Biocompatible silicon surfaces through orthogonal click chemistries and a high affinity silicon oxide binding peptide

Bioconjug Chem. 2012 Oct 17;23(10):2129-37. doi: 10.1021/bc3003875. Epub 2012 Sep 27.

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

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Azides / chemistry
  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry*
  • Biocompatible Materials / pharmacology
  • Biotin / metabolism
  • Catalysis
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Click Chemistry*
  • Copper / chemistry
  • Cycloaddition Reaction
  • Drug Design
  • Enzyme-Linked Immunosorbent Assay
  • Fluorescent Dyes / chemistry
  • Humans
  • Integrin alphaVbeta3 / metabolism
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology
  • Osteoblasts / cytology
  • Osteoblasts / drug effects
  • Peptides, Cyclic / chemical synthesis
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / pharmacology
  • Silicon / chemistry*
  • Silicon Dioxide / chemistry*
  • Surface Properties

Substances

  • Alkynes
  • Azides
  • Biocompatible Materials
  • Fluorescent Dyes
  • Integrin alphaVbeta3
  • Oligopeptides
  • Peptides, Cyclic
  • Biotin
  • Silicon Dioxide
  • Copper
  • arginyl-glycyl-aspartic acid
  • Silicon