4-Oxo-4-[[3-oxo-3-[13,24,29-tris[3-(3-carboxypropanoylamino)propanoyl]-2,3,18,19-tetrathia-8,13,24,29-tetrazapentacyclo[28.2.2.24,7.214,17.220,23]tetraconta-1(33),4,6,14,16,20(36),21,23(35),30(34),31,37,39-dodecaen-8-yl]propyl]amino]butanoic acid | 1438464-80-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-Oxo-4-[[3-oxo-3-[13,24,29-tris[3-(3-carboxypropanoylamino)propanoyl]-2,3,18,19-tetrathia-8,13,24,29-tetrazapentacyclo[28.2.2.24,7.214,17.220,23]tetraconta-1(33),4,6,14,16,20(36),21,23(35),30(34),31,37,39-dodecaen-8-yl]propyl]amino]butanoic acid
• 英文别名: 4-oxo-4-[[3-oxo-3-[13,24,29-tris[3-(3-carboxypropanoylamino)propanoyl]-2,3,18,19-tetrathia-8,13,24,29-tetrazapentacyclo[28.2.2.24,7.214,17.220,23]tetraconta-1(33),4,6,14,16,20(36),21,23(35),30(34),31,37,39-dodecaen-8-yl]propyl]amino]butanoic acid
• CAS: 1438464-80-2
• 化学式: C₆₀H₇₂N₈O₁₆S₄
• 分子量: 1289.54
• InChiKey: YBGOEMGKXGNCJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  88
• 可旋转键数：
  24
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  448
• 氢给体数：
  8
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  4,4'-二氨基二苯二硫醚 在 吡啶 、 丁二酸酐 、 氢溴酸 、 potassium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 苯酚 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 116.33h， 生成 4-Oxo-4-[[3-oxo-3-[13,24,29-tris[3-(3-carboxypropanoylamino)propanoyl]-2,3,18,19-tetrathia-8,13,24,29-tetrazapentacyclo[28.2.2.24,7.214,17.220,23]tetraconta-1(33),4,6,14,16,20(36),21,23(35),30(34),31,37,39-dodecaen-8-yl]propyl]amino]butanoic acid
  参考文献：
  名称：

  Synthesis, Guest-Binding, and Reduction-Responsive Degradation Properties of Water-Soluble Cyclophanes Having Disulfide Moieties

  摘要：

  Water-soluble cationic cyclophane having diphenyl disulfide moieties (1a) was synthesized as a reduction-responsive degradable host. The stoichiometry for the complex of 1a with anionic fluorescence guests, such as 4,4'-bis(1-anilinonaphthalene-8-sulfonate) (Bis-ANS) and 4-(1-pyrene)-butanoic acid (PBA), was confirmed to be 1:1 host:guest by a Job plot. The binding constants (K) of 1a toward Bis-ANS and PBA were evaluated to be 6.7 x 10(3) and 4.5 x 10(4) M-1, respectively, as confirmed by fluorescence spectroscopy. Reduction of disulfide bonds of 1a by dithiothreitol gave its reduced form having poor guest-binding affinity that led to release of the entrapped guest molecules to the bulk aqueous phase. Meanwhile, anionic cyclophane 1b, which was derived from 1a by a reaction with succinic anhydride, binds cationic anticancer drugs, such as daunorubicin hydrochloride (DNR) and doxorubicin hydrochloride (DOX), with a K of 2.1 x 10(3) and 7.5 x 10(2) M-1, respectively. A similar reduction-responsive guest release feature was observed when DNR and DOX were employed as a guest for complexation with 1b.

  DOI：

  10.1021/jo400591w

文献信息

• Synthesis, Guest-Binding, and Reduction-Responsive Degradation Properties of Water-Soluble Cyclophanes Having Disulfide Moieties
  作者：Osamu Hayashida、Kazuaki Ichimura、Daisuke Sato、Terutaka Yasunaga

  DOI：10.1021/jo400591w

  日期：2013.6.7

  Water-soluble cationic cyclophane having diphenyl disulfide moieties (1a) was synthesized as a reduction-responsive degradable host. The stoichiometry for the complex of 1a with anionic fluorescence guests, such as 4,4'-bis(1-anilinonaphthalene-8-sulfonate) (Bis-ANS) and 4-(1-pyrene)-butanoic acid (PBA), was confirmed to be 1:1 host:guest by a Job plot. The binding constants (K) of 1a toward Bis-ANS and PBA were evaluated to be 6.7 x 10(3) and 4.5 x 10(4) M-1, respectively, as confirmed by fluorescence spectroscopy. Reduction of disulfide bonds of 1a by dithiothreitol gave its reduced form having poor guest-binding affinity that led to release of the entrapped guest molecules to the bulk aqueous phase. Meanwhile, anionic cyclophane 1b, which was derived from 1a by a reaction with succinic anhydride, binds cationic anticancer drugs, such as daunorubicin hydrochloride (DNR) and doxorubicin hydrochloride (DOX), with a K of 2.1 x 10(3) and 7.5 x 10(2) M-1, respectively. A similar reduction-responsive guest release feature was observed when DNR and DOX were employed as a guest for complexation with 1b.