121702-03-2Relevant articles and documents
Lower rim substituted p-tert-butyl-calix[4]arene. Part 17. Synthesis, extractive and ionophoric properties of p-tert-butylcalix[4]arene appended with hydroxamic acid moieties
Kulesza,Guzinski,Bochenska,Hubscher-Bruder,Arnaud-Neu
, p. 89 - 95 (2014)
The synthesis and characterization of four p-tert-butylcalix[4]arene- hydroxamic acids are reported. The dependence of the metal ion binding, assessed by liquid-liquid extraction of the metal nitrates from water into dichloromethane in individual and competitive experiments, on the ligand structure, is presented. The results showed that those ligands could be successfully used in separation process of transition and heavy metals often present together. Two of the ligands were used as active materials in Pb-ion-selective membrane electrodes. The characteristics of these electrodes, in particular their selectivity coefficients for Pb2+ over other metal ions, are discussed.
Synthesis, X-ray crystal structure and anti-tumor activity of calix[n]arene polyhydroxyamine derivatives
An, Lin,Han, Li-Li,Zheng, You-Guang,Peng, Xian-Na,Xue, Yun-Sheng,Gu, Xiao-Ke,Sun, Jing,Yan, Chao-Guo
, p. 21 - 30 (2016)
Calixarene-based compounds are highly effective therapeutic agents against cancer. This study aims to prepare a series of calix [n]arene (n?=?4, 6, 8) polyhydroxyamine derivatives (3a–3m) and to study their potential antitumor activities. The single crystal structure of calixs[4]arene derivative 3a was determined through X-ray diffraction. We assessed the ability of the prepared calix [n]arene polyhydroxyamine derivatives to induce cytotoxicity in six cancer cell lines by performing cancer cell growth inhibition assays. Results demonstrated that compounds 3a–3d achieved IC50values ranging from 1.6?μM to 11.3?μM. Among the different compounds, 3a and 3b exerted the strongest cytotoxic effect in inhibiting the growth of SKOV3 cells. In relation to the underlying mechanisms of cytotoxic effects, cell cycle analysis revealed that the exposure of SKOV3 cells to 3a induced cell cycle arrest in the G0/G1 phase, suggesting a reduction in DNA synthesis. Immunofluorescent staining indicated that the protein expression levels of caspase-3 and p53 in cells significantly increased, whereas that of Bcl-2 was effectively suppressed. Meanwhile, no significant changes in Bax were observed in SKOV3 cells. These results highlight that calixarene 3a can be further studied as a potential anticancer agent.
Extraction of technetium(VII) by calix[4]arene tetraketones and tetraesters from acidic and basic media
Antipin,Solovieva,Stoikov,Vershinina,Pribylova,Tananaev,Myasoedov
, p. 127 - 132 (2004)
Tetrasubstituted on the lower rim calix[4]arenes, containing carbonyl and ester groups, and existing in a cone conformation are selective and efficient extracting agents for TcVII extraction from both acidic and basic solutions.
Solvent-tunable binding of hydrophilic and hydrophobic guests by amphiphilic molecular baskets
Zhao, Yan,Ryu, Eui-Hyun
, p. 7585 - 7591 (2005)
Responsive amphiphilic molecular baskets were obtained by attaching four facially amphiphilic cholate groups to a tetraaminocalixarene scaffold. Their binding properties can be switched by solvent changes. In nonpolar solvents, the molecules utilize the hydrophilic faces of the cholates to bind hydrophilic molecules such as glucose derivatives. In polar solvents, the molecules employ the hydrophobic faces of the cholates to bind hydrophobic guests. A water-soluble basket can bind polycyclic aromatic hydrocarbons including anthracene, pyrene, and perylene. The binding free energy (-ΔG) ranges from 5 to 8 kcal/mol and is directly proportional to the surface area of the aromatic hosts. Binding of both hydrophilic and hydrophobic guests is driven by solvophobic interactions.
Remarkable metal template effects on selective syntheses of p-t-butylcalix[4]arene conformers
Iwamoto,Fujimoto,Matsuda,Shinkai
, p. 7169 - 7172 (1990)
It was found that the conformer distribution in tetra-O-substitution of p-t-butylcalix[4]arene is remarkably affected by metal species in base: in particular, 100% 'cone' selectivity in the presence of Na2CO3 is changed to 100% 'partial cone' selectivity in the presence of Cs2CO3 in the reaction with ethyl bromoacetate.
Synthesis, X-Ray Crystal Structures, and Cation Transfer Properties of Alkyl Calixaryl Acetates, a New Series of Molecular Receptors
McKervey, M. Anthony,Seward, Eileen M.,Ferguson, George,Ruhl, Barbara,Harris, Stephen J.
, p. 388 - 390 (1985)
Calix-, -, and -arenes have been converted into a series of alkyl acetates which show significant phase-transfer activity and selectivity towards alkali metal picrates; the X-ray crystal structures of two members of the series, (1b) and (2d), have been determined.
