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| Other Sizes |
| Targets |
As a D-amino acid, H-D-Arg-OH·HCl does not have a specific biological target in the same way as a drug. However, it can interact with amino acid transporters and enzymes that recognize arginine. D-Arginine can be transported by some amino acid transporters, albeit with lower affinity than L-arginine. It is also a substrate for D-amino acid oxidase (DAAO), an enzyme that oxidizes D-amino acids, leading to the production of hydrogen peroxide and ammonia. D-Arginine can also compete with L-arginine for binding to nitric oxide synthase (NOS) and arginase, but with much lower affinity. Its primary utility is as a research tool for studying the stereospecificity of arginine metabolism and transport, and for investigating the roles of D-amino acids in biological systems, including their involvement in bacterial cell wall synthesis and neurobiology.
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| ln Vitro |
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro, D-arginine is used to study the stereospecificity of amino acid transporters and enzymes. It can compete with L-arginine for uptake by cells in culture, and its transport kinetics can be measured using radiolabeled or fluorescent derivatives. D-Arginine is also a substrate for D-amino acid oxidase (DAAO), and its oxidation can be monitored by measuring hydrogen peroxide production or oxygen consumption in enzymatic assays. In peptide synthesis, D-arginine can be incorporated into peptides using standard solid-phase peptide synthesis methods. These D-peptides are often used to study protein-protein interactions, as they can be resistant to proteolysis and may exhibit altered receptor binding properties. The compound does not have intrinsic pharmacological activities such as receptor agonism or antagonism; its effects are mainly mediated through its interactions with transporters and metabolic enzymes. |
| ln Vivo |
D-Arginine is not a pharmacologically active drug and does not have defined in vivo activity as a therapeutic agent. When administered to animals, D-arginine is metabolized by D-amino acid oxidase (DAAO) in the liver and kidneys, producing hydrogen peroxide, ammonia, and the corresponding α-keto acid. This metabolism leads to the rapid clearance of D-arginine from the systemic circulation. Unlike L-arginine, D-arginine is not a substrate for nitric oxide synthase (NOS) and therefore does not stimulate nitric oxide (NO) production. It may, however, compete with L-arginine for cellular uptake, potentially modulating NO production by altering intracellular L-arginine levels. D-Arginine has been used in research to study the physiological roles of D-amino acids and to investigate the effects of DAAO inhibition. It is not used clinically.
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| Enzyme Assay |
In vitro enzyme assays for H-D-Arg-OH·HCl typically focus on measuring the activity of D-amino acid oxidase (DAAO). A standard protocol involves incubating the compound with DAAO in a suitable buffer (e.g., phosphate buffer, pH 7.4) at 37°C. The reaction is initiated by addition of the substrate, and the production of hydrogen peroxide is measured using a coupled assay with horseradish peroxidase and a chromogenic substrate such as o-dianisidine or Amplex Red. Alternatively, the decrease in substrate concentration can be monitored by HPLC or by measuring oxygen consumption. The initial velocity is calculated, and kinetic parameters such as Km and Vmax can be determined. These assays are also used to screen for DAAO inhibitors, which are of interest for neurological disorders such as schizophrenia.
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| Cell Assay |
D-Arginine can be used in in vitro cellular assays to study amino acid transport and metabolism. A typical protocol involves culturing cells (e.g., endothelial cells, macrophages, or neuronal cells) in medium containing D-arginine. Cellular uptake is measured using radiolabeled D-arginine or by LC-MS/MS. The effects on cellular metabolism, such as alterations in polyamine synthesis or NO production (by competition with L-arginine), can be assessed. For example, in macrophages, D-arginine may compete with L-arginine for uptake, thereby reducing NO production. These assays help to understand the roles of D-amino acids in cell physiology and the specificity of amino acid transporters. The compound is not cytotoxic at concentrations typically used in such studies.
