A novel BODIPY-based fluorescent probe for selective detection of hydrogen sulfide in living cells and tissues

Yan, Jing; Xia, Lijun; Chen, Liu; Guo, Xiao‐Feng; Hong, Wei; Zhang, Huijuan

doi:10.1016/j.talanta.2017.12.067

Cited by 62 publications

(16 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The identical capping strategy was applied by Wang et al. (Figure ) to design a H 2 S‐responsive turn‐on probe based on the BODIPY scaffold either at the meso position ( 7 ) or linked to the para position of the 3‐vinylphenoxy moiety ( 8 ) . Lately, Jiang and co‐workers (Figure ) attached a dinitrophenyl group to the ortho ‐hydroxy of 3‐aryl of BODIPY ( 9 ) .…”

Section: Bodipy‐based Probes For Biothiolsmentioning

confidence: 99%

“…The identicalc apping strategy was applied by Wang et al (Figure 3) to design aH 2 S-responsivet urn-on probe based on the BODIPY scaffold either at the meso position (7)o rlinked to the para position of the 3-vinylphenoxy moiety (8). [41,42] Lately, Jiang and co-workers( Figure 3) attachedadinitrophenyl group to the ortho-hydroxy of 3-aryl of BODIPY (9). [43] The cleavage reactionwas induced by adding H 2 S, which led to the responding turn-off mode and the color changes can be viewed with the naked eye.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

174

View full text Add to dashboard Cite

Fluorescent probes for biothiols have aroused increasing interest owing to their potential to enable better understanding of the diverse physiological and pathological processes related to the biothiol species. BODIPY fluorophores exhibit excellent optical properties, which can be readily tailored by introducing diverse functional units at various positions of the BODIPY core. In the present review, the development of fluorescent probes based on BODIPYs for the detection of biothiols are systematically summarized, with emphasis on the preferable detection of individual biothiols, as well as simultaneous discrimination among cysteine (Cys), homocysteine (Hcy), reduced glutathione (GSH). In addition, organelle‐targeting probes for biothiols are also highlighted. The general design principles, various recognition mechanisms, and biological applications are elaboratively discussed, which could provide a useful reference to researchers worldwide interested in this area.

show abstract

Section: Bodipy‐based Probes For Biothiolsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

174

View full text Add to dashboard Cite

show abstract

“…Time-resolved fluorescence decay profile of 7a (10 –4 M) monitored at the emission maximum in MeOH–90% H 2 O (a) and pure MeOH (b) solution.…”

Section: Resultsmentioning

confidence: 99%

“…As luminescent materials, organic compounds with good optical properties and biocompatibility 1–3 are widely used in various research fields such as in light-emitting diodes, fluorescent sensors, 4–6 and biosensors. 7–9 Due to the hydrophobic conjugated system, traditional fluorescent molecules generally have a large emission wavelength and a high luminous efficiency in a single-molecule dispersion state.…”

Section: Introductionmentioning

confidence: 99%

2-(4-Boronophenyl)quinoline-4-carboxylic acid derivatives: Design and synthesis, aggregation-induced emission characteristics, and binding activity studies for D-ribose with long-wavelength emission

Fang

Wang

Bian

et al. 2019

Journal of Chemical Research

View full text Add to dashboard Cite

Long-wavelength fluorescent sensors with large Stokes shifts show useful applications in chemical biology and clinical laboratory diagnosis. We have recently reported [4-(4-{[3-(4-boronobenzamido)propyl]carbamoyl}quinolin-2-yl)phenyl]boronic acid that can selectively recognize d-ribose in a buffer solution of pH 7.4. However, the short emission wavelength (395 nm) and aggregation-caused quenching effect are not conducive to applications as a sensor. Novel diboronic acid compounds are synthesized using 2-(4-boronophenyl)quinoline-4-carboxylic acid as the building block and p-phenylenediamine as the linker. These compounds show aggregation-induced emission and fluorescence emission at about 500 nm. In addition, after binding to most carbohydrates, the aggregated state of the boronic acid–containing compounds is dissociated, resulting in fluorescence quenching. Using [4-(4-{[4-(3-borono-5-methoxybenzamido)phenyl]carbamoyl}quinoline-2-yl)phenyl]boronic acid as an example, addition of 55 mM of d-ribose resulted in the strongest quenching of 83% for all the tested carbohydrates, indicating selectively recognizing d-ribose. The reciprocal of the fluorescence intensity change showed a good linear relationship with the reciprocal of d-ribose concentration ( R2 ⩾ 0.99), indicating sensor binding to d-ribose in a ratio of 1:1 to form an inclusion complex. The fluorescence emission is red-shifted compared to 2-(4-boronophenyl)quinoline-4-carboxylic acid and its common derivatives, which provides a new method for the development of long-wavelength fluorescent sensors.

show abstract

“…As the probe shows very low LOD (51.8 nM), we have examined the in‐vitro monitoring of HS – in HepG2 cells. We have structured a comparison table (Supporting Information; Table S1 ) with few features of some recently published fluorescent probes for selective sensing of H 2 S based on thiolysis of dinitrophenyl ether . For every probe the LOD value is higher than our probe with one exception .…”

Section: Discussionmentioning

confidence: 99%

A Benzooxazole‐Based Probe for the Sensitive Detection of Hydrogen Sulfide: Kinetic and Transition‐State Studies and In Vitro Application in HepG2 Cells

et al. 2018

View full text Add to dashboard Cite

A benzooxazole based probe, 2‐[4‐(2, 4‐dinitrophenoxy)‐phenyl]‐benzooxazole has been synthesized and thoroughly characterized by mass, 1H‐NMR and FT‐IR spectroscopy. The probe exhibits sensitive and selective response towards H2S in DMSO:PBS buffer (6:4, v/v, pH 7.4) over the other reactive sulfur species especially the biological thiols like cysteine, homocysteine and glutathione. Due to thiolysis of dinitrophenyl ether, this probe displays turn‐on fluorescence response where the sensing mechanism follows inhibited photoinduced electron transfer (d‐PET) process. This thiolysis reaction proceeds through aromatic nucleophilic substitution (SNAr) type mechanism. Moreover, the transition state study shows that this process is exoergic with favorable energy barrier of 5.0 kcal/mol. The kinetic studies of the probe with HS– at various pH assist to evaluate the acid dissociation constant value (Ka1 =1.09 × 10−8 M−1) of H2S that illustrate a reasonable agreement with the literature value, Ka (9.5 x 10−8 M−1). Finally, this probe is cell permeable, non‐cytotoxic and suitable for intracellular cytoplasmic HS– sensing in live cells with a very low detection limit (51.8 nM).

show abstract

A novel BODIPY-based fluorescent probe for selective detection of hydrogen sulfide in living cells and tissues

Cited by 62 publications

References 58 publications

BODIPY‐Based Fluorescent Probes for Biothiols

BODIPY‐Based Fluorescent Probes for Biothiols

2-(4-Boronophenyl)quinoline-4-carboxylic acid derivatives: Design and synthesis, aggregation-induced emission characteristics, and binding activity studies for D-ribose with long-wavelength emission

A Benzooxazole‐Based Probe for the Sensitive Detection of Hydrogen Sulfide: Kinetic and Transition‐State Studies and In Vitro Application in HepG2 Cells

Contact Info

Product

Resources

About