N-succinimidyl 4-guanidinobutyrate | 1092706-01-8

• 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: N-succinimidyl 4-guanidinobutyrate
• 英文别名: (2,5-dioxopyrrolidin-1-yl) 4-(diaminomethylideneamino)butanoate
• CAS: 1092706-01-8
• 化学式: C₉H₁₄N₄O₄
• 分子量: 242.235
• InChiKey: YQENELIAWNUXRG-UHFFFAOYSA-N

物化性质

• 沸点：
  398.9±52.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-succinimidyl 4-guanidinobutyrate 、 2'-deoxy-[thymidinyl(3'-phospho-5')-N6-(2-aminoethyl)adenosine] 5'-triphosphate 在 碳酸氢钠 、 sodium carbonate 、 lithium perchlorate 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 生成 pentalithium 2'-deoxy-[thymidinyl(3'-phospho-5')-N6-[2-(4-guanidinobutyrylamido)ethyl]adenosine] 5'-triphosphate
  参考文献：
  名称：

  Design and synthesis of dinucleotide 5′-triphosphates with expanded functionality

  摘要：

  We propose the new approach to the synthesis of 5 '-triphosphate derivatives of natural and modified dinucleotides with expanded functionality. Our strategy includes the combination of the solution phase synthesis of necessary dimers using the wide range of nucleic acids chemistry methods and the subsequent introduction of the triphosphate residue. A number of the new potential substrates for the template dependent synthesis of nucleic acids with expanded functionality are obtained, namely, 5 '-triphosphates of dinucleotides containing the functionally active groups in heterocyclic bases, in carbohydrate -phosphate backbone, and the groups mimicking the residues of natural amino acids. The abilities of the proposed synthetic route are also demonstrated by the synthesis of 5 '-triphosphates of dinucleotides with modified carbohydrate-phosphate backbone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.029
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 γ-胍丁酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 4.0h， 生成 N-succinimidyl 4-guanidinobutyrate
  参考文献：
  名称：

  Oligopeptide Delivery Carrier for Osteoclast Precursors

  摘要：

  Dendritic amine and guanidinium group-modified nanoparticles were investigated for the delivery of model peptide drug into primary osteoclast precursor cells (bone marrow macrophages; BMMs). The model peptide drug was encapsulated into the nanoparticle by dropping the drug/carrier dissolved in dimethylsulfoxide/methylene chloride cosolvent into water containing poly(vinyl alcohol) as a stabilizer. Flow cytometry and spectrofluorimetry analysis indicated that the model drug itself was not taken up by the BMMs; however, nanoparticle systems underwent significant cellular uptake. In particular, guanidinium group-modified nanoparticles were taken up more efficiently than amine group-modified ones. Cell viability studies showed that both amine and guanidinium group-modified nanoparticles exhibited no significant cytotoxicity up to 100 mu g/mL against the cells.

  DOI：

  10.1021/bc100066k

文献信息

• Oligopeptide Delivery Carrier for Osteoclast Precursors
  作者：Bo Chi、So Jeong Park、Min Hee Park、Soo Young Lee、Byeongmoon Jeong

  DOI：10.1021/bc100066k

  日期：2010.8.18

  Dendritic amine and guanidinium group-modified nanoparticles were investigated for the delivery of model peptide drug into primary osteoclast precursor cells (bone marrow macrophages; BMMs). The model peptide drug was encapsulated into the nanoparticle by dropping the drug/carrier dissolved in dimethylsulfoxide/methylene chloride cosolvent into water containing poly(vinyl alcohol) as a stabilizer. Flow cytometry and spectrofluorimetry analysis indicated that the model drug itself was not taken up by the BMMs; however, nanoparticle systems underwent significant cellular uptake. In particular, guanidinium group-modified nanoparticles were taken up more efficiently than amine group-modified ones. Cell viability studies showed that both amine and guanidinium group-modified nanoparticles exhibited no significant cytotoxicity up to 100 mu g/mL against the cells.
• Design and synthesis of dinucleotide 5′-triphosphates with expanded functionality
  作者：Tatiana V. Abramova、Svetlana V. Vasileva、Ludmila S. Koroleva、Nina S. Kasatkina、Vladimir N. Silnikov

  DOI：10.1016/j.bmc.2008.09.029

  日期：2008.10

  We propose the new approach to the synthesis of 5 '-triphosphate derivatives of natural and modified dinucleotides with expanded functionality. Our strategy includes the combination of the solution phase synthesis of necessary dimers using the wide range of nucleic acids chemistry methods and the subsequent introduction of the triphosphate residue. A number of the new potential substrates for the template dependent synthesis of nucleic acids with expanded functionality are obtained, namely, 5 '-triphosphates of dinucleotides containing the functionally active groups in heterocyclic bases, in carbohydrate -phosphate backbone, and the groups mimicking the residues of natural amino acids. The abilities of the proposed synthetic route are also demonstrated by the synthesis of 5 '-triphosphates of dinucleotides with modified carbohydrate-phosphate backbone. (C) 2008 Elsevier Ltd. All rights reserved.