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Sensors 2008, 8(10), 6777-6790; doi:10.3390/s8106777
Article

Interfacial Recognition of Acetylcholine by an Amphiphilic p-Sulfonatocalix[8]arene Derivative Incorporated into Dimyristoyl Phosphatidylcholine Vesicles

1,2,* , 1 and 3
Received: 23 August 2008; in revised form: 17 October 2008 / Accepted: 23 October 2008 / Published: 29 October 2008
(This article belongs to the Special Issue Molecular Recognition and Sensors, Including Molecular Imprinting)
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Abstract: Dodecyl ether derivatives 1-3 of p-sulfonatocalix[n]arene were incorporated into dimyristoyl phosphatidylcholine (DMPC) vesicles, and their binding abilities for acetylcholine (ACh) were examined by using steady-state fluorescence/fluorescence anisotropy and fluorescence correlation spectroscopy (FCS). For the detection of ACh binding to the DMPC vesicles containing 5 mol % of 1-3, competitive fluorophore displacement experiments were performed, where rhodamine 6G (Rh6G) was used as a fluorescent guest. The addition of Rh6G to the DMPC vesicles containing 3 resulted in a decrease in the fluorescence intensity of Rh6G with an increase of its fluorescence anisotropy, indicating that Rh6G binds to the DMPC-3 vesicles. In the case of DMPC-1 and DMPC-2 vesicles, significant changes in the fluorescence spectra of Rh6G were not observed. When ACh was added to the DMPC-3 vesicles in the presence of Rh6G ([3]/[Rh6G]=100), the fluorescence intensity of Rh6G increased with a decrease in its fluorescence anisotropy. From the analysis of fluorescence titration data, the association constants were determined to be 7.1×105 M-1 for Rh6G-3 complex and 1.1×102 M-1 for ACh-3 complex at the DMPC-3 vesicles. To get a direct evidence for the binding of Rh6G and its displacement by ACh at the DMPC-3 vesicles, diffusion times of the Rh6G were measured by using FCS. Binding selectivity of the DMPC-3 vesicles for ACh, choline, GABA, L-aspartic acid, L-glutamic acid, L-arginine, L-lysine, L-histamine and ammonium chloride was also evaluated using FCS.
Keywords: Interfacial recognition; acetylcholine; sulfonatocalixarene; lipid bilayer; vesicle; fluorescence correlation spectroscopy Interfacial recognition; acetylcholine; sulfonatocalixarene; lipid bilayer; vesicle; fluorescence correlation spectroscopy
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Jin, T.; Fujii, F.; Ooi, Y. Interfacial Recognition of Acetylcholine by an Amphiphilic p-Sulfonatocalix[8]arene Derivative Incorporated into Dimyristoyl Phosphatidylcholine Vesicles. Sensors 2008, 8, 6777-6790.

AMA Style

Jin T, Fujii F, Ooi Y. Interfacial Recognition of Acetylcholine by an Amphiphilic p-Sulfonatocalix[8]arene Derivative Incorporated into Dimyristoyl Phosphatidylcholine Vesicles. Sensors. 2008; 8(10):6777-6790.

Chicago/Turabian Style

Jin, Takashi; Fujii, Fumihiko; Ooi, Yasuhiro. 2008. "Interfacial Recognition of Acetylcholine by an Amphiphilic p-Sulfonatocalix[8]arene Derivative Incorporated into Dimyristoyl Phosphatidylcholine Vesicles." Sensors 8, no. 10: 6777-6790.


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