title: Multivalent glycoclusters constructed by chiral self-assembly of mannose functionalized perylene bisimide.
abstract: Water-soluble perylene bisimide derivative 7 modified with six mannoses was synthesized and its self-assembled properties were studied by UV-Vis and CD spectroscopy, which revealed an interesting self-assembly with a solvent-tuning chiral conformation in H(2)O-DMSO solution. As H(2)O was added to the DMSO solution until a 60% (or 70%) v/v proportion was achieved, the self-assembly of the mannose functionalized compound 7 exhibited a left-handed helical conformation. More interestingly, when the volume of H(2)O constituted beyond 85% of the solution, the conformation of the self-assembly turned out to be a right-handed helical conformation. Furthermore, the binding interactions between the self-assembly of compound 7 and Con A were investigated by turbidity assay, CD spectra, TEM and SEM images, and ELLA experiment, which indicated that the self-assembly of compound 7 as multivalent glycoclusters exhibited specific binding to Con A with an IC(50) value of 24 μM (144 μM, valency corrected), 10 times stronger than the reference compound (α-MMP).
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China. kerangwang@hbu.edu.cn
authors.forename: Ke-Rang
authors.initials: KR
authors.lastname: Wang
authors.forename: Hong-Wei
authors.initials: HW
authors.lastname: An
authors.forename: Yue-Qing
authors.initials: YQ
authors.lastname: Wang
authors.forename: Jin-Chao
authors.initials: JC
authors.lastname: Zhang
authors.forename: Xiao-Liu
authors.initials: XL
authors.lastname: Li
mesh_terms: D002942:Circular Dichroism; D003208:Concanavalin A / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry*; D046529:Microscopy, Electron, Transmission; D008958:Models, Molecular; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007094:Imides; C510697:perylene bisimide; D003208:Concanavalin A; D010569:Perylene; D008358:Mannose