Generation of Nitric Oxide and Possibly Nitroxyl by Nitrosation of Sulfohydroxamic Acids and Hydroxamic Acids

Shirota, Frances N.; DeMaster, Eugene G.; Lee, Melinda J.C.; Nagasawa, Hiromichi

doi:10.1006/niox.1999.0257

Cited by 16 publications

(16 citation statements)

References 38 publications

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“…to Scheme 8 to produce HNO, measured as N 2 O [97]. These N-nitrohyroxamic acids were not isolatable due to their extreme instability and propensity to decompose to HNO; however, synthesizing prodrug forms of these compounds should be a challenging and worthwhile endeavor.…”

Section: Scheme (6)mentioning

confidence: 99%

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Donors of HNO

Miranda

Nagasawa

Toscano

2005

CTMC

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Recent comparisons of the pharmacological effects of nitric oxide (NO) and nitroxyl (HNO) donors have demonstrated that the responses to these redox-related nitrogen oxides are nearly universally dissimilar. These analyses have suggested the existence of mutually exclusive signaling pathways as a result of discrete chemical interactions of HNO and NO with a variety of critical biomolecules. Although the mechanisms of action are currently unresolved, the pharmacological responses to HNO are promising for clinical treatment of cardiovascular diseases such as heart failure, myocardial infarction and stroke. This review provides a detailed discussion of the most commonly utilized donors of HNO as well as a guideline for the characterization of novel donors.

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Section: Scheme (6)mentioning

confidence: 99%

“…Shirota et al [97] attempted the synthesis of hybrid compounds containing the diazeniumdiolate (NONOate) functional group of Angeli's salt and the sulfonyl components of Piloty's acid and similar sulfohydroxamic acid derivatives. Addition of aryl-and alkylsulfohyroxamic acids to an acidic nitrite solution resulted in release of NO.…”

Section: Scheme (3)mentioning

confidence: 99%

Donors of HNO

Miranda

Nagasawa

Toscano

2005

CTMC

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“…Other simple N-hydroxysulfonamides, such as N-hydroxymethanesulfonamide (CH 3 SO 2 NHOH), release HNO under basic conditions and find some use as HNO donors (76). Recent patents describe the HNO-releasing properties of a large number of Piloty's acid derivatives with various aromatic substitutions at different positions or based upon different aromatic heterocycles (85,86).…”

Section: Structure/synthesismentioning

confidence: 99%

The Chemistry of Nitroxyl-Releasing Compounds

DuMond

King

2011

Antioxidants & Redox Signaling

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Nitroxyl (HNO) demonstrates a diverse and unique biological profile compared to nitric oxide, a redox-related compound. Although numerous studies support the use of HNO as a therapeutic agent, the inherent chemical reactivity of HNO requires the use of donor molecules. Two general chemical strategies currently exist for HNO generation from nitrogen-containing molecules: (i) the disproportionation of hydroxylamine derivatives containing good leaving groups attached to the nitrogen atom and (ii) the decomposition of nitroso compounds (X-N=O, where X represents a good leaving group). This review summarizes the synthesis and structure, the HNO-releasing mechanisms, kinetics and by-product formation, and alternative reactions of six major groups of HNO donors: Angeli's salt, Piloty's acid and its derivatives, cyanamide, diazenium diolate-derived compounds, acyl nitroso compounds, and acyloxy nitroso compounds. A large body of work exists defining these six groups of HNO donors and the overall chemistry of each donor requires consideration in light of its ability to produce HNO. The increasing interest in HNO biology and the potential of HNO-based therapeutics presents exciting opportunities to further develop HNO donors as both research tools and potential treatments.

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“…Methanesulfohydroxamic acid (MHSA), the simplest member of the aliphatic sulfohydroxamic acid series, is also able to decompose to HNO at a rate comparable to Angeli's salt and PA [22][23][24]. A review addressing all the previous issues has been recently published [25].…”

Section: Introductionmentioning

confidence: 99%