Evaluation of Acetyl- and Butyrylcholinesterase Enzyme Inhibitory Activities and Cytotoxic Activities of Anthraquinone Derivatives

Abstract

In this study, the enzyme activity of anthraquinone compounds which were synthesized beforehand by our research group was investigated. Molecular docking studies were performed for compounds 1-(4-aminophenylthio)anthracene-9,10-dione (3) and 1-(4-chlorophenylthio)anthracene-9,10-dione (5). Compound 3 was synthesized from the reaction of 1-chloroanthraquinone (1) and 4aminothiophenol (2). Compound 5 was synthesized (1) from the reaction of 1-chloroanthraquinone (1) and 4-chlorothiophenol (4). Anthraquinone analogs (3, 5) were synthesized with a new reaction method made by our research group (2). Inhibitory effects of compounds 3 and 5 were investigated against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes which are related to Alzheimer's Disease (AD). Compounds 3 and 5 exhibited strong anti-acetyl-and butyryl-cholinesterase inhibition activities than galanthamine used as standard compound (92.11±1.08 and 80.95±1.77 %, respectively). The EHOMO-ELUMO values, molecular descriptors, and the calculated UV-Vis spectra of anthraquinone derivatives were computed by B3LYP/6-31+G(d,p) levels in the CHCl3 phase. Based on the fluorescence property of the anthraquinone skeleton, the fluorescence activity of the bioactive anthraquinone analogue (5) was investigated. MTT test was performed to determine the cytotoxic effects of thioanthraquinone molecules 3 and 5. In MTT analyses, 3 compounds showed the highest effect against Ishikawa cells at a dose of 10 µg/mL, while compound 5 showed the highest effect at a dose of 50 µg/mL. The cell viability for compound 3 was 84.18% for 10 µg/mL and the cell viability for compound 5 was 75.02% for 50 µg/mL.

Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone

“…A new, practical and economical synthesis method for the synthesis of amino and thio-anthraquinone molecules has been developed in previous studies of our team (1). Various amino and thioanthraquinone analogues were synthesized with this new synthesis method (29)(30)(31). It was determined that these amino and thioanthraquinone derivatives synthesized in previous studies show anticancer and antimicrobial activities (29)(30)(31).…”

“…Various amino and thioanthraquinone analogues were synthesized with this new synthesis method (29)(30)(31). It was determined that these amino and thioanthraquinone derivatives synthesized in previous studies show anticancer and antimicrobial activities (29)(30)(31). In a study by Şahin, Y.M.…”