Nω-Nitro-D-arginine
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Nω-Nitro-D-arginine

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Category
D-Amino Acids
Catalog number
BAT-003552
CAS number
66036-77-9
Molecular Formula
C6H13N5O4
Molecular Weight
219.20
Nω-Nitro-D-arginine
IUPAC Name
(2R)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoic acid
Synonyms
D-Arg(NO2)-OH; (R)-2-Amino-5-(3-Nitroguanidino)Pentanoic Acid
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.65 g/cm3
Melting Point
236-247 °C
Boiling Point
462.4°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-/m1/s1
InChI Key
MRAUNPAHJZDYCK-SCSAIBSYSA-N
Canonical SMILES
C(CC(C(=O)O)N)CN=C(N)N[N+](=O)[O-]

Nω-Nitro-D-arginine, known for its potent inhibition of nitric oxide synthase, boasts diverse applications in biomedical research and clinical investigations. Here are the key applications of Nω-Nitro-D-arginine, presented with high perplexity and burstiness:

Cardiovascular Research: At the forefront of cardiovascular research, Nω-Nitro-D-arginine serves as a pivotal tool for examining the intricate role of nitric oxide in cardiovascular functions. By suppressing nitric oxide production, researchers delve into its impact on blood pressure regulation, vascular tone, and overall cardiac functionality. This insightful approach aids in unraveling the underlying mechanisms of cardiovascular diseases and fosters the development of innovative treatment modalities.

Neurological Studies: Within the realm of neuroscience, Nω-Nitro-D-arginine emerges as a crucial component for probing the involvement of nitric oxide in neural signaling and brain function. By probing the effects of nitric oxide on processes such as synaptic plasticity, neuroprotection, and neural development, researchers gain profound insights. These revelations pave the way for identifying novel therapeutic targets for grappling with neurodegenerative ailments and cognitive anomalies.

Inflammation and Immune Response: Embarking on a journey into the realms of inflammatory pathways and immune responses, Nω-Nitro-D-arginine emerges as a key player in deciphering the impact of nitric oxide. Through modulation of nitric oxide levels, researchers unveil its influence on the production of pro-inflammatory cytokines, immune cell activation, and defense mechanisms against pathogens. This knowledge stands as a cornerstone for crafting therapeutic interventions for inflammatory disorders and fine-tuning immune responses in diverse clinical scenarios.

Cancer Research: In the dynamic field of oncology, Nω-Nitro-D-arginine takes center stage, enabling investigations into the multifaceted role of nitric oxide in tumor biology. This potent compound aids in unraveling the complex interplay between nitric oxide and tumor growth, angiogenesis, and metastasis. By deciphering these intricate relationships, researchers pave the way for designing targeted strategies to manipulate nitric oxide pathways for novel anticancer therapies.

1.Pharmacological Characterization of the Edema Caused by Vitalius dubius (Theraphosidae, Mygalomorphae) Spider Venom in Rats.
Rocha-E-Silva TA1, Linardi A2, Antunes E2, Hyslop S2. J Pharmacol Exp Ther. 2016 Jan;356(1):13-9. doi: 10.1124/jpet.115.226787. Epub 2015 Oct 15.
Bites by tarantulas (Theraphosidae, Mygalomorphae) in humans can result in mild clinical manifestations such as local pain, erythema, and edema. Vitalius dubius is a medium-sized, nonaggressive theraphosid found in southeastern Brazil. In this work, we investigated the mediators involved in the plasma extravasation caused by V. dubius venom in rats. The venom caused dose-dependent (0.1-100 μg/site) edema in rat dorsal skin. This edema was significantly inhibited by ((S)1-{2-[3(3-4-dichlorophenyl)-1-(3-iso-propoxyphenylacetyl)piperidine-3-yl]ethyl}-4-phenyl-1-azoniabicyclo[2.2.2]octone, chloride) (SR140333, a neurokinin NK1 receptor antagonist), indomethacin [a nonselective cyclooxygenase (COX) inhibitor], cyproheptadine (a serotonin 5-hydroxytryptamine1/2 and histamine H1 receptor antagonist), and N(ω)-nitro-L-arginine methyl ester (a nitric oxide synthase inhibitor). In contrast, mepyramine (a histamine H1 receptor antagonist), D-Arg-[Hyp(3),Thi(5),D-Tic(7),Oic(8)-]-BK (JE 049, a bradykinin B2 receptor antagonist), and ((S)-N-methyl-N-[4-(4-acetylamino-4-phenylpiperidino)-2-(3,4-di-chlorophenyl)butyl]benzamide) (SR48968, a neurokinin NK2 receptor antagonist) had no effect on the venom-induced increase in vascular permeability.
2.Enantioseparation of N-derivatized amino acids by micro-liquid chromatography/laser induced fluorescence detection using quinidine-based monolithic columns.
Wu H1, Wang Q2, Ruan M1, Peng K1, Zhu P1, Crommen J3, Han H4, Jiang Z5. J Pharm Biomed Anal. 2016 Mar 20;121:244-52. doi: 10.1016/j.jpba.2015.12.011. Epub 2015 Dec 15.
A novel carbamoylated quinidine based monolith, namely poly(O-9-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine-co-ethylene dimethacrylate (poly(MQD-co-EDMA)), was prepared for the micro-LC enantioseparation of N-derivatized amino acids. The influence of the mobile phase composition, including the organic modifier proportion, the apparent pH and the buffer concentration, on the enantioresolution of N-derivatized amino acids was systematically investigated. Satisfactory column performance in terms of permeability, efficiency and reproducibility was obtained in most cases. The majority of the enantiomers of the tested N-protected amino acids, including 3,5-DNB, 3,5-DClB, FMOC, 3,5-DMB, p-NB, m-ClB, p-ClB and B derivatives, could be baseline separated on the poly(MQD-co-EDMA) monolithic column within 25min. A self-assembled laser induced fluorescence (LIF) detector was employed to improve sensitivity when analyzing 7-nitro-2,1,3-benzoxadiazole (NBD) derivatives of amino acids.
3.Xylopia aethiopica fruit extract exhibits antidepressant-like effect via interaction with serotonergic neurotransmission in mice.
Biney RP1, Benneh CK2, Ameyaw EO3, Boakye-Gyasi E2, Woode E2. J Ethnopharmacol. 2016 May 26;184:49-57. doi: 10.1016/j.jep.2016.02.023. Epub 2016 Feb 20.
ETHNOPHARMACOLOGICAL RELEVANCE: Xylopia aethiopica has been used traditionally to treat some central nervous system disorders including epilepsy.
4.Vascular Actions of Angiotensin 1-7 in the Human Microcirculation: Novel Role for Telomerase.
Durand MJ1, Zinkevich NS1, Riedel M1, Gutterman DD1, Nasci VL1, Salato VK1, Hijjawi JB1, Reuben CF1, North PE1, Beyer AM2. Arterioscler Thromb Vasc Biol. 2016 Apr 14. pii: ATVBAHA.116.307518. [Epub ahead of print]
OBJECTIVE: This study examined vascular actions of angiotensin 1-7 (ANG 1-7) in human atrial and adipose arterioles.
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