Novel mitochondrial and DNA damaging fluorescent Calix[4]arenes bearing isatin groups as aromatase inhibitors: Design, synthesis and anticancer activity.

Breast cancer causes a high rate of mortality all over the world. Therefore, the present study focuses on the anticancer activity of new lower rim-functionalized calix[4]arenes integrated with isatin and the p-position of calixarenes with 1,4-dimethylpyridinium iodine against various human cancer cells such as MCF-7 and MDA-MB-231 breast cancer cell lines, as well as the PNT1A healthy epithelial cell line. It was observed that compound 6c had the lowest values in MCF-7 (8.83 µM) and MDA-MB-231 (3.32 µM). Cell imaging and apoptotic activity studies were performed using confocal microscopy and flow cytometry, respectively. The confocal imaging studies with 6c showed that the compound easily entered the cell, and it was observed that 6c accumulated in the mitochondria. The Comet assay test was used to detect DNA damage of compounds in cells. It was found that treated cells had abnormal tail nuclei and damaged DNA structures compared with untreated cells. In vitro human aromatase enzyme inhibition profiles showed that compound 6c had a remarkable inhibitory effect on aromatase. Compound 6c displayed a significant inhibition capacity on aromatase enzyme with the IC50 value of 0.104 ± 0.004 µM. Thus, not only the anticancer activity of the new fluorescent derivatives, which are the subject of this study, but the aromatase inhibitory profiles have also been proven.

A fully water-soluble Calix[4]arene probe for fluorometric and colorimetric detection of toxic hydrosulfide and cyanide ions: Practicability in living cells and food samples.

Although hydrosulfide and cyanide anions play important roles in daily life that they are available in a lot of foods. However, their excess amounts contaminate water, land, and food and cause serious problems to human health. Herein, we introduce a water-soluble macrocyclic sensor based-on Calix[4]arene (MPI-Calix[4]) with dual response sites for fluorescence recognizing cyanide (CN-) and hydrogen sulfide (HS-) under longwave light. MPI-Calix[4] exhibits a high selectivity and sensitivity in the detection of CN- and HS-, where the limits of detection were as low as 0.115 and 8.12 µmol/L, respectively. The cell imaging studies shows that this probe can be easily used in the detection of CN- and HS- on living cells. Full understanding of these results paved a fruitful system to improve an applicable analytical process for food safety and quality.

A highly branched macrocycle-based dual-channel sensor: Bodipy and pillar[5]arene combination for detection of Sn (II) &Hg (II) and bioimaging in living cells.

A highly branched pillar[5]arene-based sensor containing multiple BODIPY units has been designed and synthesized (B-P[5]arene). Systematical experiments on metal ion detection of B-P[5]arene in acetonitrile/water by emission and absorption spectra indicate that this macrocycle shows high sensitivity and selectivity to both Sn (II) and Hg(II) by dual-channels. Hg (II) ions quenched to the fluorescence intensity of B-P[5]arene, while Sn (II) caused a broader spectrum without any shifting in wavelength. The detection limits of B-P[5]arene for Hg (II) and Sn (II) were found to be 1.09 × 10-6 M and 3.18 × 10-7 M, respectively. For two complex interactions, the metal ion: ligand ratio was determined as 1:2. The complex interactions between the Hg (II)&Sn(II) metal ions and B-P[5]arene are generally stable in both basic and acidic media due to strong interaction.