(3S,7S,22S)-26-amino-5,13,20-trioxo-4,6,12,21-tetraazahexacosane-1,3,7,22-tetracarboxylic acid | 1095118-46-9

• 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: (3S,7S,22S)-26-amino-5,13,20-trioxo-4,6,12,21-tetraazahexacosane-1,3,7,22-tetracarboxylic acid
• 英文别名: (2S)-2-[[(1S)-5-[[8-[[(1S)-5-amino-1-carboxypentyl]amino]-8-oxooctanoyl]amino]-1-carboxypentyl]carbamoylamino]pentanedioic acid
• CAS: 1095118-46-9
• 化学式: C₂₆H₄₅N₅O₁₁
• 分子量: 603.67
• InChiKey: JXKIRGXULLHLQS-FHWLQOOXSA-N

物化性质

• 沸点：
  1023.4±65.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  42.0
• 可旋转键数：
  25.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  274.55
• 氢给体数：
  9.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(S)-(4-isothiocyanatobenzyl)-1,4,7-triazacyclononane-1,4,7-triacetic acid 、 (3S,7S,22S)-26-amino-5,13,20-trioxo-4,6,12,21-tetraazahexacosane-1,3,7,22-tetracarboxylic acid 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以23%的产率得到9,16,24-trioxo-1-thioxo-1-((4-(((S)-1,4,7-tris-(carboxymethyl)-1,4,7-triazonan-2-yl)methyl)phenyl)amino)-2,8,17,23,25-pentaazaoctacosane-7,22,26,28-tetracarboxylic acid
  参考文献：
  名称：

  ⁶⁴Cu-Labeled Inhibitors of Prostate-Specific Membrane Antigen for PET Imaging of Prostate Cancer

  摘要：

  Prostate-specific membrane antigen (PSMA) is a well-recognized target for identification and therapy of a variety of cancers. Here we report five (64)Cu-labeled inhibitors of PSMA, [(64)Cu]3-7, which are based on the lysine-glutamate urea scaffold and utilize a variety of macrocyclic chelators, namely NOTA(3), PCTA(4), Oxo-DO3A(5), CB-TE2A(6), and DOTA(7), in an effort to determine which provides the most suitable pharmacokinetics for in vivo PET imaging. [(64)Cu]3-7 were prepared in high radiochemical yield (60-90%) and purity (>95%). Positron emission tomography (PET) imaging studies of [(64)Cu]3-7 revealed specific accumulation in PSMA-expressing xenografts (PSMA+ PC3 PIP) relative to isogenic control tumor (PSMA- PC3 flu) and background tissue. The favorable kinetics and high image contrast provided by CB-TE2A chelated [(64)Cu]6 suggest it as the most promising among the candidates tested. That could be due to the higher stability of [(64)Cu]CB-TE2A as compared with [(64)Cu]NOTA, [(64)Cu]PCTA, [(64)Cu]Oxo-DO3A, and [(64)Cu]DOTA chelates in vivo.

  DOI：

  10.1021/jm401921j
• 作为产物：
  描述：

  (((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 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3S,7S,22S)-26-amino-5,13,20-trioxo-4,6,12,21-tetraazahexacosane-1,3,7,22-tetracarboxylic acid
  参考文献：
  名称：

  ⁶⁴Cu-Labeled Inhibitors of Prostate-Specific Membrane Antigen for PET Imaging of Prostate Cancer

  摘要：

  Prostate-specific membrane antigen (PSMA) is a well-recognized target for identification and therapy of a variety of cancers. Here we report five (64)Cu-labeled inhibitors of PSMA, [(64)Cu]3-7, which are based on the lysine-glutamate urea scaffold and utilize a variety of macrocyclic chelators, namely NOTA(3), PCTA(4), Oxo-DO3A(5), CB-TE2A(6), and DOTA(7), in an effort to determine which provides the most suitable pharmacokinetics for in vivo PET imaging. [(64)Cu]3-7 were prepared in high radiochemical yield (60-90%) and purity (>95%). Positron emission tomography (PET) imaging studies of [(64)Cu]3-7 revealed specific accumulation in PSMA-expressing xenografts (PSMA+ PC3 PIP) relative to isogenic control tumor (PSMA- PC3 flu) and background tissue. The favorable kinetics and high image contrast provided by CB-TE2A chelated [(64)Cu]6 suggest it as the most promising among the candidates tested. That could be due to the higher stability of [(64)Cu]CB-TE2A as compared with [(64)Cu]NOTA, [(64)Cu]PCTA, [(64)Cu]Oxo-DO3A, and [(64)Cu]DOTA chelates in vivo.

  DOI：

  10.1021/jm401921j

文献信息

• LOW MOLECULAR WEIGHT AND POLYAMIDOAMINE (PAMAM) DENDRIMER BASED PSMA-SPECIFIC DUAL CONTRAST AGENTS FOR OPTICAL AND PHOTOACOUSTIC IMAGING AND THERANOSTIC AGENTS FOR TREATING PROSTATE CANCER
  申请人：The Johns Hopkins University

  公开号：US20220401592A1

  公开（公告）日：2022-12-22

  Poly(amidoamine) [PAMAM] dendrimers for use as PSMA-targeted contrast agents for optical and photoacoustic imaging (PA) and theranostic agents for treating prostate cancer are disclosed.