Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 39, Pages 12830-12834Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201808400
Keywords
analytical methods; fluorescent probes; hydroxyl radicals; iron autoxidation
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Funding
- NSF of China [21535009, 21435007, 91732104, 21675159, 21820102007, 21621062]
- 973 Program [2015CB856301, 2015CB932001]
- Chinese Academy of Sciences [XDB14030102]
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The first sensitive fluorescence (OH)-O-center dot probe (1) that is capable of monitoring the generation of trace (OH)-O-center dot in iron autoxidation is presented. The probe 1 was designed by utilizing both the unique aromatic hydroxylation and the electrophilicity of (OH)-O-center dot, and prepared by incorporating a strong electron-donating methoxy group into a cyanine fluorochrome to enhance the trapping ability for (OH)-O-center dot. Reaction of 1 with (OH)-O-center dot leads to a larger pi-conjugation formation and near-infrared fluorescence off-on response. The capability of probe 1 has been demonstrated by imaging (OH)-O-center dot generated in living cells under iron autoxidation as well as various stimuli, which reveals that the basal level of (OH)-O-center dot in RAW 264.7 cells is lower than that in HeLa cells. The superior analytical performance of probe 1 makes it useful for detecting trace (OH)-O-center dot in some critical physiological and pathological processes associated with iron autoxidation.
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