1-棕榈酰基-2-戊二酰基-sn-甘油-3-磷酸胆碱 | 89947-79-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: 1-棕榈酰基-2-戊二酰基-sn-甘油-3-磷酸胆碱
• 英文名称: PGPC
• 英文别名: 1-O-palmitoyl-2-O-glutaroyl-sn-glycero-3-phosphocholine；[(2R)-2-(4-carboxybutanoyloxy)-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 89947-79-5
• 化学式: C₂₉H₅₆NO₁₀P
• 分子量: 609.738
• InChiKey: CDZVJFRXJAUXPP-AREMUKBSSA-N

物化性质

• 溶解度：
  DMSO：1mg/mL；乙醇：20mg/mL； PBS（pH 7.2）：5 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  41
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  戊二酸酐 、 溶血磷脂酰胆碱(鸡蛋) 在 吡啶 作用下， 反应 18.0h， 生成 1-棕榈酰基-2-戊二酰基-sn-甘油-3-磷酸胆碱
  参考文献：
  名称：

  Temporary membrane distortion of vascular smooth muscle cells is responsible for their apoptosis induced by platelet-activating factor-like oxidized phospholipids and their degradation product, lysophosphatidylcholine

  摘要：

  To obtain information about the mechanism of apoptosis induced by oxidized low density lipoproteins (oxLDL) in atherosclerotic plaques, we examined the effects of lysophosphatidylcholine (LPC) and platelet-activating factor (PAF)-like lipids (PAF-LL), which can be derived from oxLDL, on rat vascular smooth muscle cells (VSMC). All the lipids with different structures examined induced apoptosis of VSMC, so we studied the mechanism of induction of apoptosis by LPC. LPC-induced apoptosis was inhibited by alpha-tocopherol (alpha-T) and cholesterol (Chol), but not by other antioxidants such as palmitoyl ascorbic acid and PAF receptor antagonist. The cells temporarily became spherical and highly permeable before induction of apoptosis, and their change in shape was prevented by alpha-T and Choi. From these results, we Suggest that the apoptosis induced by oxLDL-derived phospholipids in VSMC is caused by temporary membrane distortion, not through specific receptors. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00091-4
• 作为试剂：
  描述：

  lysophosphatidylcholine 、 戊二酸酐 、 chloroform methanol 在 4-二甲氨基吡啶 1-棕榈酰基-2-戊二酰基-sn-甘油-3-磷酸胆碱 、 甲醇 、 水合甲醇 、 4-二甲氨基吡啶 、 乙醚 作用下， 以 二氯甲烷 为溶剂， 以afforded 32 mg of PGPC (42%, Rf=0.05)的产率得到1-棕榈酰基-2-戊二酰基-sn-甘油-3-磷酸胆碱
  参考文献：
  名称：

  Oxidized phospholipids

  摘要：

  本发明涉及具有以下通式(I)或(II)之一的氧化磷脂： 其中A = O，C，NH或S；B = O，C，NH或S；R2从以下组中选择：—CO—(CH2)n—CH3；—CO—(CH2)n—CHO；和—CO—(CH2)n—COOH，其中n = 3-7，但需注意，在通式(I)中，R1从以下组中选择：—CH2—(CH2)n—X；和—CO—(CH2)n—X，其中n = 5-11，X是荧光分子；在通式(II)中，R1从以下组中选择：—CH═CH—(CH2)n—CH3，其中n = 9-15；—(CH2)n—CH3，其中n = 11-17；和—CO—(CH2)n—CH3，其中n = 10-16；R3从以下组中选择：—CO—(CH2)n—X；和—SO2—(CH2)n—X，其中n = 0-5，X是荧光分子。

  公开号：

  US07906674B2

文献信息

• Oxidized Phospholipids
  申请人：Hermetter Albin

  公开号：US20090130648A1

  公开（公告）日：2009-05-21

  The invention relates to oxidized phospholipids having one of the general formulas (I) or (II) wherein A=O, C, NH, or S; B═O, C, NH, or S; and R 2 is selected from the group consisting of —CO—(CH 2 ) n —CH 3 ; —CO—(CH 2 ) b —CHO; and —CO—(CH 2 ) n —COOH, with n=3-7, with the proviso that in general formula (I), R 1 is selected from the group consisting of —CH 2 —(CH 2 ) n —X; a —CO—(CH 2 ) n —X with n=5-11, wherein X is a fluorophore; and in general formula (II), R 1 is selected from the group consisting of —CH═CH—(CH 2 ) n —CH 3 with n=9-15; —(CH 2 ) n —CH 3 with n=11-17; and —CO—(CH 2 ) n —CH 3 with n=10-16; and R 3 is selected from the group consisting of —CO—(CH 2 ) n —X; and —SO 2 —(CH 2 ) n —X, with n=0-5, wherein X is a fluorophore.

  本发明涉及具有以下一般式(I)或(II)之一的氧化磷脂，其中A = O，C，NH或S; B = O，C，NH或S; R2从以下组中选择：-CO-（CH2）n-CH3; -CO-（CH2）b-CHO; 和-CO-（CH2）n-COOH，其中n = 3-7，但在一般式(I)中，R1从以下组中选择：-CH2-（CH2）n-X; -CO-（CH2）n-X，其中n = 5-11，X是荧光染料; 而在一般式(II)中，R1从以下组中选择：-CH═CH-（CH2）n-CH3，其中n = 9-15; -（CH2）n-CH3，其中n = 11-17; 和-CO-（CH2）n-CH3，其中n = 10-16; 而R3从以下组中选择：-CO-（CH2）n-X; 和-SO2-（CH2）n-X，其中n = 0-5，X是荧光染料。
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  申请人：University of Fukui

  公开号：EP3733203A1

  公开（公告）日：2020-11-04

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  公开号：EP4061409A1

  公开（公告）日：2022-09-28
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  公开号：US20220370310A1

  公开（公告）日：2022-11-24

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  公开号：US20220401535A1

  公开（公告）日：2022-12-22

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