BODIPY based realtime, reversible and targeted fluorescent probes for biothiol imaging in living cells

He, Rongkun; Zhang, Yichuan; Madhu, Suresh; Gao, Quan; Lian, Qianjin; Raghavan, Sriram; Geng, Jin

doi:10.1039/d0cc06313d

Cited by 14 publications

(9 citation statements)

References 28 publications

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“…As the product of C was known to react with biothiol in live cells and to produce E (BOD-OHS) with the fluorescence emission shifted from 673 to 548 nm (Scheme 4a). [15] As expected, we observed that cells were fluorescent (λ ex = 488 nm) under the illumination, but without illumination they were not.…”

supporting

confidence: 83%

“…As we have reported before, formyl-BODIPY C can react with thiols via Michael addition (t 1/2 = 16 ms) to produce E (BOD-OHS). [15] We conducted several reactions to further confirm the proposed mechanism of the photorelease progress. First, A (BOD-dOH, 0.1 mmol) was illuminated to release C (BOD-OH) and D with good isolated yields for C and D, 75 % and 90 %, respectively (Scheme 3a).…”

mentioning

confidence: 87%

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C=C Bond Oxidative Cleavage of BODIPY Photocages by Visible Light

Lin

et al. 2021

Chemistry A European J

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Photocages for protection and the controlled release of bioactive compounds have been widely investigated. However, the vast majority of these photocages employ the cleavage of single bonds and high-energy ultraviolet light. The construction of a photoactivation system that uses visible light to cleave unsaturated bonds still remains a challenge. Herein, we report a regioselective oxidative cleavage of C=C bonds from a boron-dipyrrolemethene (BODIPY)-based photocage by illumination at 630 nm, resulting in a free aldehyde and a thiol fluorescent probe. This strategy was demonstrated in live HeLa cells, and the generated α-formyl-BODIPY allowed real-time monitoring of aldehyde release in the cells. In particular, it is shown that a mannose-functionalized photocage can target HepG2 cells.

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supporting

confidence: 83%

mentioning

confidence: 87%

C=C Bond Oxidative Cleavage of BODIPY Photocages by Visible Light

Lin

et al. 2021

Chemistry A European J

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“…[60] More recently, another example bearing styryl substitution on position 3 reported successful access to mitochondria by inclusion of an end triphenylphosphonium group on the meso substituent (35). [81] It was observed that the absence of the mitochondrial targeting motif in the parent system led to accumulation in different organelles. Another probe (36), sharing some structural similarities with 35 was reported.…”

Section: Bodipysmentioning

confidence: 99%

“…Utilization of trifluoromethyl substitution on neutral BODIPY based architectures ( 33 and 34 ) resulted in subcellular accumulation within the mitochondria but also in the lysosomes [60] . More recently, another example bearing styryl substitution on position 3 reported successful access to mitochondria by inclusion of an end triphenylphosphonium group on the meso substituent ( 35 ) [81] . It was observed that the absence of the mitochondrial targeting motif in the parent system led to accumulation in different organelles.…”

Section: Bodipysmentioning

confidence: 99%

“…[ 68 , 70 , 71 ] Alternatively, the first part of the synthetic protocol can be carried out by employing phosphorous oxytrichloride in the self‐condensation reaction of formylated pyrrole derivatives. [74] Along these lines, asymmetric architectures[ 34 , 58 , 59 , 60 , 61 , 63 , 64 , 65 , 75 , 76 , 77 , 78 , 79 , 80 , 81 ] can be accessed following the latter with the addition of a second pyrrole with the desired substitution. [ 54 , 82 ] It is noteworthy that a synthetic strategy to affording NIR materials bearing the BODIPY scaffold is through fused aromatic substitutions that result in a newly expanded core structure.…”

Section: Bodipysmentioning

confidence: 99%

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Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

Crawford

Dimitriadi

Bassin

et al. 2022

Chemistry A European J

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The last decade has seen an increasingly large number of studies reporting on the development of novel small organic conjugated systems for mitochondrial imaging exploiting optical signal transduction pathways. Mitochondria are known to play a critical role in a number of key biological processes, including cellular metabolism. Importantly, irregularities on their working function are nowadays understood to be intimately linked to a range of clinical conditions, highlighting the importance of targeting mitochondria for therapeutic benefits. In this work we carry out an in‐depth evaluation on the progress to date in the field to pave the way for the realization of superior alternatives to those currently existing. The manuscript is structured by commonly used chemical scaffolds and comprehensively covers key aspects factored in design strategies such as synthetic approaches as well as photophysical and biological characterization, to foster collaborative work among organic and physical chemists as well as cell biologists.

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Lysosomes Targeting pH Activable Imaging‐Guided Photodynamic Agents

et al. 2023

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Photodynamic therapy (PDT) is a photochemistry-based medical treatment combining light at a specific wavelength and a photosensitizer (PS) in the presence of oxygen. Application of PDT as a conventional treatment is limited and clearly the approval in clinics of new PS is challenging. The selective accumulation of the PS in the targeted malignant cells is of paramount importance to reduce the side effects that are typical of the current worldwide approved PS. Here we report a new series of aniline-and iodine-substituted BODIPY derivatives (1-3) as promising lysosome-targeting and pH-responsive theranostic PS, which displayed a significant in vitro lightinduced cytotoxicity, efficient imaging properties and low dark toxicity (for 2 and 3). These compounds were obtained in few reproducible synthetic steps and good yields. Spectroscopic and electrochemical measurements along with computational calculations confirmed the quenching of the emissive properties of the PS, while both fluorescence and 1 O 2 emission were obtained only under acidic conditions inducing amine protonation. The pK a values and pH-dependent emissive properties of 1-3 being established, their cellular uptake and activation in the lysosomal vesicles (pH � 4-5) were confirmed by their colocalization with the commercial LysoTracker deep red and light-induced cytotoxicity (IC 50 between 0.16 and 0.06 μM) against HeLa cancer cells.

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BODIPY based realtime, reversible and targeted fluorescent probes for biothiol imaging in living cells

Abstract: Real-time live cell imaging and quantification of biothiols dynamics are important for understanding the pathophysiological process. However, it is still challenging in the design and synthesis of rational probes that...

Cited by 14 publications

References 28 publications

C=C Bond Oxidative Cleavage of BODIPY Photocages by Visible Light

C=C Bond Oxidative Cleavage of BODIPY Photocages by Visible Light

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

Lysosomes Targeting pH Activable Imaging‐Guided Photodynamic Agents

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