Sinigrin (hydrate)
(Synonyms: 黑芥子硫苷酸钾一水；芥子甙单水合物) 目录号 : GC49002
A glucosinolate with diverse biological activities
Cas No.:64550-88-5
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
Sinigrin is a glucosinolate that has been found in Brassica and has diverse biological activities.1,2,3 It inhibits NOD-like receptor protein 3 (NLRP3) inflammasome activation in ATP-stimulated, LPS-primed RAW 264.7 cells in a concentration-dependent manner.1 Sinigrin (1-100 µg/ml) reduces LPS-induced production of nitric oxide (NO) and prostaglandin E2 , as well as NF-κB activation, in RAW 264.7 cells. It induces cell cycle arrest at the G0/G1 phase in HepG2 hepatocellular carcinoma cells when used at concentrations of 0.1 and 0.5 mM.2 Sinigrin (10 and 20 mg/kg) reduces increases in renal glomerular basement membrane thickness, as well as increases in systolic and diastolic blood pressure, in a rat model of hypertension induced by angiotensin II.3
1.Lee, H.-W., Lee, C.G., Rhee, D.-K., et al.Sinigrin inhibits production of inflammatory mediators by suppressing NF-κB/MAPK pathways or NLRP3 inflammasome activation in macrophagesInt. Immunopharmacol.45163-173(2017) 2.Jie, M., Cheung, W.M., Yu, V., et al.Anti-proliferative activities of sinigrin on carcinogen-induced hepatotoxicity in ratsPLoS One9(10)e110145(2014) 3.Cong, C., Yuan, X., Hu, Y., et al.Sinigrin attenuates angiotensin II?induced kidney injury by inactivating nuclear factor?κB and extracellular signal?regulated kinase signaling in vivo and in vitroInt. J. Mol. Med.48(2)161(2021)
| Cas No. | 64550-88-5 | SDF | |
| 别名 | 黑芥子硫苷酸钾一水；芥子甙单水合物 | ||
| Canonical SMILES | OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](SC(CC=C)=NOS([O-])(=O)=O)O1.[K+].O | ||
| 分子式 | C10H16NO9S2·K [XH2O] | 分子量 | 397.5 |
| 溶解度 | : ,DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 1 mg/ml | 储存条件 | -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 | 2.5157 mL | 12.5786 mL | 25.1572 mL |
| 5 mM | 0.5031 mL | 2.5157 mL | 5.0314 mL |
| 10 mM | 0.2516 mL | 1.2579 mL | 2.5157 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。
Allyl isothiocyanate-rich mustard seed powder inhibits bladder cancer growth and muscle invasion
Carcinogenesis 2010 Dec;31(12):2105-10.PMID:20889681DOI:10.1093/carcin/bgq202.
Allyl isothiocyanate (AITC), which occurs in many common cruciferous vegetables, was recently shown to be selectively delivered to bladder cancer tissues through urinary excretion and to inhibit bladder cancer development in rats. The present investigation was designed to test the hypothesis that AITC-containing cruciferous vegetables also inhibit bladder cancer development. We focused on an AITC-rich mustard seed powder (MSP-1). AITC was stably stored as its glucosinolate precursor (Sinigrin) in MSP-1. Upon addition of water, however, Sinigrin was readily hydrolyzed by the accompanying endogenous myrosinase. This myrosinase was also required for full conversion of Sinigrin to AITC in vivo, but the matrix of MSP-1 had no effect on AITC bioavailability. Sinigrin itself was not bioactive, whereas hydrated MSP-1 caused apoptosis and G(2)/M phase arrest in bladder cancer cell lines in vitro. Comparison between hydrated MSP-1 and pure Sinigrin with added myrosinase suggested that the anticancer effect of MSP-1 was derived principally, if not entirely, from the AITC generated from Sinigrin. In an orthotopic rat bladder cancer model, oral MSP-1 at 71.5 mg/kg (Sinigrin dose of 9 μmol/kg) inhibited bladder cancer growth by 34.5% (P < 0.05) and blocked muscle invasion by 100%. Moreover, the anticancer activity was associated with significant modulation of key cancer therapeutic targets, including vascular endothelial growth factor, cyclin B1 and caspase 3. On an equimolar basis, the anticancer activity of AITC delivered as MSP-1 appears to be more robust than that of pure AITC. MSP-1 is thus an attractive delivery vehicle for AITC and it strongly inhibits bladder cancer development and progression.
Allyl isothiocyanate induced stress response in Caenorhabditis elegans
BMC Res Notes 2011 Nov 17;4:502.PMID:22093285DOI:10.1186/1756-0500-4-502.
Background: Allyl isothiocyanate (AITC) from mustard is cytotoxic; however the mechanism of its toxicity is unknown. We examined the effects of AITC on heat shock protein (HSP) 70 expression in Caenorhabditis elegans. We also examined factors affecting the production of AITC from its precursor, Sinigrin, a glucosinolate, in ground Brassica juncea cv. Vulcan seed as mustard has some potential as a biopesticide. Findings: An assay to determine the concentration of AITC in ground mustard seed was improved to allow the measurement of AITC release in the first minutes after exposure of ground mustard seed to water. Using this assay, we determined that temperatures above 67°C decreased Sinigrin conversion to AITC in hydrated ground B. juncea seed. A pH near 6.0 was found to be necessary for AITC release. RT-qPCR revealed no significant change in HSP70A mRNA expression at low concentrations of AITC (< 0.1 μM). However, treatment with higher concentrations (> 1.0 μM) resulted in a four- to five-fold increase in expression. A HSP70 ELISA showed that AITC toxicity in C. elegans was ameliorated by the presence of ground seed from low Sinigrin B. juncea cv. Arrid. Conclusions: • AITC induced toxicity in C. elegans, as measured by HSP70 expression.• Conditions required for the conversion of Sinigrin to AITC in ground B. juncea seed were determined.• The use of C. elegans as a bioassay to test AITC or mustard biopesticide efficacy is discussed.