5(S),15(S)-二羟化二十烷四烯酸 | 82200-87-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5(S),15(S)-二羟化二十烷四烯酸
• 英文名称: 5,15-diHETE
• 英文别名: 5(S),15(S)-diHETE；5(S),15(S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid；(5S,6E,8Z,11Z,13E,15S)-5,15-dihydroxyicosa-6,8,11,13-tetraenoic acid
• CAS: 82200-87-1
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: UXGXCGPWGSUMNI-BVHTXILBSA-N

物化性质

• 溶解度：
  DMF：50mg/mL； DMSO：50mg/mL；乙醇：50mg/mL； PBS（pH 7.2）：1 mg/mL
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 储存条件：
  -20°C，密封保存，置于干燥处。

制备方法与用途

5(S)15(S)-地赫特是一种“活化”中间体，能够抑制血小板聚集，其IC50值为1.3μM。此外，5(S)15(S)-地赫特还能增强LXA4或LKB4的生物合成速率【1】。

反应信息

• 作为反应物：
  描述：

  5(S),15(S)-二羟化二十烷四烯酸 以91%的产率得到
  参考文献：
  名称：

  COREY, E. J.;SU, WEI-GUO;CLEAVER, MARTIN B., TETRAHEDRON LETT., 30,(1989) N2, C. 4181-4184

  摘要：

  DOI：
• 作为产物：
  描述：

  5(S)-羟化二十烷四烯酸 在 dipotassium hydrogenphosphate 、 soybean seed lipoxygenase-1 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 0.27h， 生成 5(S),15(S)-二羟化二十烷四烯酸
  参考文献：
  名称：

  Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2

  摘要：

  Biosynthesis of the prostaglandin endoperoxide by the cyclooxygenase (COX) enzymes is accompanied by formation of a small amount of 11R-hydroxyeicosatetraenoic acid (HETE), 15R-HETE, and 15S-HETE as by-products. Acetylation of COX-2 by aspirin abrogates prostaglandin synthesis and triggers formation of 15R-HETE as the sole product of oxygenation of arachidonic acid. Here, we investigated the formation of by-products of the transformation of 5S-HETE by native COX-2 and by aspirin-acetylated COX-2 using HPLC-ultraviolet, GC-MS, and LC-MS analysis. 5S,15S- dihydroxy (di)HETE, 5S,15R-diHETE, and 5S,11R-diHETE were identified as by-products of native COX-2, in addition to the previously described di-endoperoxide (5S,15S-dihydroxy-9S,11R,8S,12S-diperoxy-6E,13E-eicosadienoic acid) as the major oxygenation product. 5S,15R-diHETE was the only product formed by aspirin-acetylated COX-2. Both 5,15-diHETE and 5,11-diHETE were detected in CT26 mouse colon carcinoma cells as well as in lipopolysaccharide-activated RAW264.7 cells incubated with 5S-HETE, and their formation was attenuated in the presence of the COX-2 specific inhibitor, NS-398. Aspirin-treated CT26 cells gave 5,15-diHETE as the most prominent product formed from 5S-HETE. 5S,15S-diHETE has been described as a product of the cross-over of 5-lipoxygenase (5-LOX) and 15-LOX activities in elicited rat mononuclear cells and human leukocytes, and our studies implicate crossover of the 5-LOX and COX-2 pathways as an additional bio-synthetic route.-Mulugeta, S., T. Suzuki, N. T. Hernandez, M. Griesser, W. E. Boeglin, and C. Schneider. Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2. J. Lipid Res. 2010. 51: 575-585.

  DOI：

  10.1194/jlr.m001719

文献信息

• A simple and efficient synthesis of (7E, 9E, 11Z, 13E)-(5S, 6R, 15S)-trihydroxyeicosatetraenoic acid (6R-lipoxin A)
  作者：E.J. Corey、Wei-guo Su、Martin B. Cleaver

  DOI：10.1016/s0040-4039(01)80684-5

  日期：1989.1

  A practical seven-step synthetic route to 6R-lipoxin A from arachidonic acid is described which makes this biologically interesting eicosanoid easily available.

