(R)-4-Amino-3-hydroxybutyric Acid
(Synonyms: (R)-(-)-4-氨基-3-羟基丁酸) 目录号 : GC46339
A GABA receptor modulator
Cas No.:7013-07-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(R)-4-Amino-3-hydroxybutyric acid is a GABA receptor modulator.1 It binds to GABAA and GABAB receptors (IC50s = 1 and 0.35 µM, respectively) and inhibits GABA uptake in rat brain synaptosomes (IC50 = 67 µM). (R)-4-amino-3-hydroxybutyric acid is also a GABAC receptor agonist that induces currents in a patch-clamp assay using Xenopus oocytes expressing the human receptor (EC50 = 19 µM).2 In vivo, (R)-4-amino-3-hydroxybutyric acid (20 mg/animal) inhibits electrical discharges in the amygdala in a cat model of N-amidinobenzamide-induced seizures.3
1.Falch, E., Hedegaard, A., Nielsen, L., et al.Comparative stereostructure-activity studies on GABAA and GABAB receptor sites and GABA uptake using rat brain membrane preparationsJ. Neurochem.47(3)898-903(1986) 2.Hinton, T., Chebib, M., and Johnston, G.A.R.Enantioselective actions of 4-amino-3-hydroxybutanoic acid and (3-amino-2-hydroxypropyl)methylphosphinic acid at recombinant GABAC receptorsBioorg. Med. Chem. Lett.18(1)402-404(2008) 3.Katayama, Y., and Mori, A.Inhibitory action of (3R)-(-)-4-amino-3-hydroxybutanoic acid on N-amidinobenzamide induced seizure activity in cat brainIRCS Med. Sci.5(9)437(1977)
| Cas No. | 7013-07-2 | SDF | |
| 别名 | (R)-(-)-4-氨基-3-羟基丁酸 | ||
| Canonical SMILES | OC(C[C@@H](O)CN)=O | ||
| 分子式 | C4H9NO3 | 分子量 | 119.1 |
| 溶解度 | PBS (pH 7.2): 10 mg/ml | 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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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 8.3963 mL | 41.9815 mL | 83.9631 mL |
| 5 mM | 1.6793 mL | 8.3963 mL | 16.7926 mL |
| 10 mM | 0.8396 mL | 4.1982 mL | 8.3963 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Hydroxylated analogues of 5-aminovaleric acid as 4-aminobutyric acidB receptor antagonists: stereostructure-activity relationships
J Neurochem 1992 Mar;58(3):1150-9.PMID:1310720DOI:10.1111/j.1471-4159.1992.tb09374.x.
The (R) and (S) forms of 5-amino-2-hydroxyvaleric acid (2-OH-DAVA) and 5-amino-4-hydroxyvaleric acid (4-OH-DAVA) were designed as structural hybrids of the 4-aminobutyric acidB (GABAB) agonist (R)-(-)-4-Amino-3-hydroxybutyric Acid [(R)-(-)-3-OH-GABA] and the GABAB antagonist 5-aminovaleric acid (DAVA). (S)-(-)-2-OH-DAVA and (R)-(-)-4-OH-DAVA showed a moderately potent affinity for GABAB receptor sites in rat brain and showed GABAB antagonist effects in a guinea pig ileum preparation. The respective enantiomers, (R)-(+)-2-OH-DAVA and (S)-(+)-4-OH-DAVA, were markedly weaker in both test systems. All four compounds were weak inhibitors of GABAA receptor binding in rat brain, and none of them significantly affected synaptosomal GABA uptake. Based on molecular modeling studies it has been demonstrated that low-energy conformations of (R)-(-)-3-OH-GABA, (S)-(-)-2-OH-DAVA, and (R)-(-)-4-OH-DAVA can be superimposed. These conformations may reflect the shapes adopted by these conformationally flexible compounds during their interaction with GABAB receptors. The present studies emphasize the similar, but distinct, constraints imposed on agonists and antagonists for GABAB receptors.
A molecular characterization of the agonist binding site of a nematode cys-loop GABA receptor
Br J Pharmacol 2015 Aug;172(15):3737-47.PMID:25850584DOI:10.1111/bph.13158.
Background and purpose: Cys-loop GABA receptors represent important targets for human chemotherapeutics and insecticides and are potential targets for novel anthelmintics (nematicides). However, compared with insect and mammalian receptors, little is known regarding the pharmacological characteristics of nematode Cys-loop GABA receptors. Here we have investigated the agonist binding site of the Cys-loop GABA receptor UNC-49 (Hco-UNC-49) from the parasitic nematode Haemonchus contortus. Experimental approach: We used two-electrode voltage-clamp electrophysiology to measure channel activation by classical GABA receptor agonists on Hco-UNC-49 expressed in Xenopus laevis oocytes, along with site-directed mutagenesis and in silico homology modelling. Key results: The sulphonated molecules P4S and taurine had no effect on Hco-UNC-49. Other classical Cys-loop GABAA receptor agonists tested on the Hco-UNC-49B/C heteromeric channel had a rank order efficacy of GABA > trans-4-aminocrotonic acid > isoguvacine > imidazole-4-acetic acid (IMA) > (R)-(-)-4-Amino-3-hydroxybutyric Acid [R(-)-GABOB] > (S)-(+)-4-Amino-3-hydroxybutyric Acid [S(+)-GABOB] > guanidinoacetic acid > isonipecotic acid > 5-aminovaleric acid (DAVA) (partial agonist) > β-alanine (partial agonist). In silico ligand docking revealed some variation in binding between agonists. Mutagenesis of a key serine residue in binding loop C to threonine had minimal effects on GABA and IMA but significantly increased the maximal response to DAVA and decreased twofold the EC50 for R(-)- and S(+)-GABOB. Conclusions and implications: The pharmacological profile of Hco-UNC-49 differed from that of vertebrate Cys-loop GABA receptors and insect resistance to dieldrin receptors, suggesting differences in the agonist binding pocket. These findings could be exploited to develop new drugs that specifically target GABA receptors of parasitic nematodes.
Highly Diastereoselective Construction of Carbon- Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates
Front Chem 2021 Jun 2;9:613633.PMID:34150715DOI:10.3389/fchem.2021.613633.
The synthesis of the stable surrogates of an important amino acid (R)-4-Amino-3-hydroxybutyric Acid (GABOB) such as substituted hydroxy aminophosphonic acids bearing a quaternary stereogenic center is presented. Highly diastereoselective formations of fluorinated spiroepoxy alkylphosphonate or related tertiary carbon-containing oxiranes from β-keto phosphonates possessing methyl, phenyl, or cyclohexenyl substituents, are reported. Stereoselective acid-promoted epoxide opening by bromide or azide followed by reduction/protection afforded tertiary bromides or N-Boc derivatives of β-amino-γ-hydroxy alkylphosphonates in most cases, while the reactions of oxiranes with different amines yielded their β-hydroxy-γ-amino regioisomers. Surprisingly, during the synthesis of amino phosphonic acids, we observe that the acid-induced rearrangement proceeded in a high diastereospecific manner, leading finally to substituted β-hydroxy-γ-aminoalkylphosphonic acids.