Cucurbiturils: molecular nanocapsules for time-resolved fluorescence-based assays

IEEE Trans Nanobioscience. 2004 Mar;3(1):39-45. doi: 10.1109/tnb.2004.824269.

Abstract

A new fluorescent host-guest system based on the inclusion of the fluorophore 2,3-diazabicyclo[2.2.2]oct-2-ene (DBO) into the cavity of the molecular container compound cucurbit[7]uril (CB7) has been designed which possesses an exceedingly long-lived emission (690 ns in aerated water). The large binding constant of (4 +/- 1) x 10(5) M(-1) along with the resistance of the CB7.DBO complex toward external fluorescence quenchers allow the use of CB7 as an enhancer in time-resolved fluorescence-based assays, e.g., to screen enzyme activity or inhibition by using DBO-labeled peptides as substrates. The response of CB7.DBO to different environmental conditions and possible quenchers are described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Bridged-Ring Compounds / chemical synthesis
  • Bridged-Ring Compounds / chemistry*
  • Capsules
  • Fluorescent Dyes / chemistry*
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry*
  • Molecular Structure
  • Nanostructures / chemistry*
  • Spectrometry, Fluorescence

Substances

  • 2,3-diazabicyclo(2.2.2)oct-2-ene
  • Bridged Bicyclo Compounds, Heterocyclic
  • Bridged-Ring Compounds
  • Capsules
  • Fluorescent Dyes
  • Imidazoles
  • cucurbit(6)uril