Recognition and Sensing of Nucleoside Monophosphates by a Dicopper(II) Cryptate

Abstract

The dimetallic cryptate [Cu(2)(II)(1)](4+) selectively recognizes guanosine monophosphate with respect to other nucleoside monophosphates (NMPs) in a MeOH/water solution at pH 7. Recognition is efficiently signaled through the displacement of the indicator 6-carboxyfluorescein bound to the receptor, monitoring its yellow fluorescent emission. Titration experiments evidenced the occurrence of several simultaneous equilibria involving 1:1 and 2:1 receptor/NMP and receptor/indicator complexes. It was demonstrated that the added NMP displaces the indicator from the 2:1 receptor/indicator complex, forming the 1:1 receptor/analyte inclusion complex. Recognition selectivity is thus ascribed to the nature of nucleotide donor atoms involved in the coordination and their ability to encompass the Cu(II)-Cu(II) distance within the cryptate.

A Quinoline Based bis-Urea Receptor for Anions: A Selective Receptor for Hydrogen Sulfate

“…As seen in Figures 6 and 7, each anion is encapsulated within the cavity and held with four hydrogen bonds from two NHs, and two ArH protons. The CH…anion interactions are well documented in the literature [10b]. The calculated binding energies for the complexes, as shown in Table 1, correlate with the relative basicity, which is also fairly consistent with the binding data within the halide and oxoanion series.…”

“…Since the anion-ligand systems involve hydrogen- bonding interactions, it is important to choose an exchange-correlation functional which accurately captures these electronic effects. To this end, all DFT calculations were performed using the M06-2X hybrid functional which incorporates an improved description of dispersion energies, an effect which was previously found to be necessary for describing non-covalent interactions [10a]. The optimized structure of the ligand is shown in Figure 1 and the structures of anion complexes are shown in Figures 6 and 7.…”

Design Strategies for Water-Soluble Small Molecular Chromogenic and Fluorogenic Probes

“…Similar strategies have been employed by the same group for developing other chemosensing ensembles for amino acids, 385 dicarboxylates, 386 and guanosine monophosphate. 387 Another dinuclear Cu 2+ compound 155 can complex with eosine Y yielding an ensemble (K a = 5.6 × 10 4 M −1 ), which has been used for the sensitive and selective fluorescence detection of oxalate (K a = 1.3 × 10 5 M −1 ) in neutral aqueous solution. 388 Zn 2+ −DPA units have also been used to construct the corresponding ensembles for PPi assay.…”

A Multifunctional Bimetallic Molecular Device for Ultrasensitive Detection, Naked‐Eye Recognition, and Elimination of Cyanide Ions

“…Classicali ndicatord isplacementa ssays (IDAs) are generally regarded as "supramolecular ensembles" that resemblea ntibody-based immunoassays, and the target analytes in these IDAs must competef or specific molecular receptors with signaling analogues. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] However,i na ddition to an application in chemosensing, there are considerable constraints on the further development of this design because of the simplicity and monofunctionality of the components in the ensembleu nit. To overcomet his limitation, we have attempted to explore the feasibility of using an analogous approach called indicator/catalyst displacement assay (ICDA) in the design of multifunctional molecular devices that feature chemosensing, signal amplification, and advanced catalytic oxidation properties to deal with oxalic acid.…”