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Pregled bibliografske jedinice broj: 526189

Časopis

Autori: Basarić, Nikola; Cindro, Nikola; Bobinac, Damir; Mlinarić-Majerski, Kata; Uzelac, Lidija; Kralj, Marijeta; Wan, Peter
Naslov: Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity
Izvornik: Photochemical & photobiological sciences (1474-905X) 10 (2011), 12; 1910-1925
Vrsta rada: članak
Ključne riječi: antiproliferative activity ; quinone methides ; laser flash photolysis
Sažetak:
In aqueous media, photochemical excitation (S1) of hydroxyadamantyl, diphenylhydroxymethyl, and hydroxypropyl derivatives of 4-phenylphenol 5-9 leads to solvent-assisted deprotonation of the phenol OH, and protonation of the benzyl alcohol coupled with dehydration, that delivers quinone methides (QM) 14-18. The QMs react with CH3OH converting them in high quantum yields to the photosolvolysis products (overall  ~ 0.1-0.5). QMs were characterized by laser flash photolysis in CH3CN-H2O and TFE. In TFE, the zwitterionic QM 15 has a lifetime of 250 ns, whereas para QMs 16 and 17 have lifetimes of 500 μs and 1.1 s, respectively. Introduction of the steric hindrance to the parent QM structure (with the adamantyl moiety), or additional stabilization by two phenyl rings, results in an increase of QM lifetimes and selectivity in the reactions with nucleophiles. In vitro studies of antiproliferative activity of photochemicaly generated QMs 15-17 were carried out on one human cancer cell line. Irradiation of cells incubated with 7 showed enhanced antiproliferative activity compared to cells that were not irradiated, in accordance with the activity being due to the formation of QM 16.
Projekt / tema: HRZZ-UIP-02.05/25, 098-0982933-2911
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
MEDLINE
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,Temeljne medicinske znanosti
URL Internet adrese: http://pubs.rsc.org/en/content/articlelanding/2011/pp/c1pp05182b
Broj citata:
Altmetric:
DOI: 10.1039/C1PP05182B
URL cjelovitog teksta:
Google Scholar: Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity
Upisao u CROSBI: eluksa@irb.hr (eluksa@irb.hr), 20. Ruj. 2011. u 10:59 sati



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