Tetracyclic Thioxanthene Derivatives: Studies on Fluorescence and Antitumor Activity
authors Duraes, F; Silva, PMA; Novais, P; Amorim, I; Gales, L; Esteves, CIC; Guieu, S; Bousbaa, H; Pinto, M; Sousa, E
nationality International
author keywords thioxanthenes; theranostic; antitumor activity; photophysics
abstract Thioxanthones are bioisosteres of the naturally occurring xanthones. They have been described for multiple activities, including antitumor. As such, the synthesis of a library of thioxanthones was pursued, but unexpectedly, four tetracyclic thioxanthenes with a quinazoline-chromene scaffold were obtained. These compounds were studied for their human tumor cell growth inhibition activity, in the cell lines A375-C5, MCF-7 and NCI-H460. Photophysical studies were also performed. Two of the compounds displayed GI(50) values below 10 mu M for the three tested cell lines, and structure-activity relationship studies were established. Three compounds presented similar wavelengths of absorption and emission, characteristic of dyes with a push-pull character. The structures of two compounds were elucidated by X-ray crystallography. Two tetracyclic thioxanthenes emerged as hit compounds. One of the two compounds accumulated intracellularly as a bright fluorescent dye in the green channel, as analyzed by both fluorescence microscopy and flow cytometry, making it a promising theranostic cancer drug candidate.
publisher MDPI
isbn 1420-3049
year published 2021
volume 26
issue 11
digital object identifier (doi) 10.3390/molecules26113315
web of science category 13
subject category Biochemistry & Molecular Biology; Chemistry, Multidisciplinary
unique article identifier WOS:000660368900001
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journal impact factor 3.267
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