36308-36-8Relevant articles and documents
Curvature-regulated transmembrane anion transport by a trifluoromethylated bisbenzimidazole
Hong, Xiao-Qiao,Xing, Yuan-Yuan,Wang, Zhong-Kun,Mao, Qin-Chao,Chen, Wen-Hua
, p. 1653 - 1656 (2021)
In this paper, we demonstrate that modification of anion-transport active 1,3-bis(benzimidazol-2-yl)benzene with strongly electron-withdrawing trifluoromethyl and nitro groups leads to a dramatic increase in the anionophoric activity, and the activity may
Design, synthesis, and biological characterization of a new class of symmetrical polyamine-based small molecule CXCR4 antagonists
An, Jing,Fang, Xiong,Huang, Lina S.,Huang, Ziwei,Liang, Boqiang,Meng, Qian,Schooley, Robert T.,Wang, Juan,Xu, Yan,Zhang, Chaozai,Zhang, Huijun,Zhang, Xingquan,Zhu, Siyu
supporting information, (2020/06/03)
CXCR4, a well-studied coreceptor of human immunodeficiency virus type 1 (HIV-1) entry, recognizes its cognate ligand SDF-1α (also named CXCL12) which plays many important roles, including regulating immune cells, controlling hematopoietic stem cells, and directing cancer cells migration. These pleiotropic roles make CXCR4 an attractive target to mitigate human disorders. Here a new class of symmetrical polyamines was designed and synthesized as potential small molecule CXCR4 antagonists. Among them, a representative compound 21 (namely HF50731) showed strong CXCR4 binding affinity (mean IC50 = 19.8 nM) in the CXCR4 competitive binding assay. Furthermore, compound 21 significantly inhibited SDF-1α-induced calcium mobilization and cell migration, and blocked HIV-1 infection via antagonizing CXCR4 coreceptor function. The structure-activity relationship analysis, site-directed mutagenesis, and molecular docking were conducted to further elucidate the binding mode of compound 21, suggesting that compound 21 could primarily occupy the minor subpocket of CXCR4 and partially bind in the major subpocket by interacting with residues W94, D97, D171, and E288. Our studies provide not only new insights for the fragment-based design of small molecule CXCR4 antagonists for clinical applications, but also a new and effective molecular probe for CXCR4-targeting biological studies.
Exploring London Dispersion and Solvent Interactions at Alkyl–Alkyl Interfaces Using Azobenzene Switches
Strauss, Marcel A.,Wegner, Hermann A.
, p. 18552 - 18556 (2019/11/19)
Interactions on the molecular level control structure as well as function. Especially interfaces between innocent alkyl groups are hardly studied although they are of great importance in larger systems. Herein, London dispersion in conjunction with solvent interactions between linear alkyl chains was examined with an azobenzene-based experimental setup. Alkyl chains in all meta positions of the azobenzene core were systematically elongated, and the change in rate for the thermally induced Z→E isomerization in n-decane was determined. The stability of the Z-isomer increased with longer chains and reached a maximum for n-butyl groups. Further elongation led to faster isomerization. The origin of the intramolecular interactions was elaborated by various techniques, including 1H NOESY NMR spectroscopy. The results indicate that there are additional long-range interactions between n-alkyl chains with the opposite phenyl core in the Z-state. These interactions are most likely dominated by attractive London dispersion. This work provides rare insight into the stabilizing contributions of highly flexible groups in an intra- as well as an intermolecular setting.
