Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol.
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 (λ = 580 nm, τ = 690 ± 10 ns). The QM decays by protonation, giving a 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.
Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute , Bijenička cesta 54, 10 000 Zagreb, Croatia.
Đani
Đ
Škalamera
Kata
K
Mlinarić-Majerski
Irena
I
Martin-Kleiner
Marijeta
M
Kralj
Peter
P
Wan
Nikola
N
Basarić
D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D045563:Indolequinones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D007834:Lasers; D008027:Light; D010777:Photochemistry; D010782:Photolysis; D013050:Spectrometry, Fluorescence; D014270:Trifluoroethanol / Q000737:chemistry*
C000594492:2-hydroxy-3-(diphenylhydroxymethyl)anthracene; D000873:Anthracenes; D000970:Antineoplastic Agents; D045563:Indolequinones; C068040:quinone methide; D014270:Trifluoroethanol