A Fluorescent Probe for Fast and Quantitative Detection of Hydrogen Sulfide in Blood

Peng, Hanjing; Cheng, Yunfeng; Dai, Chong; King, Adrienne L.; Predmore, Benjamin L.; Lefer, David J.; Wang, Binghe

doi:10.1002/ange.201104236

Cited by 111 publications

(57 citation statements)

References 32 publications

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“…They are chemodosimeters based on the specific H 2 S‐induced reactions, such as azide reduction,8a–d quencher (such as Cu 2+ ) removal,8f,g and nucleophilic reaction to achieve strong fluorescence 8hj Most of them display a response time between 20 min to two hours, except for those that are based on the reduction of dansyl azide and Cu 2+ ‐removal sensing mechanisms reported by Wang and Nagano, respectively 8b,f. These probes, however, are not suitable for real‐time imaging of quick H 2 S‐related biological processes, and searching for quick reactions that are sensitive to H 2 S to enhance the response rate of H 2 S probes has always been attractive and challenging.…”

Section: Methodsmentioning

confidence: 99%

A Ratiometric Fluorescent Probe for Rapid Detection of Hydrogen Sulfide in Mitochondria

et al. 2013

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Section: Methodsmentioning

confidence: 99%

A Ratiometric Fluorescent Probe for Rapid Detection of Hydrogen Sulfide in Mitochondria

et al. 2013

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“…Almost during the same time when SF1/SF2 were reported, another group led by Wang disclosed a structurally different azide-based fluorescent probe dansyl azide (DNS-Az, Scheme 2). [47] DNS-Az itself is nonfluorescent, but treatment with H 2 S led to dramatic fluorescence enhancements in sodium phosphate buffers (containing Tween-20).…”

Section: Azide-based Probesmentioning

confidence: 99%

Fluorescent Probes for Hydrogen Sulfide Detection

Peng

Xian

2014

Asian J Org Chem

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Hydrogen sulfide (H 2 S) is an important signaling molecule with potent cytoprotective actions. Current results strongly suggest that modulation of H 2 S levels could have potential therapeutic values for a number of disease states, but its exact mechanisms of action are still unclear. A number of fundamental issues must be addressed to advance our understanding of the biology and clinical potential of H 2 S in the future. It is important, therefore, to understand the chemistry and properties of H 2 S and to appreciate the limitation and errors that may be generated when measuring H 2 S in biological samples. In the past several years a number of fluorescent probes for H 2 S detection have been developed. These probes are based on H 2 S-mediated reactions and are useful research tools. Herein, we provide an overview of current progress in this field. The development and properties of representative probes are discussed. Scheme 2. The structure and fluorescence turn-on mechanism of DNS-Az. Scheme 3. Strutures of R-Az, C-7Az, and Mas probe. Scheme 4. Structures of Cy-N 3 , FS1, and SHS-M2. Scheme 5. Structures of CLSS-2 and cpGFP-Tyr66pAzF. Scheme 6. Structure of SS1, P1, Eu·2, and P2. Scheme 7. Structures of nitro-based probes.

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“…H 2 S, traditionally considered to be a toxic gas with the typical smell of rotten eggs, has emerged as a member of the endogenous gaseous transmitter family of signaling molecules. [26] However, fluorescent H 2 S probes with both maximal absorption and emission wavelengths in the NIR region (650-950 nm) are relatively few, although they are highly desirable for biological imaging of H 2 S in living animals. [25a, b] H 2 S may interact with downstream proteins by posttranslational cysteine sulfhydration and binding to heme iron centers, regulating various physiological processes such as ischemia reperfusion injury, vasodilation, apoptosis, angiogenesis, neuromodulation, inflammation, insulin signaling, and oxygen sensing.…”

Section: Development Of a New Nir Fluorescent Turn-on H 2 S Probe Formentioning

confidence: 99%

“…[25e] Thus, the development of fluorescent probes for H 2 S is of high interest. [26] However, fluorescent H 2 S probes with both maximal absorption and emission wavelengths in the NIR region (650-950 nm) are relatively few, although they are highly desirable for biological imaging of H 2 S in living animals. A survey of the literature regarding the NIR fluorescent H 2 S probes indicates that the fluorescence imaging of H 2 S in living mice by NIR fluorescent probes is very rare ( www.chemeurj.org erations.…”

Section: Development Of a New Nir Fluorescent Turn-on H 2 S Probe Formentioning

confidence: 99%

Development of Unique Xanthene–Cyanine Fused Near‐Infrared Fluorescent Fluorophores with Superior Chemical Stability for Biological Fluorescence Imaging

Chen

Lin

Cui

et al. 2014

Chemistry A European J

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The development of near-infrared (NIR) functional fluorescent dyes has gained increasing attention over the last few decades. Herein, we describe the development of a unique type of xanthene-cyanine fused NIR fluorophores, XC dyes, formed by reacting chloro-substituted cyanine with resorcin or its analogues under anhydrous conditions. XC dyes are a hybrid of cyanine and xanthene. The preliminary mechanistic studies indicate that the formation of XC compounds likely includes a sequence of cyclization and oxidation. XC dyes have absorption and emission in the NIR region, and their fluorescence properties can be controlled by modifications of the key hydroxyl and amine groups. The novel XC NIR dyes are advantageous over previously developed merocyanine dyes NIR dyes in their chemical stability against strong nucleophiles. Quantum chemical calculations reveal that the distinct properties of XC and HD dyes can be attributed to their structural differences. By taking advantage of the superior properties of XC dyes, we have further constructed a new NIR fluorescent probe, XC-H2 S, which is capable of monitoring both the concentration- and time-dependent variations of H2 S in living animals, highlighting the value of XC NIR dyes. We expect that the unique XC NIR dyes developed herein will find broader applications than HD NIR dyes as fluorescent platforms for the development of a wide variety of NIR fluorescent probes, in particular, those suitable for targets of interest that have strong nucleophilic character.

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A Fluorescent Probe for Fast and Quantitative Detection of Hydrogen Sulfide in Blood

Cited by 111 publications

References 32 publications

A Ratiometric Fluorescent Probe for Rapid Detection of Hydrogen Sulfide in Mitochondria

A Ratiometric Fluorescent Probe for Rapid Detection of Hydrogen Sulfide in Mitochondria

Fluorescent Probes for Hydrogen Sulfide Detection

Development of Unique Xanthene–Cyanine Fused Near‐Infrared Fluorescent Fluorophores with Superior Chemical Stability for Biological Fluorescence Imaging

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