Swallow-tailed perylene derivative: A new tool for fluorescent imaging of lipid hydroperoxides

Nobuaki Soh, Tomoyuki Ariyoshi, Tuyoshi Fukaminato, Hizuru Nakajima, Koji Nakano, Toshihiko Imato

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)


A swallow-tailed perylene derivative including a triphenylphosphine moiety was synthesized and applied to the detection and the live-cell imaging of lipid hydroperoxides. The novel probe, named Spy-LHP, reacted rapidly and quantitatively with lipid hydroperoxides to form the corresponding oxide, Spy-LHPOx, which emits extremely strong fluorescence (Φ ∼ 1) in the visible range (λem = 535 nm, 574 nm). Spy-LHP was highly selective for lipid hydroperoxides, and the addition of other reactive oxygen species (ROS) including hydrogen peroxides, hydroxyl radical, superoxide anion, nitric oxide, peroxynitrite, and alkylperoxyl radical, caused no significant increase in the fluorescence intensity. The probe exhibited good localization to cellular membranes and was successfully applied to the confocal laser scanning microscopy (CLSM) imaging of lipid hydroperoxides in live J774A.1 cells, in which lipid peroxidation was proceeded by the stimulation of 2,2-azobis(2-amidinopropane)dihydrochloride (AAPH). These findings establish Spy-LHP as a promising new tool for investigating the physiology of lipid hydroperoxides.

Original languageEnglish
Pages (from-to)3762-3768
Number of pages7
JournalOrganic and Biomolecular Chemistry
Issue number23
Publication statusPublished - Nov 21 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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