5-Hydroxyoxindole
(Synonyms: 2-甲基-6-喹啉甲酸) 目录号 : GC61638
5-Hydroxyoxindole是尿酸的一种结构类似物。5-Hydroxyoxindole具有自由基DPPH清除活性和脂质过氧化抑制活性。5-Hydroxyoxindole可用于氧化应激介导的疾病的研究。
Cas No.:3416-18-0
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
5-Hydroxyoxindole is a structural analog of uric acid. 5-Hydroxyoxindole has DPPH radical scavenging activities and lipid peroxidation-inhibitory activities. 5-Hydroxyoxindole can be used for the research of oxidative stress-mediated disorders[1].
[1]. Daisuke Yasuda, et al. Preparation and antioxidant/pro-oxidant activities of 3-monosubstituted 5-hydroxyoxindole derivatives.
| Cas No. | 3416-18-0 | SDF | |
| 别名 | 2-甲基-6-喹啉甲酸 | ||
| Canonical SMILES | O=C1NC2=C(C=C(O)C=C2)C1 | ||
| 分子式 | C8H7NO2 | 分子量 | 149.15 |
| 溶解度 | 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 | 6.7047 mL | 33.5233 mL | 67.0466 mL |
| 5 mM | 1.3409 mL | 6.7047 mL | 13.4093 mL |
| 10 mM | 0.6705 mL | 3.3523 mL | 6.7047 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。
A 5-Hydroxyoxindole derivative attenuates LPS-induced inflammatory responses by activating the p38-Nrf2 signaling axis
Biochem Pharmacol 2018 Sep;155:182-197.PMID:29940171DOI:10.1016/j.bcp.2018.06.021.
5-Hydroxyoxindole is a urinary metabolite of indole that exhibits antioxidant activity. In the present study, we found that a 5-Hydroxyoxindole derivative (5-HI) significantly inhibited LPS-induced inflammatory effects in the murine macrophage cell line, RAW264.7. 5-HI induced the expression of the transcription factor, Nrf2, which is typically ubiquitinated by Keap1, an adaptor component of the ubiquitin E3 ligase complex, resulting in its proteasomal degradation. By utilizing Keap1-/- MEFs reconstituted with Keap1 mutants harboring substitutions in their major cysteine residues, we clarified the importance of Cys151 in Keap1 as a sensor for 5-HI in the induction of Nrf2 expression. Furthermore, 5-HI induced the activation of the MKK3/6-p38 pathway, which is required for the transcriptional activation of Nrf2. The knockdown of Nrf2 enhanced the LPS-induced expression of inflammatory mediators, including iNOS, NO, and CCL2, and effectively repressed the inhibitory effects of 5-HI on their expression. Although 5-HI and antioxidant N-acetyl cysteine (NAC) both reduced LPS-induced ROS generation, the treatment with NAC did not affect the LPS-induced expression of inflammatory mediators, suggesting that the anti-inflammatory activity of 5-HI mediated by Nrf2 is independent of redox control. Furthermore, when injected into mice with 5-HI, the expression of Nrf2 was significantly increased, and the LPS-induced mRNA expression of CXCL1, CCL2, TNFα, and IL-6 were remarkably inhibited in the kidneys, liver, and lungs, and the production of these cytokines in serum was effectively reduced. Collectively, these results suggest that 5-HI has potential in the treatment of inflammatory diseases through the activation of Nrf2.
5-Hydroxyoxindole, an indole metabolite, is present at high concentrations in brain
J Neurosci Res 2008 Jan;86(1):202-7.PMID:17722070DOI:10.1002/jnr.21475.
5-Hydroxyoxindole has been identified as a urinary metabolite of indole, which is produced from tryptophane via the tryptophanase activity of gut bacteria. We have demonstrated recently that 5-Hydroxyoxindole is an endogenous compound in blood and tissues of mammals, including humans. To date, 5-Hydroxyoxindole's role is unknown. The aim of this study was to compare 5-Hydroxyoxindole levels in plasma and cerebrospinal fluid (CSF) during day-night and seasonal changes, as a common approach to pilot physiological characterization of any compound. Simultaneous blood and CSF sampling was performed in the ewe, because its size allows collection in quantities suitable for 5-Hydroxyoxindole assay (HPLC-ED) in awake animals, without obvious physiological or behavioral disturbance. 5-Hydroxyoxindole concentration was quite stable in plasma (2-6 nM range), whereas, in CSF, it displayed marked day-night and photoperiodic variations (4-116 nM range). 5-Hydroxyoxindole levels in CSF were twofold higher at night than during the day and at least one order of magnitude higher during the long compared with the short photoperiod. These day/night and photoperiodic variations persisted after pinealectomy, indicating that 5-Hydroxyoxindole rhythms in CSF are independent of melatonin formation. In conclusion, high levels of 5-Hydroxyoxindole in the CSF during long photoperiod and its daily modulation suggest physiological involvement of 5-Hydroxyoxindole in rhythmic adjustments in the brain, independently of the pineal gland.