  描述了一种从花生四烯酸到6 R-脂蛋白A的实用的七步合成路线，该路线使这种生物学上令人感兴趣的类花生酸容易获得。
• Methods for identifying modulators of eoxin formation
  申请人：Claesson Hans-Erik

  公开号：US20090247634A1

  公开（公告）日：2009-10-01

  A method for identifying a compound for modulating the formation of 14,15-LTC 4 (Eoxin C 4 ; EoxC 4 ), 14,15-LTD 4 (Eoxin D 4 ; EoxD 4 ), or 14,15-LTE 4 (Eoxin E 4 ; EoxE 4 ) in a biological system. A method for identifying a compound with an anti-inflammatory effect, the method comprising testing the compound for an effect on formation and/or activity of 14,15-LTC 4 (Eoxin C 4 ; EoxC 4 ), 14,15-LTD 4 (Eoxin D 4 ; EoxD 4 ), or 14,15-LTE 4 (Eoxin E 4 ; EoxE 4 ) in a biological system. A method of making an anti-inflammatory composition or Eoxin formation-modulating composition comprising (i) identifying an anti-inflammatory compound or Eoxin formation-modulating compound by a method of the invention; (ii) combining the compound with a pharmaceutically acceptable excipient or carrier.

  一种用于调节生物系统中14,15-LTC4(Eoxin C4; EoxC4)、14,15-LTD4(Eoxin D4; EoxD4)或14,15-LTE4(Eoxin E4; EoxE4)形成的化合物鉴定方法。一种用于鉴定具有抗炎作用的化合物的方法，包括测试该化合物对生物系统中14,15-LTC4(Eoxin C4; EoxC4)、14,15-LTD4(Eoxin D4; EoxD4)或14,15-LTE4(Eoxin E4; EoxE4)的形成和/或活性的影响。制备抗炎组合物或Eoxin形成调节组合物的方法包括：(i)通过本发明的方法鉴定抗炎化合物或Eoxin形成调节化合物；(ii)将该化合物与药学上可接受的赋形剂或载体结合。
• Agents with leukotriene B4-like antiviral (DNA) and anti-neoplastic activities
  申请人：——

  公开号：US20040132820A1

  公开（公告）日：2004-07-08

  The present invention relates to the use of the antiviral activity of exogenous leukotriene B 4 (LTB 4 ), variants and derivatives thereof as a therapeutic agent in viral infections caused by human and animal viruses. The present invention also relates to the use of LTB 4 as an anti-neoplastic agent in the prophylaxis and treatment of cancers induced by tumor viruses and in other neoplasic diseases. The human and animal viruses are DNA viruses, such as parvoviridae, papovaviridae, adenoviridae, herpesviridae, poxyviridae and hepadnaviridae; RNA viruses, such as picornaviridae, togaviridae, orthomyxoviridae, paramyxoviridae, coronaviridae, reoviridae, and filoviridae in general, and Retroviridae such as HIV-1 and HIV-2.

  本发明涉及利用外源性白三烯 B 4 (LTB 4 )、其变体和衍生物的抗病毒活性作为人类和动物病毒引起的病毒感染的治疗剂。本发明还涉及使用 LTB 4 作为抗肿瘤剂，用于预防和治疗由肿瘤病毒诱发的癌症和其他肿瘤性疾病。人类和动物病毒包括 DNA 病毒，如副病毒科、乳头瘤病毒科、腺病毒科、疱疹病毒科、poxyviridae 和 hepadnaviridae；RNA 病毒，如 picornaviridae、togaviridae、orthomyxoviridae、paramyxoviridae、coronaviridae、reoviridae 和 filoviridae，以及逆转录病毒科，如 HIV-1 和 HIV-2。
• In vivo release of endogenous anti-microbial mediators by leukotriene B4 (LTB4) administration
  申请人：Gosselin Jean

  公开号：US20050239889A1

  公开（公告）日：2005-10-27

  The invention relates to the in vivo release of endogenous anti-microbial mediators using leukotriene B4 administration. The present invention furthermore relates to the use of leukotriene B4 for the treatment and/or prophylaxis of diseases that are positively influenced by such anti-microbial mediators.

  本发明涉及使用白三烯 B4 在体内释放内源性抗微生物介质。本发明还涉及使用白三烯 B4 治疗和/或预防受此类抗微生物介质积极影响的疾病。
• Ltb4 as vaccine adjuvant
  申请人：——

  公开号：US20040208882A1

  公开（公告）日：2004-10-21

  The present invention relates to a vaccine adjuvant for enhancing immune response of an individual to a vaccine, which comprises an immune-enhancing effective amount of an LTB4 agent in association with a pharmaceutically effective vaccine carrier.