113215-72-8Relevant articles and documents
A new chiral stationary phase for gas chromatography by use of a chiral thiacalix[4]arene derivative
Iki, Nobuhiko,Narumi, Fumitaka,Suzuki, Tomohiro,Sugawara, Atsushi,Miyano, Sotaro
, p. 1065 - 1066 (1998)
A new chiral stationary phase for capillary gas chromatography based on a chirally modified p-tert-butylthiacalix[4]arene with (S)-1-phenylethylamine was prepared to show good separations of enantiomeric amino acid, amine and alcohol derivatives, while the corresponding p-tert-butylcalix[4]arene counterpart did not differentiate the enantiomers.
Preparation and investigation of temperature-responsive calix[4]arene-based molecular gels
Cai, Xiuqin,Xu, Yunhua,Yang, Rong,Yang, Hui
, p. 28476 - 28482 (2017)
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.
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)
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.
4-tert-Butylcalix[4]arenes containing azacrown ether substituents at the narrow rim as membrane carriers
Ivanova,Prokhorova,Morzherin,Lukyanenko,Alekseeva,Basok
, p. 905 - 908 (2015)
Calixarenes substituted at the narrow rim with one or four N-methoxycarbonylmonoaza12-crown-4 moieties were used in liquid membranes to transport transition metal chlorides.
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
, p. 951 - 957 (2012)
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.
Synthesis and evaluation of the antitumor activity of Calix[4]arene L-proline derivatives
Oguz, Mehmet,Gul, Alev,Karakurt, Serdar,Yilmaz, Mustafa
, (2020)
The unique conformational properties, functionality, low toxicity, and low cost make calixarene-based compounds a valuable candidate against cancer. The aim of the present study is the synthesis of the upper rim and lower rim-functionalized L-proline-based calix[4]arene derivatives and evaluation of their cytotoxic potential for human cancerous cells as well as to determine the death mechanism. Synthesized calix[4]arene (3, 8a, 8b 13a, and 13b) derivatives were characterized by different spectroscopic techniques such as 1HNMR, 13CNMR, and FTIR. In vitro effects of compounds 3, 8a, 8b, 13a and 13b were tested on human cancerous cells (HEPG2, PC-3, A-549, and DLD-1) as well as human healthy epithelium cell (PNT1A). Results show that compounds 3, 8a, 8b and 13b have cytotoxic potential on human colorectal carcinoma cells (DLD-1) with IC50 values of 43 μM, 45.2 μM, 64.57 μM, and 29.35 μM respectively. Apoptosis ratios of cell death were investigated with flow cytometer using 7-AAD and Annexin-V as markers. Cytotoxic potential of 8a was found to be higher due to increased apoptosis, when compared with healthy cells the apoptotic cell death was significantly (p 0.0001) increased up to 1.7-fold and 2.4-fold in DLD-1 and A549 cells, respectively. In conclusion, these L-proline derived calix[4]arenes with their selective cytotoxic potential on human cancerous cells may be a potential candidate for the treatment of human CRC and lung cancer.
Nano-ranged calix[4]arene tetracarboxylic acid catalyzed expeditious protocol for spiro[dihydropyridine-oxindoles] synthesis
Sarkar, Piyali,Mukhopadhyay, Chhanda
, p. S1 - S39 (2016)
Calix[4]arene tetracarboxylic acid has been successfully established as the nanoranged organocatalyst for the synthesis of spiro[dihydropyridine-oxindoles]. Here we report a sustainable protocol for the synthesis of spiro[dihydropyridine-oxindoles], an Mannich type multi-component reaction involving the ortho-H of activated as well as un-activated aniline derivatives. A library of new spiro derivatives have been synthesized in very high yields in eco-friendly solvent water in one-pot multicomponent fashion.
Polysialosides scaffolded on p-tert-butylcalix[4]arene
Meunier, Serge J.,Roy, Rene
, p. 5469 - 5472 (1996)
p-Tert-butylcalix[4]arene (1) was transformed into known tetraethyl ester 2 to provide cone-shaped calix[4]arene used for the scaffolding of tetravalent α-sialoside. Ester 2 was transformed into acid chloride 4 which after treatment with mono-Boc-1,4-butanediamine, trifluoroacetolysis and N-chloroacetylation afforded tetraamine 7. Conjugation of α-thiosialoside 9 by nucleophilic substitution and deprotection furnished water-soluble tetravalent α-thiosialoside 12 which bound strongly to the plant lectin wheat germ agglutinin.
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)
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.
Carboxylated calixarenes bind strongly to CD69 and protect CD69+ killer cells from suicidal cell death induced by tumor cell surface ligands
Bezou?ka, Karel,?najdrová, Renata,K?enek, Karel,Van?urová, Markéta,Kádek, Alan,Adámek, David,Lhoták, Pavel,Kavan, Daniel,Hofbauerová, Kate?ina,Man, Petr,Bojarová, Pavla,K?en, Vladimír
, p. 1434 - 1440 (2010)
We have recently identified a new class of high affinity ligands for CD69 leukocyte membrane receptor, carboxylated calixarenes. Of the three compounds investigated here, thiacalix[4]arene had the highest affinity for CD69 in direct binding assays, and proved to be the most specific inhibitor of CD69 identified so far in receptor precipitation and cellular activation experiments. Carboxylated calixarenes also proved effective at protection of CD69high lymphocytes from apoptosis triggered by a multivalent ligand or antibody. Thus, carboxylated calixarenes set a new paradigm for noncarbohydrate ligands for CD69 making them attractive for protection of killer cells in combined animal tumor therapies.
Inclusion complexes of water-soluble calix[n]arenes with quercetin: preparation, characterization, water solubility, and antioxidant features
Ozyilmaz, Elif,Arpaci, Pembegul Uyar,Sayin, Serkan,Yildirim, Ayse,Ascioglu, Sebahat,Gok, Emine
, p. 201 - 209 (2022/01/20)
This study focuses on the construction of two new inclusion complexes of quercetin with p-sulfonatocalix[4]arene-tetracarboxylic acid and/or p-sulfonatocalix[8]arene-octacarboxylic acid, so that the drug gets soluble in an aqueous media. The structures of
