Construction of a water-soluble form of amino acid C-methylcalix[4]resorcinarene

Selective O-Alkylation of the Crown Conformer of Tetra(4-hydroxyphenyl)calix[4]resorcinarene to the Corresponding Tetraalkyl Ether

“…Varying the nature of the aldehyde substituent group facilitates the modification at the macrocyclic lower-rim system. At the upper rim, the obvious positions for chemical modification are the resorcinol hydroxyl group and the ortho position [ 18 , 19 , 20 ], the hydroxyl groups of the upper rim being the most common, which can be bridged to form extended cavities or substituted by functional groups for specific applications [ 21 ]. An interesting reagent for resorcinarene modification at the upper rim is glycidyl methacrylate (GMA), which can easily undergo a ring-opening reaction with nucleophilic reagents that contain hydroxyl, carboxyl, trysil or amine groups [ 18 , 22 , 23 ].…”

Aggregation and Solubilization Properties of System Based on Glycine-Calix[4]resorcinol and Sodium Dodecyl Sulfate in Aqueous Medium

“…It is known that the solubility of GC in water is low (0.02 mM), [13] but a water-soluble form can be obtained by solubilization in surfactant micelles. The aggregation behaviour of SDS in an aqueous medium in the presence of solubilized GC was studied at the first stage by tensiometry ( Figure 1a) and conductometry (Figure 1b) methods.…”

“…Syntheses of C-methylcalix [4]resorcinol with glycine groups at the upper rim [13] and 2,2'-bibenzimidazole (BBI) [18,19] were described elsewhere. 1-Phenylazo-2-naphthol (Sudan I, Acros Organics) and SDS (99%, Acros Organics) were used as received.…”

“…[8][9][10] A review of the literature shows that in recent years a significant number of calix [4]resorcinol derivatives have been synthesized, and their aggregation properties in the absence and in the presence of surfactants have been studied. [8][9][10][11][12][13][14] Despite the fact that surfactants in this case can play the role of a matrix facilitating the processes of self-aggregation, the mixed surfactant systems with calixarene containing biocompatible fragments are much less studied. Aggregation of surfactants in the presence of calixarenes containing amino acid groups has not been studied at all.…”

Amino Acid‐Functionalized Calix[4]Resorcinarene Solubilization by Mono‐ and Dicationic Surfactants

“…enhance biocompatibility and the demonstration of the specific biological effects [16,17]. Recently, we have reported syntheses of calix [4]resorcinarenes containing glycine (CR-Gly) [18] and alanine (CR-Ala) or valine (CR-Val) [17] residues at the upper rim. However, their use in aqueous solutions including almost all biological fluids, are limited because of extremely low solubility in water being less than 1 lM.…”