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M5379

Sigma-Aldrich

L-蛋氨酸亚砜酰亚胺

suitable for cell culture

别名:

L-S-(3-氨基-3-羧丙基)-S-甲基砜亚胺

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About This Item

线性分子式:
CH3S(O)(=NH)CH2CH2CH(NH2)CO2H
CAS号:
15985-39-4
分子量:
180.23
Beilstein:
6175446
MDL编号:
MFCD00002621
UNSPSC代码:
12352116
PubChem化学物质编号:
24278555
NACRES:
NA.32

质量水平

300

技术

cell based assay: suitable
cell culture | mammalian: suitable

mp

>210 °C (dec.) (lit.)

适用性

suitable for molecular biology

SMILES字符串

CS(=N)(=O)CC[C@H](N)C(O)=O

InChI

1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11?/m0/s1

InChI key

SXTAYKAGBXMACB-DPVSGNNYSA-N

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应用

L-甲硫氨酸亚砜亚胺已被用作谷氨酰胺合成酶 (GS) 活性的有效抑制剂，以研究其对肌萎缩侧索硬化症 SOD1 G93A 小鼠模型的寿命和疾病进展的影响。

使用高水平的 MSX 可以提高多种重组 GS CHO 细胞系和 GS–CHOK1SV 细胞系的生产率和生产稳定性，而不会影响产品质量。这些发现对于提高生物制品生产中使用的工业细胞培养过程的效率和可靠性具有重要意义。

MSX 是一种强效惊厥剂，已显示出对原代皮质星形胶质细胞培养物中谷氨酰胺动态具有特定且显著的影响。这使其成为研究和调节细胞培养中谷氨酰胺相关过程的有价值的化合物。

生化/生理作用

作为一种有效的谷氨酰胺合成酶(GS)活性抑制剂，该试剂可广泛用作中国仓鼠卵巢(CHO)和其他哺乳动物细胞系中质粒整合筛选剂。对用于生产治疗性重组蛋白的高产细胞库不断增长的需求导致了两种用于选择稳定和活性克隆的主要系统，二氢叶酸还原酶（DHFR）过表达细胞的甲氨蝶呤选择和谷氨酰胺合成酶过表达细胞的MSX选择。细胞在缺乏谷氨酰胺的培养基中生长，而对谷氨酰胺合成酶内源活性的抑制则导致了缺乏过表达的细胞死亡。这种MSX-谷氨酰胺合酶选择机制相对于甲氨蝶呤-DHFR系统具有更多优势，因其通常只需要单个扩增步骤便能实现产生高稳定性、高度扩增克隆时间的显著减少。L-甲硫氨酸亚砜亚胺(MSX)可通过抑制GS活性来增强小麦叶、小麦、大麦、玉米和高粱植物幼苗叶片中的NH3生产。在短暂性脑缺血模型中，MSX可提高鸟氨酸脱羧酶活性并降低存活率。

储存及稳定性

This product is stored at room temperature.

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H315,H319,H335

危险分类

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000418526
0000418527
0000411867
0000411867
0000411046

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the solubility of Product M5379, L-Methionine sulfoximine?

    We test the solubility at 50 mg/mL (0.277 M) in water; heat and/or sonication may be required.

  6. What is the solution stability of Product M5379, L-Methionine sulfoximine?

    We do not have any information available on solution stability. The following references may provide some helpful information:1. Proc. Roy. Soc., 138, 265 (1951).2. Weisbrod, R. E., and Meister, A., Studies on Glutamine Synthetase from Escherichia Coli. Formation of Pyrrolidone Carboxylate and Inhibition by Methionine Sulfoximine. J.Biol. Chem., 248(11), 3997-4002 (1973).3. Richman, P. G., et al., Inhibition of Gamma-glutamylcysteine Synthetase by L-methionine-S-sulfoximine. J. Biol. Chem., 248(19), 6684-6690 (1973).

  7. How is Product M5379, L-Methionine sulfoximine, used?

    This product has been reported as an inhibitor of glutamine synthetase by  Weisbrod, R. E., et al., J.Biol. Chem., 248(11), 3997-4002 (1973).  It has also been reported as an inhibitor of γ-glutamylcysteine synthetase by Richman, P. G., et al., J. Biol. Chem., 248(19), 6684-6690 (1973).

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Nitrate transport and not photoinhibition limits growth of the freshwater Cyanobacterium synechococcus species PCC 6301 at low temperature.
Sakamoto T and Bryant DA
Plant Physiology, 119, 785?794-785?794 (1999)
L-methionine-DL-sulfoximine induces massive efflux of glutamine from cortical astrocytes in primary culture
Albrecht J and Norenberg MD, et al.
European journal of psychotraumatology, 182(3), 587-589 (1990)
Takeshi Omasa et al.
Current pharmaceutical biotechnology, 11(3), 233-240 (2010-03-10)
Mammalian cell lines are important host cells for the industrial production of pharmaceutical proteins owing to their capacity for correct folding, assembly and post-translational modification. In particular, Chinese hamster ovary (CHO) cells are the most dependable host cells for the
Davina Chai et al.
Journal of biotechnology, 131(4), 466-472 (2007-09-11)
A key challenge in molecular breeding of orchids is the creation of efficient and reproducible gene transformation systems. In this study, we report a new transformation method utilizing L-methionine sulfoximine (MSO) as a novel agent for selection of transgenic Dendrobium
Increased MSX level improves biological productivity and production stability in multiple recombinant GS CHO cell lines
Tian Jun, et al.
Engineering in Life Sciences (2020)
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实验方案

LC/MS Analysis of L-Methionine Sulfoximine and Sulfone on Ascentis® Express OH5

LC/MS Analysis of L-Methionine Sulfoximine and Sulfone on Ascentis® Express OH5

LC/MS Analysis of L-Methionine Sulfoximine, Sulfone and Sulfoxide on Ascentis® Express HILIC

Separation of L-Methionine sulfone; L-Methionine sulfoximine; L-Methionine sulfoxide

Chromatograms

application for HPLCapplication for HPLC

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