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Cyclodextrins (CyDs) are water-soluble host molecules possessing a nanosized hydrophobic cavity. In the realm of molecular recognition, this cavity is used not only as a recognition site but also as a reaction medium, where a hydrophobic sensor recognizes a guest molecule. Based on the latter concept, we have designed a novel supramolecular sensing system composed of Zn(II)-dipicolylamine metal complex-based azobenzene ( 1-Zn ) and 3A-amino-3A-deoxy-(2A S ,3A S )- γ -cyclodextrin (3-NH 2 - γ -CyD) for sensing adenosine-5′-triphosphate (ATP).  1-Zn  showed redshifts in the UV-Vis spectra and induced circular dichroism (ICD) only when both ATP and 3-NH 2 - γ -CyD were present. Calculations of equilibrium constants indicated that the amino group of 3-NH 2 - γ -CyD was involved in the formation of supramolecular  1-Zn /3-NH 2 - γ -CyD/ATP. The Job plot of the ICD spectral response revealed that the stoichiometry of  1-Zn /3-NH 2 - γ -CyD/ATP was 2:1:1. The pH effect was examined and  1-Zn /3-NH 2 - γ -CyD/ATP was most stable in the neutral condition. The NOESY spectrum suggested the localization of  1-Zn  in the 3-NH 2 - γ -CyD cavity. Based on the obtained results, the metal coordination interaction of  1-Zn  and the electrostatic interaction of 3-NH 2 - γ -CyD were found to take place for ATP recognition. The “reaction medium approach” enabled us to develop a supramolecular sensing system that undergoes multi-point interactions in water. This study is the first step in the design of a selective sensing system based on a good understanding of supramolecular structures.

Supramolecular Zn(II)-Dipicolylamine-Azobenzene-Aminocyclodextrin-ATP Complex: Design and ATP Recognition in Water