Fluorescent Molecular Cages with Sucrose and Cyclotriveratrylene Units for the Selective Recognition of Choline and Acetylcholine

Abstract

The synthesis of four fluorescent diastereoisomeric molecular cages containing cyclotriveratrylene and sucrose moieties connected via the naphthalene linkers is reported. These diastereoisomers were found to be selective and efficient receptors for acetylcholine and choline. Compound P -5a has a better affinity for choline over acetylcholine, while cage M -5a exhibits a higher association constant for acetylcholine over choline. The highest selectivity value was observed for compound M -5a ( K ACh / K Ch = 3.1). Cages P -5a , P -5b , M -5a , and M -5b were fully characterized by the advanced NMR techniques, and ECD spectroscopy was supported by DFT calculations. The binding constants K a of these receptors were determined by fluorescence titration experiments in acetonitrile.

Purely Covalent Molecular Cages and Containers for Guest Encapsulation

“…The opposite selectivity seems to be associated with the complementarity of each guest, with the cavity size and shape of the chiral twisted ((P)-285 and (M)-285) and non twisted ((P)-284 and (M)-284) geometry of each diastereoisomer (Figure 99). 227 Alonso-Goḿez, Cid, and co-workers synthesized the two enantiomers of a helical prism-like cage (286a) to show 10fold chiroptical amplification compared to its isolated building blocks. Initial studies have revealed that the cage could encapsulate an Fc + molecule as determined by 1 H NMR and HR-ESIMS, but no encapsulation was observed for Fc (Figure The presence of methyl groups significantly enhanced binding affinities from, for example, 50 M −1 to 900 M −1 for 290 + in CD 2 Cl 2 .…”

“…Fluorescent diastereoisomeric molecular cages 284 and 285 containing cyclotriveratrylene and sucrose …”

Cucurbituril-protected dual-readout gold nanoclusters for sensitive fentanyl detection

“…14 Host-guest assembly based on the selective recognition and encapsulation between the macrocyclic host and guest ligands has been applied in the synthesis and preparation of AuNCs to realize sensing and catalysis purposes. [15][16][17][18] For example, a recent study presented cucurbit [n]uril-decorated AuNCs as novel photonic materials with fascinating luminescence properties, arousing the interest of researchers. 19 The cucurbit [7]uril (Q7) with better water solubility and optimal ability to brighten AuNCs (Table S1 †) was selected in this study.…”

Selective Detection of Choline in Pseudophysiological Medium with a Fluorescent Cage Receptor

“…Very recently, diastereoisomeric fluorescent cages with sucrose were reported by Szyszka et al for the recognition of Ch and ACh in acetonitrile. 16 Despite the fact that one of these hosts is selective for ACh (K ACh /K Ch = 3.1), the selectivity of the most efficient receptor for Ch is modest (K ACh /K Ch = 1.7). Thus, although some hosts selective for ACh exist, those for Ch are very scarce, and selective imaging of ACh or Ch with a fluorescent supramolecular host remains very challenging, more particularly in aqueous medium.…”

“…HC 4 was not able to discriminate between ACh and Ch in organic solvent, but HC 1 , 2 , and 3 , which all have a tripodal benzenic platform as the second C 3 -symmetrical unit, were found to be selective for ACh ( K ACh / K Ch = 4.1, 2.8, and 4.4, respectively). Very recently, diastereoisomeric fluorescent cages with sucrose were reported by Szyszka et al for the recognition of Ch and ACh in acetonitrile . Despite the fact that one of these hosts is selective for ACh ( K ACh / K Ch = 3.1), the selectivity of the most efficient receptor for Ch is modest ( K ACh / K Ch = 1.7).…”