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11(S)-HETE Sale

(Synonyms: 11(S)-Hydroxyeicosatetraenoic Acid) 目录号 : GC40446

A non-enzymatically derived oxylipin

11(S)-HETE Chemical Structure

Cas No.:54886-50-9

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25μg
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产品描述

11(S)-HETE is an oxylipin and the (S) enantiomer of 11(R)-HETE. It is formed non-enzymatically from arachidonic acid.[1] Levels of 11(S)-HETE are higher than those of 11(R)-HETE in isolated human plasma and serum and in LPS-stimulated isolated human plasma. Serum labels of 11(S)-HETE decrease in patients with allergic rhinitis after one year of double-mite subcutaneous immunotherapy (DM-SCIT) and are associated with an improved quality of life in regards to rhinoconjunctivitis.[2]

References:
1. Mazaleuskaya, L.L., Salamatipour, A., Saratopoulou, D., et al. Analysis of HETEs in human whole blood by chiral UHPLC-ECAPCI/HRMS. J. Lipid Res. 59(3), 564-575 (2018).
2. Zheng, P., Yan, G., Zhang, Y., et al. Metabolomics reveals process of allergic rhinitis patients with single- and double-species mite subcutaneous immunotherapy. Metabolites 11(9), 613 (2021).

Chemical Properties

Cas No. 54886-50-9 SDF
别名 11(S)-Hydroxyeicosatetraenoic Acid
Canonical SMILES CCCCC/C=C\C=C/[C@@H](O)C/C=C\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
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溶解性数据

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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
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Research Update

High fried food consumption impacts anxiety and depression due to lipid metabolism disturbance and neuroinflammation

Proc Natl Acad Sci U S A 2023 May 2;120(18):e2221097120.PMID:PMC10160962DOI:10.1073/pnas.2221097120.

Western dietary patterns have been unfavorably linked with mental health. However, the long-term effects of habitual fried food consumption on anxiety and depression and underlying mechanisms remain unclear. Our population-based study with 140,728 people revealed that frequent fried food consumption, especially fried potato consumption, is strongly associated with 12% and 7% higher risk of anxiety and depression, respectively. The associations were more pronounced among male and younger consumers. Consistently, long-term exposure to acrylamide, a representative food processing contaminant in fried products, exacerbates scototaxis and thigmotaxis, and further impairs exploration ability and sociality of adult zebrafish, showing anxiety- and depressive-like behaviors. Moreover, treatment with acrylamide significantly down-regulates the gene expression of tjp2a related to the permeability of blood-brain barrier. Multiomics analysis showed that chronic exposure to acrylamide induces cerebral lipid metabolism disturbance and neuroinflammation. PPAR signaling pathway mediates acrylamide-induced lipid metabolism disorder in the brain of zebrafish. Especially, chronic exposure to acrylamide dysregulates sphingolipid and phospholipid metabolism, which plays important roles in the development of anxiety and depression symptoms. In addition, acrylamide promotes lipid peroxidation and oxidation stress, which participate in cerebral neuroinflammation. Acrylamide dramatically increases the markers of lipid peroxidation, including (±)5-HETE, 11(S)-HETE, 5-oxoETE, and up-regulates the expression of proinflammatory lipid mediators such as (±)12-HETE and 14(S)-HDHA, indicating elevated cerebral inflammatory status after chronic exposure to acrylamide. Together, these results both epidemiologically and mechanistically provide strong evidence to unravel the mechanism of acrylamide-triggered anxiety and depression, and highlight the significance of reducing fried food consumption for mental health.

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.

Derivatization enhanced separation and sensitivity of long chain-free fatty acids: Application to asthma using targeted and non-targeted liquid chromatography-mass spectrometry approach

Anal Chim Acta 2017 Oct 9;989:59-70.PMID:28915943DOI:10.1016/j.aca.2017.08.009.

Long chain-free fatty acids (LCFFAs) play pivotal roles in various physiological functions, like inflammation, insulin resistance, hypertension, immune cell behavior and other biological activities. However, the detection is obstructed by the low contents, structural diversity, high structural similarity, and matrix interference. Herein, a fast cholamine-derivatization, within 1 min at room temperature, coupled with liquid chromatography-mass spectrometry (LC-MS) approach was developed to determine LCFFAs in complex samples. After derivatization, the ionization and separation efficiency were significantly improved, which resulted in up to 2000-fold increase of sensitivity compared with non-derivatization method, and the limits of detection were at low femtogram level. As well, this approach was applied successfully in the rapid profiling or quantification of targeted and non-targeted LCFFAs in the sera of healthy human and asthma patients. The targeted metabolomics method showed that the contents of 17 PUFAs were significantly changed in asthma patients, especially hydroxyeicosatetraenoic acids (HETEs), hydroperoxyeicosatetraenoic acid (HPETEs) and prostaglandins (PGs). The non-targeted method resulted in the tentatively identification of 35 LCFFAs including 31 saturated and mono-unsaturated LCFFAs, and 4 bile acids, except for 27 poly-unsaturated fatty acids (PUFAs), and the multivariate analysis indicated that eicosapentaenoic acid (EPA), ursodeoxycholic acid, deoxycholic acid, isodeoxycholic acid, palmitic acid, 2-lauroleic acid and lauric acid also have significant difference between healthy and asthma groups except for 17 PUFAs. To the best of our knowledge, this is the first report on the relationship of asthma with 5(S)-, 15(S)-HPETE, 8(S)-, 11(S)-HETE, 15(S)-HEPE, PGA2, PGB2, PGE1, PGF1α, PGJ2, and 13, 14-dehydro-15-keto PGF2α (DK-PGF2α).