Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol

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

doi:10.1021/jo500290y

Pregled bibliografske jedinice broj: 695559

Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol

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

Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol // Journal of organic chemistry, 79 (2014), 10; 4390-4397 doi:10.1021/jo500290y (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 695559 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol

Autori
Škalamera, Đani ; Mlinarić-Majerski, Kata ; Martin-Kleiner, Irena ; Kralj, Marijeta ; Wan, Peter ; Basarić, Nikola

Izvornik
Journal of organic chemistry (0022-3263) 79 (2014), 10; 4390-4397

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
quinone methide ; laser flash photolysis (LFP) ; 3-hydroxymethyl-2-anthrol ; anthrol

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti

POVEZANOST RADA

Projekti:
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Majerski, Kata, MZOS ) ( CroRIS)
02.05/25 - Fotokemija policikličkih molekula: od istraživanja mehanizama reakcije do novih lijekova i medicinskih primjena (Basarić, Nikola, HRZZ ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Nikola Basarić (autor)