8(S)-HETE
(Synonyms: 8(S)-Hydroxyeicosatetraenoic Acid) 目录号 : GC40463
A PKC and PPARα activator
Cas No.:98462-03-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
8(S)-HETE is a major lipoxygenase product in PMA-treated murine epidermis. It activates mouse keratinocyte protein kinase C with an IC50 of 100 µM. 8(S)-HETE also activates PPARα selectively at concentrations as low as 0.3 µM. Stereochemical assignment of the (S) enantiomer is based on comparison of chiral HPLC retention times to published results.
| Cas No. | 98462-03-4 | SDF | |
| 别名 | 8(S)-Hydroxyeicosatetraenoic Acid | ||
| Canonical SMILES | CCCCC/C=C\C\C=C\C=C/[C@@H](O)C/C=C\CCCC(=O)O | ||
| 分子式 | C20H32O3 | 分子量 | 320.5 |
| 溶解度 | 0.1 M Na2CO3: 2 mg/ml,DMF: Miscible,DMSO: Miscible,Ethanol: Miscible,PBS pH 7.2: 0.8 mg/ml | 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 | 3.1201 mL | 15.6006 mL | 31.2012 mL |
| 5 mM | 0.624 mL | 3.1201 mL | 6.2402 mL |
| 10 mM | 0.312 mL | 1.5601 mL | 3.1201 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。
Synthesis of new 8(S)-HETE analogs and their biological evaluation as activators of the PPAR nuclear receptors
J Enzyme Inhib Med Chem 2010 Oct;25(5):653-72.PMID:20518620DOI:10.3109/14756360903468171.
Structural modifications around 8-HETE (8-hydroxyeicosatetraenoic acid), a natural agonist of the PPAR (peroxisome proliferator-activated receptor) nuclear receptors have led previously to the identification of a promising analog, the quinoline S 70655. Series of novel quinoline or benzoquinoline derivatives were designed through the modification of this lead. Variations of the nature of the aromatic core and of the side chains were carried out. The SAR studies indicated the high sensitivity of the upper acid chain to modifications as well as the strong effect of the length and size of the lipophilic side chain. They afforded several new promising PPARalpha/gamma dual agonists with a high PPARalpha activity in vitro.
8(S)-hydroxyeicosatetraenoic acid is the lipoxygenase metabolite of arachidonic acid that regulates epithelial cell migration in the rat cornea
Cornea 2000 May;19(3 Suppl):S13-20.PMID:10832716DOI:10.1097/00003226-200005001-00004.
Background: We previously found that the inhibition of lipoxygenases resulted in delayed epithelial wound closure in organ-cultured rat corneas. The present study was undertaken to determine the lipoxygenase enzyme and metabolite(s) responsible for regulating reepithelialization and their mechanism of action. Methods: The effects of esculetin--an established lipoxygenase inhibitor--on endogenous hydroxyeicosatetraenoic acids (HETEs) production, epithelial wound closure, filamentous-actin (F-actin) cytoskeleton, and mitotic rate were investigated using a cell-culture assay and an organ-culture assay of rat corneal epithelium. Results: Lipoxygenase inhibition by esculetin, which resulted in the disruption of F-actin organization and a decrease in the mitotic rate, delayed wound closure in both cell- and organ-culture assays. Normal corneoscleral rims metabolized [3H]arachidonic acid to 12-HETE (major metabolite), 8-HETE, and 9-HETE. HETE synthesis was inhibited by esculetin in a dose-dependent fashion. Chiral-phase analysis revealed that they contained only (S)-enantiomers, which indicated that they were lipoxygenase metabolites. The inhibitory effects of esculetin on F-actin organization and epithelial wound closure in an organ-culture assay were totally reversed by exogenously added 8(S)-HETE, whereas 12- and 9-HETE had no effect. However, none of the HETEs reversed the decreased mitotic rate or achieved complete wound closure in the cell-culture assay. Conclusions: These results suggest that 8(S)-HETE is the key metabolite of arachidonic acid that regulates corneal epithelial cell migration during wound healing. The metabolite responsible for cell proliferation remains to be determined.
Analysis of serum polyunsaturated fatty acid metabolites in allergic bronchopulmonary aspergillosis
Respir Res 2020 Aug 5;21(1):205.PMID:32758241DOI:10.1186/s12931-020-01471-4.