Kinetics and mechanism of the dissociation of a sodium-calix [4] arene ester complex in nonaqueous solution
Jin, Takashi
, p. 1401 - 1406 (2000)
The kinetics and mechanism for the dissociation of sodium ion complexes of a calix[4]arene ester 1 were studied in nonaqueous solution by a dynamic 1H NMR. Life times τ(c) of the Na+-1 complexes and activation parameters Δ(d)H((+)) and Δ(d)S((+)) for the dissociation process were determined in five organic solvents. In methanol, the life time (8.8 x 10-3 s) of the sodium complex at 25°C was 440 times larger than that of crown ether (18C6) and was ca. 40 times less than that of cryptands (C211 and C222). The activation parameters for the dissociation process, Δ(d)H((+)) of 67, 64, 57, 57, and 46 kJ mol-1, and Δ(d)S((+)) of -22, -29, -7.7, -13, and -33 J mol-1 K-1 were determined in deuteriated nitromethane, acetonitrile, acetone, methanol, and dimethylformamide, respectively. It was observed that the activation enthalpies tend to decrease with increasing the electron- donating ability of solvents as indicated by the Gutmann donor number, while the activation enthalpies do not correlate to the donor number and all the values are negative. These results suggest that in the activated state of the Na+-1 complex, additional solvent molecules bind to the sodium ion encapsulated by ethoxycarbonylmethoxy groups in 1, and the disruption of the bonding between a sodium ion and the oxygens in the OCH2CO moieties plays a major contribution in the dissociation process. In acetonitrile, the life times of the Na+-1 complexes were not affected by the concentration of the free ligand of 1, suggesting that the dissociation proceeds via a unimolecular dissociation not a bimolecular exchange between free and complexed 1.
Efficient synthesis of water-soluble calixarenes using click chemistry
Ryu, Eui-Hyun,Zhao, Yan
, p. 1035 - 1037 (2005)
(Chemical Equation Presented) Several water-soluble calix[4]arenes were synthesized via Huisgen 1,3-dipolar cycloaddition between azides and alkynes. Cationic, anionic, and nonionic calixarenes were prepared from a common azidocalixarene intermediate. Azidocalixarenes performed better than alkynylcalixarenes as precursors. The aggregation behavior of the water-soluble calixarenes was studied by 1H NMR spectroscopy.
Luminescent behavior of pyrene-allied calix[4]arene for the highly pH-selective recognition and determination of Zn2+, Hg2+ and I-: Via the CHEF-PET mechanism: Computational experiment and paper-based device
Sutariya, Pinkesh G.,Soni, Heni,Gandhi, Sahaj A.,Pandya, Alok
supporting information, p. 9855 - 9864 (2019/07/04)
In this article, for the first time, we have reported a novel CHEF-PET fluorescence sensor L based on calix[4]arene containing four pyrene groups as binding sites, which is highly selective and sensitive towards Zn2+, Hg2+ and I-. This fluorescence probe was synthesized and characterized using the emission study, UV-vis titration, 1H NMR spectroscopy and ESI-MS investigation. The linear concentration range at pH 7 of L for Zn2+, Hg2+ and I- is 0-135 nM, 0-140 nM and 0-120 nM, respectively, with the detection limit of 6.43 nM for Zn2+, 2.94 nM for Hg2+ and 20.93 nM for I-. The binding ability was determined through Benesi-Hildebrand equation, which was found to be 7.535 × 108 M-1 for Zn2+, 9.001 × 108 M-1 for Hg2+ and 8.139 × 108 M-1 for I-. Further, we reported an easy-to-use, low-cost and disposable paper-based sensing device for the rapid chemical screening of Zn2+, Hg2+ and I-. The device comprises luminescent sensing probes embedded into a cellulose matrix, where the resonance energy transfer phenomenon seems to be the sensing mechanism. It opens up new opportunities for simple and fast screening in remote settings, where sophisticated instrumentation is not always available. The MOPAC-2016 software package was used to optimize the L using the well-established PM7 method and calculate the HOMO-LUMO energy band gap for structure L and L with Zn2+, Hg2+ and I- ion-based structures. The molecular docking study was carried out using HEX software.
FRET-based Solid-state Luminescent Glyphosate Sensor Using Calixarene-grafted Ruthenium(II)bipyridine Doped Silica Nanoparticles
Ashwin, Bosco Christin Maria Arputham,Saravanan, Chokalingam,Stalin, Thambusamy,Muthu Mareeswaran, Paulpandian,Rajagopal, Seenivasan
, p. 2768 - 2775 (2018/10/26)
Calixarene-functionalized luminescent nanoparticles were successfully fabricated for the FRET-based selective and sensitive detection of the organophosphorus pesticide glyphosate (GP). p-Tert-butylcalix[4]arene was grafted on the surface of [Ru(bpy)3]2+ incorporated SiNps to produce self-assembled nanosensors (RSC). FRET was switched on in the presence of GP by means of energy transfer due to binding with p-tert-butylcalix[4]arene grafted on the surface of the RSC. The FRET efficiency of the GP-RSC system was increased gradually with the addition of GP. The FRET efficiency was evaluated as 87.69 % and a high binding affinity was established by the binding constant value, 1.16×107 M?1, using a Langmuir binding isotherm plot. The estimated limit of detection (LOD) was 7.91×10?7 M, which was lower than the Environmental Protection Agency (EPA) recommendation. The probe also effectively responds to real sample analysis. The sensitivity and selectivity was realized due to the efficient FRET towards the fluorescence properties of the [Ru(bpy)3]2+ complex.
