Detection of Nitric Oxide and Nitroxyl with Benzoresorufin-Based Fluorescent Sensors

Apfel, Ulf Peter; Buccella, Daniela; Wilson, Justin J.; Lippard, Stephen J.

doi:10.1021/ic302793w

Cited by 82 publications

(65 citation statements)

References 60 publications

(108 reference statements)

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“…S18A†). The dynamic range of the probe is in line with values previously reported for other Cu( ii )-based HNO sensors,26,27,30 but remains significantly lower by comparison with reaction-based analogs 35,36…”

Section: Resultssupporting

confidence: 90%

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Solid-phase synthesis provides a modular, lysine-based platform for fluorescent discrimination of nitroxyl and biological thiols

et al. 2015

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Section: Resultssupporting

confidence: 90%

“…In the past decade, our group has developed several families of sensors for nitric oxide,20–26 employing a Cu( ii ) ion coordinated to the tridentate [N 2 O] motif of a quinoline-phenolate binding site, as in the parent, fluorescein-based CuFL1 (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Solid-phase synthesis provides a modular, lysine-based platform for fluorescent discrimination of nitroxyl and biological thiols

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“…97 These sensors displayed 1.5−4.8-fold emission enhancements in response to NO. Moreover, the fluorescent sensing mechanism was further explained using density functional theory calculations.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Recent Progress on the Development of Chemosensors for Gases

et al. 2015

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Introduction 7944 2. Chemosensors Based on Fluorescent Molecules 7945 2.1. Sensors for Environment Exhaust Gases 7945 2.1.1. Sensors for CO 2 7945 2.1.2. Sensors for SO 2 7949 2.1.3. Sensors for O 3 7951 2.2. Sensors for Biological Signaling Gases 7952 2.2.1. Sensors for NO 7952 2.2.2. Sensors for CO 7957 2.2.3. Sensors for H 2 S 7958 2.2.4. Sensors for 1 O 2 7962 2.3. Sensors for Highly Toxic Chemical-Warfare Agents 7963 2.3.1. Sensors for Nerve Agents 7963 2.3.2. Sensors for Sulfur Mustard 7967 3. Sensors Based on Functional Materials 7968 3.1. Sensors for Environment Gases 7968 3.1.1. Sensors for CO 2 7968 3.1.2. Sensors for O 2 7969 3.1.3. Sensors for VOCs 7971 3.1.4. Sensors for HCl 7972 3.1.5. Sensors for NH 3 7972 3.1.6. Sensors for Other Gases 7974 3.2. Sensors for High Dangerous Gases 7976 3.2.1. Sensors for Nerve Agents 7976 3.2.2. Sensors for Explosives 7976 4. Chemosensors Based on Metal Oxide Semiconductor 7978 4.1. Sensors for Environmental Gases 7978 4.1.1. Sensors for VOCs 7978 4.1.2. Sensors for CO 2 7985 4.1.3. Sensors for NO 2 7985 4.1.4. Sensors for SO 2 7987 4.1.5. Sensors for Other Gases 4.2. Sensors for Highly Toxic Gases 4.2.1. Sensors for CO 4.2.2. Sensors for H 2 S 4.2.3. Sensors for O 3 5. Conclusions and Future Perspectives Author Information

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“…25 A family of red-fluorescent sensors for HNO and NO was recently developed in our laboratory. 27 These probes, termed CuBRNO1-3, are based on the benzoresorufin fluorophore, which emits electron-rich metal chelating units can quench the emission of the fluorophore in the apo state, which reduces dramatically the dynamic range of the probe. In addition, the pK a values of electron donors and acceptors in the fluorophore need to be tuned carefully to maximize the dynamic range of the probe at pH values where the probe will be employed.…”

Section: Benzoresorufin-based Copper Complexes For Detection Of Hno Amentioning

confidence: 99%

Metal-Based Optical Probes for Live Cell Imaging of Nitroxyl (HNO)

Rivera‐Fuentes

Lippard

2015

Acc. Chem. Res.

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Conspectus: Nitroxyl (HNO) is a biological signaling agent that displays distinctive reactivity compared to nitric oxide (NO). As a consequence, these two reactive nitrogen species trigger different physiological responses. Selective detection of HNO over NO has been a challenge for chemists, and several fluorogenic molecular probes have been recently developed with that goal in mind. Common constructs take advantage of the HNO-induced reduction of Cu(II) to Cu(I).The sensing mechanism of such probes relies on the ability of the unpaired electron in a d orbital of the Cu(II) center to quench the fluorescence of a photoemissive ligand by either an electron or energy transfer mechanism. Experimental and theoretical mechanistic studies suggest that proton-coupled electron transfer mediates this process, and careful tuning of the copper coordination environment has led to sensors with optimized selectivity and kinetics.The current optical probes cover the visible and near-infrared regions of the spectrum. This palette of sensors comprises structurally and functionally diverse fluorophores such as coumarin 2 (blue/green emission), boron dipyrromethane (BODIPY, green emission), benzoresorufin (red emission), and dihydroxanthenes (near-infrared emission). Many of these sensors have been successfully applied to detect HNO production in live cells. For example, copper-based optical probes have been used to detect HNO production in live mammalian cells that have been treated with H 2 S and various nitrosating agents. These studies have established a link between HSNO, the smallest S-nitrosothiol, and HNO. In addition, a near-infrared HNO sensor has been used to perform multicolor/multianalyte microscopy, revealing that exogenously applied HNO elevates the concentration of intracellular mobile zinc. This mobilization of zinc ions is presumably a consequence of nitrosation of cysteine residues in zinc-chelating proteins such as metallothionein.Future challenges for the optical imaging of HNO include devising probes that can detect HNO reversibly, especially because ratiometric imaging can only report equilibrium concentrations when the sensing event is reversible. Another important aspect that needs to be addressed is the creation of probes that can sense HNO in specific subcellular locations. These tools would be useful to identify the organelles in which HNO is produced in mammalian cells and probe the intracellular signaling networks in which this reactive nitrogen species is involved. In addition, near-infrared emitting probes might be applied to detect HNO in thicker specimens, such as acute tissue slices and even live animals, enabling the investigation of the roles of HNO in physiological or pathological conditions in multicellular systems.

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Detection of Nitric Oxide and Nitroxyl with Benzoresorufin-Based Fluorescent Sensors

Cited by 82 publications

References 60 publications

Solid-phase synthesis provides a modular, lysine-based platform for fluorescent discrimination of nitroxyl and biological thiols

Solid-phase synthesis provides a modular, lysine-based platform for fluorescent discrimination of nitroxyl and biological thiols

Recent Progress on the Development of Chemosensors for Gases

Metal-Based Optical Probes for Live Cell Imaging of Nitroxyl (HNO)

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