A near-infrared “turn-on” fluorescent probe with a self-immolative linker for the in vivo quantitative detection and imaging of hydrogen sulfide

Park, Chul Soon; Ha, Tai Hwan; Choi, Seon-Ae; Nguyen, Duong Nguyen; Noh, Seonmyeong; Kwon, Oh Seok; Lee, Chang‐Soo; Yoon, Hyeonseok

doi:10.1016/j.bios.2016.09.093

Cited by 72 publications

(18 citation statements)

References 46 publications

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“…Near-infrared (NIR) fluorescent probes are highly required because the emission in the NIR range (>650 nm) possesses better tissue penetration, less damage to the biological samples, and lower interference from the background fluorescence. − Compared with traditional cyanine dyes, − hemicyanine dyes show high fluorescence quantum yield and good photostability that are favorable for improving the quality of the image in vivo. − Up to now, hemicyanine-based NIR probes have been employed for the detection of pH, , cysteine, superoxide radical anion, selenol, hydrogen selenide, nitroxyl, hydrazine, hydrogen peroxide, hydrogen sulfide, β-lactamase, and nitroreductase . However, the fluorescent probes based on hemicyanine dyes for ALP are still very rare.…”

mentioning

confidence: 99%

Facile and Sensitive Near-Infrared Fluorescence Probe for the Detection of Endogenous Alkaline Phosphatase Activity In Vivo

et al. 2017

Anal. Chem.

161

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Alkaline phosphatase (ALP) is an essential enzyme and widely distributes in a variety of tissues. To date, various nanomaterial and small-molecule fluorescent probes for ALP have been constructed successfully, but the emission wavelengths of these probes are in the ultraviolet or visible range, which is not beneficial for bioimaging. Herein, a hemicyanine-based near-infrared (NIR) fluorescent probe named CyP is first synthesized and used to detect ALP activity. The characteristics of probe CyP are as follows: (1) The probe possesses a facile structure, which can be obtained by easy synthetic steps. (2) The fluorescence emission of the sensing system is at 738 nm belonging to NIR region, which is suitable for bioimaging in vivo. (3) The probe exhibits high sensitivity to ALP with 10-fold fluorescence enhancement and low detection limit (0.003 U/mL) can match the level of ALP in vivo. (4) The fluorescent change of the probe is attributed to the fact that ALP-catalyzed cleavage of the phosphate group in CyP induces the transformation of CyP (fluorescence off) into CyOH (fluorescence on), which is proved by HPLC, P NMR, MS, and DFT calculation. (5) The NIR fluorescent probe is applied for the detection of endogenous ALP activity in various biological samples such as cell, tissue, and living animal with satisfactory results.

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mentioning

confidence: 99%

Facile and Sensitive Near-Infrared Fluorescence Probe for the Detection of Endogenous Alkaline Phosphatase Activity In Vivo

et al. 2017

Anal. Chem.

161

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“…Yoon et al rationally designed a turn-on NIR probe, NIR-Az , using an azide group as a recognizing moiety for the selective detection of hydrogen sulfide with excellent sensitivity and selectivity over various RSONs. 213 They introduced a self-immolative linker between the azide group and the hemicyanine dye, which could increase the reactivity and selectivity through improved accessibility of H 2 S for the azide reduction reaction. In the case of NIR-Az , fluorescence signals began to appear at 720 nm after the addition of H 2 S. Based on these advantages, H 2 S can be detected quantitatively in living cells and animals, and there was no significant toxicity when cultured with NIR-Az .…”

Section: Nir Fluorescent Probes For Small Moleculesmentioning

confidence: 99%

Activity-based NIR fluorescent probes based on the versatile hemicyanine scaffold: design strategy, biomedical applications, and outlook

et al. 2022

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“…Compared with common hemicyanine dyes, − quinolinium-xanthene dyes show longer absorption and emission wavelengths that are beneficial for improving the quality of the image in vivo. Here, a novel NIR fluorescent probe named QX-B was developed for detecting H 2 O 2 (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Monitoring the Fluctuation of Hydrogen Peroxide in Diabetes and Its Complications with a Novel Near-Infrared Fluorescent Probe

et al. 2021

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Diabetes is one of the metabolic diseases marked by hyperglycemia and is often accompanied by the occurrence of some complications. As a biomarker of oxidative stress, hydrogen peroxide (H 2 O 2 ) has close association with the occurrence and development of diabetes and its complications. Unfortunately, there is no fluorescent probe reported for imaging H 2 O 2 in diabetic mice. Here, a novel near-infrared (NIR) fluorescent probe named QX-B was designed and synthesized to detect H 2 O 2 . For the probe, the quinolinium-xanthene dye is used as the fluorophore and borate ester is chosen as the response group. After the addition of H 2 O 2 , a strong NIR fluorescence signal at 772 nm is observed. The probe not only shows high sensitivity with 10-fold enhancement but also displays excellent selectivity to H 2 O 2 over other possible interfering species. In the meantime, the possible response mechanism of QX-B toward H 2 O 2 was proposed and verified by the high-performance liquid chromatography (HPLC) experiment, mass spectra (MS) experiment, and density functional theory (DFT) calculation. Furthermore, based on the low cell cytotoxicity of QX-B, it has been applied in imaging exogenous and endogenous H 2 O 2 in HeLa cells, HCT116 cells, 4T1 cells, and zebrafish successfully. More importantly, inspired by the performance of NIR fluorescence, QX-B has been used in monitoring H 2 O 2 in diabetic mice for the first time. This provides very important information for the diagnosis and treatment of diabetes and its complications.

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A near-infrared “turn-on” fluorescent probe with a self-immolative linker for the in vivo quantitative detection and imaging of hydrogen sulfide

Cited by 72 publications

References 46 publications

Facile and Sensitive Near-Infrared Fluorescence Probe for the Detection of Endogenous Alkaline Phosphatase Activity In Vivo

Facile and Sensitive Near-Infrared Fluorescence Probe for the Detection of Endogenous Alkaline Phosphatase Activity In Vivo

Activity-based NIR fluorescent probes based on the versatile hemicyanine scaffold: design strategy, biomedical applications, and outlook

Monitoring the Fluctuation of Hydrogen Peroxide in Diabetes and Its Complications with a Novel Near-Infrared Fluorescent Probe

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