjugate Chem. 2005, 16(5):1291-1298.
9. Enami I., et al. Intramolecular cross-linking of the extrinsic 33-kDa protein leads to loss of oxygen evolution but not its ability of binding to photosystem II and stabilization of the manganese cluster. J. Biol. Chem. 1998, 273(8):4629-4634.
10. Gasparian M.E., et al. Overexpression in Escherichia coli and purification of human fibroblast growth factor (FGF-2). Biochem. Biokhimiia 2009, 74(2):221-225.
11. Hofmann S., et al. Control of in vitro tissue-engineered bone-like structures using human mesenchymal stem cells and porous silk scaffolds. Biomaterials 2007, 28(6):1152-1162.
12. Hu X.A., et al. Biomaterials from ultrasonication-induced silk fibroin-hyaluronic acid hydrogels. Biomacromolecules 2010, 11(11):3178-3188.
13. Hu X., Kaplan D., Cebe P. Determining beta-sheet crystallinity in fibrous proteins by thermal analysis and infrared spectroscopy. Macromolecules 2006, 39(18):6161-6170.
14. Hu Y., et al. The relationship between secondary structure and biodegradation behavior of silk fibroin scaffolds. Adv. Mater. Sci. Eng. 2012, 185905. (5 pp).
15. Kammerer R.A., et al. Tenascin-C hexabrachion assembly is a sequential two-step process initiated by coiled-coil alpha-helices. J. Biol. Chem. 1998, 273(17):10602-10608.
16. Karageorgiou V., et al. Bone morphogenetic protein-2 decorated silk fibroin films induce osteogenic differentiation of human bone marrow stromal cells. J. Biomed. Mater. Res., Part A 2004, 71A(3):528-537.
17. Kolb H.C., Sharpless K.B. The growing impact of click chemistry on drug discovery. Drug Discovery Today 2003, 8(24):1128-1137.
18. Kolb H.C., Finn M.G., Sharpless K.B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem., Int. Ed. 2001, 40(11):2004-2021.
19. Koren E., et al. Recommendations on risk-based strategies for detection and characterization of antibodies against biotechnology products. J. Immunol. Methods 2008, 333(1-2):1-9.
20. Li C.M., et al. Electrospun silk-BMP-2 scaffolds for bone tissue engineering. Biomaterials 2006, 27(16):3115-3124.
21. Liu R., et al. EDC/NHS crosslinked electrospun regenerated tussah silk fibroin nanofiber mats. Fibers Polymers 2012, 13(5):613-617.
22. Lopez-Alonso J.P., et al. Carbodiimide EDC induces cross-links that stabilize RNase A C-dimer against dissociation: EDC adducts can affect protein net charge, conformation, and activity. Bioconjugate Chem. 2009, 20(8):1459-1473.
23. Lucas, F., Shaw, J.T.B., Smith, S.G., 1958. Silk fibroins. In: Anfinsen, C.B., Anson, M.L., Kenneth Bailey, Edsall, John T. (Eds.), Advances in Protein Chem. Academic Press Inc, New York, vol. 13, pp. 107-242.
24. Luhmann T., et al. The induction of cell alignment by covalently immobilized gradients of the 6th Ig-like domain of cell adhesion molecule L1 in 3D-fibrin matrices. Biomaterials 2009, 30(27):4503-4512.
25. Lv Q., et al. Fibroin/collagen hybrid hydrogels with crosslinking method: preparation, properties, and cytocompatibility. J. Biomed. Mater. Res., Part A 2008, 84A(1):198-207.
26. Marsh R.E., Corey R.B., Pauling L. An investigation of the structure of silk fibroin. Biochim. Biophys. Acta 1955, 16(1):1-34.
27. Matsumoto A., et al. Mechanisms of silk fibroin sol-gel transitions. J. Phys. Chem. B 2006, 110(43):21630-21638.
28. Meinel L., et al. Engineering bone-like tissue in vitro using human bone marrow stem cells and silk scaffolds. J. Biomed. Mater. Res., Part A 2004, 71A(1):25-34.
29. Meinel L., et al. Silk implants for the healing of critical size bone defects. Bone 2005, 37(5):688-698.
30. Meinel L., et al. Osteogenesis by human mesenchymal stem cells cultured on silk biomaterials: comparison of adenovirus mediated gene transfer and protein delivery of BMP-2. Biomaterials 2006, 27(28):4993-5002.
