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Rationally Designed Fluorescence . OH Probe with High Sensitivity and Selectivity for Monitoring the Generation of . OH in Iron Autoxidation without Addition of H 2 O 2
Author(s) -
Li Hongyu,
Li Xiaohua,
Shi Wen,
Xu Yanhui,
Ma Huimin
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201808400
Subject(s) - autoxidation , chemistry , fluorescence , cyanine , photochemistry , selectivity , catalysis , organic chemistry , physics , quantum mechanics
The first sensitive fluorescence . OH probe ( 1 ) that is capable of monitoring the generation of trace . OH in iron autoxidation is presented. The probe 1 was designed by utilizing both the unique aromatic hydroxylation and the electrophilicity of . OH, and prepared by incorporating a strong electron‐donating methoxy group into a cyanine fluorochrome to enhance the trapping ability for . OH. Reaction of 1 with . OH leads to a larger π‐conjugation formation and near‐infrared fluorescence off–on response. The capability of probe 1 has been demonstrated by imaging . OH generated in living cells under iron autoxidation as well as various stimuli, which reveals that the basal level of . OH 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 in some critical physiological and pathological processes associated with iron autoxidation.