Analysis of the HNO and NO donating properties of alicyclic amine diazeniumdiolates

Bharadwaj, Gaurav; Benini, Patricia Graça Zanichelli; Basudhar, Debashree; Ramos-Colon, Cyf; Johnson, Gail M.; Larriva, Marti; Keefer, Larry K.; Andrei, Daniela; Miranda, Katrina M.

doi:10.1016/j.niox.2014.08.013

Cited by 22 publications

(12 citation statements)

References 76 publications

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“…Commonly used donors include Angeli’s salt (Na 2 N 2 O 3 ) [241, 288], Piloty’s acid (C 6 H 5 SO 2 NHOH) and derivatives [289, 290], acyl nitroso compounds [291–293], acyloxy nitroso compounds [294–296] and primary amine based diazeniumdiolates [RNH-N(O)=NO − ] [297, 298]. Among these donor classes, Angeli’s salt is the most prevalent donor used for chemical and biological studies.…”

Section: The Chemical Biology Of Hnomentioning

confidence: 99%

Biological signaling by small inorganic molecules

Basudhar

Ridnour

Cheng

et al. 2016

Coordination Chemistry Reviews

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Small redox active molecules such as reactive nitrogen and oxygen species and hydrogen sulfide have emerged as important biological mediators that are involved in various physiological and pathophysiological processes. Advancement in understanding of cellular mechanisms that tightly regulate both generation and reactivity of these molecules is central to improved management of various disease states including cancer and cardiovascular dysfunction. Imbalance in the production of redox active molecules can lead to damage of critical cellular components such as cell membranes, proteins and DNA and thus may trigger the onset of disease. These small inorganic molecules react independently as well as in a concerted manner to mediate physiological responses. This review provides a general overview of the redox biology of these key molecules, their diverse chemistry relevant to physiological processes and their interrelated nature in cellular signaling.

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Section: The Chemical Biology Of Hnomentioning

confidence: 99%

Biological signaling by small inorganic molecules

Basudhar

Ridnour

Cheng

et al. 2016

Coordination Chemistry Reviews

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“…77 A group of cyclic primary amine-based diazeniumdiolates (for example, AcOM-CPA/NO, Figure 9) release HNO with a wide-range of half-lives and hold promise in cancer cell targeting. 78 …”

Section: Advances In Hno Sourcesmentioning

confidence: 99%

Recent advances in the chemical biology of nitroxyl (HNO) detection and generation

Miao

King

2016

Nitric Oxide

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Nitroxyl or azanone (HNO) represents the redox-related (one electron reduced and protonated) relative of the well-known biological signaling molecule nitric oxide (NO). Despite the close structural similarity to NO, defined biological roles and endogenous formation of HNO remain unclear due to the high reactivity of HNO with itself, soft nucleophiles and transition metals. While significant work has been accomplished in terms of the physiology, biology and chemistry of HNO, important and clarifying work regarding HNO detection and formation has occurred within the last 10 years. This review summarizes advances in the areas of HNO detection and donation and their application to normal and pathological biology. Such chemical biological tools allow a deeper understanding of biological HNO formation and the role that HNO plays in a variety of physiological systems.

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“…It has also been suggested that HNO donors may represent a new class of inodilators for treatment of heart failure (Favaloro & Kemp‐Harper, ; Feelisch, ; Kemp‐Harper, Horowitz, & Ritchie, ; Paolocci et al, ). In addition to the cardiovascular effects observed, HNO has shown initial promise in the realm of cancer therapy (Bharadwaj et al, ; Norris et al, ).…”

Section: Introductionmentioning

confidence: 99%

Novel primary amine diazeniumdiolates—Chemical and biological characterization

Puglisi

Bradaric

Pontikis

et al. 2018

Drug Development Research

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Hit, Lead & Candidate Discovery Diazeniumdiolates, also known as NONOates, are extensively used in biochemical, physiological, and pharmacological studies due to their ability to release nitric oxide (NO ) and/or their congeneric nitroxyl (HNO). The purpose of this work was to synthesize a series of primary amine-based diazeniumdiolates as HNO/NO donors and to determine their efficacy as anticancer and antifungal agents in vivo. The seven compounds (3a-3g) were successfully synthesized and characterized, one of which had been previously reported in the literature (3g). Two compounds showed anti-proliferative effects against ovarian (ES2 and SKOV3) and AML monocyte-derived cancer cells (THP-1) when tested with standard MTT assays. Compounds 3a and 3g demonstrated reduced ovarian cancer cell proliferation when treated at doses from 0.033 to 1.0 mg/mL at the 24 hr time point. These compounds also exhibited moderate and selective antifungal activity against Fusarium oxysporum f.sp. lycopersici, one cause of opportunistic infections of immunocompromised patients, inhibiting the growth of the fungi at LD at 10 mg/mL. A third compound (3e) did not exhibit similar activities, possibly due to the alkyl chain. Our results suggest that the primary amine diazeniumdiolates may offer a versatile platform for the development of HNO/NO donors for biomedical applications.

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Analysis of the HNO and NO donating properties of alicyclic amine diazeniumdiolates

Cited by 22 publications

References 76 publications

Biological signaling by small inorganic molecules

Biological signaling by small inorganic molecules

Recent advances in the chemical biology of nitroxyl (HNO) detection and generation

Novel primary amine diazeniumdiolates—Chemical and biological characterization

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