2-[4,7-Bis(carboxymethyl)-1,4,7-triazonan-1-yl]hexanoic acid | 1325166-19-5

• 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: 2-[4,7-Bis(carboxymethyl)-1,4,7-triazonan-1-yl]hexanoic acid
• CAS: 1325166-19-5
• 化学式: C₁₆H₂₉N₃O₆
• 分子量: 359.423
• InChiKey: QDQWUTYXJLSBMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以73.6%的产率得到2-[4,7-Bis(carboxymethyl)-1,4,7-triazonan-1-yl]hexanoic acid
  参考文献：
  名称：

  Triaza-based amphiphilic chelators: Synthetic route, in vitro characterization and in vivo studies of their Ga(III) and Al(III) chelates

  摘要：

  Radiogallium chelates are important for diagnostic imaging in nuclear medicine (PET (positron emission tomography) and gamma-scintigraphy). Micelles are adequate colloidal vehicles for the delivery of therapeutic and diagnostic agents to organs and tissues. In this paper we describe the synthesis and in vitro and in vivo studies of a series of micelles-forming Ga(III) chelates targeted for the liver. The amphiphilic ligands are based on NOTA (NOTA = 1,4,7-triazacyclonoane-N,N'N ''-triacetic acid) and bear a alpha-alkyl chain in one of the pendant acetate arms (the size of the chain changes from four to fourteen carbon atoms). A multinuclear NMR study (H-1, C-13, Al-27 and Ga-71) gave some insights into the structure and dynamics of the metal chelates in solution, consistent with their rigidity and octahedral or pseudo-octahedral geometry. The critical micellar concentration of the chelates was determined using a fluorescence method and Al-27 NMR spectroscopy (Al (III) was used as a surrogate of Ga(III)), both showing similar results and suggesting that the chelates of NOTAC6 form pre-micellar aggregates. The logP (octanol-water) determination showed enhancement of the lipophilic character of the Ga(III) chelates with the increase of the number of carbons in the alpha-alkyl chain. Biodistribution and gamma-scintigraphic studies of the Ga-67(III) labeled chelates were performed on Wistar rats, showing higher liver uptake for [Ga-67](NOTAC8) in comparison to [Ga-67](NOTAC6), consistent with a longer alpha-alkyl chain and a higher lipophilicity. After 24 h both chelates were completely cleared off from the tissues and organs with no deposition in the bones and liver/spleen. [Ga-67](NOTAC8) showed high kinetic stability in blood serum. (c) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2010.06.002

文献信息

• NUCLEAR IMAGING AND RADIOTHERAPEUTICS AGENTS TARGETING CARBONIC ANHYDRASE IX AND USES THEREOF
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20190192699A1

  公开（公告）日：2019-06-27

  Highly potent and selective radionuclide-based imaging and therapy agents targeting carbonic anhydrase IX with minimum non-specific organ uptake are disclosed. Methods of imaging and/or treating carbonic anhydrase IX-expressing cells or tumors also are disclosed.
• [EN] NUCLEAR IMAGING AND RADIOTHERAPEUTICS AGENTS TARGETING CARBONIC ANHYDRASE IX AND USES THEREOF<br/>[FR] AGENTS D'IMAGERIE NUCLÉAIRE ET RADIOTHÉRAPIQUES CIBLANT L'ANHYDRASE CARBONIQUE IX ET LEURS UTILISATIONS
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2017197251A1

  公开（公告）日：2017-11-16

  Highly potent and selective radionuclide-based imaging and therapy agents targeting carbonic anhydrase IX with minimum non-specific organ uptake are disclosed. Methods of imaging and/or treating carbonic anhydrase IX-expressing cells or tumors also are disclosed.