L-Buthionine-(S,R)-sulfoximine (L-Butionine sulfoximine)
(Synonyms: 丁硫氨酸-亚砜亚胺,L-BSO) 目录号 : GC33098
An irreversible inhibitor of the γ-glutamylcysteine synthetase
Cas No.:83730-53-4
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
L-Buthionine-(S,R)-sulfoximine is an irreversible inhibitor of γ-glutamylcysteine synthetase (Ki = 25 ?M).1 It inhibits the proliferation of ZAZ and M14 melanoma cells, as well as A2780 ovarian and MCF-7 breast cancer cells (IC50s = 4.9, 18, 8.5, and 26.5 ?M, respectively).2 L-Buthionine-(S,R)-sulfoximine (100?M) induces ferroptosis in A172 and T98G glioblastoma cells.3 It increases reactive oxygen species (ROS) levels in HeLa cells when used at a concentration of 10 ?M. L-Buthionine-(S,R)-sulfoximine (1 mM), in combination with methylglyoxal, induces apoptosis of bovine aortic endothelial cells (BAECs).4 It increases the number of eye spots in the retinal pigment epithelium, an indicator of DNA deletions, in mouse pups when administered to pregnant dams at concentrations of 2 and 20 mM in the drinking water.5 L-Buthionine-(S,R)-sulfoximine decreases cysteine and glutathione (GSH) levels in fetal mice when administered to pregnant dams.
L-丝氧化-双硫仑是γ-谷氨酰半胱氨酸合成酶的不可逆抑制剂（Ki = 25μM）。1它抑制了ZAZ和M14黑色素瘤细胞、A2780卵巢和MCF-7乳腺癌细胞的增殖（分别的IC50为4.9、18、8.5和26.5μM）。2 L-丝氧化-双硫仑（100μM）会诱导A172和T98G胶质母细胞瘤细胞发生铁死亡。3在浓度为10μM时，它会增加HeLa细胞内活性氧（ROS）的水平。L-丝氧化-双硫仑（1mM）与甲基乙酰中毒结合时，可以诱导牛主动脉内皮细胞（BAECs）凋亡。4当孕母以2和20mM的浓度在饮用水中摄入时，它会增加小鼠幼仔视网膜色素上皮中的眼斑数量，这是DNA缺失的指标。5当孕母摄入时，L-丝氧化-双硫仑会降低胎儿小鼠中的半胱氨酸和谷胱甘肽（GSH）水平。
1.Griffith, O.W.Mechanism of action, metabolism, and toxicity of buthionine sulfoximine and its higher homologs, potent inhibitors of glutathione synthesisJ. Biol. Chem.257(22)13704-13712(1982) 2.Fruehauf, J.P., Zonis, S., al-Bassam, M., et al.Selective and synergistic activity of L-S,R-buthionine sulfoximine on malignant melanoma is accompanied by decreased expression of glutathione-S-transferasePigment Cell Res.10(4)236-249(1997) 3.Hayashima, K., and Katoh, H.Expression of gamma-glutamyltransferase 1 in glioblastoma cells confers resistance to cystine deprivation-induced ferroptosisJ. Biol. Chem.298(3)101703(2022) 4.Takahashi, K., Tatsunami, R., Oba, T., et al.Buthionine sulfoximine promotes methylglyoxal-induced apoptotic cell death and oxidative stress in endothelial cellsBiol. Pharm. Bull.33(4)556-560(2010) 5.Reliene, R., and Schiestl, R.H.Glutathione depletion by buthionine sulfoximine induces DNA deletions in miceCarcinogenesis27(2)240-244(2006)
|
Animal experiment: |
Mice[2]C57BL/6J pun/pun mice are used in the study. Pregnancy is timed by checking for vaginal plugs. Noon of the day of discovery is counted as 0.5 days post coitum (d.p.c.). Similarly, the time of birth of a litter is timed with the noon of discovery counted as 0.5 days post-partum (d.p.p.). Pregnant dams are given free access to drinking water supplemented by either 2 mM L-Buthionine-(S,R)-sulfoximine (BSO), 20 mM BSO, 2 mM BSO and 20 mM NAC, 20 mM NAC or unsupplemented water for 18 days from 0.5 to 18.5 d.p.c. The pH of supplemented water is as follows: 6.88, 20 mM BSO; 3.37, 2 mM BSO; 2.65, 2 mM BSO plus 20 mM NAC; and 2.58, 20 mM NAC. The pH of regular water used in our facility is ~4. To determine the DNA deletion frequency, 20-day-old offspring (23 mice in the control group and 16-17 mice per exposure group) are sacrificed to visualize eye-spots (DNA deletions) in their RPE[2]. |
|
References: [1]. Fruehauf JP, et al. Selective and synergistic activity of L-S,R-buthionine sulfoximine on malignant melanoma is accompanied by decreased expression of glutathione-S-transferase. Pigment Cell Res. 1997 Aug;10(4):236-49. |
|
| Cas No. | 83730-53-4 | SDF | |
| 别名 | 丁硫氨酸-亚砜亚胺,L-BSO | ||
| Canonical SMILES | N[C@H](C(O)=O)CCS(CCCC)(=O)=N | ||
| 分子式 | C8H18N2O3S | 分子量 | 222.31 |
| 溶解度 | Water : 41.67 mg/mL (187.44 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.4982 mL | 22.4911 mL | 44.9822 mL |
| 5 mM | 0.8996 mL | 4.4982 mL | 8.9964 mL |
| 10 mM | 0.4498 mL | 2.2491 mL | 4.4982 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。
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet