mono<6-(phenylseleno)-6-deoxy>-β-cyclodextrin | 140874-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono<6-(phenylseleno)-6-deoxy>-β-cyclodextrin
• 英文别名: mono(6-phenylseleno-6-deoxy)-β-cyclodextrin；6-(phenylseleno)-6-deoxy-β-cyclodextrin；6-phenylselenyl-6-deoxy-β-cyclodextrin；(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-(phenylselanylmethyl)-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
• CAS: 140874-31-3
• 化学式: C₄₈H₇₄O₃₄Se
• 分子量: 1274.06
• InChiKey: ATGJWZSHYPLOKQ-IHHCOHTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.77
• 重原子数：
  83
• 可旋转键数：
  9
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  534
• 氢给体数：
  20
• 氢受体数：
  34

反应信息

• 作为反应物：
  描述：

  环辛醇 、 mono<6-(phenylseleno)-6-deoxy>-β-cyclodextrin 在 phosphate buffer 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  超分子系统的分子识别研究。第19部分。†圆二色性研究有机硒改性的β-环糊精与脂肪醇的包合络合

  摘要：

  各种脂肪醇与单[6-（苄基硒代）-6-脱氧]-β-环糊精（1），单[6-（苯基硒代）-6-脱氧]-β的化学计量比为1：1的包合络合的复杂稳定性常数-环糊精（2）和mono [6-（o-，m-或p-甲苯基-6）-脱氧]-β-环糊精（3-5）是通过在磷酸盐缓冲溶液（pH = 7.2）中于25°C进行分光光度滴定而获得的。观察到的棉花效应表明芳族部分浅地渗入环糊精的疏水腔中。因此，可以将芳香族部分作为诱导圆二色性（ICD）探针来研究夹杂现象。所得结果表明，修饰的β-环糊精（1）对客体分子的大小/形状和构象刚度高度敏感，对金刚烷-1-醇/环戊醇的分子选择性高达114，并且E / Z相对较高。对香叶醇/神经醇的选择性高达2.7。有趣的是，所有使用的修饰的β-环糊精对冰片和薄荷醇的（+）-对映异构体显示出相对良好的对映选择性。从大小/形状-拟合关系和多点识别机理的角度讨论了改性β-环糊精（1-5）对脂肪醇的分子识别能力和对映选择性。

  DOI：

  10.1039/a808039i
• 作为产物：
  描述：

  在 phosphate buffer 作用下， 以 水 为溶剂， 生成 环辛醇 、 mono<6-(phenylseleno)-6-deoxy>-β-cyclodextrin
  参考文献：
  名称：

  超分子系统的分子识别研究。第19部分。†圆二色性研究有机硒改性的β-环糊精与脂肪醇的包合络合

  摘要：

  各种脂肪醇与单[6-（苄基硒代）-6-脱氧]-β-环糊精（1），单[6-（苯基硒代）-6-脱氧]-β的化学计量比为1：1的包合络合的复杂稳定性常数-环糊精（2）和mono [6-（o-，m-或p-甲苯基-6）-脱氧]-β-环糊精（3-5）是通过在磷酸盐缓冲溶液（pH = 7.2）中于25°C进行分光光度滴定而获得的。观察到的棉花效应表明芳族部分浅地渗入环糊精的疏水腔中。因此，可以将芳香族部分作为诱导圆二色性（ICD）探针来研究夹杂现象。所得结果表明，修饰的β-环糊精（1）对客体分子的大小/形状和构象刚度高度敏感，对金刚烷-1-醇/环戊醇的分子选择性高达114，并且E / Z相对较高。对香叶醇/神经醇的选择性高达2.7。有趣的是，所有使用的修饰的β-环糊精对冰片和薄荷醇的（+）-对映异构体显示出相对良好的对映选择性。从大小/形状-拟合关系和多点识别机理的角度讨论了改性β-环糊精（1-5）对脂肪醇的分子识别能力和对映选择性。

  DOI：

  10.1039/a808039i

文献信息

• Supramolecular Self-Assemblies of <i>β</i>-Cyclodextrins with Aromatic Tethers:  Factors Governing the Helical Columnar versus Linear Channel Superstructures
  作者：Yu Liu、Zhi Fan、Heng-Yi Zhang、Ying-Wei Yang、Fei Ding、Shuang-Xi Liu、Xue Wu、Takehiko Wada、Yoshihisa Inoue

  DOI：10.1021/jo034632q

  日期：2003.10.1

  Interestingly, (seleno)ethers 1-4 and ester 5 displayed distinctly different self-assembling behavior in the solid state, affording a successively threading head-to-tail polymeric helical structure for the (seleno)ethers or a mutually penetrating tail-to-tail dimeric columnar channel structure for the ester. Combining the present and previous structures reported for the relevant beta-CD derivatives, we further

