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An aggregation induced emission (AIE) fluorescent protein chromophore derivative CIC-FP for detecting protamine and heparin under physiological environment was designed and synthesized. CIC-FP exhibited good biocompatibility and a large stoke shift (91 nm), thus well attenuating the background interference, which could be used for quantitative detection of heparin and protamine . Since protamine has strong positively groups, it can interact with CIC-FP where bearing carboxyl through electrostatic interactions to form a tightly bound CIC-FP/protamine complex, thus showing superior fluorescence intensity response with a detection limit of 65.28 ng/mL. Because heparin has a stronger affinity with protamine, it would compete with CIC-FP on protamine, resulting in the release of CIC-FP and making CIC-FP change into free state with decreased fluorescence intensity . Besides, CIC-FP was successfully applied to detect spiked protamine in human serum samples. In summary, CIC-FP can be used to sensitive detection of protamine with good accuracy, which provides a new idea for designing protamine probes.
In this paper, a new ‘turn-on' fluorescence probe for the rapid, sensitive, and visual detection of hypochlorite is reported. The push–pull type trianiline–tricyanofuran-based fluorescent probe was prepared using a condensation reaction between tricyanofuran and the thiophene–trianiline derivative that had high quantum yields and showed aggregation-induced emission enhanced properties. Upon exposure to hypochlorite, prominent fluorescence enhancement of the probe was observed via the release of the fluorophore from the probe. The probe showed a ratiometric absorption change at 315 nm and 575 nm. Importantly, the probe showed an excellent detection limit for hypochlorite at 1.2 × 10 −7 M in solution and it was successfully applied for monitoring hypochlorite in waste water by test strip. This work reports a new fluorescence analytical sensing method for hypochlorite that has potential practical value in environmental monitoring and biological discrimination.
For polymer materials, both their compositions and preparation process greatly influence their service performance. Thus, the sound understanding of the relationship between materials' preparation processes and their properties is paramount. However, current research methods are partially limited due to the absence of a direct testing method to track the entire process, e.g. synthesizing, curing, ageing, and so on. With the ability for real-time sensitive characterization, fluorescence spectroscopy may be applied in testing polymer materials' performance. Here, we synthesized a novel aggregation induced emission (AIE) resin named TPE–EPOXY resin and prepared an AIE coating based on it. According to restriction of intramolecular rotation (RIR) mechanism, the preparation, curing, and aging processes for the AIE polymer resins & coatings could be studied with real-time observation. In addition, their properties could also be studied systematically. The results in this paper pave a good way to understand the relationship between the internal structure and the properties of polymer materials. Moreover, the prepared AIE polymer resins has a potential to expand the application fields of the AIE mechanism.
Fluorescent polymeric nanoparticles (FPNs) have obtained more and more attention in recent years due to their excellent performance in the fields of bioimaging, biosensing, theranostics and many other biomedical applications. In this work, we reported a novel method to fabricate amphiphilic fluorescent copolymers through host–guest interactions based on an aggregation-induced emission (AIE) active dye (named as Ad-PhNH2) and β cyclodextrin (β-CD) contained polymers, which were synthesized by free radical polymerization and subsequent ring-opening reaction. These AIE active copolymers can self assemble into FPNs (named as PEGMA–IA–β-CD/Ad-PhNH2) due to their amphiphilic properties. The hydrophobic dye was aggregated in the core and therefore can emit strong fluorescent intensity due to its AIE feature. However, the hydrophilic polymers that covered the hydrophobic core can endow good dispersibility in pure aqueous solution. Biological evaluation results demonstrated that PEGMA–IA–β-CD/Ad-PhNH2 FPNs can be effectively internalized into cells and they have shown low cytotoxicity. More importantly, the molar ratio of β-CD to Ad-PhNH2 can be facilely adjusted and the surplus β-CD can be used for carrying chemical anticancer agents. Furthermore, a large number of carboxyl groups were generated during the ring opening reaction. These negative carboxyl groups can be potentially used for further conjugation reactions and for biological delivery. The above described features of PEGMA–IA–β-CD/Ad-PhNH2 FPNs make them a prospect in biological imaging and delivery applications.
