Full Paper

Diol Appended Quenchers for Fluorescein Boronic Acid

  1. Souad A. Elfeky Dr.1,2,†,
  2. Stephen E. Flower Dr.2,†,
  3. Naoko Masumoto2,
  4. François D'Hooge Dr.2,
  5. Ludivine Labarthe2,3,
  6. Wenbo Chen Dr.1,
  7. Christophe Len Prof.4,
  8. Tony D. James Dr.2,
  9. John S. Fossey Dr.1

Article first published online: 1 FEB 2010

DOI: 10.1002/asia.200900386

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Special Issue: In dedication to the 150th anniversary of Japan–UK diplomatic relations

Volume 5, Issue 3, pages 581–588, March 1, 2010

Additional Information

How to Cite

Elfeky, S., Flower, S., Masumoto, N., D'Hooge, F., Labarthe, L., Chen, W., Len, C., James, T. and Fossey, J. (2010), Diol Appended Quenchers for Fluorescein Boronic Acid. Chemistry – An Asian Journal, 5: 581–588. doi: 10.1002/asia.200900386

Author Information

  1. 1

    School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT (UK) www:http://johnfossey.com

  2. 2

    Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY (UK)

  3. 3

    Université de Poitiers, 40, Avenue du Recteur Pineau, F-86022 Poitiers Cedex (France)

  4. 4

    Université de Technologie de Compiègne (UTC), ESCOM EA 4297 UTC/ESCOM, 1, Allée du réseau Jean-Marie Buckmaster, F-60200 Compiègne, France.

  1. †

    These authors contributed equally to this work.

Publication History

  1. Issue published online: 22 FEB 2010
  2. Article first published online: 1 FEB 2010
  3. Manuscript Received: 7 OCT 2009

Funded by

  • Royal Society for a Research Grant. Grant Number: 2007/R2
  • Leverhulme Trust. Grant Number: JSF F/00351/P
  • University of Birmingham

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article (HTML) Get PDF (427K)

Keywords:

  • boronic acid;
  • fluorophore;
  • nucleoside;
  • quencher;
  • receptor

Graphical Abstract

Thumbnail image of graphical abstract

Linking it all together! A fluorescein boronic acid derivative was prepared in one step, its interaction with readily prepared bespoke diol appended quenchers was studied revealing enhanced FRET quenching owing to ester formation. The same fluorescent boronic acid also had its fluorescence efficiently quenched by nucleosides through boronate ester formation.

Abstract

Fluorescein isothiocyanate is treated with 3-aminophenylboronic acid to provide a fluorescently tagged boronic acid derivative which is used to assess Förster resonance energy transfer (FRET) quenching upon boronate ester formation with a series of bespoke diol appended quenchers. Fluorescence spectroscopy comparison of quenching efficiency between treatment of fluorescein and its boronic acid appended congener with quencher appended diol reveals boronate ester formation (covalently linked) to be the more efficient regime and from the panel of quenchers which also included nucleosides.

View Full Article (HTML) Get PDF (427K)