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Sensors 2010, 10(3), 2438-2449; doi:10.3390/s100302438
Article

Near-Infrared Fluorescence Detection of Acetylcholine in Aqueous Solution Using a Complex of Rhodamine 800 and p-Sulfonato-calix[8]arene

WPI Immunology Frontier Research Center, Osaka University, Yamada-oka, 1-3, Suita, Osaka 565-0871, Japan
Received: 18 February 2010 / Revised: 4 March 2010 / Accepted: 9 March 2010 / Published: 23 March 2010
(This article belongs to the Special Issue Fluorescent Chemosensors)
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Abstract

The complexing properties of p-sulfonatocalix[n]arenes (n = 4: S[4], n = 6: S[6], and n = 8: S[8]) for rhodamine 800 (Rh800) and indocyanine green (ICG) were examined to develop a near-infrared (NIR) fluorescence detection method for acetylcholine (ACh). We found that Rh800 (as a cation) forms an inclusion complex with S[n], while ICG (as a twitter ion) have no binding ability for S[n]. The binding ability of Rh800 to S[n] decreased in the order of S[8] > S[6] >> S[4]. By the formation of the complex between Rh800 and S[8], fluorescence intensity of the Rh800 was significantly decreased. From the fluorescence titration of Rh800 by S[8], stoichiometry of the Rh800-S[8] complex was determined to be 1:1 with a dissociation constant of 2.2 mM in PBS. The addition of ACh to the aqueous solution of the Rh800-S[8] complex caused a fluorescence increase of Rh800, resulting from a competitive replacement of Rh800 by ACh in the complex. From the fluorescence change by the competitive fluorophore replacement, stoichiometry of the Rh800-ACh complex was found to be 1:1 with a dissociation constant of 1.7 mM. The effects of other neurotransmitters on the fluorescence spectra of the Rh800-S[8] complex were examined for dopamine, GABA, glycine, and L-asparatic acid. Among the neurotransmitters examined, fluorescence response of the Rh800-S[8] complex was highly specific to ACh. Rh800-S[8] complexes can be used as a NIR fluorescent probe for the detection of ACh (5 × 10-4−10-3 M) in PBS buffer (pH = 7.2).
Keywords: near-infrared fluorescence; fluorescence detection; acetylcholine; dopamine; rhodamine 800; p-sulfonatocalixarene near-infrared fluorescence; fluorescence detection; acetylcholine; dopamine; rhodamine 800; p-sulfonatocalixarene
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Jin, T. Near-Infrared Fluorescence Detection of Acetylcholine in Aqueous Solution Using a Complex of Rhodamine 800 and p-Sulfonato-calix[8]arene. Sensors 2010, 10, 2438-2449.

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