Screening of in Vitro Inhibition of Lactoperoxidase Enzyme by Methyl Benzoate Derivatives with Molecular Docking Studies

被引:7
作者
Abul, Nurgul [1 ]
Gerni, Serpil [1 ]
Korkmaz, Isil Nihan [1 ]
Demir, Yeliz [2 ]
Ozdemir, Hasan [1 ]
Gulcin, Ilhami [1 ]
机构
[1] Ataturk Univ, Fac Sci, Dept Chem, TR-25240 Erzurum, Turkiye
[2] Ardahan Univ, Nihat Delibalta Gole Vocat High Sch, Dept Pharm Serv, TR-75700 Ardahan, Turkiye
关键词
enzyme inhibition; lactoperoxidase; methyl benzoate; molecular docking; AROMATIC LIGANDS; DNA-DAMAGE;
D O I
10.1002/cbdv.202300687
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Lactoperoxidase enzyme (LPO) is secreted from salivary, mammary, and other mucosal glands including the bronchi, lungs, and nose, which had functions as a natural and the first line of defense towards viruses and bacteria. In this study, methyl benzoates were examined in LPO enzyme activity. Methyl benzoates are used as precursors in the synthesis of aminobenzohydrazides used as LPO inhibitors. For this purpose, LPO was purified in a single step using sepharose-4B-l-tyrosine-sulfanilamide affinity gel chromatography with a yield of 9.91 % from cow milk. Also, some inhibition parameters including the half maximal inhibitory concentration (IC50) value and an inhibition constant (K-i) values of methyl benzoates were determined. These compounds inhibited LPO with K-i values ranging from 0.033 & PLUSMN;0.004 to 1540.011 & PLUSMN;460.020 & mu;M. Compound 1 a (methyl 2-amino-3-bromobenzoate) showed the best inhibition (K-i=0.033 & PLUSMN;0.004 & mu;M). The most potent inhibitor (1 a) showed with a docking score of -3.36 kcal/mol and an MM-GBSA value of -25.05 kcal/mol, of these methyl benzoate derivatives (1 a-16 a) series are established H-bond within the binding cavity with residues Asp108 (distance of 1.79 & ANGS;), Ala114 (distance of 2.64 & ANGS;), and His351 (distance of 2.12 & ANGS;).
引用
收藏
页数:8
相关论文
共 63 条
[1]   Preparation of lactoperoxidase incorporated hybrid nanoflower and its excellent activity and stability [J].
Altinkaynak, Cevahir ;
Yilmaz, Ismail ;
Koksal, Zeynep ;
Ozdemir, Hasan ;
Ocsoy, Ismail ;
Ozdemir, Nalan .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2016, 84 :402-409
[2]   A new series of hydrazones as small-molecule aldose reductase inhibitors [J].
Altintop, Mehlika D. ;
Demir, Yeliz ;
Turkes, Cuneyt ;
Ozturk, Remzi B. ;
Canturk, Zerrin ;
Beydemir, Sukru ;
Ozdemir, Ahmet .
ARCHIV DER PHARMAZIE, 2023, 356 (04)
[3]   Design, synthesis, biological evaluation and molecular docking studies of novel 1H-1,2,3-Triazole derivatives as potent inhibitors of carbonic anhydrase, acetylcholinesterase and aldose reductase [J].
Anil, Derya Aktas ;
Aydin, Busra Ozturk ;
Demir, Yeliz ;
Turkmenoglu, Burcin .
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1257
[4]  
[Anonymous], 2022, SCHRODINGER RELEASE
[5]  
Askin S., 2021, BIOORG CHEM, P113
[6]   One-step purification of lactoperoxidase from bovine milk by affinity chromatography [J].
Atasever, Ali ;
Ozdemir, Hasan ;
Gulcin, Ilhami ;
Kufrevioglu, O. Irfan .
FOOD CHEMISTRY, 2013, 136 (02) :864-870
[7]  
BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
[8]   Discovery of novel benzenesulfonamides incorporating 1,2,3-triazole scaffold as carbonic anhydrase I, II, IX, and XII inhibitors [J].
Buza, Aida ;
Turkes, Cuneyt ;
Arslan, Mustafa ;
Demir, Yeliz ;
Dincer, Busra ;
Nixha, Arleta Rifati ;
Beydemir, Sukru .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2023, 239
[9]   Ophthalmic drugs: in vitro paraoxonase 1 inhibition and molecular docking studies [J].
Caliskan, Busra ;
Demir, Yeliz ;
Turkes, Cuneyt .
BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY, 2022, 69 (06) :2273-2283
[10]  
Castro-Vazquez D., 2022, CHEM BIOL DRUG DES, V100(2), P245