6,6'-telluro-bis(6-deoxy-β-cyclodextrin)

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-telluro-bis(6-deoxy-β-cyclodextrin)
• 英文别名: (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23S,25S,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,30,35-hexakis(hydroxymethyl)-25-[[(1S,3R,5R,6S,8S,10S,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-5,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-10-yl]methyltellanylmethyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• 化学式: C₈₄H₁₃₈O₆₈Te
• 分子量: 2363.58
• InChiKey: HXQPYRLIMMRKRK-WUGKIVSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -28.89
• 重原子数：
  153
• 可旋转键数：
  16
• 环数：
  42.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1070
• 氢给体数：
  40
• 氢受体数：
  68

反应信息

• 作为产物：
  描述：

  mono-6-deoxy-6-(p-toluenesulfonyl)-β-cyclodextrin 在 disodium telluride 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以54%的产率得到6,6'-telluro-bis(6-deoxy-β-cyclodextrin)
  参考文献：
  名称：

  Cyclodextrin-Derived Diorganyl Tellurides as Glutathione Peroxidase Mimics and Inhibitors of Thioredoxin Reductase and Cancer Cell Growth

  摘要：

  Water-soluble diorganyl tellurides of the alkyl aryl or dialkyl type were prepared by treatment of mono-6-tosyl-beta-cyclodextrin with sodium alkanetellurolates or arenetellurolates or sodium telluride. The novel cyclodextrin-derived organotelluriums were evaluated for their capacity to catalyze the reduction of hydrogen peroxide, tert-butyl hydroperoxide, and cumene hydroperoxide in the presence of glutathione, NADPH, and GSSG-reductase (coupled reductase assay). Cyclodextrins 4d and 4e, carrying 4-(N,N-dimethylamino)phenyltelluro and n-butyltelluro groups, respectively, were the most efficient glutathione peroxidase mimics. Reduction of lipophilic cumene hydroperoxide often proceeded 10-20 times faster than reduction of the more hydrophilic hydroperoxides, which cannot bind into the hydrophobic interior of the cyclodextrin. Thus, it seems that the carbohydrate moiety acts as a binding site for the hydroperoxide substrate. The cyclodextrin derivatives were also evaluated for their capacity to inhibit thioredoxin reductase/thioredoxin and cancer cell growth in culture. IC50 values for inhibition of thioredoxin or thioredoxin/thioredoxin reductase were in the submicromolar range for the best inhibitors (compounds 4d and 5). Two of the compounds (4c and 5) were found to inhibit the growth of MCF-7 cells in culture with IC50 values in the low micromolar range.

  DOI：

  10.1021/jm030916r
• 作为试剂：
  描述：

  二(对硝基苯)碳酸酯 在 6,6'-telluro-bis(6-deoxy-β-cyclodextrin) Tris-HCl buffer 作用下， 以 乙腈 为溶剂， 生成 对硝基苯酚
  参考文献：
  名称：

  Telluroxides Exhibit Hydrolysis Capacity

  摘要：

  [GRAPHIC]It has long been known that tellurium compounds are rather toxic to living organisms, and tellurium has not been found in natural biomacromolecules to date. The principles of telluride toxicity in biological processes are still controversial partly because of the lack of information on the biochemical features of tellurium. In this contribution, we report our finding for the first time that telluroxides exhibit hydrolysis capacity. For instance, 6,6'-telluroxy-bis(6-deoxy-beta-cyclodextrin) acts as a hydrolase mimic and shows a significant rate acceleration of 106 000 for the hydrolysis of 4,4'-dinitrodiphenyl carbonate.

  DOI：

  10.1021/jo0620922

文献信息

• Cyclodextrin-Derived Diorganyl Tellurides as Glutathione Peroxidase Mimics and Inhibitors of Thioredoxin Reductase and Cancer Cell Growth
  作者：Michael McNaughton、Lars Engman、Anne Birmingham、Garth Powis、Ian A. Cotgreave

  DOI：10.1021/jm030916r

  日期：2004.1.1

  Water-soluble diorganyl tellurides of the alkyl aryl or dialkyl type were prepared by treatment of mono-6-tosyl-beta-cyclodextrin with sodium alkanetellurolates or arenetellurolates or sodium telluride. The novel cyclodextrin-derived organotelluriums were evaluated for their capacity to catalyze the reduction of hydrogen peroxide, tert-butyl hydroperoxide, and cumene hydroperoxide in the presence of glutathione, NADPH, and GSSG-reductase (coupled reductase assay). Cyclodextrins 4d and 4e, carrying 4-(N,N-dimethylamino)phenyltelluro and n-butyltelluro groups, respectively, were the most efficient glutathione peroxidase mimics. Reduction of lipophilic cumene hydroperoxide often proceeded 10-20 times faster than reduction of the more hydrophilic hydroperoxides, which cannot bind into the hydrophobic interior of the cyclodextrin. Thus, it seems that the carbohydrate moiety acts as a binding site for the hydroperoxide substrate. The cyclodextrin derivatives were also evaluated for their capacity to inhibit thioredoxin reductase/thioredoxin and cancer cell growth in culture. IC50 values for inhibition of thioredoxin or thioredoxin/thioredoxin reductase were in the submicromolar range for the best inhibitors (compounds 4d and 5). Two of the compounds (4c and 5) were found to inhibit the growth of MCF-7 cells in culture with IC50 values in the low micromolar range.