Migration of Excitation Energy in Furocoumarins.

O.N Tchaikovskaya,V.S Chaidonova,E.N Bocharnikova,N.G Dmitrieva,P.V Avramov

doi:10.3389/fchem.2021.754950

Abstract

The migration of excitation energy of a number of psoralen compounds has been studied. For this, the methods of induced absorption spectroscopy, stationary electron spectroscopy, fluorescence and phosphorescence, as well as quantum chemistry were used. A comparative photostability of psoralen was achieved by exposure to a XeCl excilamp irradiation (emission wavelength λem = 308 nm) with parameters Δλ = 5–10 nm, Wpeak = 18 mW/cm2, p = 8.1 J/cm3, f = 200 kHz, pulse duration 1 μs. It was found that the singlet-triplet transition played a major role in the migration of excitation energy into triplet states. Among all tested compounds, substances with an OCH3-group in the structure have the strongest effect on the spectral-luminescent characteristics.

Highlights

Due to its sensitivity, fluorescence spectroscopy (Weber et al, 2020; Keuler et al, 2021) has become one of the most commonly used methods in biomedical research
The carbonyl group of furocoumarins participate in intermolecular interactions
Based on the data obtained as a result of optimization of the geometry of molecules by the AM1 method and quantumchemical calculation by the NPDP/s method, a diagram of the electronically excited states of the compounds under study is constructed

Summary

Introduction

Fluorescence spectroscopy (Weber et al, 2020; Keuler et al, 2021) has become one of the most commonly used methods in biomedical research. The authors of the work present studies of an anticancer inhibitor (Bai et al, 2021) based on a coumarin scaffold and low molecular weight phenolic compounds and show its therapeutic effect in the treatment of cancer by disrupting tubulin polymyrization. There is an active search for a “fluorescent linker” that can be both a diagnosis and a therapeutic agent. Such a theranostic prodrug becomes possible to create on the basis of a self-destructive coumarin linker. The wide possibilities for the synthesis of various coumarin derivatives using virtual combinatorial chemistry and spectrophotometry allowed the authors (Rauhamäki et al, 2018) to create a powerful low molecular weight cancer inhibitor based on 3-phenylcoumarin. The authors (Yañez et al, 2021) evaluated compounds of coumarin and quinoline derivatives as promising SARS-CoV-2 Mpro inhibitors

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