L-Homocysteine thiolactone hydrochloride
(Synonyms: L-高半胱氨酸硫内酯盐酸盐) 目录号 : GC32484
L-Homocysteinethiolactonehydrochloride是同型半胱氨酸的分子内硫酯;防止同型半胱氨酸转化成蛋白质。
Cas No.:31828-68-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cell experiment: | HUVEC are treated with homocysteine (1, 5, 10 mM) or homocysteine thiolactone (0.25, 0.5, 1 mM) for 3, 6, 12 and 24 h. Cell survival is determined by the MTT method. The optical density is measured at 570 nm with 630 nm as a reference[3]. |
Animal experiment: | Rats: Homocysteine thiolactone is freshly prepared in saline and administered in a volume of 1.0 mL/100 g body weight. Rats are divided into control (saline-injected) group and homocysteine thiolactone-treated group. The latter group receives different doses 5.5 mM/kg, 8.0 mM/kg, and 11.0 mM/kg, respectively. Each rat is used only once[5]. |
References: [1]. Jakubowski H, et al. Homocysteine thiolactone: metabolic origin and protein homocysteinylation in humans. J Nutr. 2000 Feb;130(2S Suppl):377S-381S. | |
L-Homocysteine thiolactone hydrochloride is an intramolecular thioester of homocysteine; prevents translational incorporation of homocysteine into proteins.
In all cell types, from bacterial to human, homocysteine is metabolized to homocysteine thiolactone by methionyl-tRNA synthetase. Elevated levels of homocysteine are an independent risk factor for cardiovascular disease in humans. Homocysteine can be harmful to human cells because of its metabolic conversion to homocysteine thiolactone, a reactive thioester. This conversion occurs in all human cell types, including endothelial cells[1]. Homocysteine thiolactone induces cell death and features of apoptosis including increased phosphotidylserine exposure on the membrane surface, increased apoptotic cells with hypoploid DNA contents, and internucleosomal DNA fragmentation in HL-60 cells[2]. Homocysteine thiolactone is cytotoxic and capable of promoting cell death, as measured by caspase-3 activation and DNA fragmentation. HcyT strongly activates IL-8 release[3].
Homocysteine thiolactone is toxic, induces epileptic seizures in rodents, and has been implicated in Alzheimer's disease[4]. Homocysteine thiolactone induces two types of seizures, the coexistence of convulsive and nonconvulsive epilepsy. The grade of seizures is dose dependent[5].
[1]. Jakubowski H, et al. Homocysteine thiolactone: metabolic origin and protein homocysteinylation in humans. J Nutr. 2000 Feb;130(2S Suppl):377S-381S. [2]. Huang RF, et al. Homocysteine thiolactone induces apoptotic DNA damage mediated by increased intracellularhydrogen peroxide and caspase 3 activation in HL-60 cells. Life Sci. 2001 May 11;68(25):2799-811. [3]. Kerkeni M, et al. Comparative study on in vitro effects of homocysteine thiolactone and homocysteine on HUVECcells: evidence for a stronger proapoptotic and proinflammative homocysteine thiolactone. Mol Cell Biochem. 2006 Oct;291(1-2):119-26. [4]. Borowczyk K, et al. Metabolism and neurotoxicity of homocysteine thiolactone in mice: evidence for a protective role of paraoxonase 1. J Alzheimers Dis. 2012;30(2):225-31. [5]. Stanojlovi? O, et al. Two types of seizures in homocysteine thiolactone-treated adult rats, behavioral and electroencephalographic study. Cell Mol Neurobiol. 2009 May;29(3):329-39.
| Cas No. | 31828-68-9 | SDF | |
| 别名 | L-高半胱氨酸硫内酯盐酸盐 | ||
| Canonical SMILES | N[C@@H](CCS1)C1=O.Cl | ||
| 分子式 | C4H8ClNOS | 分子量 | 153.63 |
| 溶解度 | Water : ≥ 23 mg/mL (149.71 mM) | 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 | 6.5091 mL | 32.5457 mL | 65.0915 mL |
| 5 mM | 1.3018 mL | 6.5091 mL | 13.0183 mL |
| 10 mM | 0.6509 mL | 3.2546 mL | 6.5091 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。
[L-[methyl-(11C)]-methionine of high enantiomeric purity production via on-line 11C-methylation of L-Homocysteine thiolactone hydrochloride]
Bioorg Khim 2011 Mar-Apr;37(2):216-22.PMID:21721254DOI:10.1134/s1068162011020051.
