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通过分子动力学模拟探究三氮唑嘧啶衍生物作为抑制剂对胚胎外胚层发育亚基的抑制机制。

Insight into the Inhibitory Mechanism of Embryonic Ectoderm Development Subunit by Triazolopyrimidine Derivatives as Inhibitors through Molecular Dynamics Simulation.

机构信息

Institute of Theoretical Chemistry, College of Chemistry, Jilin University, 2 Liutiao Road, Changchun 130023, China.

College of Biology and Food Engineering, Jilin Engineering Normal University, Changchun 130052, China.

出版信息

Molecules. 2023 Dec 7;28(24):7997. doi: 10.3390/molecules28247997.

DOI:10.3390/molecules28247997
PMID:38138487
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10745707/
Abstract

Inhibition of the Embryonic Ectoderm Development (EED) subunit in (PRC2) can inhibit tumor growth. In this paper, we selected six experimentally designed EED competitive Inhibitors of the triazolopyrimidine derivatives class. We investigated the difference in the binding mode of the natural substrate to the Inhibitors and the effects of differences in the parent nuclei, heads, and tails of the Inhibitors on the inhibitory capacity. The results showed that the binding free energy of this class of Inhibitors was close to or lower compared to the natural substrate, providing an energetic basis for competitive inhibition. For the Inhibitors, the presence of a strong negatively charged group at the 6-position of the parent nucleus or the 8'-position of the head would make the hydrogen atom on the head imino group prone to flip, resulting in the vertical movement of the parent nucleus, which significantly decreased the inhibitory ability. When the 6-position of the parent nucleus was a nonpolar group, the parent nucleus would move horizontally, slightly decreasing the inhibitory ability. When the 8'-position of the head was methylene, it formed an intramolecular hydrophobic interaction with the benzene ring on the tail, resulting in a significant increase in inhibition ability.

摘要

抑制胚胎外胚层发育 (EED) 亚基的多梳抑制复合物 2 (PRC2) 可以抑制肿瘤生长。在本文中,我们选择了六个经过实验设计的三氮唑嘧啶衍生物类 EED 竞争性抑制剂。我们研究了天然底物与抑制剂之间结合模式的差异,以及抑制剂的母体核、头部和尾部的差异对抑制能力的影响。结果表明,这类抑制剂的结合自由能接近于或低于天然底物,为竞争性抑制提供了能量基础。对于抑制剂,在母体核的 6 位或头部的 8'位存在强负电荷基团,会使头部亚氨基上的氢原子易于翻转,导致母体核的垂直运动,从而显著降低抑制能力。当母体核的 6 位为非极性基团时,母体核会横向移动,略微降低抑制能力。当头部的 8'位为亚甲基时,它与尾部的苯环形成分子内疏水相互作用,导致抑制能力显著增加。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/2941af44cc89/molecules-28-07997-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/264afab8fed7/molecules-28-07997-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/8347c282f22a/molecules-28-07997-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/b74338709dde/molecules-28-07997-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/4e11f616e743/molecules-28-07997-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/315d4a362813/molecules-28-07997-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/446f3fb2a780/molecules-28-07997-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/a9d900c22b0d/molecules-28-07997-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/dfa5cb85c92d/molecules-28-07997-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/378bc21b3925/molecules-28-07997-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/0793fb8c1758/molecules-28-07997-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/4ca90c41113d/molecules-28-07997-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/b0517bfd5e9c/molecules-28-07997-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/2941af44cc89/molecules-28-07997-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/264afab8fed7/molecules-28-07997-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/8347c282f22a/molecules-28-07997-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/b74338709dde/molecules-28-07997-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/4e11f616e743/molecules-28-07997-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/315d4a362813/molecules-28-07997-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/446f3fb2a780/molecules-28-07997-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/a9d900c22b0d/molecules-28-07997-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/dfa5cb85c92d/molecules-28-07997-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/378bc21b3925/molecules-28-07997-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/0793fb8c1758/molecules-28-07997-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/4ca90c41113d/molecules-28-07997-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/b0517bfd5e9c/molecules-28-07997-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4df/10745707/2941af44cc89/molecules-28-07997-g013.jpg

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J Med Chem. 2022 Apr 14;65(7):5317-5333. doi: 10.1021/acs.jmedchem.1c02148. Epub 2022 Mar 30.
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Recent strategies targeting Embryonic Ectoderm Development (EED) for cancer therapy: Allosteric inhibitors, PPI inhibitors, and PROTACs.针对癌症治疗的胚胎外胚层发育(EED)的最新策略:别构抑制剂、PPI 抑制剂和 PROTACs。
Eur J Med Chem. 2022 Mar 5;231:114144. doi: 10.1016/j.ejmech.2022.114144. Epub 2022 Jan 20.
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Discovery of EEDi-5273 as an Exceptionally Potent and Orally Efficacious EED Inhibitor Capable of Achieving Complete and Persistent Tumor Regression.
发现 EEDi-5273 是一种效力极高的口服有效 EED 抑制剂,能够实现完全和持久的肿瘤消退。
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gmx_MMPBSA: A New Tool to Perform End-State Free Energy Calculations with GROMACS.gmx_MMPBSA:一种使用GROMACS进行终态自由能计算的新工具。
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