The NOtizer—A Device for the Convenient Preparation of Diazen‐1‐ium‐1,2‐diolates

Konter, Joerg; Abuo‐Rahma, Gamal El‐Din A.; El‐Emam, Ali A.; Lehmann, Jochen

doi:10.1016/s0076-6879(05)96002-3

Cited by 8 publications

(6 citation statements)

References 25 publications

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“…The photocaged NONOate 1 was synthesised from pyrrolidine‐based NONOate 2 and Npom chloride ( 3 ) in good yields (Scheme ). The starting materials 2 and 3 are accessible from commercially available compounds in one and two steps, respectively, by literature protocols ,…”

Section: Resultsmentioning

confidence: 99%

“…Sodium 1‐(pyrrolidin‐1‐yl)diazen‐1‐ium‐1,2‐diolate ( 2 ) : NONOate 2 was synthesised by a modified route similar to that already described by Konter et al . but with reduced pressure and a simplified experimental setup.…”

Section: Methodsmentioning

confidence: 99%

“…Diazeniumdiolates (also called NONOates) are a particularly interesting class of NO‐releasing substances widely used to study NO‐ and cGMP‐related processes . They are stable enough to have long shelf‐lives but can be designed to release NO with half‐lives ranging from 3 s to 20 h under physiological conditions . NONOates have been further modified, to improve, for example, cellular uptake, which results in more potent prodrugs .…”

Section: Introductionmentioning

confidence: 99%

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Npom‐Protected NONOate Enables Light‐Triggered NO/cGMP Signalling in Primary Vascular Smooth Muscle Cells

et al. 2018

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Diazeniumdiolates (NONOates) are a class of nitric-oxide-releasing substances widely used in studies of NO/cGMP signalling. Because spatiotemporal control is highly desirable for such purposes, we have synthesised a new Npom-caged pyrrolidine NONOate. A kinetic analysis together with a Griess assay showed the photodependent release of NO with high quantum yield (UV light). In primary vascular smooth muscle cells (VSMCs), our compound was reliably able to induce fast increases in cGMP, as measured with a genetically encoded FRET-based cGMP sensor and further validated by the phosphorylation of the downstream target vasodilator-stimulated phosphoprotein (VASP). Thanks to their facile synthesis, good decaging kinetics and capability to activate cGMP signalling in a fast and efficient manner, Npom-protected NONOates allow for improved spatiotemporal control of NO/cGMP signalling.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Npom‐Protected NONOate Enables Light‐Triggered NO/cGMP Signalling in Primary Vascular Smooth Muscle Cells

et al. 2018

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“…Note that after recording the pressure-time plots the pressure was raised back to high pressure several times until the NO consumption in the reaction was close to zero to improve the yield of the product as reported previously. [12] Isolation and Characterization of the NONOates: The NONOates precipitated as solids during the reaction or after concentrating the final solution. Compounds 2o, 2p and 2q formed as resin-like residues after solvent evaporation.…”

Section: Methodsmentioning

confidence: 99%

“…[12] Besides several attributes that simplify the synthesis, the NOtizer features a PC-interface linked to a computer with appropriate software that allows the continuous on-line recording and graphical illustration of the pressure and temperature pattern in the reaction chamber. Further details are provided in the Experimental Section.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Diazen‐1‐ium‐1,2‐diolates Monitored by the “NOtizer” Apparatus: Relationship between Formation Rates, Molecular Structure and the Release of Nitric Oxide

Konter

Abuo‐Rahma

El-Emam³

et al. 2007

Eur J Org Chem

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Nitrogen-bound diazen-1-ium-1,2-diolates (diazeniumdiolates, "NONOates", "solid NO") are generally prepared from secondary amines and nitric oxide and are compounds of first choice for the direct release of nitric oxide (NO). First, we report on the relationships between the structures of the amines and the formation rates of the corresponding NONOates, second on the structures of the NONOates and the rate of NO release and finally between the rates of NONOate formation and NO release from these species. A series of differently sized and substituted cyclic and aliphatic amines were used to quantify the reactivity of amines towards NO by monitoring the decrease in NO pressure with the NOtizer, an apparatus developed for this study. The release of NO was measured amperometrically with an NO-sensitive electrode and the half-lives of novel diazeniumdiolates were determined by UV spectroscopy. It was found that steric hindrance

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NO-donors. Part 171: Synthesis and antimicrobial activity of novel ketoconazole–NO-donor hybrid compounds

Konter

Möllmann

Lehmann

2008

Bioorganic & Medicinal Chemistry

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The NOtizer—A Device for the Convenient Preparation of Diazen‐1‐ium‐1,2‐diolates

Cited by 8 publications

References 25 publications

Npom‐Protected NONOate Enables Light‐Triggered NO/cGMP Signalling in Primary Vascular Smooth Muscle Cells

Npom‐Protected NONOate Enables Light‐Triggered NO/cGMP Signalling in Primary Vascular Smooth Muscle Cells

Synthesis of Diazen‐1‐ium‐1,2‐diolates Monitored by the “NOtizer” Apparatus: Relationship between Formation Rates, Molecular Structure and the Release of Nitric Oxide

NO-donors. Part 171: Synthesis and antimicrobial activity of novel ketoconazole–NO-donor hybrid compounds

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