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Pregled bibliografske jedinice broj: 877363

Časopis

Autori: Škalamera, Đani; Mlinarić-Majerski, Kata; Martin-Kleiner, Irena; Kralj, Marijeta; Oake, Jessy; Wan, Peter; Bohne, Cornelia; Basarić, Nikola
Naslov: Photochemical formation of anthracene quinone methide derivatives
Izvornik: Journal of organic chemistry (0022-3263) 82 (2017), 12; 6006-6021
Vrsta rada: članak
Ključne riječi: photodehydration, photodeamination, quinone methides, anthracene, laser flash photolysis, antiproliferative activity
Sažetak:
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.
Projekt / tema: HRZZ-IP-11-2013-5660, HRZZ-IP-2014-09-6312
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://pubs.acs.org/doi/pdf/10.1021/acs.joc.6b02735
Broj citata:
Altmetric:
DOI: 10.1021/acs.joc.6b02735
URL cjelovitog teksta:
Google Scholar: Photochemical formation of anthracene quinone methide derivatives
Upisao u CROSBI: Enidija Lukša (Enidija.Luksa@irb.hr), 26. Svi. 2017. u 08:14 sati



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