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针对靶向Janus激酶3(JAK3)的吡唑并嘧啶衍生物的合理设计与虚拟筛选的计算洞察

Computational insights into rational design and virtual screening of pyrazolopyrimidine derivatives targeting Janus kinase 3 (JAK3).

作者信息

Faris Abdelmoujoud, Cacciatore Ivana, Alnajjar Radwan, Aouidate Adnane, Al Mughram Mohammed H, Elhallaoui Menana

机构信息

LIMAS, Department of Chemical Sciences, Faculty of Sciences Dhar El Mahraz, Sidi Mohamed Ben Abdellah University, Fez, Morocco.

Department of Pharmacy, University "G. d'Annunzio" of Chieti-Pescara, Chieti, Italy.

出版信息

Front Chem. 2024 Aug 12;12:1425220. doi: 10.3389/fchem.2024.1425220. eCollection 2024.

DOI:10.3389/fchem.2024.1425220
PMID:39189018
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11345245/
Abstract

The Janus kinase 3 (JAK3) family, particularly JAK3, is pivotal in initiating autoimmune diseases such as rheumatoid arthritis. Recent advancements have focused on developing antirheumatic drugs targeting JAK3, leading to the discovery of novel pyrazolopyrimidine-based compounds as potential inhibitors. This research employed covalent docking, ADMET (Absorption, Distribution, Metabolism, Excretion, Toxicity) analysis, molecular dynamics modeling, and MM/GBSA (Molecular Mechanics Generalized Born Surface Area) binding free energy techniques to screen 41 in silico-designed pyrazolopyrimidine derivatives. Initially, 3D structures of the JAK3 enzyme were generated using SWISS-MODEL, followed by virtual screening and covalent docking via AutoDock4 (AD4). The selection process involved the AMES test, binding affinity assessment, and ADMET analysis, narrowing down the candidates to 27 compounds that passed the toxicity test. Further covalent docking identified compounds 21 and 41 as the most promising due to their high affinity and favourable ADMET profiles. Subsequent development led to the creation of nine potent molecules, with derivatives 43 and 46 showing exceptional affinity upon evaluation through molecular dynamics simulation and MM/GBSA calculations over 300 nanoseconds, comparable to tofacitinib, an approved RA drug. However, compounds L21 and L46 demonstrated stable performance, suggesting their effectiveness in treating rheumatoid arthritis and other autoimmune conditions associated with JAK3 inhibition.

摘要

Janus激酶3(JAK3)家族,尤其是JAK3,在引发类风湿性关节炎等自身免疫性疾病中起关键作用。最近的进展集中在开发靶向JAK3的抗风湿药物,从而发现了新型的基于吡唑并嘧啶的化合物作为潜在抑制剂。本研究采用共价对接、ADMET(吸收、分布、代谢、排泄、毒性)分析、分子动力学建模和MM/GBSA(分子力学广义玻恩表面积)结合自由能技术,对41种计算机设计的吡唑并嘧啶衍生物进行筛选。最初,使用SWISS-MODEL生成JAK3酶的三维结构,然后通过AutoDock4(AD4)进行虚拟筛选和共价对接。筛选过程包括AMES试验、结合亲和力评估和ADMET分析,将候选化合物缩小到27种通过毒性测试的化合物。进一步的共价对接确定化合物21和41最具潜力,因为它们具有高亲和力和良好的ADMET特性。随后的研发产生了9种强效分子,通过300纳秒的分子动力学模拟和MM/GBSA计算评估,衍生物43和46表现出卓越的亲和力,与已批准的类风湿性关节炎药物托法替布相当。然而,化合物L21和L46表现出稳定的性能,表明它们在治疗类风湿性关节炎和其他与JAK3抑制相关的自身免疫性疾病方面有效。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf57/11345245/f3ec45f03761/fchem-12-1425220-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf57/11345245/4055c5817329/fchem-12-1425220-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf57/11345245/5dea562b2dc0/fchem-12-1425220-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf57/11345245/757850229014/fchem-12-1425220-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf57/11345245/f3ec45f03761/fchem-12-1425220-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf57/11345245/4055c5817329/fchem-12-1425220-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf57/11345245/5dea562b2dc0/fchem-12-1425220-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf57/11345245/757850229014/fchem-12-1425220-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf57/11345245/f3ec45f03761/fchem-12-1425220-g005.jpg

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