2-imino-2-methoxyethyl-1-thiogalactoside | 75204-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-imino-2-methoxyethyl-1-thiogalactoside
• 英文别名: 2-imino-2-methoxyethyl 1-thio-β-D-galactopyranoside；methyl 2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethanimidate
• CAS: 75204-21-6
• 化学式: C₉H₁₇NO₆S
• 分子量: 267.303
• InChiKey: QMZQMASPATYOGL-MRCFXUCSSA-N

物化性质

• 沸点：
  460.2±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-imino-2-methoxyethyl-1-thiogalactoside 、 N-(4-aminobutyl)-(cholest-5-en-3-yloxy)formamide 在 三乙胺 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 cholest-5-en-3-yl-oxy-N-(4-((1-imino-2-β-D-thiogalactosylethyl)amino)butyl)formamide
  参考文献：
  名称：

  摘要：

  Purpose. The purpose of this study is to elucidate the in vivo gene transfer for galactosylated liposomes containing cholesten-5-yloxy-N (4-((1-imino-2-beta-D-thiogalaclosylethyl)amino)butyl)formamide(Gal-C4-Chol) in relation to lipid composition and charge ratio.Methods. Galactosylated cationic liposomes containing N-[1-(2,3-dioleyloxy)propyl]-n,n,n-trimethylammonium chloride(DOTMA), Gal-C4-Chol and cholesterol(Chol), and similar liposomes were prepared. Plasmid DNA complexed with a galactosylated liposome preparation was injected intraportally into mice. The mice were sacrificed after 6 hours. The tissues were subjected to luciferase assay.Results. A markedly higher gene expression in the liver following injection of plasmid DNA that has been complexed with DOTMA/ Chol/Gal-C4-Chol(1:0.5:0.5) and DOTMA/Gal-C4-Chol(1:1) liposomes was observed. The effect was one order of magnitude higher than naked DNA and DOTMA/Chol(1:1) liposomes. Pre-exposing with galactosylated bovine serum albumin significantly reduced the hepatic gene expression. By comparison, the gene expression for galactosylated cationic liposomes containing 3 beta[N-(N',N'-dimethylaminoethane)carbamoyl]cholesterol, Gal-C4-Chol and dioleoylphosphatidylethanolamine was 10 times lower. As Ear as the charge ratio of DOTMA/ Chol/Gal-CA-Chol(1:0.5:0.5) liposomes to plasmid DNA(1.6-7.0) was concerned, complexes with charge ratios of 2.3-3.1 produced maximal gene expression in the liver. Whereas, higher ratios resulted in enhanced expression in the lung.Conclusions. By optimizing lipid composition and charge ratio, galactosylated liposome/DNA complexes allow superior in vivo gene transfection in the liver via asialoglycoprotein receptor-mediated endocytosis.

  DOI：

  10.1023/a:1007501122611
• 作为产物：
  描述：

  2-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-thiouronium bromide 在 sodium methylate 、 potassium carbonate 、 sodium hydrogensulfite 作用下， 以 水 、 丙酮 为溶剂， 反应 27.0h， 生成 2-imino-2-methoxyethyl-1-thiogalactoside
  参考文献：
  名称：

  AGENTS FOR CLEARING BIOMOLECULES FROM CIRCULATION

  摘要：

  描述了一种方法，以及其中使用的一组药剂组合，通过该方法，可以迅速清除给予受试者的药剂在循环中的存在。这是通过提供具有反应基团的给药剂（例如，用于预先靶向的探针）和提供具有另一种反应基团的清除剂来实现的，所述反应基团形成生物正交反应对。最好，反应对包括环辛烯或环辛炔作为一种反应物，二烯作为另一种反应物。该方法和组合可用于从循环中去除任何可结合分子，例如，在预先靶向方法中清除探针的过量，传递的靶向或成像剂，或已存在于循环中的任何生物分子的清除。

  公开号：

  US20130272959A1

文献信息

• Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation
  作者：Stewart R. Alexander、Antony J. Fairbanks

  DOI：10.1039/c6ob01069e

  日期：——

  Unprotected carbohydrates can be directly converted into cyanooethyl thioglycosides, which in turn may be used for protein glycosylation, in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution.

  未保护的碳水化合物可以直接转化为氰乙基硫代糖苷，然后可以通过与2-氯-1,3-二甲基咪唑氯化铵（DMC）和硫代乙腈在水溶液中反应的方式，完全立体选择性地用于蛋白质糖基化。
• Radiolabeled annexins
  申请人：NeoRx Corporation

  公开号：US20030220233A1

  公开（公告）日：2003-11-27

  Radiolabeled annexin and modified annexin conjugates useful for imaging vascular thrombi are described. Methods for making and using such radiolabeled annexin conjugates are also provided.

  本文描述了用于成像血管血栓的放射标记的Annexin和修饰的Annexin结合物。还提供了制备和使用这种放射性标记的Annexin结合物的方法。
• RADIOLABELED ANNEXINS
  申请人：Kasina Sudhakar

  公开号：US20110269943A1

  公开（公告）日：2011-11-03

  Radiolabeled annexin and modified annexin conjugates useful for imaging vascular thrombi are described. Methods for making and using such radiolabeled annexin conjugates are also provided.

  本文描述了用于成像血管血栓的放射性标记的附加素和修饰的附加素偶联物。还提供了制备和使用这种放射性标记的附加素偶联物的方法。
• Receptor mediated endocytosis type diagnostic agents
  申请人：ADVANCED MAGNETICS, INC.

  公开号：EP0670167A1

  公开（公告）日：1995-09-06

  The present invention provides a new class of diagnostic agents which are comprised of arabinogalactan and a diagnostic label and which are capable of being distributed in vivo to a selected organ or tissue of a subject by a particular cell recognition and internalization pathway.

  本发明提供了一类新的诊断剂，它由阿拉伯半乳聚糖和诊断标签组成，能够在体内通过特定的细胞识别和内化途径分布到受试者的选定器官或组织。
• Radiolabeled annexingalactose conjugates
  申请人：NEORX CORPORATION

  公开号：EP1364964A1

  公开（公告）日：2003-11-26

  Radiolabeled annexin-galactors conjugates useful for imaging vascular trombi are discussed. Methods for making such radiolabeled annexin-galactose conjugates are also addressed.

  本文讨论了可用于血管栓塞成像的放射性标记附件素-半乳糖共轭物。还讨论了制作这种放射性标记的附件素-半乳糖共轭物的方法。