Synthesis of new calix[4]arene amide derivatives and investigation of their DNA cleavage activity

Abstract

This study comprises the synthesis of new p-tert-butylcalix[4]arene with different amide functional groups and summarises an investigation of their DNA cleavage activities. The structural investigations of the synthesised compounds were examined by FTIR, 1 H NMR, 13 C NMR, elemental analysis and FAB-MS techniques. The interaction between these compounds and pBR322 plasmid DNA has been investigated via agarose gel electrophoresis and, according to the results, compounds 5, 7, 8 and 13 exhibit efficient DNA cleavage activity. In the electrophoresis images of 5, 7 and 8, Form IV which is small DNA fragment was observed in addition to supercoiled Form I, open circular Form II and linear Form III.

Nuclearity control in calix[4]arene-based zinc(ii) coordination complexes

“…Ligand (3-4H) has been designed as a tweezer for binding the zinc cations and presents a disubstituted calix [4]arene derivative bearing two carboxylic groups connected to macrocyclic platform via benzyl moieties. The synthesis of (3-4H) was achieved in high yield following a slightly modified procedure described for preparation of its p-tert-butyl analogue 39 , 40 following a two steps procedure (Figure 2). Firstly, two appended substituents containing ester junction have been successfully grafted to the macrocyclic platform using nucleophilic substitution reaction between p-H-calix [4]arene (CA) 41 and methyl 4-(bromomethyl)benzoate in the presence of potassium carbonate acting as a base, leading to 3'.…”

“…The synthesis of (4-4H) was adapted from previously reported procedures. 39,40 Synthesis of (3-4H) The synthesis of 3-4H was achieved in two steps starting from p-H-calix [4]arene 41 as initial compound.…”

Calixarenes containing modified meso bridges

“…they form inclusion complexes useful in various fields, 1 form calixarene capsules, 2 are promising as chiral NMR solvating agents, 3 form gold 4 and silver 5 nanoparticles, are useful as catalysts 6 and as liquid crystals, 7 serve for design of sensors [8][9][10] and are promising as therapeutic agents. 11,12 Calixarenes belong to the family of cage macrocycles, including besides them cyclodextrins, [13][14][15] cucurbiturils 16,17 and pillararenes. 18 All macrocycles of this family are useful in the field of supramolecular chemistry for formation of inclusion complexes 1,[19][20][21] and rotaxanes in which they serve as rings.…”