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Zwitterionic biphenyl quinone methides in photodehydration reactions of 3-hydroxybiphenyl derivatives : laser flash photolysis and antiproliferation study


Basarić, Nikola; Cindro, Nikola; Bobinac, Damir; Uzelac, Lidija; Mlinarić-Majerski, Kata; Kralj, Marijeta; Wan, Peter
Zwitterionic biphenyl quinone methides in photodehydration reactions of 3-hydroxybiphenyl derivatives : laser flash photolysis and antiproliferation study // Photochemical & photobiological sciences, 11 (2012), 2; 381-396 doi:10.1039/c1pp05338h (međunarodna recenzija, članak, znanstveni)


Naslov
Zwitterionic biphenyl quinone methides in photodehydration reactions of 3-hydroxybiphenyl derivatives : laser flash photolysis and antiproliferation study

Autori
Basarić, Nikola ; Cindro, Nikola ; Bobinac, Damir ; Uzelac, Lidija ; Mlinarić-Majerski, Kata ; Kralj, Marijeta ; Wan, Peter

Izvornik
Photochemical & photobiological sciences (1474-905X) 11 (2012), 2; 381-396

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

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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


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

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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