Effects of Substituents on the Photophysical/Photobiological Properties of Mono-Substituted Corroles

Abstract

The trans-A2B-corrole series was prepared starting with 5-(pentafluorophenyl)dipyrromethene, which was then reacted with respective aryl-substituted aldehyde by Gryko synthesis. It was further characterized by HRMS and electrochemical methods. In addition, we investigated experimental photophysical properties (absorption, emission by steady-state and time-resolved fluorescence) in several solvents and TDDFT calculations, aggregation, photostability and reactive oxygen species generation (ROS), which are relevant when selecting photosensitizers used in photodynamic therapy and many other photo-applications. In addition, we also evaluated the biomolecule-binding properties with CT-DNA and HSA by spectroscopy, viscometry and molecular docking calculations assays.

First report oftrans-A2B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays

“…In this way, the presence of C 6 F 5 groups increases the photostability of the corrole, which was also observed in other corrole derivatives in the literature. 27 Moreover, no changes in the profile of the electronic spectra of corrole was observed, possibly indicating that there was no formation of by-products under photo-bleaching conditions (see ESI – Fig. S12 and S13 † ).…”

“…The uorescence quantum yields (F f ) and Stokes Shis (SS) are measured in all solvents (Table 1) and the results are low and agree with similar uorescence properties of corrole derivatives in the literature. 27 The small SS values were observed for all solvents, and this can be attributed to the vibrational relaxation or dissipation and solvent reorganization, which can increase the separation of the energy levels of the ground and excited states. Using time-resolved uorescence decay (s f ), the corrole H 3 -LapCor presented slightly variation in the uorescence decays according to the solvent polarity (Table 1).…”

“…The uorescence lifetime measured for corrole are in agreement with those obtained for other corrole derivatives in the literature. 27 Using the radiative decay time (s r ), it is possible to see that the is very slow when compared with the uorescence lifetime in all solvents, indicating that probably for corrole H 3 LapCor the main relaxation mechanisms are probably the internal conversion (IC) and/or triplet state formation. (green).…”

Red-emission, photobiological properties and antimicrobial photodynamic assays using mono-substituted corroles contain carboxylic acid and ester units

“…The ability of each corrole derivative to produce ROS was investigated and for singlet oxygen generation species ( 1 O 2 ) was using 1,3-diphenylisobenzofuran (DPBF) in DMF, DMSO and MeCN solutions by UV-Vis spectroscopy. Using as example, Figure 6a-b show the singlet oxygen production parameters for corrole TPhCor as standard in DMSO (Φ Δ = 67.0%) [4];…”

Synthesis of anionic and cationic corroles and study of their complexing ability and photodynamic activity towards DNA and albumin

“…From the point of view of the interaction of corroles with DNA, a number of studies can be distinguished. The interaction of corroles with DNA through intercalation or interactions at major and minor grooves can cause structural changes in DNA and possible cell destruction through apoptosis or necrosis [9]. Cationic corroles interact more strongly with DNA than analogous porphyrins and form both intercalation and outside binding [10].…”