calix(4)arene and resorcinarene

calix(4)arene has been researched along with resorcinarene* in 4 studies

Other Studies

4 other study(ies) available for calix(4)arene and resorcinarene

ArticleYear
Embedding calix[4]resorcinarenes in liposomes: Experimental and computational investigation of the effect of resorcinarene inclusion on liposome properties and stability.
    Biochimica et biophysica acta. Biomembranes, 2019, 06-01, Volume: 1861, Issue:6

    Two calix[4]resorcinarenes, which differ in the length of the alkyl chain on the methylene bridge between the aromatic rings, have been embedded in unilamellar liposomes prepared from 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine in three host/guest ratios, following two different procedures. The effect of the insertion of the guests has been evaluated through the measurements of the viscosity and the kinetic stability of the liposomal systems by means of the fluorescent probes pyrene and 5(6)-carboxyfluorescein. The presence of the guests reduces the viscosity of the liposomes, suggesting a modification of the bilayer structure. However, this does not affect liposome stability. A calix[4]resorcinarene cavitand with a more rigid conformation compared to the parent resorcinarene, has been also synthetized and embedded in liposomes. The free energy of the insertion of the substrates in the lipid bilayer has been evaluated through Molecular Dynamics simulations.

    Topics: Calixarenes; Kinetics; Lipid Bilayers; Liposomes; Molecular Dynamics Simulation; Phenols; Phenylalanine; Viscosity

2019
Water-soluble calix[4]resorcinarenes with hydroxyproline groups as chiral NMR solvating agents.
    The Journal of organic chemistry, 2008, Apr-04, Volume: 73, Issue:7

    Water-soluble calix[4]resorcinarenes containing 3- and 4-hydroxyproline, d-nipecotic acid, (S)-2-(methoxymethyl)pyrrolidine, (S)-2-pyrrolidine methanol, and (S,S)-(+)-2,4-bis(methoxymethyl)pyrrolidine substituents are synthesized and evaluated as chiral NMR solvating agents. The derivatives with the hydroxyproline groups are especially effective at causing enantiomeric discrimination in the spectra of water-soluble cationic and anionic compounds with pyridyl, phenyl, and bicyclic aromatic rings. Binding studies show that mono- and ortho-substituted phenyl rings associate within the cavity of the calix[4]resorcinarenes, as do naphthyl rings with mono-, 2,3-, and 1,8-substitution patterns. Anthracene derivatives with an amino or sulfonyl group at the 1-position bind within the cavity, as well. Aromatic resonances of the substrates exhibit substantial upfield shifts because of shielding from the aromatic rings of the calix[4]resorcinarene. The effectiveness of the reagents at producing chiral recognition in 1H NMR spectra is demonstrated with sodium mandelate, the sodium salt of tryptophan, and doxylamine succinate. While no one reagent is consistently the most effective, the calix[4]resorcinarenes with trans-4-hydroxyproline and trans-3-hydroxyproline moieties generally produce the largest nonequivalence in the 1H NMR spectra of the substrates.

    Topics: Calixarenes; Hydroxyproline; Indicators and Reagents; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Structure; Phenols; Phenylalanine; Reference Standards; Solubility; Solvents; Stereoisomerism; Water

2008
Study of the Calix[4]resorcinarene--dopamine interactions in monolayers by measurement of pressure--area isotherms and Maxwell displacement currents.
    The journal of physical chemistry. B, 2007, Sep-06, Volume: 111, Issue:35

    The mechanisms of interactions between calix[4]resorcinarene and dopamine in monolayers formed at the air-water interface were studied by analyzing their mechanical, thermodynamic, and electrical properties evaluated from measurements of pressure-area isotherms and Maxwell displacement currents (MDCs). An increased concentration of dopamine in the water subphase resulted in an increase in the area per calix[4]resorcinarene molecule, an increase in the collapse pressure, and a shift in the monolayer phase transitions from the gaseous to the liquid state and from the liquid to the solid state toward higher molecular areas. A contactless method of recording MDCs enabled the monitoring of changes in the charge state of the monolayer-constituting molecules and the determination of a relationship between the phase state of the monolayer and the structural transitions of calix[4]resorcinarene. The changes of the MDC recordings started already in the gaseous state of the monolayer. On the basis of MDC values, we determined the normal component of the dipole moment of calix[4]resorcinarene, as well as that of its complex with dopamine. The dipole moment reached a maximum value of 1040 mD in the region of the phase transition from the liquid to the solid state of the monolayer. The results obtained suggest that the binding of dopamine with calix[4]resorcinarene depends on the orientation of the calixarene molecules in the monolayer. The calix[4]resorcinarene-dopamine interactions were also quantified in terms of the excess of Gibbs free energy, thereby allowing the evaluation of the energy of the calix [4]resorcinarene-dopamine bond, which was in the range from 1.95 to 8.54 kJ/mol depending on the surface pressure. This value implies weak interactions between these molecules.

    Topics: Calixarenes; Dopamine; Electrochemistry; Phenols; Phenylalanine; Pressure; Surface Properties; Thermodynamics

2007
Study of calix[4]resorcinarene-dopamine complexation in mixed phospholipid monolayers formed at the air-water interface.
    Biochimica et biophysica acta, 2006, Volume: 1758, Issue:11

    We have studied the physical properties of monolayers formed by calix[4]resorcinarene and in mixtures with dipalmitoyl phosphatidylcholine (DPPC) in various molar ratios formed at the air-water interface and at presence of dopamine in water subphase by means of measurements of surface pressure and dipole potential. We showed that both calix[4]resorcinarene as well as its mixture with DPPC form stable monolayers at the water subphase. The presence of dopamine resulted in an increase of the mean molecular area and in a decrease of the compressibility modulus of the monolayers. For mixed monolayers at higher content of calix[4]resorcinarene (> 0.2 molar fraction) a deviation from ideal miscibility took place especially for monolayers in a solid state. This can be connected with formation of aggregates of calix[4] resorcinarene. Lowest miscibility and weakest interaction of dopamine with a monolayer was observed for calix[4]resorcinarene molar fraction of 0.33 in the monolayer.

    Topics: 1,2-Dipalmitoylphosphatidylcholine; Adsorption; Air; Calixarenes; Dopamine; Phenols; Phenylalanine; Surface Properties; Water

2006
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