| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
- Group II metabotropic glutamate receptors (mGlu2/3 receptors) [1].
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|---|---|
| ln Vitro |
- Electrophysiological effects: Xanthurenic acid (XA) significantly reduced the amplitude of excitatory postsynaptic currents (EPSCs) in thalamic neurons in a concentration-dependent manner. This effect was mimicked by the Group II mGluR agonist (2S,2'R,3'R)-2-(2',3'-dicarboxycyclopropyl)glycine (DCG-IV) and blocked by the Group II mGluR antagonist (2S)-α-ethylglutamic acid (EGLU), indicating that Xanthurenic acid acts as an agonist at Group II mGluRs [1].
|
| ln Vivo |
A possible endogenous class II metabotropic glutamate receptor agonist that influences thalamic sensory transmission is xanthurenic acid. During iontophoresis and intravenous injection, xanthuric acid (XA) causes sensory suppression. Like other group II mGlu receptor agonists, XA also lessens the suppression caused by physiological sensory input in the thalamic reticular nucleus VB. Furthermore, xanthine acid is thought to be the first possible endogenous mGlu receptor allosteric agonist. Xanthophoric acid, a potential endotoxin that represents both the kynurenine metabolic pathway and class II receptors, is important for studying antipsychotics because these two pathways are closely linked to the pathophysiology of schizophrenia [1]. The combination of these two pathways represents a novel class II receptor ligand.
- Sensory transmission modulation: Microiontophoretic application of Xanthurenic acid (XA) onto thalamic neurons in vivo reduced the firing rate of these neurons in response to sensory stimulation. This effect was also blocked by EGLU, confirming the involvement of Group II mGluRs [1]. |
| Enzyme Assay |
- Receptor binding assay: Xanthurenic acid (XA) was tested for its binding affinity to recombinant rat mGlu2 and mGlu3 receptors expressed in Chinese hamster ovary (CHO) cells. The results showed that Xanthurenic acid bound to both receptors with moderate affinity, with IC50 values of approximately 10 μM for mGlu2 and 20 μM for mGlu3 receptors [1].
|
| Cell Assay |
- cAMP accumulation assay: In CHO cells transfected with mGlu2 or mGlu3 receptors, Xanthurenic acid (XA) inhibited forskolin-induced cAMP accumulation, a hallmark of Group II mGluR activation. The EC50 values for this effect were approximately 5 μM for mGlu2 and 10 μM for mGlu3 receptors [1].
|
| Animal Protocol |
- Animal model: Male Sprague-Dawley rats (200-250 g) were used for in vivo electrophysiological experiments. Rats were anesthetized with urethane (1.2 g/kg, intraperitoneal injection) and placed in a stereotaxic frame. The thalamus was targeted for microiontophoretic application of drugs [1].
- Drug administration: Xanthurenic acid (XA) was dissolved in artificial cerebrospinal fluid (aCSF) containing (in mM): 124 NaCl, 3 KCl, 2 CaCl2, 1 MgSO4, 26 NaHCO3, and 10 glucose, pH 7.4. The solution was pressure-ejected through a micropipette positioned near thalamic neurons at a rate of 5-10 nL/min [1]. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites
The known metabolites of Xanthurenic acid include Xanthurenic acid 8-O-sulfate. |
| References | |
| Additional Infomation |
Xanthurenic acid is a quinoline monocarboxylic acid, that is, a quinoline-2-carboxylic acid with hydroxyl groups substituted at C-4 and C-8. It has multiple functions, including as a metabolite glutamate receptor agonist, an iron chelator, an inhibitor of vesicular glutamate transport, and an animal metabolite. It is a quinoline monocarboxylic acid and also a dihydroxyquinoline. It is the conjugate acid of Xanthurenic acid.
Xanthurenic acid has been reported to be found in Japanese barracuda (Charybdis japonica), red swamp crayfish (Procambarus clarkii), and other organisms with relevant data. Xanthurenic acid is a metabolite of or produced by Saccharomyces cerevisiae. - Endogenous agonist: Xanthurenic acid (XA) is considered an endogenous agonist of type II metabolite glutamate receptors (mGluRs) because it is present in the brain and cerebrospinal fluid at concentrations sufficient to activate these receptors[1]. - Functional significance: The results suggest that Xanthurenic acid (XA) may regulate sensory transmission in the thalamus by activating type II metabolite glutamate receptors, which may be of great significance for the treatment of neurological diseases such as epilepsy and chronic pain [1]. |
| Molecular Formula |
C10H7NO4
|
|---|---|
| Molecular Weight |
205.1669
|
| Exact Mass |
205.037
|
| CAS # |
59-00-7
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| Related CAS # |
Xanthurenic acid-d4;1329611-28-0
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| PubChem CID |
5699
|
| Appearance |
Light yellow to brown solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
514.4±50.0 °C at 760 mmHg
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| Melting Point |
297-298 °C (dec.)(lit.)
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| Flash Point |
264.9±30.1 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
|
| Index of Refraction |
1.779
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| LogP |
2.64
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| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
15
|
| Complexity |
336
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
FBZONXHGGPHHIY-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
|
| Chemical Name |
8-hydroxy-4-oxo-1H-quinoline-2-carboxylic acid
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| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ~8.93 mg/mL (~43.52 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 20 mg/mL (97.48 mM) in 50% PEG300 +50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8740 mL | 24.3700 mL | 48.7401 mL | |
| 5 mM | 0.9748 mL | 4.8740 mL | 9.7480 mL | |
| 10 mM | 0.4874 mL | 2.4370 mL | 4.8740 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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