112269-92-8

Usage

Uses

Used in Environmental Applications:
4-SULFOCALIX[4]ARENE is used as a component in the preparation of resins for the removal of toxic metals from canola oil. Its ability to form complexes with metal ions allows for efficient and selective removal of these contaminants, contributing to the purification and safety of the oil.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, 4-SULFOCALIX[4]ARENE is used as a stabilizing agent for chrysazine, an anti-tumor compound. By inducing inhibition of the prototropic tautomerism in chrysazine, it helps maintain the compound's stability and effectiveness, potentially improving its therapeutic outcomes in cancer treatment.

InChI:InChI=1/C28H24O16S4/c29-25-13-1-14-6-22(46(36,37)38)8-16(26(14)30)3-18-10-24(48(42,43)44)12-20(28(18)32)4-19-11-23(47(39,40)41)9-17(27(19)31)2-15(25)7-21(5-13)45(33,34)35/h5-12,29-32H,1-4H2,(H,33,34,35)(H,36,37,38)(H,39,40,41)(H,42,43,44)

Upstream product

• 98-54-4 para-tert-butylphenol 
• 157432-87-6 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 
• 248590-47-8 25,26,27,28-tetrakis(hydroxy)calix[4]arene 

Relevant academic research and scientific papers

Needle-shaped amphoteric calix[4]arene as a magnetic nanocarrier for simultaneous delivery of anticancer drugs to the breast cancer cells

Background: Chemotherapy as an important tool for cancer treatment faces many obstacles such as multidrug resistance and adverse toxic effects on healthy tissues. Drug delivery systems has opened a new window to overcome these problems. There has been a strong interest development of new platform and system for delivof chemotherapeutic agents. Purpose: In the present study, a green synthesis method was chosen and performed for preparation of a novel amphoteric calix[4]arene (Calix) macrocycle with low toxicity to the human body. Materials and methods: The amphoteric Calix was coated on the surface of Fe3O4 magnetic nanoparticles and used as a magnetic nanocarrier for simultaneous delivery of two anticancer agents, doxorubicin and methotrexate, against MCF7 cancer cells. Several chemical characterizations were done for validation of prepared nanocarrier, and in vitro loading and release studies of drugs were performed with good encapsulation efficiency. Results: In vitro biological studies including hemolysis assay, erythrocytes sedimentation rate, red blood cells aggregation, cyto cellular internalization, and apoptosis evaluations were performed. Based on results, the developed nanocarrier has many advantages and capability for an efficient codelivery of DOX and MTX, which has a highly potent ability to kill cancer cells. Conclusion: All these results persuade us, this nanocarrier could be effectively used for cancer therapy of MCF7 breast cancer cells and is suitable for use in further animal studies in future investigations.

P-Sulfonic acid calix[4]arene as an efficient and reusable catalyst for the synthesis of acridinediones and xanthenes

p-Sulfonic acid calix[4]arene has been found to be an efficient catalyst for the synthesis of acridinediones and xanthenes under mild conditions in excellent yields. The present approach offers the advantages of simple methodology, short reaction time, an

Highly branched amine-functionalized: P -sulfonatocalix[4]arene decorated with human plasma proteins as a smart, targeted, and stealthy nano-vehicle for the combination chemotherapy of MCF7 cells

Nanotechnology has recently emerged as a promising field for biomedical applications, especially the targeted delivery of drugs to tumors. Besides, combination chemotherapy is common in cancer treatment and is rapidly evolving. Therefore, the successfully delivery of chemotherapeutic drugs to targeted cancers is a big challenge. In this study, we endeavour to develop a nano-vehicle, based on highly branched amine-functionalized p-sulfonatocalix[4]arene, to act as a dual-drug carrier for the co-delivery of DOX and MTX to MCF7 breast cancer cells with targeting and synergistic effects. After the synthesis and preparation of the nano-vehicle, structural characterization was also conducted (FTIR, AFM, VSM, SEM, EDX, XRD, DLS, and zeta potential analyses). Drug loading and release studies on the prepared drug-loaded nano-vehicle were conducted to optimize the formulation. The designed platform has targeting and pH-triggered drug release capabilities to improve the therapeutic index of DOX and MTX. Hemolysis assay results proved that the nano-vehicle has high blood compatibility, even for high dosage treatment. The protein-particle interactions of the nano-vehicle in human blood circulation systems were simulated via SDS-PAGE assays and the results indicated that a series of proteins were attached to the surface of the nano-vehicle. This feature gives the nano-vehicle stealth properties in the blood circulation system. The cellular uptake, from flow-cytometry and fluorescence microscopy, validated that the human plasma proteins attached to the nano-vehicle surface gave the nano-vehicle high internalization capabilities into cells due to the presence of some protein receptors on the surfaces of cancer cells, improving the tumor cell targeting properties. MTT assays and DAPI staining were also performed to show the viability and DNA fragmentation of treated cells. All results validated one another and confirmed that our designed nano-vehicle is useful for targeted and combination drug delivery systems with stealth properties.

