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Issue 5, 2019
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Competing photochemical reactions of bis-naphthols and their photoinduced antiproliferative activity

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Abstract

The photophysical properties and photochemical reactivities of a series of bis-naphthols 4a–4e and bis-anthrols 5a and 5e were investigated by preparative irradiation 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 gave rise to radical ions that were detected for 4a and 4e by LFP. Photodehydration gave 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 abovementioned 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 an 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 with QM formation. However, these QMs do not cross-link DNA. The activity is most likely associated with the alkylation of proteins present in the cell cytoplasm, as evidenced by photoinduced alkylation of bovine and human serum albumins by 4a.

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

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Article information


Submitted
20 Nov 2018
Accepted
18 Feb 2019
First published
19 Feb 2019

Photochem. Photobiol. Sci., 2019,18, 1197-1211
Article type
Paper

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

M. Sambol, K. Ester, S. Landgraf, B. Mihaljević, M. Cindrić, M. Kralj and N. Basarić, Photochem. Photobiol. Sci., 2019, 18, 1197
DOI: 10.1039/C8PP00532J

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