1,10-N,N’-bis-(β-D-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane | 1182838-47-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,10-N,N’-bis-(β-D-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane
• 英文别名: 1,10-N,N'-bis-(β-D-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane；7-N,16-N-bis[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-7,16-dicarboxamide
• CAS: 1182838-47-6
• 化学式: C₃₈H₆₈N₄O₂₆
• 分子量: 996.969
• InChiKey: HHPRROFNCBRGBT-DPQXKDDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.5
• 重原子数：
  68
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  440
• 氢给体数：
  16
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  L-赖氨酸 、 1,10-N,N’-bis-(β-D-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane 以 水 为溶剂， 反应 18.0h， 生成 N7,N16-bis((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-7,16-dicarboxamide L-lysinate
  参考文献：
  名称：

  Bis-β-cyclodextrinyl- and bis-cellobiosyl-diazacrowns: synthesis and molecular complexation behaviors toward Busulfan anticancer agent and two basic aminoacids

  摘要：

  The one-step synthesis of two C-2-symmetric receptors including two beta-cyclodextrin cores or two disaccharidyl units connected by urea linkers to a diazacrown ether organizing platform is reported. The X-ray structure of the peracetylated bis-ureidocellobiosyl podand could be determined. These molecular systems, long thought to be potent selective carriers for chiral/achiral organic guests at the supramolecular level, were found to be efficient complexing tools toward the Busulfan anticancer agent but also toward L-arginine and L-lysine basic aminoacids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.057
• 作为产物：
  描述：

  1,10-N,N’-bis-(2,3,6,2’,3’,4’,6’-hepta-O-acetyl-β-D-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 1,10-N,N’-bis-(β-D-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane
  参考文献：
  名称：

  双糖冠醚与对甲苯磺酰胺配合物的稳定性

  摘要：

  两种新的 C2 对称大环可溶于水，根据一步程序使用氮杂冠醚和叠氮糖制备。通过质子核磁共振光谱研究了它们与对甲苯磺酰胺的配合物。检查了氮杂冠醚的大小和溶剂效应对客体-主体复合物稳定性的影响。

  DOI：

  10.1002/hc.21242

文献信息

• Combined Theoretical and Experimental Investigations: Design, Synthesis, Characterization, and In Vitro Cytotoxic Activity Assessment of a Complex of a Novel Ureacellobiose Drug Carrier with the Anticancer Drug Carmustine
  作者：Marta Hoelm、Stanisław Porwański、Paweł Jóźwiak、Anna Krześlak

  DOI：10.3390/molecules29143359

  日期：——

  Drug delivery systems (DDSs) are used to transport drugs which are characterized by some pharmaceutical problems to the specific target site, enhancing therapeutic efficacy and reducing off-target accumulation in the body. In this work, one of the recently synthesized molecules, 1,10-N,N’-bis-(β-ᴅ-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane (TN), was tested as a potential drug carrier towards the anticancer drug carmustine. For this purpose, different techniques were used, from synthesis and calculations to cytotoxicity assessment. Our results showed that TN is characterized by a very compact geometry, which significantly impacts its complexation properties. Although it forms a very stable complex with carmustine, it adopts a non-inclusion geometry, as verified by both experimental and theoretical NMR analyses. The cytotoxicity study performed for all analyzed molecules (TN; carmustine; TN:carmustine complex) towards normal and cancer (breast and colon) cells revealed that TN is not toxic and that the formation of complexes with carmustine reduces the toxicity of carmustine to normal cells.