  一系列6-O-（对位取代苯基）-修饰的β-环糊精衍生物，即6-O-（4-溴苯基）-β-CD（1），6-O-（4-硝基苯基）-β -CD（2），6-O-（4-甲酰基苯基）-β-CD（3），6-苯基硒基-6-脱氧-β-CD（4）和6-O-（4-羟基苯甲酰基）-β -CD（5）的合成，并通过NMR光谱，微量量热法，晶体学和扫描隧道显微镜对它们在水溶液中的包合络合行为和固态自组装行为进行了比较研究。有趣的是，（硒）醚1-4和酯5在固态下表现出截然不同的自组装行为，从而为（硒）醚提供了连续穿线的头到尾聚合物螺旋结构或相互穿透的尾到端结构。酯的尾部二聚体柱状通道结构。结合报告的相关β-CD衍生物的当前结构和先前结构，我们进一步推断出枢轴杂原子（芳香族取代基通过该枢轴杂原子拴接到β-CD上）在确定螺旋结构（赋予2倍折叠）方面起着关键作用分别指向N / O和S / Se透视的β-CD聚集体的4倍和4倍轴。
• 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.
• Molecular Recognition Study on Supramolecular System. 14.¹ Synthesis of Modified Cyclodextrins and Their Inclusion Complexation Thermodynamics with <scp>l</scp>-Tryptophan and Some Naphthalene Derivatives
  作者：Yu Liu、Bao-Hang Han、Bin Li、Yi-Min Zhang、Peng Zhao、Yun-Ti Chen、Takehiko Wada、Yoshihisa Inoue

  DOI：10.1021/jo971466b

  日期：1998.3.1

  A series of beta-cyclodextrin derivatives, carrying pyridinio (4-6), phosphonyl (7, 8), seleno (9-11), m-and p-picolinyl (12, 13), o-chloroanilino (16), 8-quinolyl. (17), furfuryl (18), and 9-fluorenyl (19) moieties in the side chain, were newly synthesized, and their complexation behavior was assessed and discussed thermodynamically, using L-tryptophan and a few naphthalene derivatives as representative guests. Calorimetric titrations have been performed at 25.0 degrees C in buffered aqueous solution (pH 7.20) to give the complex stability constants and thermodynamic parameters for the 1:1 inclusion complexation of these guests with the native and modified alpha-, beta-, and/or gamma-cyclodextrins (1-20). All of the chemical modifications to the primary side of cyclodextrins examined led to significant changes in complex stability and thermodynamic parameters, which are elucidated in terms of the conformational, electrostatic, hydrogen-bonding, and hydration effects. Thermodynamically, the inclusion complexation is mainly enthalpy-driven with a negative or minor positive entropic contribution, which in some cases determines the complex stability. The induced circular dichroism spectral analyses of these cyclodextrin derivatives indicated that the aromatic moiety in modified beta-cyclodextrins (4-6, 9-19) only shallowly penetrates into the hydrophobic cavity of beta-cyclodextrin, while the phenyl phosphate and fluorenyl moieties in 7 and 20 are embedded into the hydrophobic cavity of beta-cyclodextrin because of the longer linking chain. Using all the thermodynamic data for a wide variety of cyclodextrin derivatives obtained in this and previous studies, the entropy changes (T Delta S) were plotted against the enthalpy changes (Delta H) to give an excellent linear relationship. The slope (alpha) of 1.02 and an intercept (T Delta S-o) of 4.3 of the regression line indicate substantial conformational changes and extensive desolvation caused upon complexation,respectively.
• Molecular recognition study on supramolecular systems. Part 19.† Circular dichroism studies of inclusion complexation of aliphatic alcohols by organoselenium modified β-cyclodextrins
  作者：Yu Liu、Bin Li、Bao-Hang Han、Takehiko Wada、Yoshihisa Inoue

  DOI：10.1039/a808039i

  日期：——

  investigate the inclusion phenomena. The results obtained demonstrate that the modified β-cyclodextrin (1) is highly sensitive to the size/shape and conformational rigidity of guest molecules, giving fairly good molecular selectivity up to 114 for adamantan-1-ol/cyclopentanol and relatively high E/Z selectivity up to 2.7 for geraniol/nerol. Interestingly, all of the modified β-cyclodextrins employed displayed

  各种脂肪醇与单[6-（苄基硒代）-6-脱氧]-β-环糊精（1），单[6-（苯基硒代）-6-脱氧]-β的化学计量比为1：1的包合络合的复杂稳定性常数-环糊精（2）和mono [6-（o-，m-或p-甲苯基-6）-脱氧]-β-环糊精（3-5）是通过在磷酸盐缓冲溶液（pH = 7.2）中于25°C进行分光光度滴定而获得的。观察到的棉花效应表明芳族部分浅地渗入环糊精的疏水腔中。因此，可以将芳香族部分作为诱导圆二色性（ICD）探针来研究夹杂现象。所得结果表明，修饰的β-环糊精（1）对客体分子的大小/形状和构象刚度高度敏感，对金刚烷-1-醇/环戊醇的分子选择性高达114，并且E / Z相对较高。对香叶醇/神经醇的选择性高达2.7。有趣的是，所有使用的修饰的β-环糊精对冰片和薄荷醇的（+）-对映异构体显示出相对良好的对映选择性。从大小/形状-拟合关系和多点识别机理的角度讨论了改性β-环糊精（1-5）对脂肪醇的分子识别能力和对映选择性。