Effects of p-Hydroxybenzaldehyde, Vanillin, and Syringaldehyde on Protein Tyrosine Phosphatase 1B Activity

Q4 Pharmacology, Toxicology and Pharmaceutics

Current Enzyme Inhibition Pub Date : 2022-06-30 DOI:10.2174/1573408018666220630140400

Joy Atule Peter, A. Olatunde, S. Aminu, I. Umar, A. Mohammed

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Abstract

The PTP 1B is a negative regulator of insulin signal transduction and hence, serves as a therapeutic target in the treatment of diabetes. The present study investigated the inhibitory effects of p-hydroxybenzaldehyde, vanillin, and syringaldehyde on the activity of protein tyrosine phosphatases phosphatase 1B (PTP 1B) in vitro. The PTP 1B inhibitory assay and mode of inhibition of the three compounds were determined using p-nitrophenyl phosphate (p-NPP) in a 96 well microplate. Molecular docking was used to predict the binding affinities of the compounds with the PTP 1B. The results showed that syringaldehyde exhibited significantly (p< 0.05) higher PTP 1B inhibitory activity (IC50: 12.75 µM) compared to p-hydroxybenzaldehyde (IC50: 33.79 µM) and vanillin (IC50: 42.82 µM) as well as the standards suramin (IC50: 28.35 µM) and ursolic acid (IC50: 19.45 µM). Syringaldehyde and vanillin showed uncompetitive inhibition whereas, p-hydroxybenzaldehyde showed a mixed inhibition type. The molecular docking simulation predicted negative binding energies of -5.0 kcal/mol, -5.5 kcal/mol, and -5.5 kcal/mol for p-hydroxybenzaldehyde, vanillin, and syringaldehyde respectively. Syringaldehyde showed higher inhibition of PTP 1B compared to other phenolic aldehydes and could be the mechanism of its antidiabetic activity. Hence, further studies are warranted to confirm the efficacy and toxicity of the compound

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对羟基苯甲醛、香兰素和丁香醛对蛋白酪氨酸磷酸酶1B活性的影响

PTP 1B是胰岛素信号转导的负调节因子，因此在糖尿病治疗中作为治疗靶点。本实验研究了对羟基苯甲醛、香兰素和丁香醛对蛋白酪氨酸磷酸酶1B (PTP 1B)活性的体外抑制作用。采用对硝基苯磷酸(p-NPP)在96孔微孔板上测定3种化合物对PTP 1B的抑制作用及抑制模式。分子对接预测了化合物与PTP 1B的结合亲和力。结果表明，丁香醛对PTP 1B的抑制活性(IC50: 12.75µM)显著高于对羟基苯甲醛(IC50: 33.79µM)和香兰素(IC50: 42.82µM)，显著高于标准品suramin (IC50: 28.35µM)和熊果酸(IC50: 19.45µM)。丁香醛和香兰素表现为非竞争性抑制，对羟基苯甲醛表现为混合型抑制。分子对接模拟预测对羟基苯甲醛、香草醛和丁香醛的负结合能分别为-5.0 kcal/mol、-5.5 kcal/mol和-5.5 kcal/mol。丁香醛对PTP 1B具有较强的抑制作用，这可能是其抗糖尿病作用的机制之一。因此，需要进一步的研究来证实该化合物的有效性和毒性

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来源期刊

Current Enzyme Inhibition Pharmacology, Toxicology and Pharmaceutics-Drug Discovery

CiteScore

1.30

自引率

0.00%

发文量

期刊介绍： Current Enzyme Inhibition aims to publish all the latest and outstanding developments in enzyme inhibition studies with regards to the mechanisms of inhibitory processes of enzymes, recognition of active sites, and the discovery of agonists and antagonists, leading to the design and development of new drugs of significant therapeutic value. Each issue contains a series of timely, in-depth reviews written by leaders in the field, covering a range of enzymes that can be exploited for drug development. Current Enzyme Inhibition is an essential journal for every pharmaceutical and medicinal chemist who wishes to have up-to-date knowledge about each and every development in the study of enzyme inhibition.