Constructing a FRET-based molecular chemodosimeter for cysteine over homocysteine and glutathione by naphthalimide and phenazine derivatives

A molecular chemodosimeter , with a naphthalimide fluorophore connected to a newly designed phenazine energy acceptor, for the selective detection of cysteine was effectively synthesized. featured efficient intramolecular fluorescence resonance energy transfer (FRET) based on spectral overlap betwee...

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Bibliographic Details
Published in:Analyst (London) 2015-01, Vol.140 (1), p.182-189
Main Authors: Yang, Lin, Qu, Weisong, Zhang, Xiao, Hang, Yandi, Hua, Jianli
Format: Article
Language:English
Subjects:
Bonding
Cellular
Cysteine
Cysteine - analysis
Derivatives
Emission
Fluorescence
Fluorescence Resonance Energy Transfer
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Fretting
Glutathione
Glutathione - analysis
HeLa Cells
Homocysteine - analysis
Humans
Molecular Structure
Naphthalimides - chemical synthesis
Naphthalimides - chemistry
Phenazines - chemical synthesis
Phenazines - chemistry
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Summary:A molecular chemodosimeter , with a naphthalimide fluorophore connected to a newly designed phenazine energy acceptor, for the selective detection of cysteine was effectively synthesized. featured efficient intramolecular fluorescence resonance energy transfer (FRET) based on spectral overlap between the emission of naphthalimide and the absorption of phenazine. A cystamine chain with a S-S bond was applied to play the role of recognition moiety and the linker part. The specific reaction between the biological thiols and gave rise to an obvious fluorescence intensity enhancement at 540 nm, which is induced by cleavage of the disulfide bond followed by elimination of the FRET effect. High sensitivity and selectivity for cysteine over homocysteine and glutathione were also achieved. In addition, upon excitation at 400 nm, a relatively weak NIR emission provided an internal standard making a promising ratiometric sensor for cellular detection of cysteine.
ISSN:0003-2654
1364-5528
DOI:10.1039/c4an01732c