Amphiphilic BODIPY-Based Photoswitchable Fluorescent Polymeric Nanoparticles for Rewritable Patterning and Dual-Color Cell Imaging

Abstract

Photoswitchable fluorescent polymeric nanoparticles (PFPNs) with controllable molecular weight, high contrast, biocompatibility, and prominent photostability are highly desirable but still scarce for rewritable printing, superresolution bioimaging, and rewritable data storage. In this study, novel amphiphilic BODIPY-based PFPNs with considerable merits are first synthesized by a facile onepot RAFT-mediated miniemulsion polymerization method. The polymerization is performed by adopting polymerizable BODIPY and spiropyran derivatives, together with MMA as monomer, and mediated by utilizing biocompatible PEO macro-RAFT agent as both control agent and reactive stabilizer. The amphiphilic BODIPY-based PFPNs not only exhibit reversibly photoswitchable fluorescence properties under the alternative UV and visible light illumination through induced intraparticle fluorescence resonance energy transfer (FRET) but also display controllable molecular weight with narrow polydispersity index (PDI), high contrast of fluorescence, tunable energy transfer efficiency, good biocompatibility, excellent photostability, favorable photoreversibility, etc. The as-prepared PFPNs are successfully demonstrated for rewritable fluorescence patterning and high-contrast dual-color fluorescence imaging of living cells, implying its potential for rewritable data storage and broad biological applications in cell biology and diagnostics.

Fluorescent Dyes Used in Polymer Carriers as Imaging Agents in Anticancer Therapy

“…The photostable amphiphilic BODIPYphotoswichable fluorescent NPs with SP derivatives were obtained as a result of copolymerization of the methyl methacrylate (MMA) in the presence of PEO as a macro-RAFT agent in the miniemulsion polymerization ( Figure 28). Both chromophores were covalently incorporated into polymer backbones and NPs displayed reversible distinct dual-color (green-red) fluorescence by irradiation of UV or visible light via occurring switchable interparticle FRET [275]. The fluorescence switching conversion of NPs occurs also thermally in the living A549 cells (human lung carcinoma).…”

FRET-based acrylic nanoparticles with dual-color photoswitchable properties in DU145 human prostate cancer cell line labeling

“…These fluorescent nanoparticles, based on fluorescence resonance energy transfer (FRET) phenomenon, have received many attentions because of some advantages over conventional fluorescent dyes as distinguishing fake positive signals by aberrant fluorescent biomolecules and targeted locations [4,5]. Hence, they have shown versatile applications in optically addressable devices [2], drug delivery [6], cell labeling and imaging [2,7,8], bioimaging and rewriteable pattering [9,10], sensing tools and optical switching [11][12][13].…”

“…Merocyanin isomer of spiropyran can receive energy from a fluorescent dye through fluorescence resonance energy transfer. Fluorescent molecules such as azocarbazole ethyl acrylate (AzoCzEA) [15], boron-dipyrromethene phenol methacrylate (BDMPA) [9] and nitrobenzoxadizole (NBD) [14] can be used in these systems as donor moieties. To achieve complete energy transfer, fluorescence emission of the fluorescent molecule must have a prominent overlap with absorption band of the acceptor chromophore.…”

“…Then, they employed these photoreversible fluorescent nanoparticles as a tool for optically addressable living cells that exhibit photoreversible red-green fluorescence in the cytosolic media. Chen et al [9] reported the preparation of amphiphilic photoswitchable fluorescent nanoparticles using borondipyrromethene (BODIPY) and spiropyran-linked methacrylate (SPMA) by RAFT polymerization.…”

FRET Phenomenon in Photoreversible Dual-Color Fluorescent Polymeric Nanoparticles Based on Azocarbazole/Spiropyran Derivatives

“…This group has already synthesized amphiphilic photoswitchable fluorescent polymeric nanoparticles by a facile one-pot RAFT-mediated miniemulsion method. 5 In their research, boron-dipyrromethene phenol methacrylate and spiropyran-linked methacrylate dyes have been covalently incorporated into the polymer backbone. The results exhibited excellent structural stability, prominent photostability, favorable photoreversibility and also lack of potential dye leakage, and aggregation that restrict their biological applications.…”