1,3-bis(2-(tert-butoxycarbonylamino)ethyl)-2-methylguanidinium iodide | 1309582-99-7

• 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: 1,3-bis(2-(tert-butoxycarbonylamino)ethyl)-2-methylguanidinium iodide
• 英文别名: tert-butyl N-[2-[[N'-methyl-N-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]carbamimidoyl]amino]ethyl]carbamate;hydroiodide
• CAS: 1309582-99-7
• 化学式: C₁₆H₃₃N₅O₄*HI
• 分子量: 487.382
• InChiKey: PCSIDMUHPWCKJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  113
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-bis(2-(tert-butoxycarbonylamino)ethyl)-2-methylguanidinium iodide 在 三氟乙酸 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以59%的产率得到1,3-bis(2-aminoethyl)-2-methylguanidine trihydrochloride
  参考文献：
  名称：

  Structure–Activity Examination of Poly(glycoamidoguanidine)s: Glycopolycations Containing Guanidine Units for Nucleic Acid Delivery

  摘要：

  In this study we synthesized a new series of polymers known as poly(glycoamidoguanidine)s (PGAGs). These new polymer structures were synthesized by copolymerizing a carbohydrate monomer (diester; galatarate or tartarate) with a diamine incorporating guanidine or methylguanidine as a charge center to create a polyamide backbone. These materials were strategically designed and compared to our previously studied DNA delivery vehicles, poly(glycoamidoamine)s (PGAAs), which contain secondary amines as the charge groups along the polymer backbone to examine the effect of charge center type on the cellular delivery efficiency of plasmid DNA (pDNA). The guanidine moieties within the PGAGs facilitate electrostatic binding with the negatively charged phosphate backbone of plasmid DNA (pDNA). Stable polymer pDNA complexes (polyplexes) with sizes in the range of 60-200 nut are formed at polymer/pDNA charge ratios (NIP) of 5 and above. When the PGAGs are complexed with Cy5-labeled pDNA (Cy5-pDNA) at N/P ratios of 10 and 25, between 80 and 95% of HeLa cells were positive for Cy5 fluorescence, indicating effective cellular internalization of the polyplexes. The toxicity of both PGAA and PGAG polyplexes was studied via MTT assays, and over 95% cell survival was observed at N/P ratios of 5,10, 15, 20, 25, and 30 in HeLa cells. Transgene expression was examined via luciferase assays at various NIP ratios in the absence and presence of serum. In the absence of serum, the PGAG polyplexes revealed similar transgene expression when compared to polyplexes formed with their analogous PGAA structures. In the presence of serum, one analog (Gg) consisting of galactarate copolymerized with the guanidine monomer yielded gene expression similar to the positive control, Glycofect Transfection Reagent. This new series of guanidine-containing oligomers are promising as a new design strategy to incorporate an alternative charge center type within the backbone of glycopolymer-based nucleic acid delivery vehicles.

  DOI：

  10.1021/bm101537f
• 作为产物：
  描述：

  {2-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]ethyl}carbamic acid tert-butyl ester 以 四氢呋喃 、 乙腈 为溶剂， 反应 28.0h， 生成 1,3-bis(2-(tert-butoxycarbonylamino)ethyl)-2-methylguanidinium iodide
  参考文献：
  名称：

  Structure–Activity Examination of Poly(glycoamidoguanidine)s: Glycopolycations Containing Guanidine Units for Nucleic Acid Delivery

  摘要：

  In this study we synthesized a new series of polymers known as poly(glycoamidoguanidine)s (PGAGs). These new polymer structures were synthesized by copolymerizing a carbohydrate monomer (diester; galatarate or tartarate) with a diamine incorporating guanidine or methylguanidine as a charge center to create a polyamide backbone. These materials were strategically designed and compared to our previously studied DNA delivery vehicles, poly(glycoamidoamine)s (PGAAs), which contain secondary amines as the charge groups along the polymer backbone to examine the effect of charge center type on the cellular delivery efficiency of plasmid DNA (pDNA). The guanidine moieties within the PGAGs facilitate electrostatic binding with the negatively charged phosphate backbone of plasmid DNA (pDNA). Stable polymer pDNA complexes (polyplexes) with sizes in the range of 60-200 nut are formed at polymer/pDNA charge ratios (NIP) of 5 and above. When the PGAGs are complexed with Cy5-labeled pDNA (Cy5-pDNA) at N/P ratios of 10 and 25, between 80 and 95% of HeLa cells were positive for Cy5 fluorescence, indicating effective cellular internalization of the polyplexes. The toxicity of both PGAA and PGAG polyplexes was studied via MTT assays, and over 95% cell survival was observed at N/P ratios of 5,10, 15, 20, 25, and 30 in HeLa cells. Transgene expression was examined via luciferase assays at various NIP ratios in the absence and presence of serum. In the absence of serum, the PGAG polyplexes revealed similar transgene expression when compared to polyplexes formed with their analogous PGAA structures. In the presence of serum, one analog (Gg) consisting of galactarate copolymerized with the guanidine monomer yielded gene expression similar to the positive control, Glycofect Transfection Reagent. This new series of guanidine-containing oligomers are promising as a new design strategy to incorporate an alternative charge center type within the backbone of glycopolymer-based nucleic acid delivery vehicles.

  DOI：

  10.1021/bm101537f

文献信息

• Structure–Activity Examination of Poly(glycoamidoguanidine)s: Glycopolycations Containing Guanidine Units for Nucleic Acid Delivery
  作者：Vijay P. Taori、Hao Lu、Theresa M. Reineke

  DOI：10.1021/bm101537f

  日期：2011.6.13

  In this study we synthesized a new series of polymers known as poly(glycoamidoguanidine)s (PGAGs). These new polymer structures were synthesized by copolymerizing a carbohydrate monomer (diester; galatarate or tartarate) with a diamine incorporating guanidine or methylguanidine as a charge center to create a polyamide backbone. These materials were strategically designed and compared to our previously studied DNA delivery vehicles, poly(glycoamidoamine)s (PGAAs), which contain secondary amines as the charge groups along the polymer backbone to examine the effect of charge center type on the cellular delivery efficiency of plasmid DNA (pDNA). The guanidine moieties within the PGAGs facilitate electrostatic binding with the negatively charged phosphate backbone of plasmid DNA (pDNA). Stable polymer pDNA complexes (polyplexes) with sizes in the range of 60-200 nut are formed at polymer/pDNA charge ratios (NIP) of 5 and above. When the PGAGs are complexed with Cy5-labeled pDNA (Cy5-pDNA) at N/P ratios of 10 and 25, between 80 and 95% of HeLa cells were positive for Cy5 fluorescence, indicating effective cellular internalization of the polyplexes. The toxicity of both PGAA and PGAG polyplexes was studied via MTT assays, and over 95% cell survival was observed at N/P ratios of 5,10, 15, 20, 25, and 30 in HeLa cells. Transgene expression was examined via luciferase assays at various NIP ratios in the absence and presence of serum. In the absence of serum, the PGAG polyplexes revealed similar transgene expression when compared to polyplexes formed with their analogous PGAA structures. In the presence of serum, one analog (Gg) consisting of galactarate copolymerized with the guanidine monomer yielded gene expression similar to the positive control, Glycofect Transfection Reagent. This new series of guanidine-containing oligomers are promising as a new design strategy to incorporate an alternative charge center type within the backbone of glycopolymer-based nucleic acid delivery vehicles.