Rotenone
(Synonyms: 鱼藤酮) 目录号 : GC16775
An inhibitor of mitochondrial complex I
Cas No.:83-79-4
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| Cell experiment [1]: | |
|
Cell lines |
differentiated SH-SY5Y neuroblastoma cells |
|
Preparation method |
The solubility of this compound in DMSO is ≥77.6mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
|
Reacting condition |
50 nM; 21 days |
|
Applications |
In differentiated SH-SY5Y neuroblastoma cells, Rotenone (50 nM) produced a biphasic survival curve with ~40% loss by 6 days and a second decline to ~60% loss between 18 and 21 days. Mitochondrial movement velocities were reduced at 8 days. |
| Animal experiment [2]: | |
|
Animal models |
20–25-weekold female BALB/c mice |
|
Dosage form |
(rotenone: 0.35 mg/kg; DMSO: 9.86 mg/kg) or vehicle (DMSO: 9.86 mg/kg); injected into the right-side nasal cavity of mice; once a day for 2 weeks |
|
Application |
In mice, rotenone attenuated the olfactory function and retarded the inhibitory input into the mitral cells, which are output neurons in the olfactory bulb (OB). Rotenone also caused neurite degeneration of DA neurons in the substantia nigra. |
|
Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
|
References: [1]. Borland MK, Trimmer PA, Rubinstein JD, et al. Chronic, low-dose rotenone reproduces Lewy neurites found in early stages of Parkinson's disease, reduces mitochondrial movement and slowly kills differentiated SH-SY5Y neural cells. Mol Neurodegener, 2008, 3: 21. [2]. Sasajima H1, Miyazono S, Noguchi T, et al. Intranasal Administration of Rotenone to Mice Induces Dopaminergic Neurite Degeneration of Dopaminergic Neurons in the Substantia Nigra. Biol Pharm Bull. 2017;40(1):108-112. |
|
Rotenone is an inhibitor of the mitochondrial complex I electron transport chain with IC50 value of 1.7 - 2.2 μM.
Electron transport chain (ETC) is a series of compounds that transfer electrons from electron donors to electron acceptors and transfer protons (H+ ions) across a membrane. The proton gradient drives ATP synthesis. Complex I is one of the main sites of production of superoxide.
Rotenone is an inhibitor of the mitochondrial complex I electron transport chain. In the transformed cell line HEK 293 and cancer cell lines U87, rotenone (50 μM) induced cell death by 30% and 40% respectively in a dose dependent way, which was mediated by reactive oxygen species (ROS). Also, rotenone significantly induced autophagy formation [1]. In SH-SY5Y cells, rotenone induced cell apoptosis in a caspase-dependent way. Also, rotenone induced phosphorylation of p38 MAP kinase, c-Jun and JNK, which indicated activation of the p38 and JNK pathways [2]. In differentiated SH-SY5Y neuroblastoma cells, rotenone (50 nM) induced cell death by 60% and slowed mitochondrial movement. While rotenone didn’t induce the formation of resembling Lewy bodies [3].
鱼藤酮是线粒体复合物I电子传输链的抑制剂，IC50值为1.7-2.2μM。
电子传输链（ETC）是一系列将电子从电子供体转移到电子受体并在膜上转移质子（H+离子）的化合物。质子梯度驱动ATP合成。复合体I是产生超氧化物的主要位点之一。
鱼藤酮是线粒体复合体I电子传递链的抑制剂。在转化细胞系HEK 293和癌症细胞系U87中，鱼藤酮（50μM）以活性氧（ROS）介导的剂量依赖性方式分别诱导30%和40%的细胞死亡。此外，鱼藤酮显著诱导自噬形成[1]。在SH-SY5Y细胞中，鱼藤酮以胱天蛋白酶依赖的方式诱导细胞凋亡。此外，鱼藤酮诱导p38 MAP激酶、c-Jun和JNK的磷酸化，这表明p38和JNK途径被激活[2]。在分化的SH-SY5Y神经母细胞瘤细胞中，鱼藤酮（50nM）诱导细胞死亡60%，并减缓线粒体运动。而鱼藤酮没有诱导类似路易体的形成[3]。
References:
[1]. Chen Y, McMillan-Ward E, Kong J, et al. Mitochondrial electron-transport-chain inhibitors of complexes I and II induce autophagic cell death mediated by reactive oxygen species. J Cell Sci, 2007, 120(Pt 23): 4155-4166.
[2]. Newhouse K, Hsuan SL, Chang SH, et al. Rotenone-induced apoptosis is mediated by p38 and JNK MAP kinases in human dopaminergic SH-SY5Y cells. Toxicol Sci, 2004, 79(1): 137-146.
[3]. Borland MK, Trimmer PA, Rubinstein JD, et al. Chronic, low-dose rotenone reproduces Lewy neurites found in early stages of Parkinson's disease, reduces mitochondrial movement and slowly kills differentiated SH-SY5Y neural cells. Mol Neurodegener, 2008, 3: 21.
| Cas No. | 83-79-4 | SDF | |
| 别名 | 鱼藤酮 | ||
| 化学名 | (2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one | ||
| Canonical SMILES | O=C1[C@H](C2=CC(OC)=C3OC)[C@@H](COC2=C3)OC4=C1C=CC5=C4C[C@H](C(C)=C)O5 | ||
| 分子式 | C23H22O6 | 分子量 | 394.42 |
| 溶解度 | ≥ 77.6mg/mL in DMSO | 储存条件 | Store at 4°C, stored under nitrogen |
| 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 | 2.5354 mL | 12.6768 mL | 25.3537 mL |
| 5 mM | 0.5071 mL | 2.5354 mL | 5.0707 mL |
| 10 mM | 0.2535 mL | 1.2677 mL | 2.5354 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。