7,8-Dihydroxycoumarin derivatives: In silico molecular docking and in vitro anticholinesterase activity

被引：3

作者：

Ozdemir, Mucahit ^{[1
]}

Taskin, Duygu ^{[2
]}

Ceyhan, Deniz ^{[3
]}

Koksoy, Baybars ^{[4
]}

Taskin, Turgut ^{[5
]}

Bulut, Mustafa ^{[1
]}

Yalcin, Bahattin ^{[1
]}

机构：

[1] Marmara Univ, Fac Arts & Sci, Dept Chem, TR-34722 Istanbul, Turkiye

[2] Univ Hlth Sci, Fac Pharm, Dept Analyt Chem, TR-34668 Istanbul, Turkiye

[3] Namik Kemal Univ, Fac Arts & Sci, Dept Chem, TR-59030 Tekirdag, Turkiye

[4] Bursa Tech Univ, Fac Engn & Nat Sci, Dept Chem, TR-16310 Bursa, Turkiye

[5] Marmara Univ, Fac Pharm, Dept Pharmacognosy, TR-34668 Istanbul, Turkiye

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2023年 / 1274卷

关键词：

Coumarin; Acetylcholinesterase; Antioxidant assay; Biological activity; Molecular docking; COUMARIN DERIVATIVES; ANTICANCER AGENTS; CRYSTAL-STRUCTURE; ANTIOXIDANT; CONDENSATION; INHIBITORS; TOXICITY; EXCHANGE; OXIDASE; COMPLEX;

D O I：

10.1016/j.molstruc.2022.134535

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

In this study, acetylcholinesterase enzyme (AChE) inhibition potential and antioxidant activity of eight different coumarin derivatives together with two ( 5 and 8 ) newly synthesized coumarins were investigated. The results showed that all compounds exhibited inhibitory activity on AChE. Compounds 1 (96.83%), 3 (96.72%), and 2 (95.48%) showed the highest inhibitory activity and the results were more significant than that of galantamine (93.14%). Compound 7 displayed the most potent inhibition of AChE (92.12%), close to galantamine. Molecular docking studies of AChE were carried out to support in vitro testing. In addition, the antioxidant activities of coumarins were performed with DPPH, FRAP, and CUPRAC methods. Among them, compound 7 had the highest results in all the assays. The pharmacokinetic properties of compounds were determined using ADMET estimates; target coumarins may be drug candidates for Alzheimer's disease, especially compound 7 may be used as an antioxidant agent in the future after detailed analysis.

引用

页数：13

共 62 条

[1] [Anonymous], 2016, GaussView
[2] Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine:: CUPRAC method
Apak, R
Güçlu, K
Özyürek, M
Karademir, SE
[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (26) : 7970 - 7981
[3] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
[J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
[4] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR
BECKE, AD
[J]. PHYSICAL REVIEW A, 1988, 38 (06): : 3098 - 3100
[5] Synthesis and protective effects of coumarin derivatives against oxidative stress induced by doxorubicin
Beillerot, Adeline
Dominguez, Juan-Carlos Rodriguez
Kirsch, Gilbert
Bagrel, Denyse
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) : 1102 - 1105
[6] The ferric reducing ability of plasma (FRAP) as a measure of ''antioxidant power'': The FRAP assay
Benzie, IFF
Strain, JJ
[J]. ANALYTICAL BIOCHEMISTRY, 1996, 239 (01) : 70 - 76
[7] The Protein Data Bank
Berman, HM
Westbrook, J
Feng, Z
Gilliland, G
Bhat, TN
Weissig, H
Shindyalov, IN
Bourne, PE
[J]. NUCLEIC ACIDS RESEARCH, 2000, 28 (01) : 235 - 242
[8] Human myeloperoxidase:: Structure of a cyanide complex and its interaction with bromide and thiocyanate substrates at 1.9 Å resolution
Blair-Johnson, M
Fiedler, T
Fenna, R
[J]. BIOCHEMISTRY, 2001, 40 (46) : 13990 - 13997
[9] Lipoxygenase interactions with natural flavonoid, quercetin, reveal a complex with protocatechuic acid in its X-ray structure at 2.1 Å resolution
Borbulevych, OY
Jankun, J
Selman, SH
Skrzypczak-Jankun, E
[J]. PROTEINS-STRUCTURE FUNCTION AND BIOINFORMATICS, 2004, 54 (01) : 13 - 19
[10] Substrate Orientation and Catalytic Specificity in the Action of Xanthine Oxidase THE SEQUENTIAL HYDROXYLATION OF HYPOXANTHINE TO URIC ACID
Cao, Hongnan
Pauff, James M.
Hille, Russ
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2010, 285 (36) : 28044 - 28053

← 1 2 3 4 5 6 7 →