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

    50 Citations (Scopus)

    Abstract

    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
    Volume5
    Issue number23
    DOIs
    Publication statusPublished - Nov 21 2007

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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