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Pregled bibliografske jedinice broj: 526189

Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity


Basarić, Nikola; Cindro, Nikola; Bobinac, Damir; Mlinarić-Majerski, Kata; Uzelac, Lidija; Kralj, Marijeta; Wan, Peter
Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity // Photochemical & photobiological sciences, 10 (2011), 12; 1910-1925 doi:10.1039/C1PP05182B (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 526189 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity

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

Izvornik
Photochemical & photobiological sciences (1474-905X) 10 (2011), 12; 1910-1925

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

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.

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

Profili:

Avatar Url Marijeta Kralj (autor)

Avatar Url Nikola Basarić (autor)

Avatar Url Kata Majerski (autor)

Avatar Url Lidija Uzelac (autor)

Avatar Url Nikola Cindro (autor)

Citiraj ovu publikaciju

Basarić, Nikola; Cindro, Nikola; Bobinac, Damir; Mlinarić-Majerski, Kata; Uzelac, Lidija; Kralj, Marijeta; Wan, Peter
Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity // Photochemical & photobiological sciences, 10 (2011), 12; 1910-1925 doi:10.1039/C1PP05182B (međunarodna recenzija, članak, znanstveni)
Basarić, N., Cindro, N., Bobinac, D., Mlinarić-Majerski, K., Uzelac, L., Kralj, M. & Wan, P. (2011) Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity. Photochemical & photobiological sciences, 10 (12), 1910-1925 doi:10.1039/C1PP05182B.
@article{article, year = {2011}, pages = {1910-1925}, DOI = {10.1039/C1PP05182B}, keywords = {antiproliferative activity, quinone methides, laser flash photolysis}, journal = {Photochemical and photobiological sciences}, doi = {10.1039/C1PP05182B}, volume = {10}, number = {12}, issn = {1474-905X}, title = {Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity}, keyword = {antiproliferative activity, quinone methides, laser flash photolysis} }

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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