17(S)-HDHA
(Synonyms: 17(S)hydroxy Docosahexaenoic Acid, 17(S)HDoHE) 目录号 : GC41208
An oxidation product of DHA
Cas No.:92693-03-3
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
17(S)-HDHA is a primary mono-oxygenation product of docosahexaenoic acid in human whole blood, human leukocytes, and mouse brain. 17(S)-HDHA serves as a precursor to 17(S)-resolvins and has intrinsic biological activity, such as the inhibition of TNF-α-induced interleukin-1β expression in human glioma cells and inhibition of TNF-α-induced leukocyte trafficking to the mouse air pouch.
| Cas No. | 92693-03-3 | SDF | |
| 别名 | 17(S)hydroxy Docosahexaenoic Acid, 17(S)HDoHE | ||
| Canonical SMILES | CC/C=C\C[C@H](O)/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O | ||
| 分子式 | C22H32O3 | 分子量 | 344.5 |
| 溶解度 | 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 | 2.9028 mL | 14.5138 mL | 29.0276 mL |
| 5 mM | 0.5806 mL | 2.9028 mL | 5.8055 mL |
| 10 mM | 0.2903 mL | 1.4514 mL | 2.9028 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。
Gram scale synthesis of specialized pro-resolving mediator 17(S)-HDHA using lipoxygenase enhanced by water-soluble reducing agent TCEP
Bioorg Med Chem Lett 2016 Jan 15;26(2):343-345.PMID:26707393DOI:10.1016/j.bmcl.2015.12.011.
17(S)-Hydroxy docosahexaenoic acid (17(S)-HDHA) is a specialized pro-resolving mediator. The oxidation of docosahexaenoic acid (DHA) to 17(S)-HDHA using soybean lipoxygenase was accomplished in the presence of the reducing agent TCEP in high yield and high enantio excess. We demonstrated application of this strategy to the synthesis of other fatty acids and to gram scale synthesis of 17(S)-HDHA.
Formation of eicosanoids and other oxylipins in human macrophages
Biochem Pharmacol 2022 Oct;204:115210.PMID:35973581DOI:10.1016/j.bcp.2022.115210.
In this review it is attempted to summarize current studies about formation of eicosanoids and other oxylipins in different human macrophages. There are several reports on M1 and M2 cells, also other phenotypes have been described. The eicosanoids formed in the largest amounts are the COX products TxB2 and PGE2. Thus shortlived bioactive TxA2 is a dominating product both in M1- and in M2-lineages, one exception seems to be MGM-CSF, TGFβ cells. 5-LOX products are produced in both M1 and M2 macrophages, as well as in not fully polarized cells of both lineages. MM-CSF as well as M2 macrophages produced LTC4 more readily compared to M1 lineage cells. In MGM-CSF, TGFβ cells LTB4 is a major eicosanoid, in line with high expression of LTA4 hydrolase. Recent reports described increased formation of leukotrienes in macrophages subjected to trained immunity with inflammatory transcriptional reprogramming. Also in macrophages derived from monocytes collected from post-COVID-19 patients. 15-LOX-1 is strongly upregulated in CD206+ M2 cells (M2a), differentiated in presence of IL-4. These macrophages also express 15-LOX-2. In incubations with pathogenic E. coli as well as other stimuli 15(S)-HETE and 17(S)-HDHA were major oxylipins formed. Also, the SPM precursor 5,15-diHETE and the SPM RvD5 were produced in considerable amounts, while other SPMs were less abundant. In M2 macrophages incubated with E. coli or S. aureus the cytosolic 15-LOX-1 enzyme accumulated to punctuate structures in a Ca2+ dependent manner with a relatively slow time course, leading to formation of mediators from endogenous substrate. Chalcones, flavone-like anti-inflammatory natural products, induced translocation of 15-LOX-1 in M2 cells, with high formation of 15-LOX derived oxylipins.
Dihydroxydocosahexaenoic acids of the neuroprotectin D family: synthesis, structure, and inhibition of human 5-lipoxygenase
J Lipid Res 2006 Nov;47(11):2462-74.PMID:16899822DOI:10.1194/jlr.M600280-JLR200.
