Self-association of a naphthalene-capped-β-cyclodextrin through cooperative strong hydrophobic interactions

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

“…Differences in the steric accessibility and acidity of the three types of hydroxyls in the molecule have been taken into account to conceive efficient position-selective and face-selective chemical functionalization methodologies. [17][18][19][20][21][22][23][24][25][26][27] A variety of multivalent conjugates with diverse architectures becomes then accessible through appropriate ligation chemistries (Fig. 1).…”

Predicting self-assembly and structure in diluted aqueous solutions of modified mono- and bis-β-cyclodextrins that contain naphthoxy chromophore groups

“…These non-covalent dimers which are stable in aqueous media dissociate in polar media. 10,27,28,30,79,80 On the other hand, circular dichroism (CD) spectra are able to provide information on the presence or absence of monoNbCD association. The simple existence of the Cotton effect in the zone of chromophore absorption is the unequivocal evidence of the interaction between the macroring appended naphthoxy group (ON) and its own cavity or a neighbouring one, providing information about its location and a mono-or a bis-derivative structure in solution.…”

“…Characteristics and measurement conditions have been previously described. 10,28,30,80 Excitation for the time-resolved measurements was carried out using sub-nanosecond pulsed NanoLED (IBH), emitting at 279 nm. Data acquisition was performed on 1024 channels at a time window width of 200 ns with a total of 10 000 counts measured at the maximum of the intensity profile.…”

Dynamic Control of the Self-Assembling Properties of Cyclodextrins by the Interplay of Aromatic and Host-Guest Interactions

“…Alternatively, prototypes featuring a two-point connected aromatic component at either the primary (Yang et al, 2008; Le Gac et al, 2016; Ménand et al, 2016, 2018; Yan et al, 2017) or the secondary rim (Balbuena et al, 2007, 2013) in a monomeric CD derivative have been reported, allowing unprecedented control over the topological and supramolecular attributes. The later architecture is particularly appealing: an aromatic component attached to the wider entrance of the inner cavity can act as gatekeeper, guest selector and/or aggregation promoter, the impact in the recognition abilities depending on the conformational bias (González-Álvarez et al, 2011, 2013). Thus, “hinge-type” o -xylylene segments connecting the vicinal secondary O -2 and O -3 positions in the same glucopyranosyl unit (e.g., 1 ) adopt a cap-like orientation that hinders inclusion and elicits instead the formation of supramolecular head-to-head (HH) dimers in which the individual constituents are closely packed (González-Álvarez et al, 2008; Mayordomo et al, 2013; Gallego-Yerga et al, 2014a).…”