Synthesis and Study of Substituted Chalcones Combined with Fluoroazobenzenes—New Photoswitches for Application in Biological Systems
Piotr Tobiasz, Damian Mielecki, Anna Stachurska-Skrodzka, Jakub Miętus, Filip Borys, Hanna Krawczyk
TL;DR
This paper introduces new light-activated chalcone compounds that can control cancer cell toxicity, with one showing strong effectiveness in a prostate cancer cell line.
Contribution
The first synthesis of visible-light-activated, photoswitchable chalcone-based microtubule inhibitors with demonstrated cytotoxicity.
Findings
One photoswitch showed light-dependent cytotoxicity in PC-3 cancer cells with an IC50 of 4.75 ± 1.00 μM.
The E conformer had slightly lower activity with an IC50 of 5.80 ± 0.80 µM.
NMR, UV spectroscopy, and computational methods confirmed the compound structures and properties.
Abstract
Chalcones have garnered significant research interest due to their various medical bioactivities. Several chalcone compounds have been approved for marketing and clinical use in the treatment of various diseases. A critical aspect of the action of chalcones is their effect on microtubules. They are considered an excellent target for chemotherapeutic agents for the treatment of cancer. Consequently, scientists are constantly developing novel chalcone drug agents and also innovative drug delivery strategies. In this manuscript, we report the first synthesis of 12 new visible-light-activated, photoswitchable chalcone-based microtubule inhibitors (17a–17l). Among the obtained compounds, one photoswitch demonstrated light-dependent cytotoxicity in the PC-3 cancer cell line. The IC50 value of the Z conformer was determined to be 4.75 ± 1.00 μM after 48 h of treatment. The E conformer…
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Taxonomy
TopicsPhotochromic and Fluorescence Chemistry · Click Chemistry and Applications · Synthesis of Organic Compounds