[¹³C₃, ¹⁵N]-choline chloride | 1129433-69-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [¹³C₃, ¹⁵N]-choline chloride
• 英文别名: 2-hydroxyethyl-tri((113C)methyl)(15N)azanium;chloride
• CAS: 1129433-69-7
• 化学式: C₅H₁₄NO*Cl
• 分子量: 143.586
• InChiKey: SGMZJAMFUVOLNK-VVMSZDRUSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.31
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [¹³C₃, ¹⁵N]-choline chloride 在 吡啶 、 四氮唑 、 ammonium hydroxide 、 水 、 碘 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 17.0h， 生成 [¹³C₃, ¹⁵N]-2-methacryloyloxyethylphosphorylcholine
  参考文献：
  名称：

  Magnetic Resonance Imaging of Tumor with a Self-Traceable Phosphorylcholine Polymer

  摘要：

  Polymers are concentration-amplified with respect to the monomeric units. We show here that a phosphorylcholine polymer enriched with C-13/N-15 at the methyl groups is self-traceable by multiple-resonance (heteronuclear-correlation) NMR in tumor-bearing mice inoculated with the mouse rectal cancer cell line (colon 26). Preliminary measurements indicated that the present polymeric nanoprobe was satisfactorily distinguished from lipids and detectable with far sub-micromolar spectroscopic and far sub-millimolar imaging sensitivities. Detailed ex vivo and in vivo studies for the tumor-bearing mice administered the probe with a mean molecular weight of 63 000 and a mean size of 13 nm, revealed the following: (1) this probe accumulates in the tumor highly selectively (besides renal excretion) and efficiently (up to 30% of the injected dose), (2) the tumor can thus be clearly in vivo imaged, the lowest clearly imageable dose of the probe being 100 mg/kg or 2.0 mg/20-g mouse, and (3) the competition between renal excretion and tumor accumulation is size-controlled; that is, the larger (higher molecular-weight) and smaller (lower molecular-weight) portions of the probe undergo tumor accumulation and renal excretion, respectively. The observed size dependence suggests that the efficient tumor-targeting of the present probe is stimulated primarily by the so-called enhanced permeability and retention (EPR) effect, that is, size-allowed invasion of the probe into the tumor tissue via defective vascular wall. Self-traceable polymers thus open an important area of magnetic resonance imaging (MRI) of tumors and may provide a highly potential tool to visualize various delivery/localization processes using synthetic polymers.

  DOI：

  10.1021/ja510479v
• 作为产物：
  描述：

  (13)C3-(15)N-choline iodide 在 silver(l) oxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 以27%的产率得到[¹³C₃, ¹⁵N]-choline chloride
  参考文献：
  名称：

  [EN] COMPOUND, DIAGNOSTIC AGENT, NUCLEAR MAGNETIC RESONANCE ANALYSIS METHOD, NUCLEAR MAGNETIC RESONANCE IMAGING METHOD, MASS SPECTROMETRY METHOD AND MASS SPECTROMETRY IMAGING METHOD
  [FR] COMPOSÉS, AGENT DE DIAGNOSTIC, PROCÉDÉ D'ANALYSE PAR RÉSONANCE MAGNÉTIQUE NUCLÉAIRE, PROCÉDÉ D'IMAGERIE PAR RÉSONANCE MAGNÉTIQUE NUCLÉAIRE, PROCÉDÉ DE SPECTROMÉTRIE DE MASSE ET PROCÉDÉ D'IMAGERIE PAR SPECTROMÉTRIE DE MASSE

  摘要：

  生物物质的标记化合物可以使用稳定同位素原子而不使用有辐射危险和处理时间限制的放射性同位素原子来生产，并且该标记化合物可以与所选生物物质的天然存在化合物分离地测量，这些化合物已经用稳定同位素原子替代。作为一种生物物质，胆碱通过用各自同位素15N和13C替换季铵基的氮原子和附着在氮原子上的甲基基团的所有碳原子来标记，并用作诊断试剂。

