Facile synthesis of polymeric fluorescent organic nanoparticles based on the self-polymerization of dopamine for biological imaging

• Published in: Materials Science & Engineering C 2017-08, Vol.77, p.972-977
• Main Authors: Shi, Yingge, Jiang, Ruming, Liu, Meiying, Fu, Lihua, Zeng, Guangjian, Wan, Qing, Mao, Liucheng, Deng, Fengjie, Zhang, Xiaoyong, Wei, Yen
• Format: Article
• Language: English
• Subjects: Addition polymerization; Biocompatibility; Biological imaging; Biomedical materials; Chemical synthesis; Cytology; Dopamine; Electron microscopy; Fluorescence; Fluorescence spectroscopy; Fourier transforms; Infrared spectroscopy; Materials science; Monomers; Nanoparticles; NMR; Nuclear magnetic resonance; Optical properties; Organic chemistry; Polyethylene glycol; Polyethyleneimine; Polyethylenes; Polymeric fluorescent organic nanoparticles; Polymerization; Polymers; Self-polymerization; Spectroscopy; Transmission electron microscopy
• ISSN: 0928-4931; 1873-0191
• DOI: 10.1016/j.msec.2017.04.033

Polymeric fluorescent organic nanoparticles (polymer-FONs) have raised considerable research attention for biomedical applications owing to their advantages as compared with fluorescent inorganic nanoparticles and small organic molecules. In this study, we presented an efficient, facile and environment-friendly strategy to produce polymer-FONs, which relied on the self-polymerization of dopamine and polyethyleneimine (PEI) in rather mild conditions. To obtain the final polymer-FONs, aldehyde group-containing copolymers (named as poly(UA-co-PEGMA)) were synthesized by reversible addition–fragmentation chain-transfer polymerization using polyethylene glycol methyl ether methacrylate (PEGMA) and 1-undecen-10-al (UA) as monomers. The dopamine was conjugated onto poly(UA-co-PEGMA) through a multicomponent reaction between UA and dopamine to obtain poly(UA-co-PEGMA)-DA, which was further utilized for preparation of polymer-FONs through self-polymerization of dopamine and PEI. 1H nuclear magnetic resonance, Fourier transform infrared spectroscopy, transmission electron microscopy and fluorescence spectroscopy were employed to characterize the structure, morphology, compositions and optical properties of these polymer-FONs. Cell viability and cell uptake behavior results suggested that these polymer-FONs possess good biocompatibility and can be potentially utilized for biomedical applications. More importantly, the method can be also applied to fabricate many other multifunctional polymer-FONs with great potential for biomedical applications. Polymeric fluorescent nanoparticles were fabricated via a novel strategy that combines the RAFT polymerization, multicomponent reaction and self-polymerization of dopamine. [Display omitted] •Dopamine-containing copolymers were synthesized by RAFT polymerization.•The dopamine-containing copolymers can be used for preparation of polymer-FONs.•Polymer-FONs are formed by self-polymerization of dopamine and PEI.•These polymer-FONs are biocompatible and promising for biological imaging.