Synthesis of novel calix[4]arenep-benzazole derivatives and investigation of their DNA binding and cleavage activities with molecular docking and experimental studies

Abstract

In this study, p-benzazole-derived calix[4]arene compounds with aromatic structures are synthesized and their DNA cleavage/binding properties are investigated.

Macrocycle-Based Antibacterial Materials

“…The p-tert-butylcalix [4]arene derivatives decorated with p-benzimidazole and benzothiazole substituents were synthesized to inhibit bacteria and eukaryotic DNA. 51 In recent years, with the rapid development of nanotechnology, supramolecular antimicrobial assemblies based on choline-modified amphiphilic macrocycles have received more and more attention. Because various substituents can be simultaneously anchored on the upper and lower rims, calix[n]arenes are also excellent candidates for amphiphilic modification and construction of self-assembled antibacterial nanomaterials.…”

“…Meanwhile, benzimidazole and benzothiazole groups were chosen to develop antibacterial materials with direct DNA binding and destroying abilities. The p - tert -butylcalix­[4]­arene derivatives decorated with p -benzimidazole and benzothiazole substituents were synthesized to inhibit bacteria and eukaryotic DNA …”

Biological activities and DNA interactions of aqueous extract of Phlomis linearis (Boiss. & Bal.)

“…DNA dodecamers PDB ID: 1BNA (Drew et al, 1981), PDB ID: 2GVR (Morsy et al, 2021), and PDB ID: 2DES (Cirilli et al, 1993), as well as the other target proteins, were selected for docking studies of the major constituents of plant extract. The DNA sequence of 1BNA is that DNA (5'-D(*CP*GP*CP*GP*AP*AP*TP*TP*CP*GP*CP*G)-3') (Alizadeh et al, 2015;El-Medani et al, 2020;Morsy et al, 2021;Ozkan et al, 2020) The 3D models of the ligands bonded to 1BNA, and their interactions was given in Figure 5. The docked ligands' conformations were ranked according to the binding energy, hydrogen bonding, and hydrophobic interactions between the ligands and the DNA (PDB ID: 1BNA, 2GVR, 2DES) (El-Medani et al, 2020).…”

Effect of Arylazo Sulfones on DNA: Binding, Cleavage, Photocleavage, Molecular Docking Studies and Interaction with A375 Melanoma and Non-Cancer Cells

“…Although most DNA-cleaving compounds are metal complexes, a significant number of research publications are devoted to organic molecules, also referred to as artificial "metalfree nucleases", aiming to identify differentiated mechanisms of action. Such compounds exhibit very diversified molecular structures, including, among the recent ones, simple oximes and hydroxylamines [5], coumarin oxime ethers [6], imidazo-phenanthrolines [7] and their carbohydrate conjugates [8], indolo-pyrimidines [9], pyridine [10] and naphthoquinone thiazole hybrids [11] and benzothiazole derivatives [12,13], bis-and tetrakis-1,2,3-triazole derivatives [14], naphthalenophanes [15], selenylated oxadiazoles [16], 2styryl-4-aminoquinazoline [17], calixarene-benzazole [18] and indolyl derivatives [19], azaenedienes [20], and the natural product Shishjimicin A [21].…”