Nitroarginine
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Nitroarginine

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Nitroarginine, or Nω-nitro-L-arginine, is a nitro derivative of the amino acid arginine. It is an inhibitor of nitric oxide synthase and hence a vaso-constrictor and coronary constrictor. As such, it finds widespread use as a biochemical tool in the study of nitric oxide and its biological effects. Nitroarginine has been used in research studying coronary constriction, in the presence of midazolam vasodilatation was unaffected by nitroarginine. Nitroarginine is currently in clinical trials for treating patients with advanced solid tumors.

Category
L-Amino Acids
Catalog number
BAT-008106
CAS number
2149-70-4
Molecular Formula
C6H13N5O4
Molecular Weight
219.20
Nitroarginine
IUPAC Name
(2S)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoic acid
Synonyms
Nitroarginine; N5-(nitroamidino)-L-Ornithine; (+)-NG-Nitroarginine; NG-nitro-L-Arginine, L-NG-Nitroarginine; L-NNA; L-NOARG; NG-Nitro-L-arginine; NG-Nitroarginine; NOLA; NSC 53662; NSC-53662; NSC53662; Nitro-L-arginine; Nω-Nitro-L-arginine; Nω-Nitro-L-arginine; ω-Nitro-L-arginine; ω-Nitroarginine
Appearance
White powder or colorless crystals
Purity
>98%
Density
1.659g/cm3
Melting Point
239-245 °C
Boiling Point
467.322°C at 760 mmHg
Storage
Store at RT
InChI
InChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1
InChI Key
MRAUNPAHJZDYCK-BYPYZUCNSA-N
Canonical SMILES
C(CC(C(=O)O)N)CN=C(N)N[N+](=O)[O-]

Nitroarginine is a potent inhibitor of nitric oxide synthase (NOS), a key enzyme in the production of nitric oxide. This compound has several notable applications in bioscience and medicine. Here are some key applications of Nitroarginine:

Cardiovascular Research: Nitroarginine is extensively used in studies focusing on cardiovascular health and diseases. By inhibiting NOS, researchers can investigate the role of nitric oxide in blood pressure regulation and vascular tone. This helps in understanding hypertension pathophysiology and developing new treatments for cardiovascular disorders.

Neurological Studies: In neurological research, Nitroarginine serves as a tool to explore the functions of nitric oxide in the brain. It is used to study its effects on neurotransmission, neurodegeneration, and brain plasticity. This is critical for investigating conditions like stroke, Alzheimer’s disease, and other neurodegenerative diseases.

Inflammation and Immune Response: Nitroarginine is used in immunological studies to examine the role of nitric oxide in inflammatory and immune responses. By blocking nitric oxide production, researchers can assess how it influences immune cell behavior and cytokine production. This is essential for understanding autoimmune diseases and developing anti-inflammatory therapies.

Cancer Research: Nitroarginine has applications in oncology, where it is used to study the relationship between nitric oxide and tumor growth. Inhibition of NOS can help researchers determine how nitric oxide contributes to cancer cell proliferation, angiogenesis, and metastasis.

