ε-{N-(pyridyl-2-methylene)N-(acetic acid)}-L-lysine | 863394-45-0

• 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: ε-{N-(pyridyl-2-methylene)N-(acetic acid)}-L-lysine
• 英文别名: (2S)-2-amino-6-[carboxymethyl(pyridin-2-ylmethyl)amino]hexanoic acid
• CAS: 863394-45-0
• 化学式: C₁₄H₂₁N₃O₄
• 分子量: 295.338
• InChiKey: RUVXZDASJUQZIF-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ε-{N-(pyridyl-2-methylene)N-(acetic acid)}-L-lysine 、 (((S)-1-carboxy-5-(8-((2,5-dioxopyrrolidin-1-yl)oxy)-8 oxooctanamido)pentyl)carbamoyl)-Lglutamicacid 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-[3-(1-carboxy-5-(7-[1-carboxy-5-(carboxymethylpyridin-2-ylmethylamino)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：

  (4-methoxyphenyl)methyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate 在 哌啶 、 三异丙基硅烷 、 三乙酰氧基硼氢化钠 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.33h， 生成 ε-{N-(pyridyl-2-methylene)N-(acetic acid)}-L-lysine
  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

• [EN] TECHNETIUM- AND RHENIUM-BIS(HETEROARYL) COMPLEXES, AND METHODS OF USE THEREOF<br/>[FR] COMPLEXES DE TECHNETIUM- ET RHENIUM-BIS(HETEROARYLE), ET LEURS PROCEDES D'UTILISATION
  申请人：MOLECULAR INSIGHT PHARM INC

  公开号：WO2005079865A1

  公开（公告）日：2005-09-01

  One aspect of the invention relates to complexes of a radionuclide with various heteroaryl ligands, e.g., imidazolyl and pyridyl ligands, and their use in radiopharmaceuticals for a variety of clinical diagnostic and therapeutic applications. Another aspect of the invention relates to imidazolyl and pyridyl ligands that form a portion of the aforementioned complexes. Methods for the preparation of the radionuclide complexes are also described. Another aspect of the invention relates to imidazolyl and pyridyl ligands based on derivatized lysine, alanine and bis-amino acids for conjugation to small peptides by solid phase synthetic methods. Additionally, the invention relates to methods for imaging regions of a mammal using the complexes of the invention.

  该发明的一个方面涉及放射性核素与各种杂环芳基配体（例如咪唑基和吡啶基配体）形成的配合物，以及它们在临床诊断和治疗应用中的放射性药物中的使用。该发明的另一个方面涉及形成前述配合物一部分的咪唑基和吡啶基配体。还描述了制备放射性核素配合物的方法。该发明的另一个方面涉及基于衍生赖氨酸、丙氨酸和双氨基酸的咪唑基和吡啶基配体，用于通过固相合成方法与小肽结合。此外，该发明涉及使用该发明的配合物来成像哺乳动物体内区域的方法。
• 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.