During aerobic oxidation of docosahexaenoic acid (DHA), soybean lipoxygenase (sLOX) has been shown to form 7,17(S)-dihydro(pero)xydocosahexaenoic acid [7,17(S)-diH(P)DHA] along with its previously described positional isomer, 10,17(S)-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid. 7,17(S)-diH(P)DHA was also obtained via sLOX-catalyzed oxidation of either 17(S)-hydroperoxydocosahexaenoic acid [17(S)-HPDHA] or 17(S)-hydroxydocosahexaenoic acid [17(S)-HDHA]. The structures of the products were elucidated by normal-phase, reverse-phase, and chiral-phase HPLC analyses and by ultraviolet, NMR, and tandem mass spectroscopy and GC-MS. 7,17(S)-diH(P)DHA was shown to have 4Z,8E,10Z,13Z,15E,19Z geometry of the double bonds. In addition, a compound apparently identical to the sLOX-derived 7,17(S)-diH(P)DHA was produced by another enzyme, potato tuber LOX, in the reactions of oxygenation of either 17(S)-HPDHA or 17(S)-HDHA. All of the dihydroxydocosahexaenoic acids (diHDHAs) formed by either of the enzymes were clearly produced through double lipoxygenation of the corresponding substrate. 7,17(S)-diHDHA inhibited human recombinant 5-lipoxygenase in the reaction of arachidonic acid (AA) oxidation. In standard conditions with 100 microM AA as substrate, the IC(50) value for 7,17(S)-diHDHA was found to be 7 microM, whereas IC(50) for 10,17(S)-DiHDHA was 15 microM. Similar inhibition by the diHDHAs was observed with sLOX, a quintessential 15LOX, although the strongest inhibition was produced by 10,17(S)-diHDHA (IC(50) = 4 microM). Inhibition of sLOX by 7,17(S)-diHDHA was slightly less potent, with an IC(50) value of 9 microM. These findings suggest that 7,17(S)-diHDHA along with its 10,17(S) counterpart might have anti-inflammatory and anticancer activities, which could be exerted, at least in part, through direct inhibition of 5LOX and 15LOX.
Novel oxylipins formed from docosahexaenoic acid by potato lipoxygenase--10(S)-hydroxydocosahexaenoic acid and 10,20-dihydroxydocosahexaenoic acid
Lipids 2005 Mar;40(3):249-57.PMID:15957250DOI:10.1007/s11745-005-1379-z.
Potato tuber lipoxygenase (ptLOX) has been shown to catalyze the aerobic formation of at least four major oxygenated derivatives of DHA. Two of the products--7,17(S)- and 10,17(S)-dihydro(pero)xy-DHA [7,17- and 10,17-diH(P)DHA]--were formed from soybean 15-LOX-derived 17(S)-hydro(pero)xy-DHA [17(S)-H(P)DHA], whereas two novel oxylipin compounds--10(S)-hydro(pero)xy-DHA and 10,20-dihydro(pero)xy-DHA [10(S)-H(P)DHA and 10,20-diH(P)DHA, respectively]--were the major direct products of DHA oxidation by ptLOX. The reactions proceeded relatively slowly but could be stimulated by catalytic amounts of SDS. Micromolar concentrations of 10(S)-HPDHA effectively abolished the kinetic lag period of ptLOX activation. Enzymatic activity with DHA or 17(S)-HPDHA as substrate was about 8% of that with linoleic acid--a standard natural ptLOX substrate--whereas 17(S)-HDHA was converted at a rate of approximately 1%. The enzyme was relatively unstable and quickly inactivated during the reaction with DHA on with 17(S)-HPDHA (first-order kinetic constant of inactivation kin = 1.5 +/- 0.3 min(-1)), but not with 17(S)-HDHA. Both 7,17- and 10,20-diH(P)DHA were clearly products of double oxygenation catalyzed by soybean 15-LOX and/or ptLOX. Our observation that ptLOX could convert 17-HDHA to 10,17-diH(P)DHA indicates that this dihydroxylated derivative of DHA also can be formed via a double lipoxygenation mechanism.