Amphiphilic BODIPY derivatives: the solvophobic effect on their photophysical properties and bioimaging in living cells

Abstract

Three novel amphiphilic BODIPY derivatives were prepared and their photophysical properties in THF/water mixtures with varying fractions of water were investigated. BDP-1 could self-assemble into different vesicle architectures in aqueous solution, while BDP-2 and BDP-3 with more hydrophilic abilities formed spherical and worm-like micelles. The BODIPY derivatives could be absorbed by HeLa cells and showed no apparent toxicity during the course of the test. In particular, unlike traditional amines or morpholinyl functionalized lysosome fluorescent probes, BDP-1 nanovesicles without targeted groups exhibit red emission and show effective lysosome biological imaging. Co-staining experiments with lysosome specific trackers further confirmed the disassembly of BDP-1 nanovesicles in lysosomes. This research provides a new avenue of using probes without targeting the structural unit to stain special organelles and shows potential applications in cell imaging fields.

Photoresponsive, Water‐Soluble Supramolecular Dendronized Polymer with Specific Lysosome‐Targetable Bioimaging Application in Living Cells

“…Laser scanning fluorescence microscopy (LSFM) was used to investigate the cell bioimaging potential of SDP. Based on our previous experience that the fluorescent intensities might be dependent on the incubation time due to the large aggregate size, we collected the images at different time intervals and found that the SDP showed red emission, which was consistent with our previous observation. In addition, the intensities were correlated with the incubation time as well ( Figure ).…”

Near‐Infrared‐Emissive Amphiphilic BODIPY Assemblies Manipulated by Charge‐Transfer Interaction: From Nanofibers to Nanorods and Nanodisks

“…Formyl‐modified OEG dendrons 1 followed a classic synthetic pathway to BODIPY derivatives to afford target molecule 2 . Then, compound 2 underwent a Knoevenagel reaction with 1‐pyrenecarboxaldehyde to generate the final BBDP product . PBI and MV were obtained according to the literature .…”

“…BBDP: Compound 2 (100 mg, 0.11 mmol), 1‐pyrenecarboxaldehyde (100 mg, 0.44 mmol), and p ‐toluenesulfonic acid ( p ‐TsOH, 10 mg) were dissolved in a mixture of toluene (25 mL) and piperidine (1 mL). The mixture was stirred at 120 °C for 2 h under the protection of N 2 .…”

“…[18][19][20][21][22][23][24][25] Amphiphilic BODIPY derivatives with ah ydrophobic planara romatic ring and hydrophilic parts have the potential to aggregate in aqueous solu-tions, which resultsi nt he formation of versatile topological structures such as nanowires, nanotubes, nanoribbons, and so on. [26][27][28][29][30] These sophisticated topological morphologies are commonly attributed to the complicated molecular structures. However, few studies report tuning of amphiphilic NIR-emissive BODIPY derivatives elf-assemblies by noncovalentd riving forces.…”

Imine‐linked porous organic polymers showing mesoporous microspheres architectures with tunable surface roughness

“…For example, the luminescent POPs with tunable surface morphologies have rarely been referred. We have been interested in fluorescent amphiphilic 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BDP) derivatives since 2014 . Very recently, a novel about dimeric BDP molecules based POPs could be realized by using FeCl 3 at room temperature was reported .…”