31. Meinel L., et al. The inflammatory responses to silk films in vitro and in vivo. Biomaterials 2005, 26(2):147-155.
32. Min B.M., et al. Regenerated silk fibroin nanofibers: water vapor-induced structural changes and their effects on the behavior of normal human cells. Macromol. Biosci. 2006, 6(4):285-292.
33. Murphy A.R., Kaplan D.L. Biomedical applications of chemically-modified silk fibroin. J. Mater. Chem. 2009, 19(36):6443-6450.
34. Murphy A.R., John P.S., Kaplan D.L. Modification of silk fibroin using diazonium coupling chemistry and the effects on hMSC proliferation and differentiation. Biomaterials 2008, 29(19):2829-2838.
35. Nakayama K., Endo M., Majima T. A hydrophilic azobenzene-bearing amino acid for photochemical control of a restriction enzyme BamHI. Bioconjugate Chem. 2005, 16(6):1360-1366.
36. Pantoliano M.W., et al. Multivalent ligand-receptor binding interactions in the fibroblast growth-factor system produce a cooperative growth-factor and heparin mechanism for receptor dimerization. Biochemistry 1994, 33(34):10229-10248.
37. Patten P.A., Schellekens H. The immunogenicity of biopharmaceuticals. Lessons learned and consequences for protein drug development. Dev. Biol. (Basel) 2003, 112:81-97.
38. Rosenberg A.S. Effects of protein aggregates: an immunologic perspective. Aaps J. 2006, 8(3):E501-E507.
39. Sampaio S., et al. Preparation of silk fibroin-poly(ethylene glycol) conjugate films through click chemistry. Polym. Int. 2011, 60(12):1737-1744.
40. Schellekens H. Factors influencing the immunogenicity of therapeutic proteins. Nephrol. Dial. Transplant. 2005, 20:3-9.
41. Sofia S., et al. Functionalized silk-based biomaterials for bone formation. J. Biomed. Mater. Res. 2001, 54(1):139-148.
42. Squires C.H., et al. Production and characterization of human basic fibroblast growth factor from Escherichia coli. J. Biol. Chem. 1988, 263(31):16297-16302.
43. Uebersax L., et al. Effect of scaffold design on bone morphology in vitro. Tissue Eng. 2006, 12(12):3417-3429.
44. Uebersax L., et al. Silk fibroin matrices for the controlled release of nerve growth factor (NGF). Biomaterials 2007, 28(30):4449-4460.
45. Uebersax L., Merkle H.P., Meinel L. Insulin-like growth factor I releasing silk fibroin scaffolds induce chondrogenic differentiation of human mesenchymal stem cells. J. Controlled Release 2008, 127(1):12-21.
46. van de Weert M., et al. Fourier transform infrared spectrometric analysis of protein conformation: effect of sampling method and stress factors. Anal. Biochem. 2001, 297(2):160-169.
47. Vepari C.P., Kaplan D.L. Covalently immobilized enzyme gradients within three-dimensional porous scaffolds. Biotechnol. Bioeng. 2006, 93(6):1130-1137.
48. Vepari C., Kaplan D.L. Silk as a biomaterial. Prog. Polym. Sci. 2007, 32(8-9):991-1007.
49. Vepari C., et al. Surface modification of silk fibroin with poly(ethylene glycol) for antiadhesion and antithrombotic applications. J. Biomed. Mater. Res., Part A 2010, 93A(2):595-606.
50. Vunjak-Novakovic G., et al. Bioengineering heart muscle: a paradigm for regenerative medicine. Annu. Rev. Biomed. Eng. 2011, 13:245-267.
51. Wang Y.Z., et al. Stem cell-based tissue engineering with silk biomaterials. Biomaterials 2006, 27(36):6064-6082.
52. Wenk E., et al. The use of sulfonated silk fibroin derivatives to control binding, delivery and potency of FGF-2 in tissue regeneration. Biomaterials 2010, 31(6):1403-1413.
53. Yagi T., et al. Preparation of double-raschel knitted silk vascular grafts and evaluation of short-term function in a rat abdominal aorta. J. Artificial Organs 2011, 14(2):89-99.
54. Zhou C.Z., et al. Silk fibroin: structural implications of a remarkable amino acid sequence. Proteins: Struct., Funct., Genet. 2001, 44(2):119-122.