A novel water-soluble fluorescent polymer based on perylene bisimides dyes: one-pot preparation and its bio-imaging

• Published in: Journal of biomaterials science. Polymer ed. Vol. 27; no. 6; pp. 455 - 471
• Main Authors: Tan, Haijian, Liu, Hongmei, Liu, Yaojun, Duan, Wenfeng, Yi, Xuegang, Wu, Yonggang, Zhao, Hongchi, Bai, Libin
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 12.04.2016
• Subjects: bio-imaging; Biological; Biological Transport; Cell Survival - drug effects; Chemical reactions; Chemistry Techniques, Synthetic; Conversion; cytotoxicity; Dyes; Fluorescence; Fluorescent Dyes - chemistry; Fluorescent Dyes - metabolism; Fluorescent Dyes - toxicity; HeLa Cells; Humans; Imides - chemistry; Molecular Imaging - methods; one-pot method; Optical Phenomena; Perylene - analogs & derivatives; Perylene - chemistry; perylene bisimides; Photoluminescence; Polymers - chemistry; Polymers - metabolism; Polymers - toxicity; Solubility; Spectra; Spectrometry, Fluorescence; Thiols; Water - chemistry; Water-soluble fluorescent polymer; bio-imaging; cytotoxicity; Water-soluble fluorescent polymer; one-pot method; perylene bisimides
• ISSN: 0920-5063; 1568-5624
• DOI: 10.1080/09205063.2015.1136860

Perylene bisimides dye-based water-soluble fluorescent polymer P3, N,N'-bis(3-amyl)-1-bromo-7-{4'-[3''-(S-poly(N-acryloyl ethylene diamine hydrochloride)-2'''-methyl propionic acid)propionyloxy hexyloxy]phenyl} perylene-3,4:9,10-tetracarboxylic bisimides, was synthesized with polyelectrolyte modification via one-pot reaction (the reduction reaction of trithioester and click reaction between the thiol group and carbon-carbon double bond were simultaneously conducted in one pot with high conversion). One-pot method can overcome the limitation that usual click reaction between thiol and other groups has low conversion because thiol group is subject to rapid oxidation during purification and storage. Chemical, structural, and optical properties of P3 and intermediate products were fully characterized by nuclear magnetic resonance spectroscopy, Fourier transform infrared, gel permeation chromatograph, UV-vis spectra, and fluorescence spectra, respectively. The results revealed that P3 displayed excellent water solubility and not only exhibited red strong fluorescence emission band in water but also had the similar photoluminescent spectra to those of intermediate products (M4 and P2) in chloroform. Allowing for the potential application in biological detection field, cell viability and live cell imaging with the presence of P3 were further investigated with Hela cells. The results showed that P3 had low cytotoxicity with strong intracellular fluorescence entry. Meanwhile, with the augment of concentration of P3 (0-0.500 mg mL −1 ), the cell uptake and accumulation of P3 increased and thereby result in enhancement of the intracellular fluorescence. These experiment results suggested that P3 had enormous potential as a fluorescence probe to be an important component in biological detection field.