Xanthurenic acid
(Synonyms: 4,8-二羟基喹啉-2-甲酸) 目录号 : GC11459
Xanthurenic acid是一种内源性II组代谢型谷氨酸受体激动剂，参与丘脑的感觉传递。
Cas No.:59-00-7
Sample solution is provided at 25 µL, 10mM.
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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.
Xanthurenic acid是一种内源性II组代谢型谷氨酸受体激动剂，参与丘脑的感觉传递[1]。Xanthurenic acid由3-羟基犬尿氨酸（3-HK）合成，可能在注意力和认知过程中发挥生理作用[2]。Xanthurenic acid能够与Bcl-2家族蛋白相互作用，诱导线粒体凋亡途径并损害线粒体功能[3]。Xanthurenic acid能够诱导寄生性疟原虫的配子发生[4]。
在体外，Xanthurenic acid（20μM）处理血管平滑肌细胞和视网膜色素上皮细胞3h，诱导了线粒体损伤，导致线粒体迁移、细胞色素c释放以及线粒体和细胞核的破坏[5]。
在体内，Xanthurenic acid（100mg/kg）通过腹腔注射处理成年雄性白化Wistar大鼠21天，显著减少了腹侧被盖区（VTA）中每条通道的活跃神经元数量，但不会改变黑质致密部（SN）中放电神经元的数量[6]。
| 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: | |
| Cas No. | 59-00-7 | SDF | |
| 别名 | 4,8-二羟基喹啉-2-甲酸 | ||
| 化学名 | 8-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acid | ||
| Canonical SMILES | OC1=C(C2=CC=C1)NC(C(O)=O)=CC2=O | ||
| 分子式 | C10H7NO4 | 分子量 | 205.17 |
| 溶解度 | 0.1 M NaOH: 2 mg/ml | 储存条件 | Store at RT |
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.874 mL | 24.37 mL | 48.7401 mL |
| 5 mM | 0.9748 mL | 4.874 mL | 9.748 mL |
| 10 mM | 0.4874 mL | 2.437 mL | 4.874 mL |
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Quality Control & SDS
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- Purity: >99.50%
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