Hrvatska znanstvena bibliografija (CROSBI)



Pregled bibliografske jedinice broj: 541397

Časopis

Autori: Basarić, Nikola; Cindro, Nikola; Bobinac, Damir; Uzelac, Lidija; Mlinarić-Majerski, Kata; Kralj, Marijeta; Wan, Peter
Naslov: Zwitterionic biphenyl quinone methides in photodehydration reactions of 3-hydroxybiphenyl derivatives : laser flash photolysis and antiproliferation study
Izvornik: Photochemical & photobiological sciences (1474-905X) 11 (2012), 2; 381-396
Vrsta rada: članak
Ključne riječi: 3-hydroxybiphenyl derivatives ; quinone methides ; antiproliferative activity
Sažetak:
In aqueous media, photochemical excitation to S1 of 3-phenylphenols 4-8 leads to deprotonation of the phenol OH, coupled with protonation of the benzyl alcohol and overall dehydration that delivers zwitterions 17-21. The zwitterions react with nucleophiles (CH3OH, CF3CH2OH and ethanolamine) converting them in high quantum yields to the corresponding adducts and photosolvolysis products (for photomethanolysis  ~ 0.1-0.5). Zwitterions 20 and 21 were characterized by laser flash photolysis in CH3CN-H2O (τ~7.5 and 25μs, respectively) and the associated quenching rate constants with nucleophiles azide and ethanolamine determined. In vitro studies of antiproliferative activity of the photochemicaly generated QMs and zwitterions formed from 2-, 3- and 4-phenylphenols were carried out on three human cancer cell lines HCT 116 (colon), MCF-7 (breast), and H 460 (lung). Irradiation of cells incubated with 3, 6, and 26 showed enhanced antiproliferative activity compared to the cells that were not irradiated. 3-Phenylphenol derivatives 4-8 are photoreactive and give rise to the corresponding QMs with zwitterionic structures. Irradiation of cells incubated with alkyl derivatives of 4-phenylphenol 3 and 26, and 3-phenylphenol 6, leads to enhanced antiproliferative effect compared to the cells that were kept in dark.
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/2012/pp/c1pp05338h
Broj citata:
Altmetric:
DOI: 10.1039/c1pp05338h
URL cjelovitog teksta:
Google Scholar: Zwitterionic biphenyl quinone methides in photodehydration reactions of 3-hydroxybiphenyl derivatives : laser flash photolysis and antiproliferation study
Upisao u CROSBI: eluksa@irb.hr (eluksa@irb.hr), 16. Stu. 2011. u 11:08 sati