2-amino-4-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraaza-cyclododec-1-yl)-acetylamino]-butyric acid hydrochloride | 1248343-72-7

• 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: 2-amino-4-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraaza-cyclododec-1-yl)-acetylamino]-butyric acid hydrochloride
• 英文别名: (2S)-2-amino-4-[[2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetyl]amino]butanoic acid;hydrochloride
• CAS: 1248343-72-7
• 化学式: C₂₀H₃₆N₆O₉*ClH
• 分子量: 541.002
• InChiKey: PRNMOUOBVPWYCO-RSAXXLAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  217
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  (S)-2,2',2''-(10-(2-((4-(tert-butoxy)-3-((tert-butoxycarbonyl)amino)-4-oxobutyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 2-amino-4-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraaza-cyclododec-1-yl)-acetylamino]-butyric 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

文献信息

• [EN] Heterocycle-amino acid derivatives for targeting cancer tissue and radioactive or non-radioactive labeled compounds thereof<br/>[FR] DÉRIVÉS D'ACIDE AMINÉ-HÉTÉROCYCLE DESTINÉS À CIBLER UN TISSU CANCÉREUX ET COMPOSÉS MARQUÉS RADIOACTIFS OU NON RADIOACTIFS CORRESPONDANTS
  申请人：SNU R&DB FOUNDATION

  公开号：WO2010114308A1

  公开（公告）日：2010-10-07

  The present invention relates to novel amino acid derivatives containing heterocyclic chelating residues thereof; radioactive or nonradioactive metal complexes thereof; methods for preparation thereof; and apyrogenic and sterile preparative kits of the composition for targeting cancer cells. The compounds of the present invention can easily be taken up to cancer cells as they contain amino acid residues thereof; radioactive or nonradioactive metals can be labeled easily as they contain heterocyclic chelating residues thereof; cancer lesion can be imaged easily by targeting using the present invention.

  本发明涉及含有杂环螯合残基的新型氨基酸衍生物；其放射性或非放射性金属配合物；其制备方法；以及用于靶向癌细胞的无热原和无菌制剂组合。本发明的化合物含有氨基酸残基，因此可以轻松地被癌细胞吸收；含有杂环螯合残基，因此可以轻松地标记放射性或非放射性金属；使用本发明可以轻松地靶向癌症病变进行成像。
• Synthesis and evaluation of macrocyclic amino acid derivatives for tumor imaging by gallium-68 positron emission tomography
  作者：Dinesh Shetty、Jae Min Jeong、Chang Hwan Ju、Young Ju Kim、Ji-Youn Lee、Yun-Sang Lee、Dong Soo Lee、June-Key Chung、Myung Chul Lee

  DOI：10.1016/j.bmc.2010.09.022

  日期：2010.11

  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.