(2S)-2-amino-6-[bis(1H-imidazol-2-ylmethyl)amino]hexanoic acid | 1448302-58-6

• 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: (2S)-2-amino-6-[bis(1H-imidazol-2-ylmethyl)amino]hexanoic acid
• CAS: 1448302-58-6
• 化学式: C₁₄H₂₂N₆O₂
• 分子量: 306.368
• InChiKey: DQPLLPMXHIVATF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-6-[bis(1H-imidazol-2-ylmethyl)amino]hexanoic acid 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-(3-[1-carboxy-5-(7-(1-carboxy-5-[(6-hydrazinopyridine-3-carbonyl)amino]pentylcarbamoyl)heptanoylamino)pentyl]ureido)pentanedioic acid
  参考文献：
  名称：

  Effect of Chelators on the Pharmacokinetics of ^99mTc-Labeled Imaging Agents for the Prostate-Specific Membrane Antigen (PSMA)

  摘要：

  Technetium-99m, the most commonly used radionuclide in nuclear medicine, can be attached to biologically important molecules through a variety of chelating agents, the choice of which depends upon the imaging application. The prostate-specific membrane antigen (PSMA) is increasingly recognized as an important target for imaging and therapy of prostate cancer (PCa). Three different Tc-99m-labeling methods were employed to investigate the effect of the chelator on the biodistribution and PCa tumor uptake profiles of 12 new urea-based PSMA-targeted radiotracers. This series includes hydrophilic ligands for radiolabeling with the [Tc-99m(CO)(3)](+) core (L8-L10), traditional NxSy-based chelating agents with varying charge and polarity for the Tc-99m-oxo core (L11-L18), and a Tc-99m-organohydrazine-labeled radioligand (L19). Tc-99m(I)-Tricarbonyl-labeled [Tc-99m]L8 produced the highest PSMA+ PC3 PIP to PSMA- PC3 flu tumor ratios and demonstrated the lowest retention in normal tissues including kidney after 2 h. These results suggest that choice of chelator is an important pharmacokinetic consideration in the development of Tc-99m-labeled radiopharmaceuticals targeting PSMA.

  DOI：

  10.1021/jm400823w
• 作为产物：
  描述：

  N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 在 哌啶 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (2S)-2-amino-6-[bis(1H-imidazol-2-ylmethyl)amino]hexanoic acid
  参考文献：
  名称：

  Effect of Chelators on the Pharmacokinetics of ^99mTc-Labeled Imaging Agents for the Prostate-Specific Membrane Antigen (PSMA)

  摘要：

  Technetium-99m, the most commonly used radionuclide in nuclear medicine, can be attached to biologically important molecules through a variety of chelating agents, the choice of which depends upon the imaging application. The prostate-specific membrane antigen (PSMA) is increasingly recognized as an important target for imaging and therapy of prostate cancer (PCa). Three different Tc-99m-labeling methods were employed to investigate the effect of the chelator on the biodistribution and PCa tumor uptake profiles of 12 new urea-based PSMA-targeted radiotracers. This series includes hydrophilic ligands for radiolabeling with the [Tc-99m(CO)(3)](+) core (L8-L10), traditional NxSy-based chelating agents with varying charge and polarity for the Tc-99m-oxo core (L11-L18), and a Tc-99m-organohydrazine-labeled radioligand (L19). Tc-99m(I)-Tricarbonyl-labeled [Tc-99m]L8 produced the highest PSMA+ PC3 PIP to PSMA- PC3 flu tumor ratios and demonstrated the lowest retention in normal tissues including kidney after 2 h. These results suggest that choice of chelator is an important pharmacokinetic consideration in the development of Tc-99m-labeled radiopharmaceuticals targeting PSMA.

  DOI：

  10.1021/jm400823w

文献信息

• Effect of Chelators on the Pharmacokinetics of ^99mTc-Labeled Imaging Agents for the Prostate-Specific Membrane Antigen (PSMA)
  作者：Sangeeta Ray Banerjee、Mrudula Pullambhatla、Catherine A. Foss、Alexander Falk、Youngjoo Byun、Sridhar Nimmagadda、Ronnie C. Mease、Martin G. Pomper

  DOI：10.1021/jm400823w

  日期：2013.8.8

  Technetium-99m, the most commonly used radionuclide in nuclear medicine, can be attached to biologically important molecules through a variety of chelating agents, the choice of which depends upon the imaging application. The prostate-specific membrane antigen (PSMA) is increasingly recognized as an important target for imaging and therapy of prostate cancer (PCa). Three different Tc-99m-labeling methods were employed to investigate the effect of the chelator on the biodistribution and PCa tumor uptake profiles of 12 new urea-based PSMA-targeted radiotracers. This series includes hydrophilic ligands for radiolabeling with the [Tc-99m(CO)(3)](+) core (L8-L10), traditional NxSy-based chelating agents with varying charge and polarity for the Tc-99m-oxo core (L11-L18), and a Tc-99m-organohydrazine-labeled radioligand (L19). Tc-99m(I)-Tricarbonyl-labeled [Tc-99m]L8 produced the highest PSMA+ PC3 PIP to PSMA- PC3 flu tumor ratios and demonstrated the lowest retention in normal tissues including kidney after 2 h. These results suggest that choice of chelator is an important pharmacokinetic consideration in the development of Tc-99m-labeled radiopharmaceuticals targeting PSMA.