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

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

Pages : 729-740

Doi:10.18596/jotcsa.963290

View : 13 | Download : 5

Publication Date : 2022-08-31

Article Type : Research Paper

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-insert ignore into journalissuearticles values(4-aminophenylthio);anthracene-9,10-dione insert ignore into journalissuearticles values(3); and 1-insert ignore into journalissuearticles values(4-chlorophenylthio);anthracene-9,10-dione insert ignore into journalissuearticles values(5);. Compound 3 was synthesized from the reaction of 1-chloroanthraquinone insert ignore into journalissuearticles values(1); and 4-aminothiophenol insert ignore into journalissuearticles values(2);. Compound 5 was synthesized insert ignore into journalissuearticles values(1); from the reaction of 1-chloroanthraquinone insert ignore into journalissuearticles values(1); and 4-chlorothiophenol insert ignore into journalissuearticles values(4);. Anthraquinone analogs insert ignore into journalissuearticles values(3, 5); were synthesized with a new reaction method made by our research group insert ignore into journalissuearticles values(2);. Inhibitory effects of compounds 3 and 5 were investigated against acetylcholinesterase insert ignore into journalissuearticles values(AChE); and butyrylcholinesterase insert ignore into journalissuearticles values(BuChE); enzymes which are related to Alzheimer’s Disease insert ignore into journalissuearticles values(AD);. Compounds 3 and 5 exhibited strong anti-acetyl- and butyryl-cholinesterase inhibition activities than galanthamine used as standard compound insert ignore into journalissuearticles values(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+Ginsert ignore into journalissuearticles values(d,p); levels in the CHCl3 phase. Based on the fluorescence property of the anthraquinone skeleton, the fluorescence activity of the bioactive anthraquinone analogue insert ignore into journalissuearticles values(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.
Keywords : anthraquinone, cytotoxicity, anti Alzheimer, in silico, thio anthraquinone