An O-GlcNAcase responsive fluorogenic probe for biological applications

Jung, Hyoje; Park, Sang‐Hyun; Yang, Won Ho; Cho, Jin Won; Shin, Injae

doi:10.1016/j.snb.2022.132093

Cited by 7 publications

(4 citation statements)

References 32 publications

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“…10a). 89 Because it distributed over the whole cell including the cytoplasm and the nucleus, a coumarin-conjugated fluorescein dye was chosen as a fluorophore in the design of the probes. Accordingly, 30a–d were composed of a coumarin-conjugated fluorescein dye linked to β- N -acylated glucosaminide.…”

Section: Fluorescent Probesmentioning

confidence: 99%

Glycosidase-targeting small molecules for biological and therapeutic applications

Kim,

Li,

Choi

et al. 2023

Chem. Soc. Rev.

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Section: Fluorescent Probesmentioning

confidence: 99%

Glycosidase-targeting small molecules for biological and therapeutic applications

Kim,

Li,

Choi

et al. 2023

Chem. Soc. Rev.

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“…Grad characteristic and can discriminate Ga 3+ and Pa 2+ in H 2 O/DMF (1/9, v/v) solution [33]. Compared with other analytical skills, the technology of fluorescent sensing has garnered significant attention due to its high sensitivity, fast response, excellent selectivity, and low biological toxicity [34][35][36][37][38][39][40][41]. However, practical applications still face inconveniences such as complex preparation, cumbersome separation, and challenging purification processes [42][43][44][45].…”

Section: Introductionmentioning

confidence: 99%

A comparative study of two thienopyrimidine Schiff base probes for sequential monitoring of Ga³⁺ and Pd²⁺

Shi,

Li,

Kang

et al. 2024

Luminescence

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Two Schiff base probes (S1 and S2) were prepared and synthesized by incorporating thienopyrimidine into salicylaldehyde or 3‐ethoxysalicylaldehyde individually, with the aim of detecting Ga3+ and Pd2+ sequentially. Upon chelation with Ga3+, S1 and S2 exhibited fluorescence enhancement in DMSO/H2O buffer. Both S1–Ga3+ and S2–Ga3+ were quenched by Pd2+. The limit of detection for S1 in response to Ga3+ and Pd2+ was 2.86 × 10−7 and 4.4 × 10−9 M, respectively. For S2, the limit of detection for Ga3+ and Pd2+ was 4.15 × 10−8 and 3.0 × 10−9 M, respectively. Furthermore, the complexation ratios of both S1 and S2 with Ga3+ and Pd2+ were determined to be 1:2 through Job's plots, ESI‐MS analysis, and theoretical calculations. Two molecular logic gates were constructed, leveraging the response behaviors of S1 and S2. Moreover, the potential utility of S1 and S2 for monitoring Ga3+ and Pd2+ in domestic water was verified.

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“…Recently, fluorescent probes have been developed to determine the individual activities of OGA and phosphatase in cells. For example, a coumarin-based activity probe and a coumarinconjugated fluorescein-based probe have been created to capture and detect OGA in cells (Hyun et al, 2019;Jung et al, 2022). While only two fluorescent probes for OGA have been devised to date, numerous fluorescent probes are available for detection of phosphatases Liu et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

A fluorescent probe to simultaneously detect both O-GlcNAcase and phosphatase

Boo

Lee²,

Kim³

et al. 2023

Front. Chem.

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O-GlcNAc modification of proteins often has crosstalk with protein phosphorylation. These posttranslational modifications are highly dynamic events that modulate a wide range of cellular processes. Owing to the physiological and pathological significance of protein O-GlcNAcylation and phosphorylation, we designed the fluorescent probe, βGlcNAc-CM-Rhod-P, to differentially detect activities of O-GlcNAcase (OGA) and phosphatase, enzymes that are responsible for these modifications. βGlcNAc-CM-Rhod-P was comprised of a βGlcNAc-conjugated coumarin (βGlcNAc-CM) acting as an OGA substrate, a phosphorylated rhodol (Rhod-P) as a phosphatase substrate and a piperazine bridge. Because the emission wavelength maxima of CM and Rhod liberated from the probe are greatly different (100 nm), spectral interference is avoided. The results of this study revealed that treatment of βGlcNAc-CM-Rhod-P with OGA promotes formation of the GlcNAc-cleaved probe, CM-Rhod-P, and a consequent increase in the intensity of fluorescence associated with free CM. Also, it was found that exposure of the probe to phosphatase produces a dephosphorylated probe, βGlcNAc-CM-Rhod, which displays strong fluorescence arising from free Rhod. On the other hand, when incubated with both OGA and phosphatase, βGlcNAc-CM-Rhod-P was converted to CM-Rhod which lacked both βGlcNAc and phosphoryl groups, in conjunction with increases in the intensities of fluorescence arising from both free CM and Rhod. This probe was employed to detect activities of OGA and phosphatase in cell lysates and to fluorescently image both enzymes in cells. Collectively, the findings indicate that βGlcNAc-CM-Rhod-P can be utilized as a chemical tool to simultaneously determine activities of OGA and phosphatase.

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An O-GlcNAcase responsive fluorogenic probe for biological applications

Cited by 7 publications

References 32 publications

Glycosidase-targeting small molecules for biological and therapeutic applications

Glycosidase-targeting small molecules for biological and therapeutic applications

A comparative study of two thienopyrimidine Schiff base probes for sequential monitoring of Ga³⁺ and Pd²⁺

A fluorescent probe to simultaneously detect both O-GlcNAcase and phosphatase

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An O-GlcNAcase responsive fluorogenic probe for biological applications

Cited by 7 publications

References 32 publications

Glycosidase-targeting small molecules for biological and therapeutic applications

Glycosidase-targeting small molecules for biological and therapeutic applications

A comparative study of two thienopyrimidine Schiff base probes for sequential monitoring of Ga3+ and Pd2+

A fluorescent probe to simultaneously detect both O-GlcNAcase and phosphatase

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Product

Resources

About

A comparative study of two thienopyrimidine Schiff base probes for sequential monitoring of Ga³⁺ and Pd²⁺