Fluorescence imaging, especially specific organelle imaging, has become a significant technology to comprehending cell transplantation, migration, division, fusion, and lysis. In this paper, we designed and synthesized a water soluble and fluorescent polymer named as Poly(AA-TPA-d), which was pH-responsive by the fluorescence channel due to the presence of poly acrylic acid as the polymer backbone. The research results demonstrated that Poly(AA-TPA-d) exhibits novel aggregation-induced-emission (AIE) property. Additionally, due to the hydrogen bond formation and C=O···π interactions between methyl acrylate groups, Poly(AA-TPA-d) was of excellent hydrogel formation ability. Moreover, Poly(AA-TPA-d) displayed good bio-compatibility with the living MPC5 cells and highly specific cytoplasm-targeting ability by MTT assay and cell staining experiment respectively.
Fabrication of water dispersible, biocompatible and ultrabright luminescent polymeric nanoprobes (LPNs) has been the subject of great research interest. Although a number of LPNs have been fabricated previously through different strategies, the preparation of luminescent carbohydrate polymers with aggregation-induced emission (AIE) characterstic has received only limited attention. In this work, we reported for the first time that AIE-active luminescent starch can be facilely fabricated via mixing the aldehyde-contained AIE dye 4-(1,2,2-triphenylvinyl) benzaldehyde (TPE-CHO) with carboxyl methyl starch sodium (CMS) and amino phenylboronic acid in a one-pot procedure, in which aminophenylboronic acid can serve as the linkage for conjugation of TPE-CHO and CMS. The final products (TPE-CMS LPNs) were characterized by a number of characterization techniques such as 1 H nuclear magnetic resonance spectroscopy, transmission electron microscopy, Fourier transform infrared spectroscopy and fluorescence Spectroscopy in detail. To examine their biomedical application potential, the biocompatibility as well as cell uptake behavior of TPE-CMS LPNs were further determined. We demonstrated that TPE-CMS LPNs showed high water dispersibility and strong fluorescence, well biocompatibility and efficient cell internalization behavior, making them promising candidates for various biomedical applications.
In the present study, an amphiphilic polymer was prepared by conjugating methoxy poly(ethylene glycol) (mPEG) with tetraphenylethene (TPE) via disulfide bonds (Bi(mPEG-S-S)-TPE). The polymer could self-assemble into micelles and solubilize hydrophobic anticancer drugs such as paclitaxel (PTX) in the core. Combining the effect of TPE, mPEG, and disulfide bonds, the Bi(mPEG-S-S)-TPE micelles exhibited excellent AIE feature, reduced protein adsorption, and redox-sensitive drug release behavior. An in vitro intracellular uptake study demonstrated the great imaging ability and efficient internalization of Bi(mPEG-S-S)-TPE micelles. The excellent anticancer effect and low systemic toxicity were further evidenced by the in vivo anticancer experiment. The Bi(mPEG-S-S)-TPE micelles were promising drug carriers for chemotherapy and bioimaging.Keywords:polymeric micelles;aggregation-induced emission;bioimaging;redox-sensitive;anticancer drug delivery
Stimuli-responsive supramolecular materials have attracted much attention because of their controllable microstructure and luminescence behavior. In this study, the fluorescent molecule ((1E)-1-((4-(1,2,2-triphenylvinyl)benzylidene)hydrazineylide-ne)ethyl)ferrocene (FcMe-TPE) with aggregation-induced emission (AIE) property and redox activity was synthesized. The morphology as well as fluorescence behavior could be modulated by changing solvent, adding oxidant or applying voltage, and the translation mechanism was explored in detail by means of density functional theory (DFT). Based on the presence of competitive hydrogen bonding, FcMe-TPE assemblies showed different aggregate behaviors and properties under different water contents (f w ). As f w increased from 20% to 60%, the morphology of assemblies could be transformed from 2D sheet to elliptical crystal structure, then the precipitation gradually disappeared for the further increase of f w . At the same time, the addition of oxidant as well as the application of voltage could also cause changes in the fluorescence intensity of the assemblies. When the voltage increased from 0 V to 3 V, the fluorescence intensity increased and reached the maximum value at 1 V. Based on this property, the electrofluorochromic (EFC) device with low trigger voltage was made. This work provides a feasible strategy for controllable self-assembly and the fabrication of multiple fluorescence switches, which has potential practical application in the field of advanced anti-counterfeiting, intelligent display and information encryption.
