Heat-initiated detection for reduced glutathione with 19F NMR probes based on modified gold nanoparticles

Narufumi Kitamura, Kazuo Tanaka, Yoshiki Chujo

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

For detecting reduced glutathione (GSH) with a 19F NMR spectroscopy with time-specificity, we developed the probes based on gold nanoparticles modified with the fluorinated groups via the thermally-cleavable linkers. Before the heating treatment with the probe, the maleimide moiety as a binding site with GSH in the probe is inactivated by cycloaddition of furan. At this silent state, the magnitude of 19F NMR signals from the fluorinated groups was suppressed. By heating for the activation of the probe, the maleimide moiety was produced via retro Diels-Alder reaction, and 19F NMR signals were observed. From this moment, GSH started the reaction with the probe via Michael addition to the maleimide moiety, leading to the observation of the new peak in 19F NMR spectra. Finally, the amounts of GSH were determined from the increase of the magnitude of 19F NMR signals.

Original languageEnglish
Pages (from-to)281-286
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number1
DOIs
Publication statusPublished - 2013 Jan 1
Externally publishedYes

Keywords

  • F NMR
  • Gold nanoparticle
  • Molecular probe
  • Reduced glutathione
  • Retro Diels-Alder reaction

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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