Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Tanabe, K. et al.

Kazuhito Tanabe, Nao Hirata, Hiroshi Harada, Masahiro Hiraoka, Sei-Ichi Nishimoto,

Emission under hypoxia: one-electron reduction and fluorescence characteristics of an indolequinone-coumarin conjugate.

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.[1]

References

Emission under hypoxia: one-electron reduction and fluorescence characteristics of an indolequinone-coumarin conjugate. Tanabe, K., Hirata, N., Harada, H., Hiraoka, M., Nishimoto, S. Chembiochem (2008) [Pubmed]

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