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

作者：

Funda OZKOK , Mehmet BOĞA , Muhammed TUNEG , Vildan ENİSOĞLU ATALAY , Nihal ONUL , Kamala ASGAROVA , Rabia TIĞLI , Sıla ARSLAN , Dilan AKAGÜNDÜZ , Rumeysa CEBECİOĞLU , Tunç ÇATAL

作者单位：

Organic Chemistry Division, Department of Chemistry, Faculty of Engineering, Istanbul UniversityCerrahpaşa, Avcılar, 34320, Istanbul, Turkey , Dicle University, Faculty of Pharmacy, Department of Analytical Chemistry, 21280, Diyarbakir, Turkey , Uskudar University, Faculty of Engineering and Natural Sciences, Department of Molecular Biology and Genetics, 34662, Uskudar, Istanbul, Turkey , Istanbul Protein Research-Application and Inovation Center (PROMER), Uskudar University 34662 Uskudar, Istanbul, Turkey

摘要：

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 4-aminothiophenol (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.

语种：

DOI：

10.18596/jotcsa.963290

来源期刊：

Journal of the Turkish Chemical Society, Section A: Chemistry

出版商：

Turkish Chemical Society

年，卷（期）：

2022;9(3):729-74