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).

Chiral Perylene Diimides: Building Blocks for Ionic Self‐Assembly

“…Factors that promote a fast aggregation rate, such as rapid cooling and high concentration, can lead to self‐assembly processes that occur by a kinetically controlled pathway 49. This behaviour has been demonstrated recently by investigations in which tuneable helicity of PDI materials was achieved by employing non‐equilibrium conditions using solvent,17 ultrasound,36b, 50 and concentration 51. It is likely that the formation of left‐handed helical aggregates occurs by a kinetically controlled pathway for BTPPP films cast from MeOH.…”

Synthesis and Predetermined Supramolecular Chirality of Carbohydrate‐Functionalized Perylene Bisimide Derivatives

“…Finally, in water a bisignate CD signal crossing over at 507 nm was observed with three negative CD signals at approximately 371, 390, and 483 nm, and with three positive CD signals at approximately 552, 585, and 627 nm. The shape of the bisignate negative/positive Cotton effect with increasing wavelength indicated that PBI‐4 lac‐2 lac molecules in the assembly adopted a right‐handed supramolecular stacking in the thermodynamically equilibrated state induced by the chiral D ‐lactose moieties 9a–d. 21…”

“…With a further increase in H 2 O in the solution, the intensity of the CD signals increased. The shape of the bisignate positive/negative Cotton effect with increasing wavelength indicated that PBI‐4 Man‐2 Man molecules adopted a left‐handed supramolecular stacking in the thermodynamically equilibrated state induced by the chiral D ‐mannose moieties 9a–d. 21…”

Tetraphenylethylene-based glycoclusters with aggregation-induced emission (AIE) properties as high-affinity ligands of bacterial lectins

“…Glycoclusters have been designed with a large series of aromatic cores 1 among which several inherently fluorescent scaffolds. [2][3][4][5][6][7][8][9][10][11][12] We have recently applied perylenediimide (PDI) to the antiadhesive strategy 13 against Pseudomonas aeruginosa (PA) and evaluated successfully PDI-based glyco-dots in the context of cancer cells detection. 14 As a continuation of these investigations, we report here the tetraphenylethylene(TPE)-based glycoclusters as multivalent lectin ligands and also for their antiadhesive evaluation against PA.…”