1. Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol
- Author
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Nikola Basarić, Irena Martin-Kleiner, Kata Mlinarić-Majerski, Peter Wan, Marijeta Kralj, and Đani Škalamera
- Subjects
Light ,Photochemistry ,Antineoplastic Agents ,Protonation ,chemistry.chemical_compound ,Reaction rate constant ,Cell Line, Tumor ,Humans ,Hydroxymethyl ,Indolequinones ,Cell Proliferation ,Anthracenes ,quinone methide ,laser flash photolysis (LFP) ,3-hydroxymethyl-2-anthrol ,anthrol ,Anthracene ,Photolysis ,Lasers ,Organic Chemistry ,Trifluoroethanol ,Chromophore ,Quinone methide ,Chemistry ,Spectrometry, Fluorescence ,chemistry ,Flash photolysis ,Visible spectrum - Abstract
Excitation of 2-hydroxy-3-(diphenylhydroxymethyl)anthracene (7) to S1 initiates photodehydration giving the corresponding quinone methide (QM) that was detected by laser flash photolysis (LFP) in 2, 2, 2-trifluoroethanol TFE (λ = 580 nm, τ = 690 ± 10 ns). The QM decays by protonation, giving cation (λ = 520 nm, τ = 84 ± 3 μs) which subsequently reacts with nucleophiles. The rate constants in the reactions with nucleophiles were determined by LFP, whereas the adducts were isolated via preparative photolyses. The photogeneration of QMs in the anthrol series is important for potential use in biological systems since the chromophore absorbs at wavelengths > 400 nm. Antiproliferative investigations conducted with 2-anthrol derivative 7 on three human cancer cell lines showed higher activity for irradiated cells.
- Published
- 2014