α-picolyl-N,N'-dimethylacetate | 1283655-70-8

• 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: α-picolyl-N,N'-dimethylacetate
• 英文别名: Methyl 2-[(2-methoxy-2-oxoethyl)-(pyridin-3-ylmethyl)amino]acetate
• CAS: 1283655-70-8
• 化学式: C₁₂H₁₆N₂O₄
• mdl: MFCD18046268
• 分子量: 252.27
• InChiKey: NNTAJEASILCUFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-picolyl-N,N'-dimethylacetate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以83%的产率得到
  参考文献：
  名称：

  99mTc-tricarbonyl labeled agents for cell labeling: Development, biodistribution in normal mice and preliminary in vitro evaluation

  摘要：

  We have developed four Tc-99m(CO)(3)-labeled lipophilic tracers as potential radiolabeling agents for cells based on a hexadecyl tail. Tc-99m(CO)(3)-hexadecylamino-N,N'-diacetic acid (negatively charged), Tc-99m(CO)(3)-hexadecylamino-N-alpha-picolyl-N'-acetic acid (uncharged), Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine (positively charged), Tc-99m(CO)(3)-N-hexadecylaminoethyl-N'-aminoethylamine (positively charged) were prepared in a radiolabeling yield: >90%. Preliminary cell uptake studies were performed in mixed blood cells with or without plasma and were compared with Tc-99m-d,l-HMPAO and [F-18]FDG. In plasma-free blood cells, maximum uptake (78%) was obtained for Tc-99m(CO)(3)-N-hexadecylaminoethyl-N'-aminoethylamine after 60 min incubation (compared to 55% and 23% for Tc-99m-d,l-HMPAO and [F-18]FDG, respectively) while in plasma-rich medium, Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine was best bound (54%, similar to the binding of 99mTc-d, l-HMPAO). Biodistribution in normal mice showed mainly hepatobiliary clearance of the agents and initial high lung uptake. The radiolabeled compounds showed good blood clearance with maximally 7.9% injected dose per gram at 60 min post injection. While the least lipophilic agent (Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine, log P = 1.3) showed the best cell uptake, there appears to be no direct correlation between lipophilicity and tracer uptake in mixed blood cells. In view of its comparable cell uptake to well known cell labeling agent Tc-99m-d,l-HMPAO, Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine merits further evaluation as a potential cell labeling agent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.045
• 作为产物：
  描述：

  2-氨甲基吡啶 、 溴乙酸甲酯 在 三乙胺 作用下， 以 甲醇 为溶剂， 以43%的产率得到α-picolyl-N,N'-dimethylacetate
  参考文献：
  名称：

  99mTc-tricarbonyl labeled agents for cell labeling: Development, biodistribution in normal mice and preliminary in vitro evaluation

  摘要：

  We have developed four Tc-99m(CO)(3)-labeled lipophilic tracers as potential radiolabeling agents for cells based on a hexadecyl tail. Tc-99m(CO)(3)-hexadecylamino-N,N'-diacetic acid (negatively charged), Tc-99m(CO)(3)-hexadecylamino-N-alpha-picolyl-N'-acetic acid (uncharged), Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine (positively charged), Tc-99m(CO)(3)-N-hexadecylaminoethyl-N'-aminoethylamine (positively charged) were prepared in a radiolabeling yield: >90%. Preliminary cell uptake studies were performed in mixed blood cells with or without plasma and were compared with Tc-99m-d,l-HMPAO and [F-18]FDG. In plasma-free blood cells, maximum uptake (78%) was obtained for Tc-99m(CO)(3)-N-hexadecylaminoethyl-N'-aminoethylamine after 60 min incubation (compared to 55% and 23% for Tc-99m-d,l-HMPAO and [F-18]FDG, respectively) while in plasma-rich medium, Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine was best bound (54%, similar to the binding of 99mTc-d, l-HMPAO). Biodistribution in normal mice showed mainly hepatobiliary clearance of the agents and initial high lung uptake. The radiolabeled compounds showed good blood clearance with maximally 7.9% injected dose per gram at 60 min post injection. While the least lipophilic agent (Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine, log P = 1.3) showed the best cell uptake, there appears to be no direct correlation between lipophilicity and tracer uptake in mixed blood cells. In view of its comparable cell uptake to well known cell labeling agent Tc-99m-d,l-HMPAO, Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine merits further evaluation as a potential cell labeling agent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.045

文献信息

• 99mTc-tricarbonyl labeled agents for cell labeling: Development, biodistribution in normal mice and preliminary in vitro evaluation
  作者：Humphrey Fonge、Lixin Jin、Jan Cleynhens、Guy Bormans、Alfons Verbruggen

  DOI：10.1016/j.bmc.2009.10.045

  日期：2010.1

  We have developed four Tc-99m(CO)(3)-labeled lipophilic tracers as potential radiolabeling agents for cells based on a hexadecyl tail. Tc-99m(CO)(3)-hexadecylamino-N,N'-diacetic acid (negatively charged), Tc-99m(CO)(3)-hexadecylamino-N-alpha-picolyl-N'-acetic acid (uncharged), Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine (positively charged), Tc-99m(CO)(3)-N-hexadecylaminoethyl-N'-aminoethylamine (positively charged) were prepared in a radiolabeling yield: >90%. Preliminary cell uptake studies were performed in mixed blood cells with or without plasma and were compared with Tc-99m-d,l-HMPAO and [F-18]FDG. In plasma-free blood cells, maximum uptake (78%) was obtained for Tc-99m(CO)(3)-N-hexadecylaminoethyl-N'-aminoethylamine after 60 min incubation (compared to 55% and 23% for Tc-99m-d,l-HMPAO and [F-18]FDG, respectively) while in plasma-rich medium, Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine was best bound (54%, similar to the binding of 99mTc-d, l-HMPAO). Biodistribution in normal mice showed mainly hepatobiliary clearance of the agents and initial high lung uptake. The radiolabeled compounds showed good blood clearance with maximally 7.9% injected dose per gram at 60 min post injection. While the least lipophilic agent (Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine, log P = 1.3) showed the best cell uptake, there appears to be no direct correlation between lipophilicity and tracer uptake in mixed blood cells. In view of its comparable cell uptake to well known cell labeling agent Tc-99m-d,l-HMPAO, Tc-99m(CO)(3)-N,N'-dipicolylhexadecylamine merits further evaluation as a potential cell labeling agent. (C) 2009 Elsevier Ltd. All rights reserved.