B2640
DL-丁硫氨酸-(S,R)-亚砜亚胺
synthetic (organic), ≥98% (TLC), γ-glutamylcysteine synthetase inhibitor, powder
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线性分子式:
CH3(CH2)3S(O)(=NH)CH2CH2CH(NH2)CO2H
化学文摘社编号:
分子量:
222.31
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77
MDL number:
产品名称
DL-丁硫氨酸-(S,R)-亚砜亚胺,
SMILES string
CCCCS(=N)(=O)CCC(N)C(O)=O
InChI key
KJQFBVYMGADDTQ-UHFFFAOYSA-N
InChI
1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)
biological source
synthetic (organic)
assay
≥98% (TLC)
form
powder
mp
215 °C (dec.) (lit.)
solubility
water: 50 mg/mL, clear to very slightly hazy, colorless to yellow
storage temp.
2-8°C
Quality Level
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Application
DL-丁硫氨酸-(S,R)-亚砜亚胺已用于：
- 诱发椋鸟的氧化应激
- 耗竭出生两天的大鼠幼崽中的脉络膜谷胱甘肽(GSH)
- 检测其对克氏锥虫(T. cruzi)的γ-谷氨酰半胱氨酸合成酶和 trypanothione（一种锥虫谷胱甘肽）合成酶(TryS)的抑制作用
DL-丁硫氨酸-(S,R)-亚砜亚胺已被用于消耗视网膜神经节细胞 5 (RGC-5) 细胞系中的细胞谷胱甘肽水平。
Biochem/physiol Actions
耗竭细胞谷胱甘肽，下调 GST 级别。
Features and Benefits
这种化合物是 ADME 毒性研究的特色产品。点击此处发现更多特色 ADME 毒性产品。在sigma.com/discover-bsm可了解更多关于生物活性小分子的其他研究领域。
General description
DL-丁硫氨酸-SR-亚砜亚胺（BSO）是一种氨基酸类似物，可作为γ-谷氨酰半胱氨酸合成酶的抑制剂。BSO可提高克氏锥虫对抗寄生虫药物（如硝呋莫司或苄硝唑）的敏感性。
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Buthionine sulfoximine increases the toxicity of nifurtimox and benznidazole to Trypanosoma cruzi
Faundez M, et al.
Antimicrobial Agents and Chemotherapy, 49(1), 126-130 (2005)
Glutathione: interorgan translocation, turnover, and metabolism
Griffith OW and Meister A
Proceedings of the National Academy of Sciences of the USA, 76(11), 5606-5610 (1979)
Experimental inhibition of a key cellular antioxidant affects vocal communication
Messina S, et al.
Functional Ecology, 1101-1110 (2017)
Citlali Vázquez et al.
FEBS letters, 591(23), 3881-3894 (2017-11-12)
Buthionine sulfoximine (BSO) induces decreased glutathione (GSH) and trypanothione [T(SH)2 ] pools in trypanosomatids, presumably because only gamma-glutamylcysteine synthetase (γECS) is blocked. However, some BSO effects cannot be explained by exclusive γECS inhibition; therefore, its effect on the T(SH)2 metabolism
Brain-derived neurotrophic factor released from engineered mesenchymal stem cells attenuates glutamate-and hydrogen peroxide-mediated death of staurosporine-differentiated RGC-5 cells
Harper MM, et al.
Experimental Eye Research, 89(4), 538-548 (2009)
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