L-[methyl-(11C)]-methionine ([11C]MET), labelled with carbon-11 (T1/2 = 20 min), is the most commonly used amino acid radiotracer for PET diagnostics of brain tumors. The production of [11C]MET via on-line 11C-methylation of L-Homocysteine thiolactone hydrochloride (lactone) on C18 solid-phase extraction cartridge creates a problem of insufficient enantiomeric purity (content of L-isomer) of the product. The results of a systematic study of the influence of reaction parameters (lactone/base and the EtOH/H20 ratios, time of 11C-methylation) on the content of L-isomer in the preparation are presented. The developed method of on-line [11C]MET synthesis allows to obtain a product with a sufficiently high radiochemical yield (75 +/- 3%, n = 100, based on [11C]CH3I) and reliably high content of L-isomer (93.7 +/- 0.5%) satisfying the requirements of clinical applications. [11C] MET synthesis was performed on a fully automated module designed by the Institute of Human Brain (IHB RAS).
Efficient preparation of [11C]CH3Br for the labeling of [11C]CH3-containing tracers in positron emission tomography clinical practice
Nucl Med Commun 2011 Jun;32(6):466-74.PMID:21519304DOI:10.1097/MNM.0b013e3283438f9a.
Background and aim: [C]methyl iodide ([C]CH3I) is the most extensively used methylation agent for the preparation of a majority of C-labeled positron emission tomography (PET) radiotracers, which is commonly produced by the wet method and the gas-phase method. On account of the complexity of the gas-phase method, a simple automated synthesis of [C]methyl bromide ([C]CH3Br) as an analog of [C]CH3I is derived by the wet method in this study. Radiosynthesis of L-[S-methyl-C]methionine (MET), L-[S-methyl-C]cysteine (MCYS), [N-methyl-C]choline (CH), [C]methyl triflate ([C]CH3OSO2CF3), and [C]-2-β-carbomethoxy-3-β-(4-fluorophenyl)-tropane (CFT) by methylation reaction with [C]CH3Br, and PET imaging of patients are also described. Methods: The preparation of [C]CH3Br by a one-pot wet method involved the following steps: reduction of [C]carbon dioxide with lithium aluminium hydride (LiAlH4) solution, treatment with hydrobromic acid, and distillation of [C]CH3Br under continuous nitrogen flow. [C]methylation of L-Homocysteine thiolactone hydrochloride, L-cysteine, 2-dimethylaminoethanol, silver triflate, and nor-β-CFT as precursors with [C]CH3Br and purification with Sep-Pak cartridges gave MET, MCYS, CH, [C]CH3OSO2CF3, and CFT, respectively. In addition, PET imaging of brain cancer and Parkinson's disease was carried out. Results: The uncorrected radiochemical yield of [C]CH3Br was (37.8±2.5%) based on [C]carbon dioxide within a total synthesis time of 10 min and the radiochemical purity of [C]CH3Br was greater than 95%. The uncorrected yields of MET, MCYS, CH, [C]CH3OSO2CF3, and CFT were 70.1±0.5%, 70.2±2.3%, 60.3±1.8%, 95.1±2.2%, and 60.1±1.5% (from [C]CH3OSO2CF3) within a total synthesis time of 2, 2, 5, 1, and 8 min, respectively. The radiochemical purity of MET, MCYS, CH, [C]CH3OSO2CF3, and CFT was more than 95%. Good PET images in the patients are obtained. Conclusion: Automated synthesis of [C]CH3Br can be done by the wet method on the commercial [C]CH3I synthesizer. [C]CH3Br can be used for a [C]methylation reaction to produce C-labeled tracers for clinical PET imaging.