1-O-palmityl-D-glucuronic acid | 127910-63-8

• 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: 1-O-palmityl-D-glucuronic acid
• 英文别名: (2S,3S,4S,5R)-6-hexadecoxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 127910-63-8
• 化学式: C₂₂H₄₂O₇
• 分子量: 418.571
• InChiKey: QFUQXEVPTHAOHS-QAKXDBDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (2S,3S,4S,5R)-3,4,5-triacetyloxy-6-hexadecoxyoxane-2-carboxylate 生成 1-O-palmityl-D-glucuronic acid
  参考文献：
  名称：

  NAMBA, YUKIHIRO;SAKAKIBARA, TOSHIYUKI;MASADA, MIKIO;ITO, FUMIAKI;OKU, NAO+, CHEM. LETT.,(1989) N2, C. 2145-2148

  摘要：

  DOI：

文献信息

• Lipid-derivatized bisphosphonic acid
  申请人：Greb Wolfgang

  公开号：US20070154537A1

  公开（公告）日：2007-07-05

  A bisphosphonic acid of the general formula (I) wherein R 1 is H, OH, C 1 -C 6 alkyl C 1 -C 6 alkoxy, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 1 -C 6 halogen alkyl X is a direct bond, alkylen group with 1 to 20 carbon atoms, (CH 3 ) m —(OCR 3 HCH 2 ) n —(O) o — wherein R 3 is H or CH 3 and m is 0 or a number from 1 to 6, n is a number from 1 to 10, preferably 1 to 6, and o is 0 or 1, —(CR 4 HCH 2 O) p — wherein R 4 is H or CH 3 , p is a number from 1 to 10, preferably 1 to 6, (CH 3 ) q —(OCR 5 HCH 2 ) r —(O) s —(CH 3 ) t —, wherein R 5 is H or CH 3 and q is 0 or a number from 1 to 6, r is a number from 1 to 10, preferably 1 to 6, and s is 0 or 1, and t is a number from 1 to 6, R 2 is a group of the formula (II) as well as their physiologically compatible derivatives, in particular salts and trimethyl silyl derivatives.

  通用式（I）的双膦酸 其中R 1 为H、OH、C 1 -C 6 烷基、C 1 -C 6 烷氧基、C 1 -C 6 羟基烷基、C 1 -C 6 氨基烷基、C 1 -C 6 卤代烷基 X为直链键、含有1至20个碳原子的烷基基团、（CH 3 ） m —（OCR 3 HCH 2 ） n —（O） o —其中R 3 为H或CH 3 ，m为0或1至6的数字，n为1至10的数字，优选1至6，o为0或1， —（CR 4 HCH 2 O） p —其中R 4 为H或CH 3 ，p为1至10的数字，优选1至6， （CH 3 ） q —（OCR 5 HCH 2 ） r —（O） s —（CH 3 ） t —，其中R 5 为H或CH 3 ，q为0或1至6的数字，r为1至10的数字，优选1至6，s为0或1，t为1至6的数字， R 2 为式（II）的基团 以及它们的生理相容衍生物，特别是盐和三甲基硅烷衍生物。
• Glucuronate-modified liposomes with prolonged circulation time.
  作者：Yukihiro NAMBA、Toshiyuki SAKAKIBARA、Mikio MASADA、Fumiaki ITO、Naoto OKU

