Sulfide-selective chemosignaling by a Cu2+ complex of dipicolylamine appended fluorescein

Choi, Myung Gil; Cha, Sunyoung; Lee, Haekyung; Jeon, Hye Lim; Chang, Suk‐Kyu

doi:10.1039/b916476f

Cited by 330 publications

(157 citation statements)

References 37 publications

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“…62 The probe was designed based on a Cu 2+ complex of fluorescein containing a dipicolylamine chelator. The detection limit was 420 nM in aqueous solution.…”

Section: Fluorescent Probes Based On Copper Sulfide Precipitationmentioning

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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“…62 The probe was designed based on a Cu 2+ complex of fluorescein containing a dipicolylamine chelator. The detection limit was 420 nM in aqueous solution.…”

Section: Fluorescent Probes Based On Copper Sulfide Precipitationmentioning

confidence: 99%

Fluorescent probes for hydrogen sulfide detection and bioimaging

2014

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“…•− including colorimetry, 28 electrochemicalanalysis, 29 and gas chromatography. 30 However, these technologies often require post-mortem processing and destruction of tissues or cells.…”

Section: Introductionmentioning

confidence: 99%

Near-Infrared Fluorescence Probe for in Situ Detection of Superoxide Anion and Hydrogen Polysulfides in Mitochondrial Oxidative Stress

et al. 2016

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H 2 S plays important physiological and pathological roles in cardiovascular system and nervous system. But recent evidences imply that hydrogen polysulfides (H 2 S n ) are the actual signaling molecules in cells. Although H 2 S n have been demonstrated to be responsible for mediating tumor suppressors, ion channels, and transcription factors, more of their biological effects are still need to be elaborated. On one hand, H 2 S n have been suggested to be generated from endogenous H 2 S upon reaction with reactive oxygen species (ROS). On the other hand, H 2 S n derivatives are proposed to be a kind of direct antioxidant against intracellular oxidative stress. This conflicting results should be attributed to the regulation of redox homeostasis between ROS and H 2 S n . Superoxide anion (O 2 •− ) is undoubtedly the primary ROS existing in mitochondria. We reason that the balance of O 2•− and H 2 S n are pivotal in physiological and pathological processes. Herein, we report two near-infrared fluorescent probes Hcy-Mito and Hcy-Biot for the detection of O 2•− and H 2 S n in cells and in vivo. Hcy-Mito is conceived to be applied in mitochondria, and Hcy-Biot is designed to target tumor tissue. Both of the probes were successfully applied for visualizing exogenous and endogenous O 2•− and H 2 S n in living cells and in tumor mice models. The results demonstrate that H 2 S n can be promptly produced by mitochondrial oxidative stress. Flow cytometry assays for apoptosis suggest that H 2 S n play critical roles in antioxidant systems.

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“…[9][10][11][12][13][14][15][16][17][18][19][20] These probes can detect H 2 S in aqueous solution with high sensitivity and selectivity. Existing fluorescencebased probes implemented so far have been subdivided into four different categories (depending on the reaction mechanism by which analyte recognition occurs): [1,19] (i) azide-toamine reduction; [12,[21][22][23][24][25][26][27] (ii) nucleophilic addition; [28][29][30][31] (iii) copper displacement; [32][33][34][35][36] and (iv) nitro-to-amine reduction. [37,38] All the sensors belonging to the above categories make use of organic molecules that change their fluorescence intensity when interacting with H 2 S. Sensors belonging to category (iii) constitute an exception since in this case the molecule acting as the recognition element is a metal complex.…”

Section: Introductionmentioning

confidence: 99%

“…generally produce fluorescence turn-on changes via H 2 Smediated precipitation of Mt-S. [1,[32][33][34][39][40][41][42] Despite all the advantages of the above mentioned probes (e.g. high selectivity and sensitivity), some shortcomings typically involve slow response and poor water solubility.…”

Section: Introductionmentioning

confidence: 99%

A Copper Porphyrin for Sensing H₂S in Aqueous Solution via a “Coordinative‐Based” Approach

et al. 2015

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Sulfide-selective chemosignaling by a Cu2+ complex of dipicolylamine appended fluorescein

Cited by 330 publications

References 37 publications

Fluorescent probes for hydrogen sulfide detection and bioimaging

Fluorescent probes for hydrogen sulfide detection and bioimaging

Near-Infrared Fluorescence Probe for in Situ Detection of Superoxide Anion and Hydrogen Polysulfides in Mitochondrial Oxidative Stress

A Copper Porphyrin for Sensing H₂S in Aqueous Solution via a “Coordinative‐Based” Approach

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Sulfide-selective chemosignaling by a Cu2+ complex of dipicolylamine appended fluorescein

Cited by 330 publications

References 37 publications

Fluorescent probes for hydrogen sulfide detection and bioimaging

Fluorescent probes for hydrogen sulfide detection and bioimaging

Near-Infrared Fluorescence Probe for in Situ Detection of Superoxide Anion and Hydrogen Polysulfides in Mitochondrial Oxidative Stress

A Copper Porphyrin for Sensing H2S in Aqueous Solution via a “Coordinative‐Based” Approach

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A Copper Porphyrin for Sensing H₂S in Aqueous Solution via a “Coordinative‐Based” Approach