Polymerizable aggregation-induced emission dye for preparation of cross-linkable fluorescent nanoprobes with ultra-low critical micelle concentrations

• Published in: Materials Science & Engineering C 2017-07, Vol.76, p.586-592
• Main Authors: Huang, Long, Liu, Meiying, Mao, Liucheng, Zhang, Xiqi, Xu, Dazhuang, Wan, Qing, Huang, Qiang, Shi, Yingge, Deng, Fengjie, Zhang, Xiaoyong, Wei, Yen
• Format: Article
• Language: English
• Subjects: Addition polymerization; Agglomeration; Aggregation-induced emission; Biocompatibility; Biological effects; Biological imaging; Biomedical materials; Chain transfer; Copolymers; Critical micelle concentrations; Cross-linkable; Cross-Linking Reagents; Crosslinking; Cytotoxicity; Dyes; Emission; Fluorescence; Fluorescent Dyes; Hydrophobicity; Low cytotoxicity; Materials science; Methacrylates; Methacryloyloxyethyl phosphorylcholine; Micelles; Monomers; Nanoparticles; Nanostructures; Optical properties; Phosphorylcholine; Phosphorylcholine - analogs & derivatives; Polymerization; Polymers; Toxicity
• ISSN: 0928-4931; 1873-0191
• DOI: 10.1016/j.msec.2017.03.122

In recent years, aggregation-induced emission (AIE) dyes based fluorescent organic nanoparticles (FONs) have achieved significant progress in various biomedical applications. In this work, we developed a covalent strategy to prepare biocompatible AIE-active dyes based cross-linked copolymers (MPC-POSS-PhE) via controllable reversible addition fragmentation chain transfer (RAFT) polymerization using zwitterionic 2-methacryloyloxyethyl phosphorylcholine (MPC), polymerizable AIE dye (named as PhE) and 8-vinyl polyoctahedral silsesquioxanes (POSS) as monomers. Due to the existence of hydrophilic MPC and hydrophobic PhE, the resultant copolymers will self-assemble into core-shell nanoparticles in aqueous solution with ultra-low critical micelle concentration (CMC). This could effectively overcome the drawbacks of non-crosslinked micelles and show more attractive properties and better performance for biomedical applications. Furthermore, the characterization results and biological assays demonstrated that the final MPC-POSS-PhE FONs show stable aqueous stability, uniform size and morphology, high water dispersity, desirable optical properties and low cytotoxicity. These remarkable properties make the resultant AIE-active nanoprobes great potential for biomedical applications. Cross-linked fluorescent organic nanoparticles with aggregation-induced emission were fabricated through reversible addition fragmentation chain transfer polymerization using 8-vinyl polyoctahedral silsesquioxanes as the linkage and utilized for biological imaging. [Display omitted] •Preparation of aggregation-induced emission fluorescent organic nanoparticles•Cross-linked fluorescent copolymers with ultra-low critical micelle concentrations•These cross-linked AIE-active FONs show excellent optical properties and biocompatibility.•These cross-linked AIE-active FONs are promising candidates for biological imaging.