Naslov
Synthesis and antiproliferative activity of anthrols and the corresponding quinone methides

Autori
Sambol, Matija ; Škalamera, Đani ; Basarić, Nikola ; Mlinarić-Majerski, Kata ; Martin- Kleiner, Irena ; Kralj, Marijeta

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
MACROCYCLES - synthesis, medicinal chemistry and biological activity / - Zagreb, 2014

Skup
MACROCYCLES - synthesis, medicinal chemistry and biological activit

Mjesto i datum
Zagreb, Hrvatska, 28.04.2014. - 29.04.2014

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
anthrols ; anthracene derivatives ; photodehydration ; quinone methides ; antiproliferative activity

Sažetak
Quinone methides (QM) are commonly encountered reactive intermediates in chemistry of phenols. [1] They are associated to the biological activity of numerous natural and synthetic compounds, as anticancer drugs, or mechanism- based enzyme inactivators.[1] Photochemical methods provide a mild approach for the generation of QMs, since they allow for formation of QMs inside living cells. Consequently, photochemical approach to generate QMs is very appropriate for the use in biological systems, e. g. for cancer treatment. Within the on-going interest in our laboratory in photochemical formation of QMs and their antiproliferative activity, [2] we have prepared precursors of anthracene QMs that on excitation with near-visible light (>350 nm) give QMs. Herein we report synthesis of compounds 1a-1e, 2 and 3 and investigation of their antiproliferative activity with and without exposure of cells to irradiation. Whereas derivatives 1 undergo photodehydration or photodeamination to furnish QMs [3], compounds 2, 3 and 4 cannot give QMs, so they were chosen as reference compounds. Antiproliferative activity of compounds 1-4 was investigated on three human cancer cell lines (colon HCT 116, breast MCF-7, and lung H 460), with and without exposure of cells to irradiation (350 nm, 420 nm and white light). Interestingly, enhancement of the antiprolieferative effect was observed also with compounds that cannot give QMs. The mechanism of potential biological action will be discussed.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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