| Identification | Back Directory | [Name]
2-[amino-(4-amino-4-carboxy-butyl)imino-methyl]aminobutanedioic acid | [CAS]
2387-71-5 | [Synonyms]
Arginosuccinic acid
L-Arginosuccinic acid
L-Argininosuccinic acid
Arginosuccinic acid 13C4
(N(omega)-L-arginino)succinic acid
N-[[(S)-4-Amino-4-carboxybutyl]amino(imino)methyl]-L-aspartic acid
N-[[[(S)-4-Amino-4-carboxybutyl]amino](imino)methyl]-L-aspartic acid
2-[amino-(4-amino-4-carboxy-butyl)imino-methyl]aminobutanedioic acid
L-Aspartic acid, N-[[[(4S)-4-amino-4-carboxybutyl]amino]iminomethyl]- | [Molecular Formula]
C10H18N4O6 | [MDL Number]
MFCD00871403 | [MOL File]
2387-71-5.mol | [Molecular Weight]
290.27 |
| Hazard Information | Back Directory | [Uses]
Argininosuccinic acid participates in the fourth step of the urea cycle, with being cleaved to arginine and fumaric acid by argininosuccinic acid lyase (ASL). Argininosuccinic acid reduces reduced glutathione (GSH) level, and increases the production of reactive oxygen species in cerebral cortex and striatum. Argininosuccinic acid causes lipid peroxidation and protein oxidation, and induces oxidative stress in the developing rat brain[1][2]. | [in vivo]
Argininosuccinic acid (2 μM for 2 μL; ICV; single dose) significantly induces oxidative stress in 30-day-old rats[1].
| Animal Model: | 30-day-old rats with two small holes drilled in the skull[1] | | Dosage: | 2 μL of a 1.0 M concentration (2 μmol in 2 μL) | | Administration: | Injection; euthanized 2 h after treatment | | Result: | Significantly induced lipid oxidation (MDA levels) and protein oxidation (carbonyl formation), increased ROS and RNS generation (DCFH oxidation).
Significantly decreased GSH concentrations.
|
| [Purification Methods]
A likely impurity is fumaric acid. In neutral or alkaline solution it readily undergoes ring closure to the 'anhydride' (see below). Crystallise it from water by adding 1.5 volumes of EtOH. The barium salt is stable at 0-5o if dry. [Westfall Biochem J 77 135 1960, Ratner & Kunkemueller Biochemistry 5 1821 1966.] | [References]
[1] Seminotti B, et al. Free Radical Scavengers Prevent Argininosuccinic Acid-Induced Oxidative Stress in the Brain of Developing Rats: a New Adjuvant Therapy for Argininosuccinate Lyase Deficiency? Mol Neurobiol. 2020 Feb;57(2):1233-1244. DOI:10.1007/s12035-019-01825-0
[2] Nagamani SCS, et al. GeneReviews? [Internet]. Seattle (WA): University of Washington, Seattle; 1993–2023. PMID:21290785 |
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