Water-soluble aminocalix[4]arene receptors with hydrophobic and hydrophilic mouths

Biological applications of functionalized calixarenes

“…[42][43][44][45] Based on the knowledge of the mixed-self assembled monolayer and the molecular recognition properties of the imincalix [4]arene 5, and aminocalix [4]arnes 6-9, recently, T. Kim et al introduced the phenomenon of molecular recognition to immobilize oligonucleotides on aminocalix [4]arene (AMCA) slides for the production of 9G DNAChips. 46 The preparation of the 9G DNAChip and the hybridization thereafter is briefly explained in Scheme 4.…”

“…64 In 2005, Oshima et al reported that a calix [6]arene carboxylic acid derivative exhibited a high affinity for cationic proteins such as cytochrome c (Cyt c) by promoting its extraction in organic media. The same group has also investigated several calix [4,6,8]arenes as protein extraction agents, which revealed that the large cavities of the carboxylic acid derivatives of p-tert-octylcalix [6]arene and ptert-octylcalix [8]arene exhibit high extraction capacities for proteins compared with the p-tert-octylcalix [4]arene. 65 Though the enzymatic reactions in organic media are reported to be difficult, 66 they have several advantages over those in water due to the unique property and widespread utilities of the water-insoluble substrates.…”

“…Furthermore, hexyl and octyl chains confer to these calixarenes cell transfection capabilities. Conversely, larger and conformationally mobile calix [6]-and calix [8]arene methoxy derivatives 41 and 42 form intermolecular aggregates characterized by ''gorgonlike'' structures composed of multiple plectomenes. These adducts, in which interstrand connections are dominated by electrostatic interactions, fail to promote cell transfection.…”

“…Biological tests, performed in vivo by the immunization of mice, showed that the target construct possesses higher immunostimulating activity with respect to the corresponding monovalent analogues, emphasizing the presence of a cluster effect and the important role of the calixarene macrocycle. 147 In the same year, Geraci et al extended their study on the anticancer activity of calixarene derivatives by using a calix [8]arene derivative instead of calix [4]arenes. Glycocalix [8]arenes 148 93, 94 exposing multiple N-acetylglucosamine (GlcNAc) residues and urido functionalities inhibit the rat C6 glioma cell migration and proliferation in a scratch wound model.…”

Water-Soluble Calix[4]arene Derivatives: Binding Stoichiometry and Spectroscopic Evaluation of the Host-Guest Recognition Mechanism

“…The new water-soluble aminocalix [4]arene hosts 11 and 12 with deep hydrophobic cavity facilitate hydrophilic mouth and hydrophobic mouth, respectively. 64 The 1 H NMR titrations revealed that host 12 shows high selectivity for neutral guests (18 and 19), with log K of 4.2 and 4.6, respectively. The host 11 shows log K of 4.9 for binding with guest 39.…”