The endogenous oxindoles 5-Hydroxyoxindole and isatin are antiproliferative and proapoptotic
Biochem Biophys Res Commun 2000 Sep 16;276(1):379-84.PMID:11006132DOI:10.1006/bbrc.2000.3477.
Oxindole-core synthetic molecules are currently being developed as anticancer drugs that target protein tyrosine kinases associated with growth factor receptors. Oxindole, 5-Hydroxyoxindole, and 2, 3-dioxindole [isatin] are natural molecules found in mammalian body fluids and tissues and we addressed the question of similar properties of endogenous oxindoles. 5-Hydroxyoxindole and isatin, but not oxindole, inhibited N1E-115, BALB/c3T3, BBC, PC12, and HL60 proliferation at submicromolar concentrations. Acute treatment with 5-Hydroxyoxindole and isatin reduced the activity of extracellular signal regulated protein kinases (ERKs) by 35% at 100 microM and ERK1 activity was strongly inhibited by 5-Hydroxyoxindole at 10 microM. Survival of PMA-differentiated HL60 and FGF(2)-differentiated PC12 cells was not affected by 5-Hydroxyoxindole and isatin treatment, suggesting that endogenous oxindoles interact with growth factors signaling. The physiological implications of these data and the potential utility of 5-Hydroxyoxindole and isatin as antitumor agents are discussed.
Preparation and antioxidant/pro-oxidant activities of 3-monosubstituted 5-Hydroxyoxindole derivatives
J Clin Biochem Nutr 2016 Nov;59(3):165-173.PMID:27895383DOI:10.3164/jcbn.16-24.
Antioxidant treatments have been expected to be a novel therapeutics for various oxidative stress-mediated disorders. Our previous study revealed that 5-Hydroxyoxindole and its 3-phenacyl-3-hydroxy derivatives showed excellent antioxidant activities such as 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and lipid-peroxidation inhibitory activity. However, the DPPH radical scavenging activity of the 3,3-disubstituted derivatives was lower than that of the original 5-Hydroxyoxindole. In the present study, we synthesized novel 3-monosubstituted 5-Hydroxyoxindole derivatives that exhibited stronger DPPH radical scavenging activities and lipid peroxidation-inhibitory activities than the 3,3-disubstituted 5-hydroxyoxindoles. Moreover, the 3-monosubstituted 5-Hydroxyoxindole derivatives showed neither an iron-mediated pro-oxidant effect nor a remarkable cytotoxicity against HL-60 cell lines except some of the highly lipophilic compounds. These results indicate that 3-monosubstituted 5-hydroxyoxindoles can be used as a promising antioxidant scaffold for drug discovery.
Antioxidant activities of 5-Hydroxyoxindole and its 3-hydroxy-3-phenacyl derivatives: the suppression of lipid peroxidation and intracellular oxidative stress
Bioorg Med Chem 2013 Dec 15;21(24):7709-14.PMID:24216095DOI:10.1016/j.bmc.2013.10.021.
The antioxidant activities of 5-Hydroxyoxindole (1) and newly synthesized 3,5-dihydroxy-3-phenacyl-2-oxindole derivatives against rat liver microsome/tert-butylhydroperoxide system-induced lipid peroxidation and hydrogen peroxide-induced intracellular oxidative stress were investigated. Compound 1 and its derivatives showed significant suppression of lipid peroxidation and an intracellular oxidative stress. The effects of the more lipophilic derivatives tended to be greater than that of the original compound 1. The cytotoxicity of all of the oxindole derivatives on human promyelocytic leukemia HL60 cells was lower than that of 2,6-di(tert-butyl)-4-hydroxytoluene (BHT), a widely used phenolic antioxidant. These results show that compound 1 and its 3-substituted derivatives could be good lead candidates for future novel antioxidant therapeutics.