11beta-PGF2alpha-EA

• 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: 11beta-PGF2alpha-EA
• 英文别名: (Z)-7-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide
• 化学式: C₂₂H₃₉NO₅
• 分子量: 397.5
• InChiKey: XCVCLIRZZCGEMU-WMTHMIERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氢(+1)阳离子 、 NADPH(4-) 、 (5Z,8Xi,13E)-9,15-二羟基-N-(2-羟基乙基)-11-氧代前列腺-5,13-二烯-1-酰胺 生成 11beta-PGF2alpha-EA 、 NADP⁺
  参考文献：
  名称：

  Synthesis of prostaglandin F ethanolamide by prostaglandin F synthase and identification of Bimatoprost as a potent inhibitor of the enzyme: new enzyme assay method using LC/ESI/MS

  摘要：

  Prostaglandin (PG) D-2 ethanolamide (prostamide D-2) was reduced to 9alpha, 11beta-PGF(2) ethanolamide (9alpha, 11beta-prostamide F-2) by PGF synthase, which also catalyzes the reduction of PGH(2) and PGD(2) to PGF(2alpha) and 9alpha11beta-PGF(2), respectively. These enzyme activities were measured by a new method, the liquid chromatographic-electrospray ionization-mass spectrometry (LC/ESI/MS) technique, which could simultaneously detect the substrate and all products. PGF(2alpha), 9alpha,l lbeta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2 were separated on a TSKgel ODS 80Ts column, ionized by electrospray, and detected in the negative mode. Selected ion monitoring (SIM) of m/z 353 ([M-H](-)), 353 ([M-H](-)), 351 ([M-H](-)) 333 ([M-H-H2O](-)) 456 ([M+59](-)), and m/z 358 ([M-37](-)) was used for quantifying PGF(2alpha), 9alpha,11beta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2, respectively. The detection limit for PGF(2alpha) and 9alpha,11beta-PGF(2) was 0.01 pmol, that for PGH(2) and PGD(2), 0.1 pmol; and that for prostamide D-2 and 9alpha,11beta-prostamide F-2, 0.5 and 0.03 pmol, respectively. The LC/ESI/MS technique for measuring PGF synthase activity showed higher sensitivity than other methods. Using this method, we found that Bimatoprost, the ethyl amide analog of 17-phenyl-trinor PGF(2alpha) and an anti-glaucoma agent, inhibited all three reductase activities of PGF synthase when used at a low concentration. These results suggest that Bimatoprost also behaves as a potent PGF synthase inhibitor in addition to having prostamide-like activity. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2004.02.009

文献信息

• Synthesis of prostaglandin F ethanolamide by prostaglandin F synthase and identification of Bimatoprost as a potent inhibitor of the enzyme: new enzyme assay method using LC/ESI/MS
  作者：Noriko Koda、Yasutaka Tsutsui、Haruki Niwa、Seiji Ito、David F Woodward、Kikuko Watanabe

  DOI：10.1016/j.abb.2004.02.009

  日期：2004.4

  Prostaglandin (PG) D-2 ethanolamide (prostamide D-2) was reduced to 9alpha, 11beta-PGF(2) ethanolamide (9alpha, 11beta-prostamide F-2) by PGF synthase, which also catalyzes the reduction of PGH(2) and PGD(2) to PGF(2alpha) and 9alpha11beta-PGF(2), respectively. These enzyme activities were measured by a new method, the liquid chromatographic-electrospray ionization-mass spectrometry (LC/ESI/MS) technique, which could simultaneously detect the substrate and all products. PGF(2alpha), 9alpha,l lbeta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2 were separated on a TSKgel ODS 80Ts column, ionized by electrospray, and detected in the negative mode. Selected ion monitoring (SIM) of m/z 353 ([M-H](-)), 353 ([M-H](-)), 351 ([M-H](-)) 333 ([M-H-H2O](-)) 456 ([M+59](-)), and m/z 358 ([M-37](-)) was used for quantifying PGF(2alpha), 9alpha,11beta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2, respectively. The detection limit for PGF(2alpha) and 9alpha,11beta-PGF(2) was 0.01 pmol, that for PGH(2) and PGD(2), 0.1 pmol; and that for prostamide D-2 and 9alpha,11beta-prostamide F-2, 0.5 and 0.03 pmol, respectively. The LC/ESI/MS technique for measuring PGF synthase activity showed higher sensitivity than other methods. Using this method, we found that Bimatoprost, the ethyl amide analog of 17-phenyl-trinor PGF(2alpha) and an anti-glaucoma agent, inhibited all three reductase activities of PGF synthase when used at a low concentration. These results suggest that Bimatoprost also behaves as a potent PGF synthase inhibitor in addition to having prostamide-like activity. (C) 2004 Elsevier Inc. All rights reserved.