Pillar[5]arene-Derived endo-Functionalized Molecular Tube for Mimicking Protein-Ligand Interactions
Wang, Zhuo1,2,3; Chen, Tao1,3; Liu, Hua2; Zhao, Xiao-Li4; Hu, Wei-Bo1; Yang, Hui1,2; Liu, Yahu A.5; Wen, Ke1,2
2021-05-07
发表期刊JOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
EISSN1520-6904
卷号86期号:9页码:6467-6477
DOI10.1021/acs.joc.1c00314
摘要Artificial tubular molecular pockets bearing polar functionalities on their inner surface are useful model systems for understanding the mechanisms of protein-ligand interactions in living systems. We herein report a pillar[S]arene-derived molecular tube, [P4-(OH)BPO], whose endo conformational isomer endo-[P4-(OH)BPO] possesses an inwardly pointing hydrogen-bond (H-bond) donor (OH) in its deep cavity and a strong H-bond acceptor (C=O) on its predominantly hydrophobic inner surface, rendering it a perfect protein binding pocket mimetic. A fragment-based drug design model was established using endo-[P4-(OH)BPO] and a library of various shape-complementary fragment ligands (1-38). On the A basis of the binding affinity data for fragment-pocket complexes G subset of endo-[P4-(OH)BPO] (G = 1-38), two rationally designed lead molecules (39 and 40) were identified as being able to enhance binding affinity significantly by forming H-bonds with both the donor and acceptor of endo-[P4-(OH)BPO]. The described work opens new avenues for developing pillar[n]arene-derived protein binding pocket-mimetic systems for studies of protein-ligand interactions and mechanisms of enzymatic reactions.
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收录类别SCIE ; EI
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000649101400038
出版者AMER CHEMICAL SOC
原始文献类型Article
引用统计
文献类型期刊论文
条目标识符https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/126942
专题物质科学与技术学院_博士生
物质科学与技术学院_特聘教授组_杨辉组
物质科学与技术学院_特聘教授组_文珂组
物质科学与技术学院_公共科研平台_分析测试平台
通讯作者Hu, Wei-Bo; Yang, Hui; Liu, Yahu A.; Wen, Ke
作者单位1.Chinese Acad Sci, Shanghai Adv Res Inst, Shanghai 201210, Peoples R China;
2.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China;
3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China;
4.East China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China;
5.ChemBridge Res Labs, Med Chem, San Diego, CA 92127 USA
第一作者单位物质科学与技术学院
通讯作者单位物质科学与技术学院
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Wang, Zhuo,Chen, Tao,Liu, Hua,et al. Pillar[5]arene-Derived endo-Functionalized Molecular Tube for Mimicking Protein-Ligand Interactions[J]. JOURNAL OF ORGANIC CHEMISTRY,2021,86(9):6467-6477.
APA Wang, Zhuo.,Chen, Tao.,Liu, Hua.,Zhao, Xiao-Li.,Hu, Wei-Bo.,...&Wen, Ke.(2021).Pillar[5]arene-Derived endo-Functionalized Molecular Tube for Mimicking Protein-Ligand Interactions.JOURNAL OF ORGANIC CHEMISTRY,86(9),6467-6477.
MLA Wang, Zhuo,et al."Pillar[5]arene-Derived endo-Functionalized Molecular Tube for Mimicking Protein-Ligand Interactions".JOURNAL OF ORGANIC CHEMISTRY 86.9(2021):6467-6477.
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