A highly selective, colorimetric and ratiometric fluorescent probe for NH2NH2 and its bioimaging

In this work, we report a novel approach which employed substrate-triggered intramolecular addition-cyclization cascade to develop a highly selective fluorescent probe E)-3-(4-(1H-phenanthro[9,10-d]imidazol-2-yl)phenyl)-1-(2-hydroxylphenyl) prop-2-en-1-one (P-OH) for NH2NH2. The new sensing mechanis...

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Published inTalanta (Oxford) Vol. 180; pp. 199 - 205
Main Authors Xu, Hai, Gu, Biao, Li, Yaqian, Huang, Zhen, Su, Wei, Duan, Xiaoli, Yin, Peng, Li, Haitao, Yao, Shouzhuo
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.04.2018
Subjects
Addition-cyclization
color
colorimetry
fluorescence
fluorescence emission spectroscopy
fluorescent dyes
Living cells
mass spectrometry
NH2NH2
nuclear magnetic resonance spectroscopy
primary amines
Ratiometric
Selectivity
titration
NH2NH2
Addition-cyclization
Selectivity
Living cells
Ratiometric
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Summary:In this work, we report a novel approach which employed substrate-triggered intramolecular addition-cyclization cascade to develop a highly selective fluorescent probe E)-3-(4-(1H-phenanthro[9,10-d]imidazol-2-yl)phenyl)-1-(2-hydroxylphenyl) prop-2-en-1-one (P-OH) for NH2NH2. The new sensing mechanism of P-OH for NH2NH2 was investigated in detail by fluorescence spectroscopy, 1H NMR titration, mass spectrometry and control experiments. The synthesized probe showed ratiometric fluorescent response to NH2NH2 with naked-eye color changes from yellow to colorless. It's noteworthy that this probe displayed high sensitivity and selectivity to NH2NH2 over other species, including primary amines, Cys, Hcy, GSH, HS- and HSO3-. Furthermore, the probe can not only detect NH2NH2 in real water samples but also image NH2NH2 in living cells, indicating its potential utility for NH2NH2 sensing in environmental and biological samples. [Display omitted] •A novel fluorescent probe for NH2NH2 was developed based on NH2NH2-triggered intramolecular addition-cyclization cascade.•It showed high sensitivity and selectivity toward NH2NH2 with obvious colorimetric and ratiometic fluorescence responses.•It could detect NH2NH2 in vitro and in vivo without interference from other amines and reductive species.
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ISSN:0039-9140
1873-3573
1873-3573
DOI:10.1016/j.talanta.2017.12.039