3-carboxypropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-carboxypropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• 英文别名: 4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxybutanoic acid
• 化学式: C₃₈H₄₂O₈
• 分子量: 626.747
• InChiKey: BMAKKQREGOINNN-MQPLVFOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-carboxypropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 反应 2.5h， 生成
  参考文献：
  名称：

  Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery

  摘要：

  Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(W) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(W) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 mu M) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.

  DOI：

  10.1021/acs.jmedchem.7b00433
• 作为产物：
  描述：

  1-硫代-b-甲基葡萄糖甙-4-甲基苯酯 在 N-碘代丁二酰亚胺 、 sodium hydride 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.66h， 生成 3-carboxypropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery

  摘要：

  Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(W) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(W) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 mu M) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.

  DOI：

  10.1021/acs.jmedchem.7b00433

文献信息

• Use of <i>n</i>-Pentenyl Glycosides as Precursors to Various Spacer Functionalities
  作者：Therese Buskas、Eva Söderberg、Peter Konradsson、Bert Fraser-Reid

  DOI：10.1021/jo9909554

  日期：2000.2.1

  Pent-4-enyl beta-D-glucopyranoside and its peracetylated and perbenzylated derivatives are shown to be excellent substrates for preparation of a wide variety of spacer functionalities. The spacer derivatives so obtained are promising substrates for preparing agents such as neo-glycoconjugates, micelles, and liquid crystalline phases, which are of interest for studying various biological and physiological phenomena of carbohydrates.
• Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery
  作者：Jing Ma、Qingpeng Wang、Zhonglv Huang、Xiande Yang、Quandeng Nie、Wenpei Hao、Peng George Wang、Xin Wang

  DOI：10.1021/acs.jmedchem.7b00433

  日期：2017.7.13

  Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(W) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(W) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 mu M) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.