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| Animal Protocol |
In vivo animal studies with D-arginine are typically conducted to study amino acid metabolism and the role of D-amino acids in physiology. A common protocol involves administering D-arginine to rodents via intraperitoneal or intravenous injection at doses ranging from 10 to 100 mg/kg. Blood and tissue samples are collected at various time points to measure D-arginine and its metabolites (e.g., D-ornithine, α-keto acid) using chiral chromatography or mass spectrometry. The compound's effects on plasma arginine levels, NO production, or blood pressure may be assessed. D-Arginine can also be used in studies of DAAO activity in vivo, for example, by measuring the production of hydrogen peroxide or by using DAAO inhibitors to alter D-arginine levels. These studies help to elucidate the physiological significance of D-amino acids and their metabolism.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for D-arginine are limited, as it is not a drug candidate. When administered exogenously, D-arginine is rapidly metabolized by D-amino acid oxidase (DAAO) in the liver and kidneys, leading to a short half-life in the circulation. The compound is distributed to various tissues, but its uptake is less efficient than that of L-arginine due to stereospecificity of transporters. D-Arginine is predominantly cleared by renal excretion and metabolism. Its pharmacokinetics are dose-dependent and are influenced by the activity of DAAO. In research settings, D-arginine is often used as a tool to modulate DAAO activity or to study arginine transport. Due to its rapid metabolism, sustained plasma concentrations are difficult to achieve without using DAAO inhibitors. The compound has a solubility of ≥10 mg/mL in water and is stable under recommended storage conditions.
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| Toxicity/Toxicokinetics |
The toxicity of D-arginine is generally considered to be low, as it is a naturally occurring D-amino acid that is metabolized by DAAO. At high doses, the production of hydrogen peroxide and ammonia by DAAO could potentially lead to oxidative stress and toxicity. However, typical research doses (e.g., up to 100 mg/kg in rodents) do not cause significant adverse effects. The compound may cause mild irritation to skin, eyes, and mucous membranes. It is not classified as a carcinogen, mutagen, or reproductive toxicant. Standard laboratory safety precautions, including the use of personal protective equipment, are recommended. The compound should be handled in a well-ventilated area to avoid inhalation of the powder. No specific toxicological data are available for chronic exposure, but based on its metabolism and use, it is considered relatively safe for laboratory use.
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| References |
[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.
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| Additional Infomation |
D-Arginine hydrochloride (H-D-Arg-OH·HCl, CAS 64960-75-4) is a D-amino acid derivative used as a research tool in biochemistry and peptide synthesis. Its chemical formula is C₆H₁₄N₄O₂·HCl and molecular weight is 210.66. The compound appears as a white to off-white crystalline powder with a purity of ≥98% and a melting point of approximately 240-245°C (dec.). It is soluble in water (≥10 mg/mL) and is typically stored at 2-8°C for long-term stability. D-Arginine is used to study stereospecificity in amino acid transport and metabolism, as a substrate for D-amino acid oxidase (DAAO), and as a building block for the synthesis of D-peptides. It is not approved for human use and is intended for research purposes only.
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| Molecular Formula |
C8H15NO4
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|---|---|
| Molecular Weight |
189.209
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| Exact Mass |
189.1
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| CAS # |
64960-75-4
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| PubChem CID |
7018828
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
318.7±37.0 °C at 760 mmHg
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| Flash Point |
146.5±26.5 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.476
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| LogP |
0.94
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
13
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| Complexity |
207
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC(C)(C)OC(=O)C[C@H](C(=O)O)N
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| InChi Key |
MXWMFBYWXMXRPD-RXMQYKEDSA-N
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| InChi Code |
InChI=1S/C8H15NO4/c1-8(2,3)13-6(10)4-5(9)7(11)12/h5H,4,9H2,1-3H3,(H,11,12)/t5-/m1/s1
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| Chemical Name |
(2R)-2-amino-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2851 mL | 26.4257 mL | 52.8513 mL | |
| 5 mM | 1.0570 mL | 5.2851 mL | 10.5703 mL | |
| 10 mM | 0.5285 mL | 2.6426 mL | 5.2851 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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