97600-39-0Relevant academic research and scientific papers
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.
Preparation and investigation of temperature-responsive calix[4]arene-based molecular gels
Cai, Xiuqin,Xu, Yunhua,Yang, Rong,Yang, Hui
, p. 28476 - 28482 (2017/07/07)
A novel calix[4]arene-based tetracholesteryl derivative was synthesized, and its gelation behaviours in 30 organic solvents were studied. It showed that 1 gelled long chain alkane, some of alcohol, kerosene, ethyl acetate benzene and toluene. Interestingly the gel of 1/kerosene possessed special property, which was that the mixture solution of the compound 1/kerosene heating for a while was put on the flat contact heater and formed a gel film at 25 °C and 65 °C. Unlike ordinary film, gel film had higher strength and toughness at 65 °C, by contrast other was fragile and broken easily at 25 °C, this phenomenon was few reported before. In order to explore the phenomenon, the mechanism of the gel of 1/kerosene was discussed by Scanning Electron Microscope (SEM), High Nuclear Magnetic Resonance (H NMR), Fourier Transform Infrared Spectrometer (IR) and micro-rheology. SEM revealed that the xerogel of 1/kerosene assembled network through some long and thick fibers at 65 °C, with concentration reducing fibers become thin and its networks were clearly observed. In contrast the morphology of xerogel was porous at low concentration and was a bulk at high temperature system. According to EI data in micro-rheology, the gelation process could be divided into three stages at 65 °C and they could be that some cholesterol segments in the gelator interacting with each other formed some small aggregation in the first stage, and other cholesterol section of the gelator sufficiently were cross-linked with time and assembled into large assembly in the second plateau. In the final moment the large assembly build gel network and the system of gel tended to stable. But there are two stages at low temperature and could be some cholesterol segments that didn't take part in assembly, which may be the cause that the performance of gel was fragile.
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 (2016/08/01)
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.
Calix[4]arene-based low molecular mass gelators to form gels in organoalkoxysilanes
Yang, Hui,Zhang, Shaofei,Liu, Kaiqiang,Fang, Yu
, p. 109969 - 109977 (2016/11/30)
Three calix[4]arene derivatives (CMA, CDA and CTA) appended with one, two or four carboxyl acid structures were prepared. Gelation behaviours of the compounds and calix[4]arene itself in ten common organoalkoxysilanes were studied. It was found that at a concentration of 2% (w/v), only the compound with the most carboxyl groups (CTA) functions as a gelator, and only this compound gels with three of the liquids tested; however, the as created gels possess smart thixotropic and thermo-reversible phase transition properties. In particular, the CTA/trimethoxyphenylsilane (PTMS) gel exhibits superior mechanical strength with a storage modulus (G′) greater than 1.9 × 106 Pa and a yield stress exceeding 3600 Pa at a concentration of 6.0% (w/v). Further testing demonstrated that the gel could be used as a substrate for sensing film fabrication, injection molding and melting-free deposition molding. Moreover, the objects from the molding and fabrication could be turned into permanent structures through further hydrolysis and condensation reactions. It is believed that the LMMGs based organoalkoxysilane gels have the potential to be used as smart materials for 3D printing and pre-cursors to a functionality-oriented solid matrix.
Design, synthesis and characterization of quinoline-pyrimidine linked calix[4]arene scaffolds as anti-malarial agents
Shah, Rahul B.,Valand, Nikunj N.,Sutariya, Pinkesh G.,Menon, Shobhana K.
, p. 173 - 178 (2016/07/29)
In this paper, we report a series of quinolinepyrimidine linked calix[4]arene derivatives functionalized with 8-amino quinoline, 5-amino quinoline, 8-hydroxy quinoline, 2-amino pyrimidine and 4-amino 3-methyl quinoline. The synthesized compounds were purified and characterized by elemental analysis, FT-IR,1H NMR and ESI-MS and screened for their anti-malarial activity against plasmodium falciparum strains. Two synthesized compounds with 8-hydroxy quinoline and 2-amino pyrimidine substituents showed good antimalarial activity with IC50 0.073 and 0.043 μg/ml respectively which is comparable with the standard drug chloroquine. The present study provides valuable information for developing calix[4]arene conjugates quinoline-pyrimidine based derivatives as an effective antimalarial agents. Graphical Abstract In this paper, we report a series of quinoline-pyrimidine linked calix [4]arenes derivatives functionalised with 8-amino quinoline, 5-amino quinoline, 8-hydroxy quinoline, 2-amino pyrimidine and 4-amino 3-methyl quinoline and screened for antimalarial activity. Two synthesized compounds with 8-hydroxy quinoline and 2-amino pyrimidine substituents showed good antimalarial activity with IC50 0.073 and 0.043 μg/mL respectively, which is comparable with the standard drug chloroquine. The present study provides valuable information for developing calix[4]arene conjugates quinoline-pyrimidine derivatives.
Synthesis, structure and coordination properties of novel bifunctional carboxylic derivatives of 1,3-alternate tetrathiacalix[4]arene
Podyachev, Sergey N.,Gimazetdinova, Gulnaz Sh.,Gubaidullin, Aidar T.,Syakaev, Victor V.,Sudakova, Svetlana N.,Gabidullin, Bulat M.,Ivanov, Vladimir T.,Gogolashvili, Edward L.,Konovalov, Alexander I.
, p. 19531 - 19544 (2016/02/27)
New bifunctional derivatives of 1,3-alternate tetrathiacalix[4]arene decorated with carboxylic, ester, hydrazide and/or hydrazone groups have been synthesized with good yields using the tetrathiacalix[4]arene derivatives with incorporated pairs of carboxylic and ester groups as versatile building blocks. The structural peculiarities of the obtained bifunctional compounds have been investigated by means of X-ray analysis, IR and NMR spectroscopy. The recognition ability of the synthesized macrocycles towards some alkali, alkali-earth and transition metal ions has been investigated applying a solvent extraction method. The results showed that the structure of a calix[4]arene platform as well as the nature of functional substitutes located on opposite sides of the macrocycle are critical for the coordination properties of the synthesized compounds.
MATERIALS COATED WITH CALIXARENES
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Paragraph 0157; 0158, (2015/03/16)
This invention relates to the direct grafting of a calixarene mostly onto the surface of a material, as well as to a grafting process, and certain calixarene intermediates useful for carrying the grafting process.
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 (2014/05/20)
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.
Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as iminosugar mimics
Marradi, Marco,Cicchi, Stefano,Sansone, Francesco,Casnati, Alessandro,Goti, Andrea
supporting information; experimental part, p. 951 - 957 (2012/08/29)
The preparation of low-generation dendrimers based on a simple calix[4]arene scaffold by insertion of the iminosugar-analogue C 2-symmetric 3, 4-dihydroxypyrrolidine is described. This methodology allows a rapid incorporation of a considerable number of iminosugar-like moieties in a reduced volume and in a well-defined geometry. The inclusion of alkali-metal ions (sodium and potassium) in the polar cavity defined by the acetamide moieties at the lower rim of the calixarene was demonstrated, which allows also the rigidification of the dendrimer structure and the iminosugar presentation in the clusters. The combination of the supra-molecular properties of calixarenes with the advantage of a dendrimeric presentation of repetitive units opens up the possibility of generating well-defined multivalent and multifaceted systems with more complex and/or biologically relevant iminosugars.
