Interfacial Interactions of Cations with Amphiphilic Dihydroxyphosphonyl-calix-[4]-arene Mesosystems

Abstract

Two novel amphiphilic phosphorylated-calix- [4]-arenes, 5,11,17,23-tetrakis(dihydroxyphosphonyl)-25,-26,27,28-tetradecyloxy-calix-[4]-arene and 5,11,17,23-tetrakis(dihydroxyphosphonyl)-25,26,27,28-tetradodecyloxy-calix-[4]-arene, have been synthesized, and their interactions with the cations Na + , K + , Mg 2+ , and Ca 2+ have been measured at varying concentrations of the chloride salts. The systems were studied both at the air-water interface and in aqueous suspension as colloidal nanostructures. In the Langmuir experiments, monolayer expansion and increase in collapse pressure were observed for Na + at a concentration of 145 mM. For Mg 2+ , there was monolayer expansion accompanied by the formation of a second phase at a subphase concentration of 30 mM. In contrast, in the case of Ca 2+ there is an apparent contraction of the monolayer. The nanostructures were imaged by means of atomic force microscopy in the noncontact mode. As aqueous dispersions, no change in size or stability of the colloidal systems was observed with the monovalent cations; however, for the divalent cations at concentrations above 3 mM for Mg 2+ and 3 mM for Ca 2+ there is aggregation and flocculation of the dispersions.

Langmuir films of (α-amino) phosphorus amphiphiles on various ion-containing subphases

“…Calcium can thus easily form complexes with various bond lengths. This difference between calcium and magnesium was also observed for dihydroxyphosphoryl calixarenes [27].…”

Solid Lipid Nanoparticle-Based Calix[n]arenes and Calix-Resorcinarenes as Building Blocks: Synthesis, Formulation and Characterization

“…A 20 μL portion of a suspension of the SLNs was deposited, and imaging was performed after drying for 24 h at 25 °C [86]. …”

“…The amphiphilic dihydroxyphosphonyl-calix[ 4 ]arenes, 14 – 15 , were prepared from the previously synthesized tetrabromotetraalkyl-calix[ 4 ]arenes [ 85 ] ( 10 – 11 ) according to the literature procedure [ 86 ] via an Arbuzov reaction yielding the intermediate di-isopropyl phosphites ( 12 – 13 ), followed by de-protection ( Figure 17 ).…”

Kinetic properties of Na(+),K(+)-АТРase of spermatozoa from fertile and infertile men under effect of calix[4]arene C-107

“…Due to the amphiphilicity of calix [4]arenas molecule (hydrophilic acid groups and lipophilic macrocycle skeleton), calix [4]arenes might be embedded in lipid biomembranes, forming channels for the transport of cations [20,21]. Therefore calix [4]arenas can potentially affect enzymatic or transport activity of membrane-bound proteins.…”