  DOI：10.1248/cpb.38.1663

  日期：——

  For the purpose of obtaining liposomes with long circulation time in blood, we synthesized 1-O-palmityl-D-glucuronic acid (PGlcUA) and incorporated it into the liposomal membranes. The clearance of the PGlcUA-liposomes composed of dipalmitoylphosphatidylcholine (DPPC), choleterol, and PGlcUA (40 : 40 : 20 as a molar ratio) from blood and their tissue distribution were compared with those of dipalmitoylphosphatidylglycerol (DPPG)-liposomes (DPPC/cholesterol/DPPG=40 : 40 : 20). When [3H]inulin-loaded PGlcUA-liposomes and DPPG-liposomes were intravenously injected into rats, the half-life of the PGlcUA-liposomes in the blood appeared to be 1.7-fold longer than that of DPPG-liposomes. Radioactivities present in plasma and various tissues were measured 22h after administration of these liposomes, and radioactivity remaining in the plasma was 2.5-fold greater when PGlcUA-liposomes were injected. The distribution pattern of [3H]inulin in PGlcUA-liposomes was similar to that in DPPG-liposomes. The radioactivity recovered in urine was 25% lower in rats treated with PGlcUA-liposomes than in those treated wit DPPG-liposomes. Since both PGlcUA-and DPPG-liposomes exhibited similar size distribution and ζ-potential, glucuronic acid, rather than negative charge, on the liposomal surface appears to endow liposomes with a longer circulation time in the bloodstream.

  为了获得在血液中循环时间较长的脂质体，我们合成了 1-O-棕榈酰-D-葡萄糖醛酸（PGlcUA），并将其加入脂质体膜中。我们比较了由二棕榈酰磷脂酰胆碱（DPPC）、胆固醇和 PGlcUA（摩尔比为 40 : 40 : 20）组成的 PGlcUA 脂质体与二棕榈酰磷脂酰甘油（DPPG）脂质体（DPPC/胆固醇/DPG=40 : 40 : 20）在血液中的清除率及其组织分布情况。给大鼠静脉注射[3H]菊粉负载的 PGlcUA 脂质体和 DPPG 脂质体时，PGlcUA 脂质体在血液中的半衰期似乎比 DPPG 脂质体长 1.7 倍。注射这些脂质体 22 小时后，测量了血浆和各种组织中的放射性活度，结果显示，注射 PGlcUA 脂质体后，血浆中残留的放射性活度是 DPPG 脂质体的 2.5 倍。PGlcUA 脂质体中[3H]菊粉的分布模式与 DPPG 脂质体相似。接受 PGlcUA 脂质体治疗的大鼠尿液中回收的放射性比接受 DPPG 脂质体治疗的大鼠低 25%。由于 PGlcUA 和 DPPG 脂质体的大小分布和ζ电位相似，脂质体表面的葡萄糖醛酸而不是负电荷似乎使脂质体在血液中的循环时间更长。
• Drug delivery system for use in the treatment of vascular and vessel-related pathologies
  申请人：Academisch Medisch Centrum

  公开号：EP2210590A1

  公开（公告）日：2010-07-28

  The present invention relates to a drug delivery system for use in the treatment of vascular and vessel-related pathologies, comprising a drug delivery platform that comprises at least one compound capable of exerting an effect on the formation and/or maintenance of a thrombus in the vessel to be treated. The platform is preferably formed by liposomes that are sterically stabilized by grafting of poly(ethylene glycol) onto the liposome surface. The liposomes may further comprise photosensitizers and targeting molecules. The liposomes may be thermosensitive. The compound is suitably tranexamic acid. The drug delivery system is preferably used for the treatment of port wine stains.

  本发明涉及一种用于治疗血管和血管相关病症的给药系统，该系统包括一个给药平台，该平台包含至少一种能够对待治疗血管中血栓的形成和/或维持产生影响的化合物。该平台最好由脂质体形成，脂质体表面接枝聚乙二醇使其立体稳定。脂质体可进一步包含光敏剂和靶向分子。脂质体可具有热敏性。化合物宜为氨甲环酸。该给药系统最好用于治疗波特酒渍。
• NAMBA, YUKIHIRO;SAKAKIBARA, TOSHIYUKI;MASADA, MIKIO;ITO, FUMIAKI;OKU, NAO+, CHEM. LETT.,(1989) N2, C. 2145-2148
  作者：NAMBA, YUKIHIRO、SAKAKIBARA, TOSHIYUKI、MASADA, MIKIO、ITO, FUMIAKI、OKU, NAO+

  DOI：——

  日期：——
• LIPID- DERIVATISIERTE BISPHOSPHONSÄURE
  申请人：MCS Micro Carrier Systems GmbH

  公开号：EP1706415B1

  公开（公告）日：2011-10-05