A near-infrared fluorescent turn-on probe for fluorescence imaging of hydrogen sulfide in living cells based on thiolysis of dinitrophenyl ether

Cao, Xiaowei; Lin, Weiying; Zheng, Kaibo; He, Longwei

doi:10.1039/c2cc34031c

Cited by 284 publications

(142 citation statements)

References 38 publications

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“…57 The dinitrophenyl group has often been used to protect tyrosine in peptide synthesis. Thiols could remove the dinitrophenyl group under basic conditions.…”

Section: Fluorescent Probes Based On a Thiolysis Reactionmentioning

confidence: 99%

Fluorescent probes for hydrogen sulfide detection and bioimaging

2014

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In comparison with other biological detection technologies, fluorescence bioimaging technology has become a powerful supporting tool for intracellular detection, and can provide attractive facilities for investigating physiological and pathological processes of interest with high spatial and temporal resolution, less invasiveness, and a rapid response. Due to the versatile roles of hydrogen sulfide (H 2 S) in cellular signal transduction and intracellular redox status regulation, fluorescent probes for the detection of this third signalling gasotransmitter have rapidly increased in number in recent years. These probes can offer powerful means to investigate the physiological actions of H 2 S in its native environments without disturbing its endogenous distribution. In this feature article, we address the synthesis and design strategies for the development of fluorescent probes for H 2 S based on the reaction type between H 2 S and the probes. Moreover, we also highlight fluorescent probes for other reactive sulfur species, such as sulfane sulfurs and SO 2 derivatives.

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“…57 The dinitrophenyl group has often been used to protect tyrosine in peptide synthesis. Thiols could remove the dinitrophenyl group under basic conditions.…”

Section: Fluorescent Probes Based On a Thiolysis Reactionmentioning

confidence: 99%

Fluorescent probes for hydrogen sulfide detection and bioimaging

2014

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“…In this work, we introduced dinitrophenyl ether group into 4 position of 1,8-naphthalimide, which acted as the H 2 S reactive site [42], and easily obtained the two-photo fluorescent probe NIeNHS [36]. The synthesis of NIeNHS is shown in Scheme 1, which is quite straightforward started from the cheap commercial available material 4-bromo-1,8-naphthalic anhydride.…”

Section: Introductionmentioning

confidence: 99%

A two-photon fluorescent probe for imaging hydrogen sulfide in living cells

Zhang

Qiao

et al. 2013

Dyes and Pigments

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“…He (34,35) and Xian (36,37) have reported elegantly designed probes with dual proximate electrophilic sites for trapping H 2 S. Furthermore, Nagano (38) as well as Zeng and Bai (39) have developed copper sulfide precipitation strategies for H 2 S detection. Nucleophilic addition (40)(41)(42) and related tactics (43)(44)(45) have also appeared in the recent literature. This ever-expanding palette of fluorescent probes has been used for the optical detection of exogenous H 2 S in live cells, blood, and in vitro enzyme assays.…”

mentioning

confidence: 99%

Cell-trappable fluorescent probes for endogenous hydrogen sulfide signaling and imaging H ₂ O ₂ -dependent H ₂ S production

Lin¹,

Lippert

Chang

2013

Proc. Natl. Acad. Sci. U.S.A.

352

223

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Hydrogen sulfide (H 2 S) is a reactive small molecule generated in the body that can be beneficial or toxic owing to its potent redox activity. In living systems, disentangling the pathways responsible for H 2 S production and their physiological and pathological consequences remains a challenge in part due to a lack of methods for monitoring changes in endogenous H 2 S fluxes. The development of fluorescent probes with appropriate selectivity and sensitivity for monitoring production of H 2 S at biologically relevant signaling levels offers opportunities to explore its roles in a variety of systems. Here we report the design, synthesis, and application of a family of azide-based fluorescent H 2 S indicators, Sulfidefluor-4, Sulfidefluor-5 acetoxymethyl ester, and Sulfidefluor-7 acetoxymethyl ester, which offer the unique capability to image H 2 S generated at physiological signaling levels. These probes are optimized for cellular imaging and feature enhanced sensitivity and cellular retention compared with our previously reported molecules. In particular, Sulfidefluor-7 acetoxymethyl ester allows for direct, real-time visualization of endogenous H 2 S produced in live human umbilical vein endothelial cells upon stimulation with vascular endothelial growth factor (VEGF). Moreover, we show that H 2 S production is dependent on NADPH oxidase-derived hydrogen peroxide (H 2 O 2 ), which attenuates VEGF receptor 2 phosphorylation and establishes a link for H 2 S/H 2 O 2 crosstalk. molecular imaging | redox biology | thiol | VEGFR

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A near-infrared fluorescent turn-on probe for fluorescence imaging of hydrogen sulfide in living cells based on thiolysis of dinitrophenyl ether

Abstract: We have constructed a novel NIR fluorescent turn-on hydrogen sulfide probe suitable for fluorescent imaging in living cells based on thiolysis of dinitrophenyl ether.

Cited by 284 publications

References 38 publications

Fluorescent probes for hydrogen sulfide detection and bioimaging

Fluorescent probes for hydrogen sulfide detection and bioimaging

A two-photon fluorescent probe for imaging hydrogen sulfide in living cells

Cell-trappable fluorescent probes for endogenous hydrogen sulfide signaling and imaging H ₂ O ₂ -dependent H ₂ S production

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A near-infrared fluorescent turn-on probe for fluorescence imaging of hydrogen sulfide in living cells based on thiolysis of dinitrophenyl ether

Abstract: We have constructed a novel NIR fluorescent turn-on hydrogen sulfide probe suitable for fluorescent imaging in living cells based on thiolysis of dinitrophenyl ether.

Cited by 284 publications

References 38 publications

Fluorescent probes for hydrogen sulfide detection and bioimaging

Fluorescent probes for hydrogen sulfide detection and bioimaging

A two-photon fluorescent probe for imaging hydrogen sulfide in living cells

Cell-trappable fluorescent probes for endogenous hydrogen sulfide signaling and imaging H 2 O 2 -dependent H 2 S production

Contact Info

Product

Resources

About

Cell-trappable fluorescent probes for endogenous hydrogen sulfide signaling and imaging H ₂ O ₂ -dependent H ₂ S production