1.Perinatal Resveratrol Supplementation to Spontaneously Hypertensive Rat Dams Mitigates the Development of Hypertension in Adult Offspring.
Care AS1, Sung MM1, Panahi S1, Gragasin FS1, Dyck JR1, Davidge ST1, Bourque SL2. Hypertension. 2016 May;67(5):1038-44. doi: 10.1161/HYPERTENSIONAHA.115.06793. Epub 2016 Feb 29.
This study was undertaken to determine whether perinatal maternal resveratrol (Resv)-a phytoalexin known to confer cardiovascular protection-could prevent the development of hypertension and improve vascular function in adult spontaneously hypertensive rat offspring. Dams were fed either a control or Resv-supplemented diet (4 g/kg diet) from gestational day 0.5 until postnatal day 21. Indwelling catheters were used to assess blood pressure and vascular function in vivo; wire myography was used to assess vascular reactivity ex vivo. Perinatal Resv supplementation in dams had no effect on fetal body weights, albeit continued maternal treatment postnatally resulted in growth restriction in offspring by postnatal day 21; growth restriction was no longer evident after 5 weeks of age. Maternal perinatal Resv supplementation prevented the onset of hypertension in adult offspring (-18 mm Hg;P=0.007), and nitric oxide synthase inhibition (withl-NG-nitroarginine methyl ester) normalized these blood pressure differences, suggesting improved nitric oxide bioavailability underlies the hemodynamic alterations in the Resv-treated offspring.
2.Neuroprotective Role of L-NG-Nitroarginine Methyl Ester (L-NAME) against Chronic Hypobaric Hypoxia with Crowding Stress (CHC) Induced Depression-Like Behaviour.
Deep SN1, Baitharu I2, Sharma A3, Gurjar AK4, Prasad D1, Singh SB1. PLoS One. 2016 Apr 15;11(4):e0153371. doi: 10.1371/journal.pone.0153371. eCollection 2016.
Improper neuroimmune responses following chronic stress exposure have been reported to cause neuronal dysfunctions leading to memory impairment, anxiety and depression like behaviours. Though several factors affecting microglial activation and consequent alteration in neuro-inflammatory responses have been well studied, role of NO and its association with microglia in stress induced depression model is yet to be explored. In the present study, we validated combination of chronic hypobaric hypoxia and crowding (CHC) as a stress model for depression and investigated the role of chronic stress induced elevated nitric oxide (NO) level in microglia activation and its effect on neuro-inflammatory responses in brain. Further, we evaluated the ameliorative effect of L-NG-Nitroarginine Methyl Ester (L-NAME) to reverse the stress induced depressive mood state. Four groups of male Sprague Dawley rat were taken and divided into control and CHC stress exposed group with and without treatment of L-NAME.
3.[PARTICIPATION OF NO-ERGIC MECHANISMS IN REALIZATION OF RESPIRATORY EFFECTS OF PRO-INFLAMMATORY CYTOKINE INTERLEUKIN-1-BETA].
Aleksandrov VG, Aleksandrova NP, Tumanova TS, Evseeva AD, Merkuriev VA. Ross Fiziol Zh Im I M Sechenova. 2015 Dec;101(12):1372-84.
The role of NO-ergic mechanisms in the realization of the respiratory effects of pro-inflammatory cytokine IL-1beta was investigated in acute experiments on anesthetized rats. To achieve this, we studied the effect of intravenous administration of IL-1beta during inhibition of NO-synthase by N-nitro-L-arginine methyl ester (L-NAME, a non-specific blocker of NO-synthase) on the parameters of breathing and the Hering-Breuer inspiratory-inhibitory reflex. It was shown that the effect of L-NAME eliminates the IL-1beta-dependent increase of the Hering-Breuer reflex, whereas effects on breathing pattern does not change: the increase in IL-1beta system-level evokes an increase in respiratory rate, tidal volume and lung ventilation. It is assumed that one of the mechanisms of enhance in the strength inspiratory-inhibitory reflex by increasing circulatory IL-1beta level is the increased glutamate-ergic transmission on pump-neurons induced by increase in nitric oxide synthesis in cerebrovascular endothelial cells.
4.Diagnostic Ultrasound High Mechanical Index Impulses Restore Microvascular Flow in Peripheral Arterial Thromboembolism.
Porter TR1, Radio S2, Lof J2, Everbach C3, Powers JE4, Vignon F5, Shi WT5, Xie F2. Ultrasound Med Biol. 2016 Apr 12. pii: S0301-5629(16)00062-4. doi: 10.1016/j.ultrasmedbio.2016.02.001. [Epub ahead of print]
We sought to explore mechanistically how intermittent high-mechanical-index (MI) diagnostic ultrasound impulses restore microvascular flow. Thrombotic microvascular obstruction was created in the rat hindlimb muscle of 36 rats. A diagnostic transducer confirmed occlusion with low-MI imaging during an intravenous microbubble infusion. This same transducer was used to intermittently apply ultrasound with an MI that produced stable or inertial cavitation (IC) for 10 min through a tissue-mimicking phantom. A nitric oxide inhibitor, L-Nω-nitroarginine methyl ester (L-NAME), was pre-administered to six rats. Plateau microvascular contrast intensity quantified skeletal microvascular blood volume, and postmortem staining was used to detect perivascular hemorrhage. Intermittent IC impulses produced the greatest recovery of microvascular blood volume (p < 0.0001, analysis of variance). Nitric oxide inhibition did not affect the skeletal microvascular blood volume improvement, but did result in more perivascular hemorrhage.
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