A calix[4]arene-based ternary supramolecular nanoassembly with improved fluoroquinolone photostability and enhanced NO photorelease

Micellar-like nanoassemblies of a sulfonate amphiphilic calix[4]arene (1) are able to effectively co-entrap the fluoroquinolone antibacterial norfloxacin (2) and a hydrophobic nitric oxide (NO) photodonor (3), leading to a ternary supramolecular complex having a diameter of ca. 150 nm and a zeta potential of -48 mV. Outstanding photochemical stabilization of the otherwise photolabile fluoroquinolone 2 is observed under UVA excitation. Besides, visible light excitation leads to a remarkable enhancement of the NO photorelease efficiency of 3. Both the results can be explained on the basis of a "cage effect" of the micellar host that, in the case of 2, hinders the formation of the precursor complex responsible for the photodegradation, whereas in the case of 3 it provides a low polarity environment and easily abstractable hydrogens, which facilitate the radical-mediated mechanism involved in NO photorelease. Therefore, this supramolecular ternary nanoassembly simultaneously overcomes the main limitations of the free individual guests such as photolability and low photoreactivity. In view of the well-known antibacterial properties of the NO radical and the biocompatibility of the calixarene host, this nanoassembly represents a suitable bimodal system to be tested in antibacterial research.

Synthesis of para-sulfonatocalix[4]arene-modified silver nanoparticles as colorimetric histidine probes

This Communication reports a novel colorimetric sensor to probe histidine in water based on para-sulfonatocalix[4]arene-modified silver nanoparticles; this highly selective sensor allows a rapid quantitative assay of histidine down to a concentration of 5 × 10-6 M, providing a new tool for the direct measurement of histidine. The Royal Society of Chemistry.

Novel catanionic vesicles from calixarene and single-chain surfactant

The mixed system between p-sulfonatocalix[4]arene and tetradecyltrimethylammonium bromide forms unilamellar vesicles after sonication of the aqueous dispersion. Furthermore these vesicles can be stored, without use of lyoprotectants, by lyophilization and

P-Sulfonic acid calix[n]arenes as organocatalysts for the transesterification reaction of Passiflora seed oil

The catalytic activity of p-sulfonic acid calix[4]arene was studied in the transesterification reactions of Passiflora seed oil with methanol or ethanol. Calix[n]arenes are highly versatile organocatalysts and conversion rates >98 % were obtained for the transformation of Passiflora seed oil to its methyl or ethyl esters after 5 h of reaction in the presence of p-sulfonic acid calix[4]arene (3.52 mol % in ethanol; 5.28 mol % in methanol). Moreover, the organocatalyst was recovered and reused in two subsequent cycles without a significant decrease in the activity or selectivity. The use of a non-corrosive and reusable organocatalyst is the positive aspect of this process.

Investigation of hydrogen bonding in p-sulfonatocalix[4]arene and its thermal stability by vibrational spectroscopy

The vibrational spectra of p-sulfonatocalix [4] arene were studied. The geometrical parameters, the energies, the frequencies and the intensities of the bands in the IR and Raman spectra are calculated for four conformations. The most stable conformation of the p-sulfonatocalix[4]arene is the cone due to the cooperative cyclic intramolecular hydrogen bonding system. The strength of the hydrogen bonds depends on the type of substituent on the upper rim of the calixarene molecules. We studied the process of destruction of calixarenes using IR spectroscopy and TGA methods. Characteristic bands for each conformation were selected. HOMO covers aromatic units with notable conjugation, and LUMO belongs to sulfonate groups.

Synthesis and anti-HIV evaluation of water-soluble calixarene-based bithiazolyl podands

Nine anionic water-soluble calix[4]arene species, incorporating sulfonate, carboxylate or phosphonate groups, six of them incorporating two 2,2′-bithiazole subunits in alternate position at the lower rim, have been synthesised and evaluated as anti-HIV agents on various HIV strains and cells of the lymphocytic lineage (HIV-1 III B/MT4, HIV-1 LAI/CEM-SS, HIV-1 Bal/PBMC), using AZT as reference compound. A toxicity was detected for a minority of compounds on PBMC whereas for the others no cellular toxicity was measured at concentrations up to 100 μM. Most of the compounds have an antiviral activity in a 10-50 μM range, and one of them, sulfonylated, displays its activity, whatever the tropism of the virus, at a micromolar concentration.

NMR evidence of slow monomer-micelle exchange in a calixarene-based surfactant

The self-aggregation of amphiphilic p-sulfonatocalix[4]arene was studied by fluorescence and NMR techniques. Pyrene fluorescence spectra were used to determine the critical micelle concentration and the value obtained was confirmed using Diffusion-Ordered NMR Spectroscopy (DOSY). It was found from the 1H NMR spectra that exchange between the monomers in the bulk and in the micelles is slow on the NMR time scale. This finding was confirmed by 2D EXSY experiments and the rate constants of the process at different temperatures were extracted using the latter technique.