(±)-7,8-epoxy-4Z,10Z,13Z,16Z,19Z-docosapentaenoic acid | 895127-66-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (±)-7,8-epoxy-4Z,10Z,13Z,16Z,19Z-docosapentaenoic acid
• 英文别名: 7,8-epoxydocosapentaenoic acid；7,8-epoxidocosapentaenoic；7,8-EDP；7(8)-EpDPE；(Z)-6-[3-[(2Z,5Z,8Z,11Z)-tetradeca-2,5,8,11-tetraenyl]oxiran-2-yl]hex-4-enoic acid
• CAS: 895127-66-9
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: OHYKIJBTVXMLKX-MPQBXPHNSA-N

物化性质

• 沸点：
  486.9±40.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50mg/mL； DMSO：50mg/mL；乙醇：50mg/mL； PBS（pH 7.2）：1 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  -20°C，密闭保存，置于干燥处

制备方法与用途

( \pm )7(8)-EpDPA是一种由细胞色素P450环氧酶作用生成的DHA衍生物。

反应信息

• 作为反应物：
  描述：

  (±)-7,8-epoxy-4Z,10Z,13Z,16Z,19Z-docosapentaenoic acid 、 C.I.酸性橙108 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成 (Z)-N-(2-hydroxyethyl)-6-[3-[(2Z,5Z,8Z,11Z)-tetradeca-2,5,8,11-tetraenyl]oxiran-2-yl]hex-4-enamide
  参考文献：
  名称：

  Antitumorigenic Properties of Omega-3 Endocannabinoid Epoxides

  摘要：

  Accumulating studies have linked inflammation to tumor progression. Dietary omega-3 fatty acids, such as docosahexaenoic acid (DHA), have been shown to suppress tumor growth through their conversion to epoxide metabolites. Alternatively, DHA is converted enzymatically into docosahexaenoylethanolamide (DHEA), an endocannabinoid with antiproliferative activity. Recently, we reported a novel class of anti-inflammatory DHEA-epoxide derivative called epoxydocospentaenoic-ethanolamide (EDP-EA) that contain both ethanolamide and epoxide moieties. Herein, we study the antitumorigenic properties of EDP-EAs in an osteosarcoma (OS) model. First, we show similar to 80% increase in EDP-EAs in metastatic versus normal lungs of mice. We found significant differences in the apoptotic and antimigratory potencies of the different EDPEA regioisomers, which were partially mediated through cannabinoid receptor 1 (CB1). Next, we synthesized derivatives of the most pro-apoptotic regioisomer. These derivatives had reduced hydrolytic susceptibility to fatty acid amide hydrolase (FAAH) and increased CB1-selective binding. Collectively, we report a novel class of EDP-EAs that exhibit antiangiogenic, antitumorigenic, and antimigratory properties in OS.

  DOI：

  10.1021/acs.jmedchem.8b00243
• 作为产物：
  描述：

  all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester 、 间氯过氧苯甲酸 生成 (±)-7,8-epoxy-4Z,10Z,13Z,16Z,19Z-docosapentaenoic acid
  参考文献：
  名称：

  VANROLLINS, MIKE;FRADE, PETER D.;CARRETERO, OSCAR A., J. LIPID RES., 30,(1989) N, C. 275-286

  摘要：

  DOI：

文献信息

• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATION<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE TRAITEMENT D'UNE INFLAMMATION
  申请人：RESOLVYX PHARMACEUTICALS INC

  公开号：WO2010120719A1

  公开（公告）日：2010-10-21

  The invention relates to novel resolvin compounds and pharmaceutical preparations thereof. The invention further relates to methods of treatment using the novel resolvin compounds of the invention.

  这项发明涉及新型利用新型resolvin化合物和其药物制剂的治疗方法。
• [EN] COMPOSITIONS AND METHODS FOR ORGAN PRESERVATION<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE CONSERVATION D'ORGANE
  申请人：RESOLVYX PHARMACEUTICALS INC

  公开号：WO2010091226A1

  公开（公告）日：2010-08-12

  The invention relates to reducing, preventing or reversing organ damage, reducing and/or preventing stem cell damage and/or death, enhancing organ preservation and/or survival, or enhancing stem cell preservation and/or survival comprising administering a compound of formula A, a compound of any one of formulae 1-49 or I-III, a lipoxin compound, an oxylipin compound, or a combination of aspirin and an omega-3 fatty acid.

  该发明涉及减少、预防或逆转器官损伤，减少和/或预防干细胞损伤和/或死亡，增强器官保存和/或存活，或增强干细胞保存和/或存活的方法，包括给予化合物A的化合物，任何一个化合物1-49或I-III的化合物，脂氧合素化合物，氧脂素化合物，或阿司匹林和ω-3脂肪酸的组合。
• COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATORY DISEASE
  申请人：Gjorstrup Per

  公开号：US20110190242A1

  公开（公告）日：2011-08-04

  The invention relates to methods of treating inflammatory disease comprising administering a compound of formula A, a compound of any one of formulae 1-49 or I-III, a lipoxin compound, or an oxylipin compound.

  该发明涉及治疗炎症性疾病的方法，包括给予公式A的化合物、任何一个公式1-49或I-III的化合物、脂氧素化合物或氧脂素化合物。
• Topical formulations and uses thereof
  申请人：OCULAR TECHNOLOGIES SARL

  公开号：US10441630B2

  公开（公告）日：2019-10-15

  Provided herein include formulations for topical administration, such as ophthalmic formulations, and methods of using such formulations. In some aspects and embodiments the formulations may include a polyoxyl lipid or fatty acid, and or a polyalkoxylated alcohol and may include nanomicelles. Also include methods of treating or preventing diseases or conditions, such as ocular diseases or conditions.

  本文提供了用于局部用药的制剂，如眼科制剂，以及使用此类制剂的方法。在某些方面和实施方案中，制剂可包括聚氧乙烯脂质或脂肪酸，以及或聚烷氧基化醇，并可包括纳米细胞。还包括治疗或预防疾病或病症（如眼部疾病或病症）的方法。
• Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450
  作者：Danièle Lucas、Sophie Goulitquer、Jan Marienhagen、Maude Fer、Yvonne Dreano、Ulrich Schwaneberg、Yolande Amet、Laurent Corcos

  DOI：10.1194/jlr.m003061

  日期：2010.5

  Cytochromes P450 (CYPs) metabolize polyunsaturated long-chain fatty acids (PUFA-LC) to several classes of oxygenated metabolites. Through use of human recombinant CYPs, we recently showed that CYP1A1, -2C19, -2D6, -2E1, and -3A4 are mainly hydroxylases, whereas CYP1A2, -2C8, -2C9, and -2J2 are mainly epoxygenases of arachidonic acid (AA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), respectively. It is worth noting that the last double bond of these PUFAs, i.e., omega 6 in AA or omega 3 in EPA and DHA, respectively, was preferentially epoxidized. In this study, we have characterized the stereoselectivity of this epoxidation reaction by comparison with the PUFA-LC epoxide stereoisomers obtained from the enantioselective bacterial CYP102A1 F87V. The stereoselectivity of the epoxidation of the last olefin of AA (omega 6), EPA (omega 3), or DHA (omega 3) differed between the CYP isoforms but was similar for EPA and DHA. These data give additional insight into the PUFA-LC epoxide enantiomers generated by the hepatic CYPs.-Lucas, D., S. Goulitquer, J. Marienhagen, M. Fer, Y. Dreano, U. Schwaneberg, Y. Amet, and L. Corcos. Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450. J. Lipid Res. 2010. 51: 1125-1133.