Interactions of a few azole derivatives with a transport protein: role of heteroatoms

Abstract

The interaction of a few azole derivatives, 2-(4'-N,N-dimethylaminophenyl)benzimidazole, 2-(4'-N,N-dimethylaminophenyl)benzoxazole, 2-(4'-N,N-dimethylaminophenyl)oxazolo[4,5-b]pyridine with bovine serum albumin (BSA) were examined by absorption and fluorescence spectroscopy. The results were compared with the previously studied imidazopyridine derivative 2-(4'-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine. Displacement studies were carried out with site selective probes to locate the binding site of these ligands. The spectral shifts and the binding constant vary depending on the nature of the ligand. The fluorescence intensity of both oxazole derivatives 2-(4'-N,N-dimethylaminophenyl)benzoxazole and 2-(4'-N,N-dimethylaminophenyl) oxazolo[4,5-b]pyridine increases substantially in the presence of BSA, whereas the intensity of 2-(4'-N,N-dimethylaminophenyl)benzimidazole decreases. However, hypsochromic shift is observed in presence of BSA. The results obtained from the docking studies are also in good agreement with the experimental results. The location and orientation of binding depend upon the nature of the ligand. The studies revealed that apart from hydrophobic interaction, hydrogen bonding also plays a vital role in the molecular binding. Oxazoles have higher binding affinity than imidazoles and substitution of extra nitrogen further increases the binding affinity.

Tetraconazole-induced Programmed Cell Death in Schizosaccharomyces pombe

“…Azoles are antifungal agents showing variation in activity, toxicity, and interaction potential [1]. While some azoles can potentially inhibit oxidative drug-metabolizing enzyme systems [2][3][4], others were shown to interact with transporter proteins [5]. Among azole antifungal agents, tetraconazole is a systemic triazole fungicide, which is formed by a chiral carbon atom and two enantiomers and is widely used as an eradicant and protectant against fungal infections [6,7].…”

Nanoparticle and surfactant controlled switching between proton transfer and charge transfer reaction coordinates

“…The TICT emissions of dimethylamino derivative imidazopyridines were also enhanced in constrained less polar environments such as cyclodextrin (CD), proteins, and surfactants including TX-100. [59][60][61] At higher concentrations, TX-100 replaces DHP completely. With the addition of TX-100 the SPR band becomes relatively narrower and shifted hypsochromically compared to that in SDS or without surfactant.…”