Poor cellular permeability greatly hampers the utilization of anionic Ir(III) complexes, though efficiently emissive and remarkably stable, in cell-based diagnosis. To overcome this barrier, we present the development of an alkaline phosphatase (ALP)-responsive, anionic, and aggregation-induced emission (AIE)-active Ir(III) complex (Ir1) for specific recognition of osteosarcoma cells. Containing phosphate moieties, Ir1 exhibits a net −1 charge, enabling charge repulsion from the cell membrane and resulting in low cellular uptake and good biocompatibility in normal osteoblast cells. Upon ALP-mediated hydrolysis of phosphate groups, the resulting dephosphorylated product, Ir2, demonstrates a positive charge and increased lipophilicity, promoting cellular uptake and activating its AIE properties for specific recognition of osteosarcoma cells that express elevated levels of ALP. This study elucidates the role of ALP as an ideal trigger for enhancing the cellular permeability of phosphate ester-containing Ir(III) complexes, thus expanding the potential of anionic Ir(III) complexes for biomedical applications.
This work report the first AIE-based fluorescence sensor that can simultaneously detect three kinds of IIB elements (Zn 2+ , Cd 2+ and Hg 2+ ) in aqueous media. The thiourea-bridging bis-tetraphenylethylene ( Bis-TPE ) was synthesized by the condensation reaction of formyltetraphenylethylene and bis-thiosemicarbazide derivative in 82 % yield. Due to the AIE effect in the aqueous medium, the long-wavelength fluorescence was observed at 500–526 nm. It displayed high selective Zn 2+ -sensing ability with red-to-green fluorescence change, selective Cd 2+ -sensing ability with red-to-yellow fluorescence change and selective Hg 2+ -sensing ability with fluorescence enhancement, respectively. Moreover, it could detect simultaneously Zn 2+ , Cd 2+ and Hg 2+ in the mixed solution of these three kinds of cations by the fluorescence change with the assistance of Cl − and ATP. The sensing mechanism was confirmed as 1:1 stoichiometric ratio between host and guest. The detection limits were as low as 8.22×10 -8 M, 2.36×10 -7 M and 3.43×10 -8 M for Zn 2+ , Cd 2+ and Hg 2+ , respectively. These sensing abilities were applied as test strips for detecting Zn 2+ , Cd 2+ and Hg 2+ , and were used for living cell imaging, implying a high efficient and simple method for analyzing trace IIB elements (Zn 2+ , Cd 2+ and Hg 2+ ) simultaneously in complex environments and living bodies.
Macromolecular architecture control of fluorescent polymers presents an important approach to diverse self-assembled nanostructures and tailored functions. Herein, tetraphenylethylene (TPE) derivatives with different bromopropionate and hydroxyl functionalities were synthesized efficiently. Based on the single electron transfer living radical polymerization (SET-LRP) of oligo(ethylene glycol) methyl ether acrylate (OEGA) and the mechanistic transition to reversible addition−fragmentation chain transfer (RAFT) dispersion polymerization of benzyl methacrylate (BzMA), well-defined aggregation-induced emission (AIE)-active miktoarm star TPE-(POEGA)n-(PBzMA)4-n (n = 1−3) nanoassemblies were synthesized for the first time. The nanoassemblies were utilized as an ideal platform to probe the intricate interplay between macromolecular architecture, self-assembly behavior, and fluorescence properties. Results showed that the arm engineering (changing the respective arm numbers) of miktoarm star polymers can bring about drastic alterations in the self-assembled morphology and photoluminescence characteristics. This arises from the influences of macromolecular structure on molecular packing, intermolecular interactions and intramolecular motions. This work highlights the unique advantage of miktoarm star architecture design and has far-reaching implications for the rational design of high-performance intelligent fluorescence systems.
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