N²,N²-bis[2-[bis(carboxymethyl)amino]ethyl]-N-[(3β,5β,7α,12α)-7,12-dihydroxy-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl]-L-glutamine | 280766-03-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N²,N²-bis[2-[bis(carboxymethyl)amino]ethyl]-N-[(3β,5β,7α,12α)-7,12-dihydroxy-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl]-L-glutamine
• 英文别名: N2-bis[2-[bis(carboxymethyl)amino]ethyl]-N-[(3β,5β,7α,12α)-7,12-dihydroxy-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl]-L-glutamine；(2S)-2-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]-5-[[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-17-[(2R)-5-oxo-5-(2-sulfoethylamino)pentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]-5-oxopentanoic acid
• CAS: 280766-03-2
• 化学式: C₄₃H₇₁N₅O₁₇S
• 分子量: 962.126
• InChiKey: SLAYJJGXIPEQKC-FILLJEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  66
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  358
• 氢给体数：
  10
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  gadolinium(III) oxide 、 N²,N²-bis[2-[bis(carboxymethyl)amino]ethyl]-N-[(3β,5β,7α,12α)-7,12-dihydroxy-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl]-L-glutamine 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 6.0h， 以82%的产率得到gadolinium complex of N2-bis[2-[bis(carboxymethyl)amino]ethyl]-N-[(3β,5β,7α,12α)-7,12-dihydroxy-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl]-L-glutamine salified with sodium (1:3)
  参考文献：
  名称：

  Blood pool agents for nuclear magnetic resonance diagnostics

  摘要：

  公开号：

  EP1935435B1
• 作为产物：
  描述：

  (3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid phenyl methyl ester 在 5%-palladium/activated carbon 氰基磷酸二乙酯 、 氢气 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.33h， 生成 N²,N²-bis[2-[bis(carboxymethyl)amino]ethyl]-N-[(3β,5β,7α,12α)-7,12-dihydroxy-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl]-L-glutamine
  参考文献：
  名称：

  Blood pool agents for nuclear magnetic resonance diagnostics

  摘要：

  公开号：

  EP1935435B1

文献信息

• Conjugates of Gadolinium Complexes to Bile Acids as Hepatocyte-Directed Contrast Agents for Magnetic Resonance Imaging
  作者：Pier Lucio Anelli、Luciano Lattuada、Vito Lorusso、Giovanna Lux、Alberto Morisetti、Pierfrancesco Morosini、Michele Serleti、Fulvio Uggeri

  DOI：10.1021/jm0310683

  日期：2004.7.1

  A series of structurally different Gd(III) conjugates incorporating a bile acid moiety have been prepared. Polyaminopolycarboxylic ligands such as diethylenetriaminepentaacetic acid (DTPA) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid (DOTA) have been selected as chelating subunit for the Gd(III) ion. Cholic acid, cholylglycine, and cholyltaurine have been incorporated as the bile acid moieties. In first generation conjugates the Gd(III) complex is linked to the carboxyl group of cholic acid. Second generation conjugates feature the attachment of the Gd(III) complex to the 3 position of the steroidic backbone of the bile acid. Finally, in third generation conjugates the Gd(III) complex is attached to the E nitrogen atom of cholyllysine. The conjugates are eliminated through the biliary route to a various extent (7.5 to 77% in rats) according to their structural features. Among the most promising terms, a second generation conjugate in which the Gd(III) complex is linked to cholic acid through the 3alpha hydroxy group seems to enter hepatocytes using the Na+/taurocholate transporter. Noticeably, some of the second generation conjugates are characterized by very high tolerabilities (LD50 up to 9.5 mmol/kg) after intravenous administration in mice.
• BLOOD POOL AGENTS FOR NUCLEAR MAGNETIC RESONANCE DIAGNOSTICS
  申请人：BRACCO IMAGING S.p.A.

  公开号：EP1140209B1

  公开（公告）日：2008-08-20
• Use of bile acid derivatives conjugated with metal ion chelated complexes for the diagnostic assessment of microvascular permeability
  申请人：Cavagna Friedrich

  公开号：US20070059246A1

  公开（公告）日：2007-03-15

  The use of contrast agents of molecular weight lower than 5000 Dalton and including at least one residue of a biliary acid for the preparation of diagnostic contrast compositions for the microvascular permeability assessment is disclosed.