L-(-)-threo-3-Hydroxyaspartic acid 是一种天然存在的、具有特定立体化学构型的氨基酸衍生物。L-(-)-threo-3-Hydroxyaspartic acid是谷氨酸受体（特别是NMDA受体）的一种选择性激动剂。
Cas No.:7298-99-9
Sample solution is provided at 25 µL, 10mM.
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L-(-)-threo-3-Hydroxyaspartic acid is a naturally occurring amino acid derivative with a specific stereochemical configuration. L-(-)-threo-3-Hydroxyaspartic acid is a selective agonist for glutamate receptors, particularly the NMDA receptor[1-2]. L-(-)-threo-3-Hydroxyaspartic acid is primarily used in neuroscience research as a tool compound for studying glutamatergic neurotransmission and receptor pharmacology[3-4].
In vitro, when Xenopus oocytes expressing EAAT4 were incubated with L-(-)-threo-3-Hydroxyaspartic acid (100μM). L-(-)-threo-3-Hydroxyaspartic acid competed with L-aspartate for binding to EAAT4 and induced an inward current[5]. L-(-)-threo-3-Hydroxyaspartic acid (100μM) was directly applied to migrating human U87MG glioma cells on Matrigel for 15 minutes. L-(-)-threo-3-Hydroxyaspartic acid increased the oscillation frequency of cells with spontaneous calcium oscillations and induced calcium oscillations in previously quiescent cells[6].
In vivo, L-(-)-threo-3-Hydroxyaspartic acid (833μM; 0.3±0.1µl) was locally injected into the substantia nigra pars compacta of rats three times a week for three weeks (a total of 9 injections). L-(-)-threo-3-Hydroxyaspartic acid resulting in morphological damage to neurons in the substantia nigra pars compacta[7]. L-(-)-threo-3-Hydroxyaspartic acid (100μM) was locally applied via pressure ejection (50ms pulses) from a glass micropipette near parenchymal arterioles in the somatosensory cortex of anesthetized C57BL/6J mice while monitoring changes in vascular diameter. L-(-)-threo-3-Hydroxyaspartic acid significantly increased arteriole diameter, mimicking the neurovascular coupling response[8].
References:
[1] Hara R, Nakano M, Kino K. One-Pot Production of L-threo-3-Hydroxyaspartic Acid Using Asparaginase-Deficient Escherichia coli Expressing Asparagine Hydroxylase of Streptomyces coelicolor A3(2). Appl Environ Microbiol. 2015 Jun;81(11):3648-54.
[2] Munir M, Correale DM, Robinson MB. Substrate-induced up-regulation of Na(+)-dependent glutamate transport activity. Neurochem Int. 2000 Aug-Sep;37(2-3):147-62.
[3] Jensen AA, Bräuner-Osborne H. Pharmacological characterization of human excitatory amino acid transporters EAAT1, EAAT2 and EAAT3 in a fluorescence-based membrane potential assay. Biochem Pharmacol. 2004 Jun 1;67(11):2115-27.
[4] Wang Z, Li W, Mitchell CK, et al. Activation of protein kinase C reduces GLAST in the plasma membrane of rat Müller cells in primary culture. Vis Neurosci. 2003 Nov-Dec;20(6):611-9.
[5] Shigeri Y, Shimamoto K, Yasuda-Kamatani Y, et al. Effects of threo-beta-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5). J Neurochem. 2001 Oct;79(2):297-302.
[6] Hamadi A, Giannone G, Takeda K, et al. Glutamate involvement in calcium-dependent migration of astrocytoma cells. Cancer Cell Int. 2014 May 19;14:42.
[7] Loopuijt LD. Local application of L- threo-hydroxyaspartate and malonate in rats in vivo induces rigidity and damages neurons of the substantia nigra, pars compacta. J Neural Transm (Vienna). 2002 Oct;109(10):1275-94.
[8] Jackson JG, Krizman E, Takano H, et al, Activation of Glutamate Transport Increases Arteriole Diameter in vivo: Implications for Neurovascular Coupling. Front Cell Neurosci. 2022 Mar 4;16:831061.
