Direct encapsulation of AIE-active dye with β cyclodextrin terminated polymers: Self-assembly and biological imaging.

Aggregation-induced emission (AIE) phenomenon has attracted great attention recently and been extensively explored for biomedical applications. Nevertheless, the direct utilization of AIE-active dyes for biomedical applications has demonstrated to be enormous challenge owing to the hydrophobic nature of these AIE-active dyes. In this work, we reported the fabrication of amphiphilic AIE-active copolymers through the specific host-guest interaction between β cyclodextrin (β-CD) and an adamantine terminating tetraphenylethene derivative (TPE-Ad). In this construction system, β-CD was acted as the bridge to link TPE-Ad with PEG. The TPE-β-CD-PEG copolymers were characterized by various equipments in detail. Cytocompatibility and cell uptake behavior of TPE-β-CD-PEG were also examined to evaluate their biomedical application potential. Results demonstrated that TPE-β-CD-PEG copolymers were prone to self-assemble into luminescent nanoparticles, which exhibited high water dispersity, AIE feature and excellent biocompatibility. These features endowed TPE-β-CD-PEG great potential for biomedical applications.

[1]  Hui Zhou,et al.  Highly Efficient Supramolecular Aggregation-Induced Emission-Active Pseudorotaxane Luminogen for Functional Bioimaging. , 2017, Biomacromolecules.

[2]  K. Harata,et al.  The Circular Dichroism Spectra of the β-Cyclodextrin Complex with Naphthalene Derivatives , 1975 .

[3]  Yen Wei,et al.  One-step preparation of AIE-active dextran via formation of phenyl borate and their bioimaging application , 2016 .

[4]  Ben Zhong Tang,et al.  Aggregation-induced emission. , 2011, Chemical Society reviews.

[5]  Yang Liu,et al.  Changing the Behavior of Chromophores from Aggregation‐Caused Quenching to Aggregation‐Induced Emission: Development of Highly Efficient Light Emitters in the Solid State , 2010, Advanced materials.

[6]  Q. Tao,et al.  Polymeric hollow spheres assembled from ALG-g-PNIPAM and β-cyclodextrin for controlled drug release. , 2016, International journal of biological macromolecules.

[7]  L. Pannell,et al.  Hydroxypropyl-β-cyclodextrin: preparation and characterization; effects on solubility of drugs , 1986 .

[8]  Ian D. Williams,et al.  Effect of the counterion on light emission: a displacement strategy to change the emission behaviour from aggregation-caused quenching to aggregation-induced emission and to construct sensitive fluorescent sensors for Hg2+ detection. , 2014, Chemistry.

[9]  Ben Zhong Tang,et al.  Aggregation‐Induced Emission: The Whole Is More Brilliant than the Parts , 2014, Advanced materials.

[10]  Ben Zhong Tang,et al.  Protein detection and quantitation by tetraphenylethene-based fluorescent probes with aggregation-induced emission characteristics. , 2007, The journal of physical chemistry. B.

[11]  Qiang Yan,et al.  Voltage-responsive vesicles based on orthogonal assembly of two homopolymers. , 2010, Journal of the American Chemical Society.

[12]  K. Otsuka,et al.  Electrokinetic chromatography with 2-O-carboxymethyl-β-cyclodextrin as a moving “stationary” phase , 1985 .

[13]  Yen Wei,et al.  Fabrication and biological imaging application of AIE-active luminescent starch based nanoprobes. , 2016, Carbohydrate polymers.

[14]  Yen Wei,et al.  Facile Fabrication of PEGylated Fluorescent Organic Nanoparticles with Aggregation-Induced Emission Feature via Formation of Dynamic Bonds and Their Biological Imaging Applications. , 2016, Macromolecular rapid communications.

[15]  B. Tang,et al.  Conjugation‐Induced Rigidity in Twisting Molecules: Filling the Gap Between Aggregation‐Caused Quenching and Aggregation‐Induced Emission , 2015, Advanced materials.

[16]  B. Tang,et al.  Fabrication of fluorescent silica nanoparticles hybridized with AIE luminogens and exploration of their applications as nanobiosensors in intracellular imaging. , 2010, Chemistry.

[17]  D. Armstrong,et al.  (S)-2-Hydroxyprophyl-β-cyclodextrin, a new chiral stationary phase for reversed-phase liquid chromatography , 1990 .

[18]  A. Entezami,et al.  Fabrication of biodendrimeric β-cyclodextrin via click reaction with potency of anticancer drug delivery agent. , 2015, International journal of biological macromolecules.

[19]  Yaling Zhang,et al.  Fabrication of water-dispersible and biocompatible red fluorescent organic nanoparticles via PEGylation of aggregate induced emission enhancement dye and their cell imaging applications. , 2014, Colloids and surfaces. B, Biointerfaces.

[20]  H. Nowotny,et al.  Separation of enantiomers on diluted permethylated β-cyclodextrin by high-resolution gas chromatography , 1988 .

[21]  Yen Wei,et al.  Fabrication of aggregation induced emission active luminescent chitosan nanoparticles via a "one-pot" multicomponent reaction. , 2016, Carbohydrate polymers.

[22]  Yen Wei,et al.  Ultrafast Preparation of AIE-Active Fluorescent Organic Nanoparticles via a "One-Pot" Microwave-Assisted Kabachnik-Fields Reaction. , 2016, Macromolecular rapid communications.

[23]  Hiroyuki Kono,et al.  Cyclodextrin-grafted chitosan hydrogels for controlled drug delivery. , 2015, International journal of biological macromolecules.