Background: The importance of lipid mediators in allergic diseases has been long recognized, whereas little is known about their role in allergic bronchopulmonary aspergillosis (ABPA). We investigated whether lipid mediators are associated with ABPA. Methods: We recruited 12 ABPA patients, 23 asthma patients and 12 healthy control in our study. Serum of 11 ABPA patients were collected before and following treatment. 36 polyunsaturated fatty acid metabolites were measured in serum samples by using liquid chromatography-mass spectrometry. This study was approved by the Ethics Committee of the First Affiliated Hospital of Guangzhou Medical University, with ethics number GYFYY-2016-73. Results: Levels of arachidonic acid (AA), 15(S)-hydroxyeicosatetraenoic acid (HETE), 12(S)-HETE, 8(S)-HETE, 5(S)-HETE, LTB4, PGB2, 12(S)-hydroxyeicosapentaenoic acid (HEPE), 12-hydro-xyheptadecatrienoic acid (HHTrE) were significantly higher in ABPA patients than that in HC groups. Compared with asthma group, ABPA group expressed lower levels of 15(S)-hy-droperoxyeicosatetraenoic acid (HPETE), 5(S)-HPETE, 13(S)-hydroperoxyoctadecadienoic acid (HPODE) and 9(S)-HPODE. In APBA patients, AA level was positively correlated with serumtotal IgE (tIgE). The levels of 12(S)-HPETE, 15(S)-HEPE and 12(S)-HEPE correlated with Asp-ergillus fumigatus specific IgE(A. fumigatus sIgE) positively. Peripheral blood eosinophilia correlated with high levels of 12(S)-HETE and 15(S)-HETE. In addition, the serum levels of15(S)-HETE and 12(S)-HETE in ABPA subjects both declined with the decrease of tIgE, A. fumigatus sIgE and sIgG concentrations after treatment. Conclusions: We present data regarding the role of polyunsaturated fatty acid metabolites in APBA for the first time. Most of the tested metabolites increased in ABPA when co-mpared with healthy controls and 15(S)-HETE and 12(S)-HETE may play a role in the pat-hogenesis of ABPA. These findings can provide new ideas for diagnosis, therapy and mon-itor of ABPA.
Investigation of the mechanism of biosynthesis of 8-hydroxyeicosatetraenoic acid in mouse skin
Biochim Biophys Acta 1991 Feb 5;1081(3):347-54.PMID:1900207DOI:10.1016/0005-2760(91)90292-p.
One of the many changes induced by topical application of phorbol ester or calcium ionophore A23187 to mouse skin is the appearance of an enzymic activity which will convert arachidonic acid to its 8-hydroxyeicosatetraenoic acid metabolite (8-HETE) (Gschwendt, M., et al (1986) Carcinogenesis 7, 449-455). Induction of this activity is lower in strains of mice with a weak inflammatory response to TPA, and the 8-HETE may be involved in the inflammation or hyperplasia. To further characterize the activity, we first measured the chirality of the product; it is almost exclusively the 8DS)-hydroxy enantiomer (8S-HETE). The 8(S)-HETE is formed from octadeuterated arachidonic acid with complete retention of deuterium labels, indicating that a keto intermediate is not involved in the biosynthesis. Using arachidonic acids labeled with a prochiral tritium in either the 10DR or 10LS positions, we found that the biosynthesis of 8S-HETE is associated with the stereoselective abstraction of the 10DR hydrogen from the 10-carbon of the substrate. This stereoselective hydrogen removal conforms to the properties of an 8S-lipoxygenase. This is the only lipoxygenase known to catalyze solely 8S-oxygenation of arachidonic acid. The recent characterization of stereoselective biological effects for other HETEs serve as strong precedents to suggest that 8S-HETE has a specific role in the cellular tissue response to TPA.
Metabolomics Reveals Process of Allergic Rhinitis Patients with Single- and Double-Species Mite Subcutaneous Immunotherapy
Metabolites 2021 Sep 9;11(9):613.PMID:34564431DOI:10.3390/metabo11090613.
Allergen immunotherapy (AIT) is the only treatment that can change the course of allergic diseases. However, there has not been any research on metabolic reactions in relation to AIT with single or mixed allergens. In this study, patients with allergic rhinitis caused by Dermatophagoides pteronyssinus (Der p) and Dermatophagoides farinae (Der f) were treated with single-mite (Der p) and double-mite (Der p:Der f = 1:1) subcutaneous immunotherapy (SCIT), respectively. To compare the efficacy and the dynamic changes of inflammation-related single- and double-species mite subcutaneous immunotherapy (SM-SCIT and DM-SCIT), we performed visual analogue scale (VAS) score, rhinoconjunctivitis quality of life questionnaire (RQLQ) score and serum metabolomics in allergic rhinitis patients during SCIT. VAS and RQLQ score showed no significant difference in efficacy between the two treatments. A total of 57 metabolites were identified, among which downstream metabolites (5(S)-HETE (Hydroxyeicosatetraenoic acid), 8(S)-HETE, 11(S)-HETE, 15(S)-HETE and 11-hydro TXB2) in the ω-6-related arachidonic acid and linoleic acid pathway showed significant differences after approximately one year of treatment in SM-SCIT or DM-SCIT, and the changes of the above serum metabolic components were correlated with the magnitude of RQLQ improvement, respectively. Notably, 11(S)-HETE decreased more with SM-SCIT, and thus it could be used as a potential biomarker to distinguish the two treatment schemes. Both SM-SCIT and DM-SCIT have therapeutic effects on patients with allergic rhinitis, but there is no significant difference in efficacy between them. The reduction of inflammation-related metabolites proved the therapeutic effect, and potential biomarkers (arachidonic acid and its downstream metabolites) may distinguish the options of SCIT.