A Fast and Selective Near-Infrared Fluorescent Sensor for Multicolor Imaging of Biological Nitroxyl (HNO)

Wrobel, Alexandra T.; Johnstone, Timothy C.; Liang, Alexandria Deliz; Lippard, Stephen J.; Rivera‐Fuentes, Pablo

doi:10.1021/ja500315x

Cited by 203 publications

(127 citation statements)

References 48 publications

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“…The integration of multiresponse to multi-species by a single probe can demonstrate the redox homeostasis process more clearly. [32][33][34][35][36][37][38][39] Moreover, the multiresponse probes can benefit from inaccurate calibration. And they can also avoid potobleaching rates of individual probes, uneven probe loading, nonhomogeneous distribution uncontrollable localization, larger invasive effects, metabolisms, and interference of spectral overlap.…”

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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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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“…Because of their protonation property at physiological conditions, macrocyclic polyamines often act as positive-charged units in constructing DNA condensation agents and non-viral gene vectors [5][6][7][8]. As a binding unit, macrocyclic polyamines have been frequently applied in the development of artificial nucleases [9][10][11][12] and a number of chemical sensors to monitor biologically-and environmentally-relevant metal and anion ions [13][14][15][16]. Our group has recently focused on the design and synthesis of various macrocyclic polyamine [12]aneN 3 compounds and their applications in artificial nucleases, DNA condensation agents, non-viral gene vectors, and chemical sensors [17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

[12]aneN3-based BODIPY as a selective and sensitive off–on sensor for the sequential recognition of Cu2+ ions and ADP

Zhang

Gao

Shi

et al. 2015

Chinese Chemical Letters

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“…11 Understanding the role of small molecules such as NO and HNO in biological signal transduction has resulted in important advances in medicine. 12,13 To shed light on the role of HSNO in vivo, sensors are currently being developed to image this elusive molecule. However, the biochemistry (formation, transport, decomposition) of HSNO remains poorly understood and the structure of the molecule has not been determined to date.…”

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confidence: 99%

Spontaneous and Selective Formation of HSNO, a Crucial Intermediate Linking H₂S and Nitroso Chemistries

et al. 2016

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Thionitrous acid (HSNO), a potential key intermediate in biological signaling pathways, has been proposed to link NO and H 2 S biochemistries, but its existence and stability in vivo remains controversial. We establish that HSNO is spontaneously formed in high concentration when NO and H 2 S gases are mixed at room temperature in the presence of metallic surfaces. Our measurements reveal that HSNO is formed by the reaction H 2 S + N 2 O 3 → HSNO + HNO 2 , where N 2 O 3 is a product of NO disproportionation. These studies also suggest that further reaction of HSNO with H 2 S may form HNO and HSSH. The length of the SN bond has been derived to high precision, and is found to be unusually long: 1.84 Å the longest SN bond reported to date for an R-SNO compound. The present structural and, particularly, reactivity investigations of this elusive molecule provide a rm foundation to better understand its potential physiological chemistry and propensity to undergo SN bond clevage in vivo.The intriguing similarities between the biological proles of NO and H 2 S, two important gasotransmitters acting notably as blood pressure mediators, have raised questions about the possibility of`cross-talk' between the two species. 1Such an interaction could explain the surprisingly benecial eects of these signaling molecules as it may allow H 2 S to modulate the availability of NO within the body.2 The vast majority of NO in vivo is bound as S-nitrosothiols (RSNO), a family of molecules well known for their crucial role in response to oxygen deprivation 35 as well as for being important biological reservoir for NO. 6,7 RSNOs are typically formed through the reaction of nitrosylating agents with thiols (RSH), 8 Once formed, RSNOs can also act as nitrosylating agents thus highlighting their role as NO shuttles at the cellular level.The simplest RSNO, thionitrous acid (HSNO), has been proposed to be the product of the reaction between NO and H 2 S; 9 other possible species have been implicated in this cross-talk', including nitrosopersulde (SSNO − ) and Nnitrosohydroxylamine-N -sulfonate.10 Unlike larger RSNOs, HSNO is thought to be able to freely diuse through cell membranes 2 suggesting that it has the ability to transnitrosate proteins removed from the sites where NO is synthesized, and therefore could play a key role in cellular redox regulation.11 Understanding the role of small molecules such as NO and HNO in biological signal transduction has resulted in important advances in medicine. 12,13 To shed light on the role of HSNO in vivo, sensors are currently being developed to image this elusive molecule. However, the biochemistry (formation, transport, decomposition) of HSNO remains poorly understood and the structure of the molecule has not been determined to date. HSNO has been spectroscopically characterized by infrared measurements in low temperature argon matrices.14,15 The molecule was produced from photolysis of HNSO, a low-lying stable structural isomer of HSNO (∆H ≥ 10 kcal/mol, 16 see Supplementary Information). ...

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A Fast and Selective Near-Infrared Fluorescent Sensor for Multicolor Imaging of Biological Nitroxyl (HNO)

Cited by 203 publications

References 48 publications

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

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

[12]aneN3-based BODIPY as a selective and sensitive off–on sensor for the sequential recognition of Cu2+ ions and ADP

Spontaneous and Selective Formation of HSNO, a Crucial Intermediate Linking H₂S and Nitroso Chemistries

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A Fast and Selective Near-Infrared Fluorescent Sensor for Multicolor Imaging of Biological Nitroxyl (HNO)

Cited by 203 publications

References 48 publications

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

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

[12]aneN3-based BODIPY as a selective and sensitive off–on sensor for the sequential recognition of Cu2+ ions and ADP

Spontaneous and Selective Formation of HSNO, a Crucial Intermediate Linking H2S and Nitroso Chemistries

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Spontaneous and Selective Formation of HSNO, a Crucial Intermediate Linking H₂S and Nitroso Chemistries