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A Hemicyanine‐Embedded Diphenylselenide‐Containing Probe “HemiSe” in which SePh 2 Stays Reduced for Selective Detection of Superoxide in Living Cells
Author(s) -
Halle Mahesh B.,
Lee Kyung Jin,
Yudhistira Tesla,
Choi Jae Hyuck,
Park HeeSung,
Churchill David G.
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801339
Subject(s) - superoxide , detection limit , chemistry , fluorescence , quantum yield , fluorophore , photochemistry , xanthine , quenching (fluorescence) , photoinduced electron transfer , selectivity , yield (engineering) , electron transfer , xanthine oxidase , chemiluminescence , biochemistry , enzyme , organic chemistry , chromatography , materials science , catalysis , physics , quantum mechanics , metallurgy
A simple one‐step synthesis of fluorescent probe HemiSe has been developed for the detection of superoxide (O 2 .− ). The probe undergoes reaction specifically with O 2 .− when in the presence of other competitive ROS/RNS/metal ions. The diphenylselenide was incorporated to completely quench the fluorescence of the hemicyanine unit through the action of a photoinduced electron transfer (PET) photomechanism. However, after the addition of O 2 .− , the latent fluorophore regains its fluorescence owing to the reaction at the C=C bond of the hemicyanine with O 2 .− through nucleophilic attack; the increase in blue emission is due to a reaction of the double bond within HemiSe followed by an increase in fluorescence quantum yield ( Φ ) up to 0.45; the limit of detection (LOD) is 11.9 n m . A time‐dependent study shows that HemiSe can detect superoxide within 13 min with high sensitivity, high selectivity, over a wide pH range, and through confirmation with a xanthine/xanthine oxidase biochemical assay ( λ em =439 nm). A study in the RAW 264.7 macrophage living cells also shows that HemiSe is not toxic, cell permeable (experimental log P =2.11); confocal imaging results show that HemiSe can detect O 2 .− in endogenous and exogeneous systems.