Skatole(3-Methylindole)
(Synonyms: 粪臭素; 3-Methylindole; 3-Methyl-1H-indole) 目录号 : GC30646
Skatole (3-methylindole, Scatole) is a mildly toxic white crystalline organic compound that occurs naturally in feces. It has a fairly broad bacteriostatic effect.
Cas No.:83-34-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Skatole (3-methylindole, Scatole) is a mildly toxic white crystalline organic compound that occurs naturally in feces. It has a fairly broad bacteriostatic effect.
3MI causes pulmonary edema in goats, sheep, rats, and some strains of mice. Response to 3-methylindole (3MI) varies among species. Mice recover from 3MI-induced bronchiolar epithelial injury but sustain persistent olfactory mucosal injury with scarring and epithelial metaplasia. In contrast, 3MI induces obliterative bronchiolitis in horses and ponies. It also causes severe olfactory mucosal damage and fibrosis in rodents (in addition to small airways disease)[2].
[1] Doran E, et al. Chem Biol Interact. 2002, 140(1):81-92. [2] Miller MA, et al. Vet Pathol. 2003, 40(4):363-70.
| Cas No. | 83-34-1 | SDF | |
| 别名 | 粪臭素; 3-Methylindole; 3-Methyl-1H-indole | ||
| Canonical SMILES | C2=C(C1=CC=CC=C1[NH]2)C | ||
| 分子式 | C9H9N | 分子量 | 131.17 |
| 溶解度 | DMSO: 100 mg/mL (762.37 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。 |
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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 | 7.6237 mL | 38.1185 mL | 76.2369 mL |
| 5 mM | 1.5247 mL | 7.6237 mL | 15.2474 mL |
| 10 mM | 0.7624 mL | 3.8118 mL | 7.6237 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。
Skatole (3-Methylindole) Is a Partial Aryl Hydrocarbon Receptor Agonist and Induces CYP1A1/2 and CYP1B1 Expression in Primary Human Hepatocytes
Skatole (3-methylindole) is a product of bacterial fermentation of tryptophan in the intestine. A significant amount of skatole can also be inhaled during cigarette smoking. Skatole is a pulmonary toxin that induces the expression of aryl hydrocarbon receptor (AhR) regulated genes, such as cytochrome P450 1A1 (CYP1A1), in human bronchial cells. The liver has a high metabolic capacity for skatole and is the first organ encountered by the absorbed skatole; however, the effect of skatole in the liver is unknown. Therefore, we investigated the impact of skatole on hepatic AhR activity and AhR-regulated gene expression. Using reporter gene assays, we showed that skatole activates AhR and that this is accompanied by an increase of CYP1A1, CYP1A2 and CYP1B1 expression in HepG2-C3 and primary human hepatocytes. Specific AhR antagonists and siRNA-mediated AhR silencing demonstrated that skatole-induced CYP1A1 expression is dependent on AhR activation. The effect of skatole was reduced by blocking intrinsic cytochrome P450 activity and indole-3-carbinole, a known skatole metabolite, was a more potent inducer than skatole. Finally, skatole could reduce TCDD-induced CYP1A1 expression, suggesting that skatole is a partial AhR agonist. In conclusion, our findings suggest that skatole and its metabolites affect liver homeostasis by modulating the AhR pathway.
Inhibitory effect of skatole (3-methylindole) on enterohemorrhagic Escherichia coli O157:H7 ATCC 43894 biofilm formation mediated by elevated endogenous oxidative stress
We investigated the effects of skatole (3-methylindole), which is one of the indole derivatives on the biofilm formation of EHEC O157:H7. Notably, skatole (100 μg ml??) significantly reduced EHEC O157:H7 ATCC 43894 biofilm formation by 52% in 96-well polystyrene plates under quiescent conditions, with no effect on planktonic cell growth. The skatole sample was maintained in stable conditions for 24 h without degradation or evaporation via EHEC O157:H7 ATCC 43894. Importantly, skatole negatively triggered the expression of catalase in EHEC strains, as well as altered EHEC surface morphology. Our finding indicated that suppressed catalase activity via skatole might have been responsible for elevated endogenous oxidative stress and increment in oxidative metabolites might have led to damaged cell surfaces and a reduction in biofilm formation of EHEC O157:H7 ATCC 43894.
Significance and impact of the study: Our findings suggest that inefficient catalase activity of skatole-exposed enterohemorrhagic Escherichia coli (EHEC) O157:H7 ATCC 43894 may account for elevated endogenous oxidative stress, leading to damaged cell surfaces and reduction in biofilm formation. Our results also provide that skatole as a new candidate for bacterial signalling may be applied for inhibiting bacterial biofilms in food and feed industry.
Skatole: A thin red line between its benefits and toxicity
Skatole (3-methylindole) is a heterocyclic compound naturally found in the feces of vertebrates and is produced by certain flowers. Skatole has been used in specific products of the perfume industry or as a flavor additive in ice cream. Additionally, skatole is formed by tryptophan pyrolysis of tobacco and has been demonstrated to be a mutagen. Skatole-induced pulmonotoxicity was reliably described in ruminants and rodents, but no studies have been conducted in humans. Initially, we provide basic knowledge and a historical overview of skatole. Then, skatole bacterial formation in the intestine is described, and the importance of the microbiome during this process is evaluated. Increased skatole concentrations could serve as a marker for intestinal disease development. Therefore, the human molecular targets of skatole that may have significant effects on various processes in the human body are described. Ultimately, we suggest a link between skatole intestinal formation in humans and skatole-induced pulmonotoxicity, which should be explored further in the future.
Rapid and accurate high-performance liquid chromatographic method for the determination of 3-methylindole (skatole) in faeces of various species
A rapid method for the determination of skatole (3-methylindole) in faeces by reversed-phase high-performance liquid chromatography is described. Samples of 0.5 g were extracted with 2 ml of methanol. The extract was purified on Amberlite XAD-8. The lower limit of detection was 2.5 ng per injection (0.2 microgram/g faeces). The mean recovery of skatole was 95%, and the mean coefficients of variation were 7.0% (intra-assay) and 11.8% (inter-assay). Skatole concentrations were clearly lower in faeces from ruminants (average 2.6 micrograms/g for goat, sheep and cattle) than in those from monogastrics. Mean concentrations in human samples were 15.5 micrograms/g, and 10 micrograms/g in mature domestic pigs. An effect of the anabolic status on skatole concentrations in faeces of pigs is likely.
High-performance liquid chromatographic method for the determination of 3-methylindole (skatole) and indole in adipose tissue of pigs
A rapid method for the determination of skatole (3-methylindole) and indole in adipose tissue of pigs by reversed-phase high-performance liquid chromatography has been developed. Tissue samples were melted in a microwave oven, and 100 microliters of the liquid fat were dissolved in 1 ml of n-hexane and extracted with acetonitrile-water (75:25, v/v). Portions of 100 microliters of the solution were used for chromatographic analysis. Elution was performed on a reversed-phase column with a mobile phase composed of acetic acid and isopropanol (70:30, v/v). A fluorescence detector was used for quantification. The detection limit was 4 ng/g fat. The mean recoveries of added amounts of skatole and indole were 98.9 and 93.8%, respectively. The mean coefficients of variation were: inter-assay, 6.6% (skatole) and 8.8% (indole); intra-assay, 4.2% (skatole) and 2.9% (indole). Mean skatole concentrations in fat samples from boars (40 ng/g; n = 349) were not significantly higher than those from barrows (24 ng/g; n = 98).