Novel fluorescent probe for detecting hydroperoxides with strong emission in the visible range

Nobuaki Soh, Tomoyuki Ariyoshi, Tuyoshi Fukaminato, Koji Nakano, Masahiro Irie, Toshihiko Imato

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A novel fluorescent probe, a swallow-tailed perylene derivative for detecting hydroperoxides (Spy-HP), containing perylene 3,4,9,10-tetracarboxyl bisimide as the main skeleton in the structure, was developed. Spy-HP reacted rapidly with hydroperoxides such as m-chloroperbenzoic acid (MCPBA) and cumene hydroperoxide to form its oxidized derivative, Spy-HPOx, and emitted an extremely strong fluorescence (Φ ∼ 1) in the visible range (λex = 524 nm and λem = 535 nm), as the result of canceling the photoinduced electron transfer (PET) effect. The reaction between Spy-HP and hydroperoxides proceeded quantitatively in strict stoichiometry, without being affected by autoxidation or photobleaching. Because of these prominent properties, Spy-HP is expected to be a novel and useful fluorescent probe to 'spy' on hydroperoxides in biosamples.

Original languageEnglish
Pages (from-to)2943-2946
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume16
Issue number11
DOIs
Publication statusPublished - Jun 1 2006

All Science Journal Classification (ASJC) codes

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

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