1418130-91-2

Upstream product

• 128-69-8 perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride 
• 34596-27-5 4-(prop-2-yn-1-yloxy)phenol 
• 1419865-47-6 N,N’-bis-propargyl-1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic diimide 

Relevant academic research and scientific papers

Perylenediimide-based glycoclusters as high affinity ligands of bacterial lectins: Synthesis, binding studies and anti-adhesive properties

The synthesis of eight perylenediimide-based glycoclusters was readily performed from hexa- and tetra-propargylated cores through azide-alkyne "click" conjugation. Variations in the carbohydrate epitope (Glc, Gal, Man, Fuc) and the linker arm provided molecular diversity. Interactions with LecA and LecB, two proteins involved in the adhesion of Pseudomonas aeruginosa to host tissues, were evaluated by microcalorimetry (ITC). In both cases high affinities were obtained with Kd values in the nanomolar range. Further evaluation of their anti-adhesive properties using cultured epithelial cells demonstrated their potent anti-adhesive activities against Pseudomonas aeruginosa with only 30-40% residual adhesion observed. The fluorescence properties of the PDI core were then investigated by confocal microscopy on cell-bacteria cultures. However, the red fluorescence signal of the PDI-based glycocluster was too weak to provide significant data. The present study provides another type of anti-adhesive glycocluster against bacterial infection with a large aromatic PDI core.

Multivalent glycoclusters constructed by chiral self-assembly of mannose functionalized perylene bisimide

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 H2O-DMSO solution. As H2O 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 H2O 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 IC50 value of 24 μM (144 μM, valency corrected), 10 times stronger than the reference compound (α-MMP).