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

Funda Ozkok, Mehmet Boga, Muhammed Tuneg, Vildan Enisoglu Atalay, Nihal Onul*, Kamala Asgarova, Rabia Tigli, Sıla Arslan, Dilan Akagunduz, Rumeysa Cebecioglu, Tunc Çatal

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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)anthracene9,10-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.

Original languageEnglish
Pages (from-to)729-740
Number of pages12
JournalJournal of the Turkish Chemical Society, Section A: Chemistry
Volume9
Issue number3
DOIs
Publication statusPublished - 2022
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2022, Turkish Chemical Society. All rights reserved.

Keywords

  • Anthraquinone
  • anti-Alzheimer
  • cytotoxicity
  • in-silico
  • thioanthraquinone

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