GLPBio

Xanthurenic acid

Catalog No.: GC11459Purity:>98.00%Synonyms: NSC 401570, Xanthurenate
COASDSData Sheet
Xanthurenic acid is an endogenous group II metabotropic glutamate receptor agonist involved in sensory transmission in the thalamus.

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Xanthurenic acid
Cas No.: 59-00-7
10mM (in 1mL DMSO)In Stock
$19.00
1
25mgIn Stock
$17.00
1
50mgIn Stock
$25.00
1
100mgIn Stock
$35.00
1
500mgIn Stock
$86.00
1
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Description

Xanthurenic acid is an endogenous group II metabotropic glutamate receptor agonist involved in sensory transmission in the thalamus[1]. Xanthurenic acid is synthesized from 3-hydroxykynurenine (3-HK) and may play a physiological role in attention and cognitive processes[2]. Xanthurenic acid can interact with Bcl-2 family proteins, induce mitochondrial apoptosis pathways and impair mitochondrial function[3]. Xanthurenic acid can induce gametogenesis in parasitic Plasmodium[4].

In vitro, Xanthurenic acid (20μM) treatment of vascular smooth muscle cells and retinal pigment epithelial cells for 3h induced mitochondrial damage, resulting in mitochondrial migration, cytochrome c release, and destruction of mitochondria and nucleus[5].

In vivo, Xanthurenic acid (100mg/kg) treated by intraperitoneal injection for 21 days in adult male albino Wistar rats significantly reduced the number of active neurons per channel in the ventral tegmental area (VTA), but did not change the number of firing neurons in the substantia nigra pars compacta (SN)[6].

References:
[1] Copeland C S, Neale S A, Salt T E. Actions of Xanthurenic acid, a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus[J]. Neuropharmacology, 2013, 66: 133-142.
[2] Sathyasaikumar K V, Tararina M, Wu H Q, et al. Xanthurenic acid formation from 3-hydroxykynurenine in the mammalian brain: neurochemical characterization and physiological effects[J]. Neuroscience, 2017, 367: 85-97.
[3] Malina H Z, Hess O M. Xanthurenic acid translocates proapoptotic Bcl-2 family proteins into mitochondria and impairs mitochondrial function[J]. BMC cell biology, 2004, 5: 1-7.
[4] Billker O, Lindo V, Panico M, et al. Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito[J]. Nature, 1998, 392(6673): 289-292.
[5] Malina H Z, Richter C, Mehl M, et al. Pathological apoptosis by xanthurenic acid, a tryptophan metabolite: activation of cell caspases but not cytoskeleton breakdown[J]. BMC physiology, 2001, 1: 1-8.
[6] Taleb O, Maammar M, Klein C, et al. A role for xanthurenic acid in the control of brain dopaminergic activity[J]. International Journal of Molecular Sciences, 2021, 22(13): 6974.

Protocol

Cell experiment [1]:

Cell lines

Primary vascular smooth muscle cells (VSMCs), Retinal pigment epithelium (RPE) cells

Preparation Method

Confluent cells culture were pre-incubated without or with Xanthurenic acid (20μM) in MEM medium for 3h. The medium was removed and replaced with medium containing 100nM Mitotracker CMXRos. After an incubation for 45min Mitotracker CMXRos was removed and replaced by MEM medium. cells were cultivated for the next 20h, stained additionally with antibody against gelsolin and then observed by fluorescence microscopy.

Reaction Conditions

20μM; 3h

Applications

Xanthurenic acid induces mitochondrial damage.
Animal experiment [2]:

Animal models

Adult male albino Wistar rats

Preparation Method

Animals were treated during 21 consecutive days with Xanthurenic acid (100mg/kg/day; dissolved in 1% bicarbonate solution). The drug was i.p injected in a 1mL volume. The Xanthurenic acid effect was compared to that of the neuroleptic haloperidol (0.5mg/kg i.p in 1mL) given daily for 21 days. Control animals were daily i.p injected with 1mL of vehicle for the same period. After the treatment schedule (i.e., on day 22) spontaneously firing dopaminergic neurons within the substantia nigra compacta (SN) and the ventral tegmental area (VTA) nucleus were counted.

Dosage form

100mg/kg for 21 days; i.p.

Applications

Xanthurenic acid treatment reduced significantly the number of active neurons per track in the VTA. In contrast, Xanthurenic acid treatment did not change the number of firing neurons in the SN.

References:
[1]Malina H Z, Richter C, Mehl M, et al. Pathological apoptosis by xanthurenic acid, a tryptophan metabolite: activation of cell caspases but not cytoskeleton breakdown[J]. BMC physiology, 2001, 1: 1-8.
[2]Taleb O, Maammar M, Klein C, et al. A role for xanthurenic acid in the control of brain dopaminergic activity[J]. International Journal of Molecular Sciences, 2021, 22(13): 6974.

Product Documents

Purity:>98.00%Appearance:A solid
COASDSData Sheet

Chemical Properties

CAS No.
59-00-7
Synonyms
NSC 401570, Xanthurenate
Chemical Name
8-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acid
SMILES
OC1=C(C2=CC=C1)NC(C(O)=O)=CC2=O
Molecular Formula
C10H7NO4
Molecular Weight
205.17
Solubility
0.1 M NaOH: 2 mg/ml
Storage
Store at 2-8°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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