L-(-)-threo-3-Hydroxyaspartic acid 是一种天然存在的、具有特定立体化学构型的氨基酸衍生物。L-(-)-threo-3-Hydroxyaspartic acid是谷氨酸受体（特别是NMDA受体）的一种选择性激动剂[1-2]。L-(-)-threo-3-Hydroxyaspartic acid主要用于神经科学研究，作为研究谷氨酸能神经传递和受体药理学的工具化合物[3-4]。
在体外，在L-(-)-threo-3-Hydroxyaspartic acid（100μM）孵育表达EAAT4的卵母细胞时。L-(-)-threo-3-Hydroxyaspartic acid与L-天冬氨酸竞争结合EAAT4，可诱导内向电流[5]。L-(-)-threo-3-Hydroxyaspartic acid（100μM）直接处理在基质胶上迁移的人U87MG胶质瘤细胞15分钟。L-(-)-threo-3-Hydroxyaspartic acid能够增加具有自发性钙振荡细胞的振荡频率，并诱导原本静止的细胞产生钙振荡[6]。
在体内，L-(-)-threo-3-Hydroxyaspartic acid（833μM；0.3±0.1µl）局部注射至大鼠黑质致密部，每周三次，持续三周（共9次注射），可导致大鼠黑质致密部神经元的形态学损伤[7]。L-(-)-threo-3-Hydroxyaspartic acid（100μM）通过玻璃微管局部压力注射（50ms脉冲），应用于麻醉的C57BL/6J小鼠体感皮层小动脉附近，同时监测血管直径变化。L-(-)-threo-3-Hydroxyaspartic acid显著增加了小动脉直径，模拟了神经血管耦合反应[8]。
| Cell experiment [1]: | |
Cell lines | Human U87MG astrocytoma/glioma cells |
Preparation Method | U87MG cells were maintained in EMEM supplemented with 10% heat-inactivated fetal calf serum (FCS) at 37°C, 5% CO₂. For migration and calcium imaging assays, cells were plated on Matrigel-coated dishes or coverslips. For calcium measurements, cells were loaded with the fluorescent Ca²⁺ indicator Oregon Green 488 BAPTA-1 AM for 45 minutes prior to imaging. The glutamate reuptake inhibitor L-(-)-threo-3-Hydroxyaspartic acid (100μM) was added during the imaging period. |
Reaction Conditions | 100μM; 15min. |
Applications | L-(-)-threo-3-Hydroxyaspartic acid increased the frequency of spontaneous, migration-associated intracellular Ca²⁺ oscillations in oscillating cells and induced Ca²⁺ oscillations in previously quiescent cells. This enhancement of Ca²⁺ signaling contributes to the glutamate-mediated autocrine loop that promotes the migration of astrocytoma cells. |
| Animal experiment [2]: | |
Animal models | Male Sprague-Dawley rats |
Preparation Method | Rats were anesthetized and stereotactically implanted with bilateral guide cannulas above the substantia nigra, pars compacta (SNc). A solution containing either L-(-)-threo-3-Hydroxyaspartic acid alone, L-(-)-threo-3-Hydroxyaspartic acid plus malonate, or vehicle was bilaterally pressure-injected (0.3 ± 0.1 µl over 1 minute) directly into the brain tissue near the SNc. Injections were administered 3 times a week for a total of 9 times over three weeks. Behavior (rigidity, catalepsy, locomotion) was assessed 24 hours after injections. After the treatment period, the rats were sacrificed, and their brains were processed for histological analysis of the SNc. |
Dosage form | 833µM in 0.3 ± 0.1µl; Local pressure injection into the brain; 9 injections over 3 weeks. |
Applications | Local injection of L-(-)-threo-3-Hydroxyaspartic acid plus the mitochondrial inhibitor malonate induced a transient, mild rigidity in rats. The combination treatment resulted in more extensive neuronal damage in the ventral part of the SNc compared to L-(-)-threo-3-Hydroxyaspartic acid treatment alone. The observed neuronal damage was characterized by shrunken nucleoli and faintly stained cytoplasm in the affected neurons, indicating morphological and functional impairment, which may underlie the rigidity behavior. |
References: | |
| Cas No. | 7298-99-9 | SDF | |
| 别名 | L(-)-THREO-3-羟基天冬氨酸 | ||
| 化学名 | (2S,3S)-2-amino-3-hydroxysuccinic acid | ||
| Canonical SMILES | O[C@H](C(O)=O)[C@@H](C(O)=O)N | ||
| 分子式 | C4H7NO5 | 分子量 | 149.1 |
| 溶解度 | Soluble to 100 mM in 1eq. NaOH | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.7069 mL | 33.5345 mL | 67.0691 mL |
| 5 mM | 1.3414 mL | 6.7069 mL | 13.4138 mL |
| 10 mM | 670.7 μL | 3.3535 mL | 6.7069 mL |
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动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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