In the recent decades, the interest on substituted furan containing compounds has dramatically increased, mainly because these classes of compounds have unique and interesting biological properties from medicinal chemistry points of view. Thiadiazole and thiazoline compounds have, extensively, found outstanding pharmacological applications. They have a sulfur atom that provides better lipohilicity than other substituted furan. These compounds easily penetrate cellular membranes and interact with various biological targets. Thiadiazole and thiazoline derivatives are used as anticancer, antiepileptic, antiviral, antibacterial, anti-fungal, antidiabetic, analgesic, and anti-inflammatory drugs. The two new thiadiazole and thiazoline FCP24A, FCP27A derivatives were selected. They represent 1,6-anhydrosugars functionalized at C-4 position. We compared biological properties between FCP24A and FCP27A in the context of their anticancer properties. We used a human ovarian cancer cell line (A2780) as a cancer model. Cytotoxicity and cell viability was tested by Resazurin based assay. Genotoxicity was evaluated with the alkaline version of comet assay. The level of oxidative stress was analyzed by flow cytometry as well as modified comet assay with hOGG1 enzyme and spin traps. Apoptosis and necrosis was performed using flow cytometry and colorimetric assay. Colorimetric assay was also used to test thioredoxin reductase (TrxR) (EC 1.8.1.9) and glutathione reductase (EC 1.8.1.7). Both compound exhibited significantly high anticancer activities compared to cisplatin (positive control) with IC<sub>50</sub> values 56.5 ± 1.2, 47.29 ± 1.5, respectively but the anticancer mechanism seems to be different. FCP24A induced DNA lesions, whereas, FCP27A did not. These DNA lesions were oxidative modified bases with oxidative stress origin. FCP24A evoke high oxidative stress correlated with TrxR inhibition. FCP27A shows high toxicity without inducing apoptosis and oxidative stress. Despite the similar IC<sub>50</sub> value, the 1,6-anhydrosugar functionalized at C-4 position with amino thiadiazole moiety induces necrotic cell death at a much higher level than 1,6-anhydrosugars functionalized at C-4 position with thiazoline and has high oxidative properties.

Comparison of biological activity of 1,6-anhydrosugars functionalized at C-4 position with amino thiadiazole and thiazoline moieties: Key role of triazole moiety in oxidative stress and necrosis induction

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.