Rational Design of Ratiometric Near-Infrared Aza-BODIPY-Based Fluorescent Probe for in Vivo Imaging of Endogenous Hydrogen Peroxide

Abstract

Precise in vivo tracking of hydrogen peroxide is still challenging due to its dynamic complexity and intrinsic background interference. Herein, we describe a rational design strategy to construct asymmetric aza-boron-dipyrromethane derivative (BODIPY)-based ratiometric probes for in vivo tracking H 2 O 2 , which are composed of a near-infrared aza-BODIPY core, active targeting group, and H 2 O 2 -specific recognition unit. We take advantage of two terminal functionalized conjunctions in the bis-condensed aza-BODIPY by rationally introducing carbonyl group as an electrondeficiency linker for regulating intramolecular charge transfer-induced wavelength shift and by attaching hydrophilic polyethylene glycol-biotin segment as the active targeting moiety. The probe BP 5 -NB-OB features several striking characteristics: (i) ratiometric near infrared response in both absorption and emission spectra; (ii) active targeting ability (biotin receptor-mediated endocytosis) with excellent biocompatibility; and (iii) in vivo tracking of endogenous H 2 O 2 . It was demonstrated that the probe BP 5 -NB-OB was successfully utilized for tracking endogenous H 2 O 2 in living cells and tumorbearing mice, providing opportunities to insight into H 2 O 2 related diseases for clinical application.

A Bright Deep-Red AIEgen with Locked Noncoplanar Conformation for Lipid Droplet-Specific Imaging

“…Luminescent molecules with bright and deep-red emission generally are favorable in bio-imaging applications since they hold the advantages of non-invasiveness, deep penetration depth, superior anti-photobleaching capability, and low photodamage to cell or tissue. 56,57 On the other hand, researchers have found that lipid droplets (LDs), used to be considered only as inert reservoirs of lipids for energy storage, have an essential influence on the normal function of cells. 58 The abnormalities of LDs will lead to several like chronic hepatitis and liver cirrhosis etc.…”

Near‐InfraredFluorescent Nanoprobe for Detecting Hydrogen Peroxide in Inflammation and Ischemic Kidney Injury

“…Fluorescence detection technique is one of the effective and convenient imaging tools to identify the target biomarkers in bio‐system. [ 11‐20 ] Compared to other methods, fluorescence technique shows higher sensitivity, simple operation process and non‐destructive imaging capability. [ 21‐24 ] To date, various fluorescent probes especially those with long‐wavelength emission have been synthesized for H 2 O 2 detection, as summarized in Table S1.…”

Red/NIR Thermally Activated Delayed Fluorescence from Aza‐BODIPYs

“…[35] These effectsc an be enlarged through the peripherical arylationo ft he aza-BODIPYc hromophoric core. [32][33][34] Recently,e fficient and long-lastingf luorescent and laser emission in the target red/NIR spectralr egion have been recordedf rom polyarylateda za-BODIPYs under drastic pumping conditions. [36] In this work, we report for the first time to the best of our knowledge red/NIR TADF emitters based on heavy-atom-free aza-BODIPY derivatives.…”

“…In fact, the simple replacement of the meso ‐methine group at the BODIPY core by an electronegative nitrogen atom induces a pronounced bathochromic shift of both the absorption and emission transitions as well as a drastic decrease of the energy gap between excited singlet and triplet states without promoting phosphorescence emission [35] . These effects can be enlarged through the peripherical arylation of the aza‐BODIPY chromophoric core [32–34] . Recently, efficient and long‐lasting fluorescent and laser emission in the target red/NIR spectral region have been recorded from polyarylated aza‐BODIPYs under drastic pumping conditions [36] …”

“…Among the chemical structures tested to design red TADF probes,l ong-wavelength emitting aza-BODIPY fluorophores has never being considered for this application despite dyes based on this aza-BODIPY scaffold stand out as bright, stable, and compact red/NIR emitters. [32][33][34] In fact, the simple replacement of the meso-methine group at the BODIPY core by an electronegative nitrogena tom induces ap ronounced bathochromic shift of both the absorption and emission transitions as wella sad rastic decrease of the energy gap between excited singlet and triplets tates withoutp romoting phosphorescence emission. [35] These effectsc an be enlarged through the peripherical arylationo ft he aza-BODIPYc hromophoric core.…”