  公开号：

  WO2009031712A1

文献信息

• [EN] COMPOUND, DIAGNOSTIC AGENT, NUCLEAR MAGNETIC RESONANCE ANALYSIS METHOD, NUCLEAR MAGNETIC RESONANCE IMAGING METHOD, MASS SPECTROMETRY METHOD AND MASS SPECTROMETRY IMAGING METHOD<br/>[FR] COMPOSÉS, AGENT DE DIAGNOSTIC, PROCÉDÉ D'ANALYSE PAR RÉSONANCE MAGNÉTIQUE NUCLÉAIRE, PROCÉDÉ D'IMAGERIE PAR RÉSONANCE MAGNÉTIQUE NUCLÉAIRE, PROCÉDÉ DE SPECTROMÉTRIE DE MASSE ET PROCÉDÉ D'IMAGERIE PAR SPECTROMÉTRIE DE MASSE
  申请人：UNIV KYOTO

  公开号：WO2009031712A1

  公开（公告）日：2009-03-12

  To produce a labeled compound for a selected biological substance not using a radioisotope atom which has a risk of exposure to radioactivity and limitation on handling time but using a stable isotope atom; and that the labeled compound can be measured with good sensitivity separably from naturally occurring compounds of the selected biological substance which are substituted with the stable isotope atom. Choline as a biological substance is labeled by substituting the nitrogen atom of the quaternary ammonium group and all the carbon atoms of the methyl group attached to the nitrogen atom with respective isotopes 15N and 13C and used as a diagnostic agent.

  生物物质的标记化合物可以使用稳定同位素原子而不使用有辐射危险和处理时间限制的放射性同位素原子来生产，并且该标记化合物可以与所选生物物质的天然存在化合物分离地测量，这些化合物已经用稳定同位素原子替代。作为一种生物物质，胆碱通过用各自同位素15N和13C替换季铵基的氮原子和附着在氮原子上的甲基基团的所有碳原子来标记，并用作诊断试剂。
• Magnetic Resonance Imaging of Tumor with a Self-Traceable Phosphorylcholine Polymer
  作者：Hisatsugu Yamada、Yoshinori Hasegawa、Hirohiko Imai、Yuki Takayama、Fuminori Sugihara、Tetsuya Matsuda、Hidehito Tochio、Masahiro Shirakawa、Shinsuke Sando、Yu Kimura、Akio Toshimitsu、Yasuhiro Aoyama、Teruyuki Kondo

  DOI：10.1021/ja510479v

  日期：2015.1.21

  Polymers are concentration-amplified with respect to the monomeric units. We show here that a phosphorylcholine polymer enriched with C-13/N-15 at the methyl groups is self-traceable by multiple-resonance (heteronuclear-correlation) NMR in tumor-bearing mice inoculated with the mouse rectal cancer cell line (colon 26). Preliminary measurements indicated that the present polymeric nanoprobe was satisfactorily distinguished from lipids and detectable with far sub-micromolar spectroscopic and far sub-millimolar imaging sensitivities. Detailed ex vivo and in vivo studies for the tumor-bearing mice administered the probe with a mean molecular weight of 63 000 and a mean size of 13 nm, revealed the following: (1) this probe accumulates in the tumor highly selectively (besides renal excretion) and efficiently (up to 30% of the injected dose), (2) the tumor can thus be clearly in vivo imaged, the lowest clearly imageable dose of the probe being 100 mg/kg or 2.0 mg/20-g mouse, and (3) the competition between renal excretion and tumor accumulation is size-controlled; that is, the larger (higher molecular-weight) and smaller (lower molecular-weight) portions of the probe undergo tumor accumulation and renal excretion, respectively. The observed size dependence suggests that the efficient tumor-targeting of the present probe is stimulated primarily by the so-called enhanced permeability and retention (EPR) effect, that is, size-allowed invasion of the probe into the tumor tissue via defective vascular wall. Self-traceable polymers thus open an important area of magnetic resonance imaging (MRI) of tumors and may provide a highly potential tool to visualize various delivery/localization processes using synthetic polymers.