(S)-2,2',2''-(10-(2-((2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid | 1258385-21-5

• 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: (S)-2,2',2''-(10-(2-((2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
• CAS: 1258385-21-5
• 化学式: C₂₅H₄₄N₆O₁₁
• 分子量: 604.658
• InChiKey: RNMZGKSGTLYBBE-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.36
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  218.59
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (S)-2,2',2''-(10-(2-((2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以67%的产率得到(S)-2-amino-3-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraaza-cyclododec-1-yl)-acetylamino]-propionic acid hydrochloride
  参考文献：
  名称：

  Synthesis and evaluation of macrocyclic amino acid derivatives for tumor imaging by gallium-68 positron emission tomography

  摘要：

  Ga-68 PET imaging in clinical oncology represents a notable development because the availability of Ga-68 is not dependent on a cyclotron. Furthermore, labeled amino acid derivatives have been proven to be useful for the imaging many tumor types. In the present study, we synthesized beta-aminoalanine, gamma-aminohomoalanine, and lysine conjugates of macrocyclic bifunctional chelating agents, such as, NOTA (1a-c) and DOTA (2a-c). The compounds produced were found to be potential useful as Ga-68-PET imaging agents. In particular, they showed high tumor uptakes in vitro and in vivo, and had high labeling yields and excellent stabilities. The co-ordination chemistry of NOTA-monoamide compound 1a was studied by multinuclear NMR. In vitro studies showed that the synthesized compounds were taken up by cancer cells more than controls (Ga-68-NOTA and Ga-68-DOTA). Furthermore, in vivo studies showed that they have high tumor to muscle and tumor to blood ratios, and small-animal PET imaging revealed high tumor uptakes as compared with other organs, and high bladder activities, indicating rapid renal excretion. These results might motivate the use of Ga-68 amino acid PET for tumor diagnosis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.022
• 作为产物：
  描述：

  1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸 、 3-氨基-N-Boc-L-丙氨酸甲酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以50%的产率得到(S)-2,2',2''-(10-(2-((2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
  参考文献：
  名称：

  Synthesis and evaluation of macrocyclic amino acid derivatives for tumor imaging by gallium-68 positron emission tomography

  摘要：

  Ga-68 PET imaging in clinical oncology represents a notable development because the availability of Ga-68 is not dependent on a cyclotron. Furthermore, labeled amino acid derivatives have been proven to be useful for the imaging many tumor types. In the present study, we synthesized beta-aminoalanine, gamma-aminohomoalanine, and lysine conjugates of macrocyclic bifunctional chelating agents, such as, NOTA (1a-c) and DOTA (2a-c). The compounds produced were found to be potential useful as Ga-68-PET imaging agents. In particular, they showed high tumor uptakes in vitro and in vivo, and had high labeling yields and excellent stabilities. The co-ordination chemistry of NOTA-monoamide compound 1a was studied by multinuclear NMR. In vitro studies showed that the synthesized compounds were taken up by cancer cells more than controls (Ga-68-NOTA and Ga-68-DOTA). Furthermore, in vivo studies showed that they have high tumor to muscle and tumor to blood ratios, and small-animal PET imaging revealed high tumor uptakes as compared with other organs, and high bladder activities, indicating rapid renal excretion. These results might motivate the use of Ga-68 amino acid PET for tumor diagnosis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.022