15-deoxy-delta prostaglandin J2 | 64222-94-2

• 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: 15-deoxy-delta prostaglandin J2
• 英文别名: 15-deoxyprostaglandin J₂；15-deoxy-PGJ₂；15d-prostaglandin J2；15d-PJ2；(5Z,13E)-11-oxo-5,9,13-prostatrienoic acid；15-d-PGJ2；15-deoxyprostaglandin J2；(Z)-7-[(1S,5R)-5-[(E)-oct-1-enyl]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid
• CAS: 64222-94-2
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: AWSUSADYFDCYML-KUPUPYBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5Z,13E)-11-oxo-5,9,13-prostatrienoic acid diphenylmethyl ester 在 三氯化铝 作用下， 以 硝基甲烷 、 二氯甲烷 、 苯甲醚 为溶剂， 以75%的产率得到15-deoxy-delta prostaglandin J2
  参考文献：
  名称：

  Treatment for hypertension or glaucoma in eyes

  摘要：

  本发明涉及一种用于治疗眼部高血压或青光眼的方法，包括将眼部表面与公式（I）的15-去氧前列腺素衍生物的治疗量接触：其中##STR2##是从组成的一组中选择的5元环，##STR3##R.sup.1是氢或较低烷基；R.sup.2是C.sub.6 -C.sub.12烷基，C.sub.6 -C.sub.12烯基或C.sub.6 -C.sub.12烷二烯基或其药学上可接受的盐。该发明还涉及一种用于递送治疗青光眼的局部溶液的工具包，包括（a）包含公式（I）化合物的溶液的容器，以及（b）用于将所述溶液以受控剂量递送至眼部的局部递送手段。

  公开号：

  US05292754A1

文献信息

• Δ¹²-Prostaglandin J₂ as a Product and Ligand of Human Serum Albumin: Formation of an Unusual Covalent Adduct at His146
  作者：Satoru Yamaguchi、Giancarlo Aldini、Sohei Ito、Nozomi Morishita、Takahiro Shibata、Giulio Vistoli、Marina Carini、Koji Uchida

  DOI：10.1021/ja908878n

  日期：2010.1.20

  Human serum albumin (HSA), the most abundant protein in plasma, has a very unique function, catalyzing the conversion of prostaglandin J(2) (PGJ(2)), a dehydration product of PGD(2), to yield Delta(12)-PGJ(2). These PGD(2) metabolites are actively transported into cells and accumulated in the nuclei, where they act as potent inducers of cell growth inhibition and cell differentiation, and exhibit their own unique spectrum of biological effects. The facts that (i) arachidonic acid metabolites bind to human serum albumin (HSA) and the metabolism of these molecules is altered as a result of binding, (ii) HSA catalyzes the transformation of PGJ(2) into Delta(12)-PGJ(2), and (iii) Delta(12)-PGJ(2) is stable in serum suggest that HSA may bind and stabilize Delta(12)-PGJ(2) in a specific manner. A molecular interaction analysis using surface plasmon resonance (Biacore) indeed suggested the presence of a specific Delta(12)-PGJ(2)-binding site in HSA. To investigate the molecular details of the binding of this PGD(2) metabolite to albumin, we analyzed the cocrystal structure of the HSA-Delta(12)-PGJ(2)-myristate complex by X-ray crystallography and found that two Delta(12)-PGJ(2) molecules bind to a primary site in subdomain IB of the protein. The electron density results suggested that one of the two Delta(12)-PGJ(2) molecules that specifically bind to the site covalently interacted with a histidine residue (His146). Using nano-LC-MS/MS analysis of the HSA-Delta(12)-PGJ(2) Complex, the formation of an unusual Delta(12)-PGJ(2)-histidine adduct at His146 was confirmed. Thus, our crystallographic and mass spectrometric analyses of the HSA-Delta(12)-PGJ(2) complex provided intriguing new insights into the molecular details of how this electrophilic ligand interacts with its primary producer and transporter.
• 15-DEOXYPROSTAGLANDIN DERIVATIVE
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0471856B1

  公开（公告）日：1995-03-22
• US5292754A
  申请人：——

  公开号：US5292754A

  公开（公告）日：1994-03-08
• US5599837A
  申请人：——

  公开号：US5599837A

  公开（公告）日：1997-02-04
• Treatment for hypertension or glaucoma in eyes
  申请人：Shionogi & Co., Ltd.

  公开号：US05292754A1

  公开（公告）日：1994-03-08

  The present invention relates to a method for treating hypertension or glaucoma in the eye comprising contacting the surface of the eye with a therapeutic amount of a 15-deoxyprostaglandin derivative of the formula (I): ##STR1## in which ##STR2## is a 5 membered ring which is selected from a group consisting of ##STR3## R.sup.1 is hydrogen or lower alkyl; R.sup.2 is C.sub.6 -C.sub.12 alkyl, C.sub.6 -C.sub.12 alkenyl or C.sub.6 -C.sub.12 alkadienyl or a pharmaceutically acceptable salt thereof. The invention also relates to a kit for delivery of a topical solution for treatment of glaucoma which comprises (a) container having a solution including a compound of the formula (I), and (b) means for topical delivery of said solution to the eye in a controlled dosage.

  本发明涉及一种用于治疗眼部高血压或青光眼的方法，包括将眼部表面与公式（I）的15-去氧前列腺素衍生物的治疗量接触：其中##STR2##是从组成的一组中选择的5元环，##STR3##R.sup.1是氢或较低烷基；R.sup.2是C.sub.6 -C.sub.12烷基，C.sub.6 -C.sub.12烯基或C.sub.6 -C.sub.12烷二烯基或其药学上可接受的盐。该发明还涉及一种用于递送治疗青光眼的局部溶液的工具包，包括（a）包含公式（I）化合物的溶液的容器，以及（b）用于将所述溶液以受控剂量递送至眼部的局部递送手段。