1-(4,4'-dimethoxytrityl)-D-(+)-biotinol tosylate | 159333-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(4,4'-dimethoxytrityl)-D-(+)-biotinol tosylate
• 英文别名: 5-[(3aR,6S,6aS)-3-[bis(4-methoxyphenyl)-phenylmethyl]-2-oxo-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-6-yl]pentyl 4-methylbenzenesulfonate
• CAS: 159333-27-4
• 化学式: C₃₈H₄₂N₂O₆S₂
• 分子量: 686.893
• InChiKey: ARMHXCBTZBLDHO-KVBYWJEESA-N

物化性质

• 沸点：
  868.6±65.0 °C(predicted)
• 密度：
  1.237±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(4,4'-dimethoxytrityl)-D-(+)-biotinol tosylate 在 15-冠醚-5 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 18.17h， 生成 1-<2,2a,4,5,5a,6-hexahydro-3H-4-oxothieno<3,4-d>imidazol-2-yl>-5-(2-nitroimidazol-1-yl)pentane
  参考文献：
  名称：

  Bioreductive Markers for Hypoxic Cells: 2-Nitroimidazoles with Biotinylated 1-Substituents

  摘要：

  The interference by oxygen with the bioreductive metabolism and binding within cells of 2-nitroimidazoles has been used to identify hypoxic cells. Three novel compounds were synthesized with a 1-substituent containing a biotin moiety. Bound adducts of these compounds could be identified in hypoxic cells in vitro by the biotin binding proteins, avidin or streptavidin, labeled with fluorescein. The metabolism and discrimination of these compounds between well-oxygenated and hypoxic cells was evaluated by flow cytometry. Ester or amide links between the 2-nitroimidazole and the biotin were degraded in the presence of mouse serum, but a compound with a C5 hydrocarbon link was stable, and this compound was suitable for evaluation in an in vivo tumor model.

  DOI：

  10.1021/jm00051a012
• 作为产物：
  描述：

  1-N-(4,4'-dimethoxytrityl)-D(+)-biotinol 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 24.0h， 以76%的产率得到1-(4,4'-dimethoxytrityl)-D-(+)-biotinol tosylate
  参考文献：
  名称：

  Bioreductive Markers for Hypoxic Cells: 2-Nitroimidazoles with Biotinylated 1-Substituents

  摘要：

  The interference by oxygen with the bioreductive metabolism and binding within cells of 2-nitroimidazoles has been used to identify hypoxic cells. Three novel compounds were synthesized with a 1-substituent containing a biotin moiety. Bound adducts of these compounds could be identified in hypoxic cells in vitro by the biotin binding proteins, avidin or streptavidin, labeled with fluorescein. The metabolism and discrimination of these compounds between well-oxygenated and hypoxic cells was evaluated by flow cytometry. Ester or amide links between the 2-nitroimidazole and the biotin were degraded in the presence of mouse serum, but a compound with a C5 hydrocarbon link was stable, and this compound was suitable for evaluation in an in vivo tumor model.

  DOI：

  10.1021/jm00051a012

文献信息

• Bioreductive Markers for Hypoxic Cells: 2-Nitroimidazoles with Biotinylated 1-Substituents
  作者：Richard J. Hodgkiss、John Parrick、Manuchehr Porssa、Michael R. L. Stratford

  DOI：10.1021/jm00051a012

  日期：1994.12

  The interference by oxygen with the bioreductive metabolism and binding within cells of 2-nitroimidazoles has been used to identify hypoxic cells. Three novel compounds were synthesized with a 1-substituent containing a biotin moiety. Bound adducts of these compounds could be identified in hypoxic cells in vitro by the biotin binding proteins, avidin or streptavidin, labeled with fluorescein. The metabolism and discrimination of these compounds between well-oxygenated and hypoxic cells was evaluated by flow cytometry. Ester or amide links between the 2-nitroimidazole and the biotin were degraded in the presence of mouse serum, but a compound with a C5 hydrocarbon link was stable, and this compound was suitable for evaluation in an in vivo tumor model.