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Competing photochemical reactions of bis-naphthols and their photoinduced antiproliferative activity


Sambol, Matija; Ester, Katja; Landgraf, Stephan; Mihaljević, Branka; Cindrić, Mario; Kralj, Marijeta; Basarić, Nikola
Competing photochemical reactions of bis-naphthols and their photoinduced antiproliferative activity // Photochemical & photobiological sciences, 18 (2019), 1197-1211 doi:10.1039/c8pp00532j (međunarodna recenzija, članak, znanstveni)


Naslov
Competing photochemical reactions of bis-naphthols and their photoinduced antiproliferative activity

Autori
Sambol, Matija ; Ester, Katja ; Landgraf, Stephan ; Mihaljević, Branka ; Cindrić, Mario ; Kralj, Marijeta ; Basarić, Nikola

Izvornik
Photochemical & photobiological sciences (1474-905X) 18 (2019); 1197-1211

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

Ključne riječi
Naphthols, photodehydration, quinone methides, antiproliferative activity, DNA cross-linking, photoinduced electron transfer, protein alkylation

Sažetak
Photophysical properties and photochemical reactivity for a series of bis-naphthols 4a-4e and bis-anthrols 5a and 5e were investigated by preparative irradiations in CH3OH, fluorescence spectroscopy and laser flash photolysis (LFP). Methanolysis taking place via photodehydration (bis-naphthols ΦR = 0.04-0.05) is in competition with symmetry breaking charge separation (SB-CS). The SB-CS gives rise to radical ions that were for 4a and 4e detected by LFP. Photodehydration gives quinone methides (QMs) that were also detected by LFP (λmax = 350 nm, τ ≈ 1-2 ms). In the aqueous solvent, excited state proton transfer (ESPT) competes with the above mentioned processes, giving rise to naphtholates, but the process is inefficient and can only be observed in the buffered aqueous solution at pH >7. Since the dehydration of bis-naphthols delivers QMs, their potential antiproliferative activity was investigated by MTT test on three human cancer cell lines (NCI-H1299, lung carcinoma ; MCF-7, breast adenocarcinoma ; and SUM159, pleomorphic breast carcinoma). Cells were treated with 4 or 5 with or without irradiation (350 nm). An enhancement of the activity (up to 10-fold) was observed upon irradiation, which may be associated to the QM formation. However, these QMs do not cross-link DNA. The activity is most likely associated to the alkylation of proteins present in the cell cytoplasm, as evidenced by photoinduced alkylation of bovine and human serum albumins by 4a.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2013-11-5660 - Mulitidisciplinarni pristup otkriću lijekova s ciljanim djelovanjem na matične stanice tumora – uloga transporta kalija (Marijeta Kralj, )
HRZZ-IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (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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