PMID:18224643
| Citation |
Tanabe, K, Hirata, N, Harada, H, Hiraoka, M and Nishimoto, S (2008) Emission under hypoxia: one-electron reduction and fluorescence characteristics of an indolequinone-coumarin conjugate. Chembiochem 9:426-32 |
|---|---|
| Abstract |
A characteristic feature of the reactivity of indolequinone derivatives, substituents of which can be removed by one-electron reduction under hypoxic conditions, was applied to the development of a new class of fluorescent probes for disease-relevant hypoxia. A reducing indolequinone parent molecule conjugated with fluorescent coumarin chromophores could suppress efficiently the fluorescence emission of the coumarin moieties by an intramolecular electron-transfer quenching mechanism and a conventional internal-filter effect. Under hypoxic conditions, however, the conjugate, denoted IQ-Cou, underwent a one-electron reduction triggered by X irradiation or the action of a reduction enzyme to release a fluorescent coumarin chromophore, whereupon an intense fluorescence emission with a maximum intensity at 420 nm was observed. The one-electron reduction of IQ-Cou was suppressed by molecular oxygen under aerobic conditions. IQ-Cou also showed intense fluorescence in a hypoxia-selective manner upon incubation with a cell lysate of the human fibrosarcoma cell line HT-1080. The IQ-Cou conjugate has several unique properties that are favorable for a fluorescent probe of hypoxia-specific imaging. |
| Links |
PubMed Online version:10.1002/cbic.200700458 |
| Keywords |
Anoxia/metabolism; Coumarins/chemistry; Electrons; Indolequinones/chemistry; Oxidation-Reduction; Spectrometry, Fluorescence/methods |
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