Chiral self-assembled (β,d)-RIB-TPE micron vesicles with AIE characteristics used as targeting-drug carriers†

Abstract

A novel chiral fluorescent probe, tetraphenylvinyltriazole-ribosyl ribose derivative (β,D)-RIB-TPE, was prepared by Click reaction. It can self-assemble into amphiphilic micron vesicles in methanol solution. (β,D)-RIB-TPE has good AIE properties with a large Stokes shift (redshift 61.8 nm), self-assembles into J-aggregates in a mixed solution with 98% water content, and exhibits a relative fluorescence intensity α_AIE = 24, emitting bright blue fluorescence. In addition to the micron vesicles, (β,D)-RIB-TPE self-assembled into J-aggregates in different mixtures, showing different morphologies, such as a cross-linked network structure and an irregular bulk stacking structure. The fluorescent probe (β,D)-RIB-TPE could achieve high efficiency and rapid multi-channel detection of clopidogrel S-(+)-sulfate by fluorescence chromatography and CD spectroscopy. Infrared, nuclear magnetic titration, scanning electron microscopy and DFT calculations confirmed that the probe (β,D)-RIB-TPE recognized S-(+)-clopidogrel sulfate by an ICT mechanism. (β,D)-RIB-TPE and S-(+)-clopidogrel sulfate were co-assembled in methanol to form single-target drug-carrying micron vesicles with a smaller particle size than the self-assembled (β,D)-RIB-TPE vesicles and good drug embedding capacity.