Fabrication of aggregation induced emission active luminescent chitosan nanoparticles via a “one-pot” multicomponent reaction

Abstract

Chitosan based nanomaterials have been extensively examined for biomedical applications for their biodegradability, low toxicity, biological activity and low cost. In this work, a novel strategy for fabrication of luminescent polymeric nanoparticles (LPNs) based on aggregation induced emission (AIE) dye and water soluble chitosan (WS-Chitosan) were firstly developed via a highly efficient mercaptoacetic acid (MA) locking imine reaction. In this multicomponent reaction (MCR), MA serves as "lock" to connect 9,10-Bis(aldehydephenl)anthracene dye (An-CHO) and amino-containing WS-Chitosan under mild reaction conditions. The obtained WS-Chitosan@An-CHO LPNs show strong yellow emission and great water dispersibility. Biological evaluation results demonstrated that synthetic luminescent polymeric nanoparticles possess desirable cytocompatibility and distinct imaging properties. Therefore, we have developed a facile and useful method to fabricate AIE active nanoprobes with desirable properties for various biomedical applications. This strategy should be a general and easy handling tool to fabricate many other AIE dye based materials.

Facile Fabrication of AIE-Active Fluorescent Polymeric Nanoparticles with Ultra-Low Critical Micelle Concentration Based on Ce(IV) Redox Polymerization for Biological Imaging Applications

“…Therefore, these unique performances contained strong fluorescence, small size, great water dispersibility, and excellent biocompatibility make PEG‐poly(Phe‐alc) FPNs be expected to have important biomedical application value for cell imaging, targeted tracing, and cancer treatment. Furthermore, this work firstly introduces that fabrication of AIE‐active FPNs based redox polymerization in aqueous solution, which provide an important inspiration for the construction of natural glycosylation based AIE‐active FPNs because of poor solubility in organic solvents and abundant hydroxyl groups of saccharides …”

AIEgen-Based Fluorescent Nanomaterials: Fabrication and Biological Applications

“…To prepare AIEgen-based nanomaterials through covalent binding, people can first covalently link the functionalized AIEgens to polymers with corresponding reactive groups and use modified polymers to fabricate AIEgen-based nanomaterials, Figure 3 G,H. [ 41 , 42 , 43 ] For example, the isothiocyanate group on TPE-ICT can react with the amino group on chitosan (CS), a natural biopolymer, via Schiff’s base reaction, Figure 3 G [ 39 , 44 ]. For instance, Wang and co-authors have succeeded in covalently attaching TPE-ITC to CS and used the resultant TPE-CS for long-term cell tracking [ 41 ].…”

Recent Advances and Future Prospects of Aggregation‐induced Emission Carbohydrate Polymers

“…Therefore, the fabrication of multifunctional carbohydrate polymers for biomedical applications has become one of the research frontiers in polymer, material, and biomedical science . Over the past years, the interactions between AIE‐active dyes and carbohydrate polymers have also been investigated by some groups . Some conjugation reactions related to the AIE‐active dyes and carbohydrate polymers or biological small molecules have also reported .…”