Abstract
Multifunctionality is gaining more and more importance in the field of improved biomaterials. Especially peptides feature a broad chemical variability and are versatile mediators between inorganic surfaces and living cells. Here, we synthesized a unique peptide that binds to SiO(2) with nM affinity. We equipped the peptide with the bioactive integrin binding c[RGDfK]-ligand and a fluorescent probe by stepwise Diels-Alder reaction with inverse electron demand and copper(I) catalyzed azide-alkyne cycloaddition. For the first time, we report the generation of a multifunctional peptide by combining these innovative coupling reactions. The resulting peptide displayed an outstanding binding to silicon oxide and induced a significant increase in cell spreading and cell viability of osteoblasts on the oxidized silicon surface.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkynes / chemistry
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Azides / chemistry
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Biocompatible Materials / chemical synthesis
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Biocompatible Materials / chemistry*
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Biocompatible Materials / pharmacology
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Biotin / metabolism
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Catalysis
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Cell Line, Tumor
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Cell Survival / drug effects
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Click Chemistry*
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Copper / chemistry
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Cycloaddition Reaction
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Drug Design
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Enzyme-Linked Immunosorbent Assay
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Fluorescent Dyes / chemistry
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Humans
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Integrin alphaVbeta3 / metabolism
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Oligopeptides / chemical synthesis
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Oligopeptides / chemistry*
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Oligopeptides / pharmacology
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Osteoblasts / cytology
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Osteoblasts / drug effects
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Peptides, Cyclic / chemical synthesis
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Peptides, Cyclic / chemistry*
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Peptides, Cyclic / pharmacology
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Silicon / chemistry*
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Silicon Dioxide / chemistry*
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Surface Properties
Substances
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Alkynes
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Azides
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Biocompatible Materials
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Fluorescent Dyes
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Integrin alphaVbeta3
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Oligopeptides
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Peptides, Cyclic
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Biotin
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Silicon Dioxide
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Copper
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arginyl-glycyl-aspartic acid
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Silicon