A Reversible Fluorescent Probe for Real‐Time Live‐Cell Imaging and Quantification of Endogenous Hydropolysulfides

Umezawa, Keitaro; Kamiya, Mako; Urano, Yasuteru

doi:10.1002/ange.201804309

Cited by 16 publications

(13 citation statements)

References 29 publications

(22 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Since incorporation of 4-fluorobenzenesulfonamide transformed rhodamine 500R into a highly fluorogenic SNAP-tag probe (23), we also applied this structural change to CPY to obtain 32 (Figure 6e). We then measured the absorbance and fluorescence increase of 32 upon binding to the SNAP-tag in-vitro and compared its fluorogenicity to the original CPY SNAP-tag probe (30). Despite a reduced brightness, 32 yielded a significantly increased turn-on in the presence of the SNAP-tag compared to 30 (Figure 6f).…”

Section: Extending the Strategy To Other Rhodamine-based Dyesmentioning

confidence: 99%

“…12,17 Xanthenes with reduced electron density are also known to display enhanced reactivity towards intracellular nucleophiles, which can decrease fluorophore brightness. 16,[29][30] Furthermore, modification of the xanthene core often requires multi-step syntheses and the development of sophisticated methodologies. 8,12,[31][32] With respect to probes for SMLM techniques, stable rhodamine spirolactams were previously introduced which could be photoactivated to form a fluorescent state.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Systematic Tuning of Rhodamine Spirocyclization for Super-Resolution Microscopy

Lardon

Wang

Tschanz

et al. 2021

Preprint

View full text Add to dashboard Cite

Rhodamines are the most important class of fluorophores for applications in live-cell fluorescence microscopy. This is mainly because rhodamines exist in a dynamic equilibrium between a fluorescent zwitterion and a non-fluorescent but cell-permeable spirocyclic form. Different imaging applications require different positions of this dynamic equilibrium, which poses a challenge for the design of suitable probes. We describe here how the conversion of the ortho-carboxy moiety of a given rhodamine into substituted acyl benzenesulfonamides and alkylamides permits the systematic tuning of the equilibrium of spirocyclization with unprecedented accuracy and over a large range. This allows to transform the same rhodamine into either a highly fluorogenic and cell-permeable probe for live-cell stimulated emission depletion (STED) microscopy, or into a spontaneously blinking dye for single molecule localization microscopy (SMLM). We used this approach to generate differently colored probes optimized for different labeling systems and imaging applications.

show abstract

Section: Extending the Strategy To Other Rhodamine-based Dyesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Systematic Tuning of Rhodamine Spirocyclization for Super-Resolution Microscopy

Lardon

Wang

Tschanz

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

“…As shown in Figures 4a, 4b, 4d, and 4e, when the cells were stimulated with LPS, IFN-γ, and PMA, the fluorescence of the red channel was enhanced compared with that of the green channel. Next, we added TEMPO and GREs, which produce GSH, 59,60 to the cells after stimulation with LPS, IFN-γ, and PMA, and the imaging experiments were performed 30 min later. The results indicated that the fluorescence in the red channel was weaker than that in the green channel and the F R / G value was lower (Figures 4b, 4c, 4e, and 4f).…”

Section: Reversible Sensing Of Intracellular Exogenous and Endogenous Onoo − And Gsh Using Ucnps-1@pei@nb3mentioning

confidence: 99%

Engineering of Reversible Luminescent Probes for Real-Time Intravital Imaging of Liver Injury and Repair

Liu

Gong

et al. 2022

CCS Chem

View full text Add to dashboard Cite

As the major organ for drug metabolism and detoxification, the liver is prone to damage and severely impaired functionality. The treatment of liver diseases is based on a clear understanding of the process underlying liver injury and repair. However, intravital real-time imaging of liver injury and repair is still limited due to the lack of in vivo reversible visualization methods. To this end, we proposed a rational design strategy for the development of a reversible upconversion luminescence nanoprobe that allows real-time and in vivo imaging of liver injury and repair processes. As a proof of concept, we first developed a small molecule probe NB3 which can reversibly respond to related analytes of early liver injury [peroxynitrite (ONOO − )] and liver repair [glutathione (GSH)]. The small molecule probe was then integrated with a core-shell upconversion nanoparticle to form a sophisticated nanoprobe. Compared with traditional small molecule probes, this nanoprobe exhibited a higher selectivity to ONOO − , longer retention time in liver, and wider dynamic response range to GSH after oxidation by ONOO − . The novel nanoprobe facilitated the successful monitoring and discrimination among the different degrees of liver injury and repair in a mouse model.

show abstract

“…As shown in Figure 4A-B and Figure 4D-E, when the cells were stimulated with LPS, IFN-γ, and PMA, the fluorescence of the red channel was enhanced compared to that of the green channel. Next, we added TEMPO and GSH reduced ethyl ester (GREs), which produce GSH, 59,60 to the cells after stimulation with LPS, IFN-γ and PMA, and the imaging experiments were performed 30 min later. The results indicated that the fluorescence in the red channel was weaker than that in the green channel and the F R / G value was lower (Figure 4B-C and 4E-F).…”

Section: Reversible Sensing Of Intracellular Exogenous and Endogenous Onooand Gsh Using Ucnps-1@pei@nb3mentioning

confidence: 99%

Engineering of Reversible Luminescent Probes for Real-time Intravital Imaging of Liver Injury and Repair

Liu¹,

He²,

Gong³

et al. 2021

CCS Chem.

View full text Add to dashboard Cite

As the primary organ for drug metabolism and detoxification, the liver is prone to be damaged and its functionality is severely impaired. The treatment of liver diseases is based on a clear understanding of the process underlying liver injury and repair. However, intravital real-time imaging of liver injury and repair is still limited due to the lack of in vivo reversible visualization methods. To this end, we proposed a rational design strategy for the development of reversible upconversion luminescence nanoprobe that allows real-time and in vivo imaging of liver injury and repair processes. As a proof of demonstration, we first developed a small molecule probe NB3 which can reversibly respond to related analytes of early liver injury (peroxynitrite, ONOO-) and liver repair (glutathione, GSH). The small molecule probe was then integrated with a core-shell upconversion nanoparticle to form a sophisticated nanoprobe. Compared to traditional small molecule probes, this nanoprobe exhibited higher selectivity to ONOO − , longer retention time in liver, and a wider response dynamic range to GSH after oxidized by ONOO -. The novel nanoprobe facilitated the successful monitoring and discrimination among the different degrees of liver injury and repair in a mouse model.

show abstract

A Reversible Fluorescent Probe for Real‐Time Live‐Cell Imaging and Quantification of Endogenous Hydropolysulfides

Cited by 16 publications

References 29 publications

Systematic Tuning of Rhodamine Spirocyclization for Super-Resolution Microscopy

Systematic Tuning of Rhodamine Spirocyclization for Super-Resolution Microscopy

Engineering of Reversible Luminescent Probes for Real-Time Intravital Imaging of Liver Injury and Repair

Engineering of Reversible Luminescent Probes for Real-time Intravital Imaging of Liver Injury and Repair

Contact Info

Product

Resources

About