Laser-induced twisting of phosphorus functionalized thiazolotriazole as a way of cholinesterase activity change

Dmitrii Pankin, Anastasia Khokhlova, Ilya Kolesnikov, Anna Vasileva, Anna Pilip, Anastasia Egorova, Elena Erkhitueva, Vladislav Zigel, Maxim Gureev, Alina Manshina

Research outputpeer-review

Abstract

Herein, the synthesis, design, and the physicochemical characterization of phosphorus functionalized thiazolotriazole (PFT) compound are presented. The PFT tests on the biological activity revealed butyrylcholinesterase inhibition that was confirmed and explained with molecular docking studies. The pronounced reduction of optical density and biological activity was found as a result of irradiation of the PFT water solution with laser beam at wavelength 266 nm. The observed phenomenon was explained on the base of molecular dynamics, docking, and density functional theory modeling by the formation of PFT conformers via laser-induced phosphonate group twisting. The reorganization of the PFT geometry was found to be a reason of butyrylcholinesterase inhibition mechanism change and the site-specificity loss. These results demonstrate that PFT combines photoswitching and bioactive properties in one molecule that makes it promising as a molecular basis for the further design of bioactive substances with photosensitive properties based on the mechanism of the phosphonate group phototwisting.

Original languageEnglish
Article number118979
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume246
DOIs
Publication statusPublished - 5 Feb 2021

Scopus subject areas

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

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