39909-72-3Relevant articles and documents
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.
18F-Labeled Benzyldiamine Derivatives as Novel Flexible Probes for Positron Emission Tomography of Cerebral β-Amyloid Plaques
Li, Zijing,Zhang, Xuran,Zhang, Xiaoyang,Cui, Mengchao,Lu, Jie,Pan, Xiaodong,Zhang, Xianzhong
, p. 10577 - 10585 (2016/12/16)
Early noninvasive visualization of cerebral β-amyloid (Aβ) plaques with positron emission tomography (PET) is the most feasible way to diagnose Alzheimer’s disease (AD). In this study, a series of flexible benzyldiamine derivatives (BDA) were proposed for
Fine tuning of molecular and supramolecular properties of simple trianglimines-the role of the functional group
Gajewy,Szymkowiak,Kwit
, p. 53358 - 53369 (2016/06/14)
Chiral, triangular poly-azamacrocycles (trianglimines) readily available from enantiomerically pure trans-1,2-diaminocyclohexane and various aromatic dialdehydes, differ in their nature and substitution pattern. The highly symmetrical macrocycle having two electron-donating groups attached to the aryl moieties is formed under thermodynamic control that fulfilled the so called entropy of symmetry rule. Conversely, from the 2-nitroterephthaldehyde a kinetic product of trivial C1 symmetry is solely obtained, whereas from 2-methoxyterepthaldehyde a mixture of C3- and C1-symmetrical macrocycles are formed. The factors that contribute to the mechanism of the macrocycle formation were determined on the basis of an experimental/theoretical approach. The non-symmetrical structure of the macrocycle resulted from a symmetrical intermediate that appeared during cyclocondensation. The chiroptical properties of the trianglimines were studied by means of experimental ECD and VCD methods supported by quantum-chemical calculations. The nitro-substituted trianglimine appeared to be a simple, low molecular weight supergelator forming in polar media of stable chiral organogels. The structure of the gel is affected by the nature and chirality of the dopant. The hexaimine macrocycles after reduction of the CN imine bonds formed trianglamines-useful chiral ligands in stereoselective synthesis. The Zn-trianglamine complexes were employed as catalysts for asymmetric hydrosilylation of prochiral ketones, providing products of enantiomeric excess up to 98%. This remains the best result obtained for Zn-diamine catalysed asymmetric hydrosilylation of ketones so far.
Selective fluorescence sensing of cyanide with an o-(carboxamido)trifluoroacetophenone fused with a cyano-1,2-diphenylethylene fluorophore
Lee, Hanna,Chung, Yun Mi,Ahn, Kyo Han
, p. 5544 - 5547 (2008/12/22)
A novel fluorescence probe has been synthesized, which consists of o-(carboxamido)trifluoroacetophenone moiety as the recognition element and cyano-1,2-diphenylethylene moiety as the signaling unit. Fluorescence titrations of the probe with anions such as F-, Cl-, I-, CN-, SCN-, AcO-, H2 PO4-, HSO4-, and ClO4- as their Bu4N+ salts in acetonitrile show that CN- is the most efficient quencher, AcO- and F- follow it, and other anions show little changes. In an aqueous medium, MeOH-water (9:1), the probe shows fluorescence quenching only toward cyanide and no changes toward the other anions.
Synthesis of a new hydrophilic o-nitrobenzyl photocleavable linker suitable for use in chemical proteomics
Piggott, Andrew M.,Karuso, Peter
, p. 8241 - 8244 (2007/10/03)
Linkers currently used in solid phase synthesis are generally short and hydrophobic, limiting their usefulness in biological systems. Herein, we describe a facile synthesis of a long, hydrophilic, o-nitrobenzyl photocleavable linker, suitable for construc
Synthesis and photophysical studies of bis-enediynes as tunable fluorophores
Hwang, Gil Tae,Son, Hyung Su,Ku, Ja Kang,Kim, Byeang Hyean
, p. 11241 - 11248 (2007/10/03)
We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the π-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.
