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Photochemical formation of anthracene quinone methide derivatives (CROSBI ID 239520)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Škalamera, Đani ; Mlinarić-Majerski, Kata ; Martin-Kleiner, Irena ; Kralj, Marijeta ; Oake, Jessy ; Wan, Peter ; Bohne, Cornelia ; Basarić, Nikola Photochemical formation of anthracene quinone methide derivatives // Journal of organic chemistry, 82 (2017), 12; 6006-6021. doi: 10.1021/acs.joc.6b02735

Podaci o odgovornosti

Škalamera, Đani ; Mlinarić-Majerski, Kata ; Martin-Kleiner, Irena ; Kralj, Marijeta ; Oake, Jessy ; Wan, Peter ; Bohne, Cornelia ; Basarić, Nikola

engleski

Photochemical formation of anthracene quinone methide derivatives

Anthrols 2-7 were synthesized and their photochemical reactivity investigated by irradiations in aq. CH3OH. Upon excitation with visible light (λ > 400 nm) in methanolic solutions they undergo photodehydration or photodeamination and deliver methyl ethers, most probably via quinone methides (QMs), with methanolysis quantum efficiencies ΦR = 0.02-0.3. Photophysical properties of 2-7 were determined by steady-state fluorescence and time-correlated single photon counting. Generally, anthrols 2-7 are highly fluorescent in aprotic solvents (ΦF = 0.5-0.9), whereas in aqueous solutions the fluorescence is quenched due to excited state proton transfer (ESPT) to solvent. The exception is amine 4 that undergoes excited state intramolecular proton transfer (ESIPT) in neat CH3CN where photodeamination is probably coupled to ESIPT. Photodehydration may take place via ESIPT (or ESPT) that is coupled to dehydration, or via a hitherto undisclosed pathway that involves photoionization and deprotonation of radical-cation, followed by homolytic cleavage of the alcohol OH group from the phenoxyl radical. QMs were detected by laser flash photolysis (LFP) and their reactivity with nucleophiles investigated. Biological investigation of 2-5 on human cancer cell lines showed enhancement of antiproliferative effect upon exposure of cells to irradiation by visible light, probably due to formation of electrophilic species such as QMs.

photodehydration, photodeamination, quinone methides, anthracene, laser flash photolysis, antiproliferative activity

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Podaci o izdanju

82 (12)

2017.

6006-6021

objavljeno

0022-3263

1520-6904

10.1021/acs.joc.6b02735

Povezanost rada

Kemija

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