Intramolecular Indicator Displacement Assay for Anions: Supramolecular Sensor for Glyphosate

One of the well-known strategies for anion sensing is an indicator (dye) displacement assay. However, the disadvantage of the dye displacement assays is the low sensitivity due to the excess of the dye used. To overcome this setback, we have developed an “Intramolecular Indicator Displacement Assay...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-08, Vol.136 (32), p.11396-11401
Main Authors: Minami, Tsuyoshi, Liu, Yuanli, Akdeniz, Ali, Koutnik, Petr, Esipenko, Nina A, Nishiyabu, Ryuhei, Kubo, Yuji, Anzenbacher, Pavel
Format: Article
Language:English
Subjects:
Anions
Chlorides - chemistry
Diphosphates - chemistry
Discriminant Analysis
Electrolytes
Fluorescent Dyes - chemistry
Glycine - analogs & derivatives
Glycine - chemistry
Glyphosate
Herbicides - chemistry
Magnetic Resonance Spectroscopy
Multivariate Analysis
Phosphates - chemistry
Polymers - chemistry
Sodium Chloride - chemistry
Water - chemistry
X-Ray Diffraction
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Summary:One of the well-known strategies for anion sensing is an indicator (dye) displacement assay. However, the disadvantage of the dye displacement assays is the low sensitivity due to the excess of the dye used. To overcome this setback, we have developed an “Intramolecular Indicator Displacement Assay (IIDA)”. The IIDAs comprise a receptor and a spacer with an attached anionic chromophore in a single-molecule assembly. In the resting state, the environment-sensitive anionic chromophore is bound by the receptor, while the anionic substrate competes for binding into the receptor. The photophysical properties of the dye exhibit change in fluorescence when displaced by anions, which results in cross-reactive response. To illustrate the concept, we have prepared IID sensors 1 and 2. Here, the characterization of sensors and microtiter arrays comprising the IIDA are reported. The microtiter array including IID sensors 1 and 2 is capable of recognizing biological phosphates in water. The utility of the IIDA approach is demonstrated on sensing of a phosphonate herbicide glyphosate and other biologically important anions such as pyrophosphate in the presence of interferent sodium chloride.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja504535q