[(S)-2-(3-((S)-1-carboxy-5-(2-(4-iodo-1H-1,2,3-triazol-1-yl)acetamido)pentyl)ureido)pentanedioic acid]123I | 1360607-76-6

• 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-(3-((S)-1-carboxy-5-(2-(4-iodo-1H-1,2,3-triazol-1-yl)acetamido)pentyl)ureido)pentanedioic acid]123I
• 英文别名: (2S)-2-[[(1S)-1-carboxy-5-[[2-(4-(123I)iodanyltriazol-1-yl)acetyl]amino]pentyl]carbamoylamino]pentanedioic acid
• CAS: 1360607-76-6
• 化学式: C₁₆H₂₃IN₆O₈
• 分子量: 550.394
• InChiKey: PKJJZSIIPXTZFD-XGNCGABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  213
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-叠氮基乙酸甲酯 、 (S)-di-tert-butyl 2-(3-((S)-6-amino-1-(tert-butoxy)-1-oxohexan-2-yl)ureido)pentanedioate 、 乙炔基溴化镁 在 (3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)3SnI 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 [(S)-2-(3-((S)-1-carboxy-5-(2-(4-iodo-1H-1,2,3-triazol-1-yl)acetamido)pentyl)ureido)pentanedioic acid]123I
  参考文献：
  名称：

  Triazole Appending Agent (TAAG): A New Synthon for Preparing Iodine-Based Molecular Imaging and Radiotherapy Agents

  摘要：

  A new prosthetic group referred to as the triazole appending agent (TAAG) was developed as a means to prepare targeted radioiodine-based molecular imaging and therapy agents. Tributyltin-TAAG and the fluorous analogue were synthesized in high yield using simple click chemistry and the products labeled in greater than 95% RCY with I-123. A TAAG derivative of an inhibitor of prostate-specific membrane antigen was prepared and radiolabeled with I-123 in 85% yield where biodistribution studies in LNCap prostate cancer tumor models showed rapid clearance of the agent from nontarget tissues and tumor accumulation of 20% injected dose g(-1) at 1 h. The results presented demonstrate that the TAAG group promotes minimal nonspecific binding and that labeled conjugates can achieve high tumor uptake and exquisite target-to-nontarget ratios.

  DOI：

  10.1021/ml300003v

文献信息

• Triazole Appending Agent (TAAG): A New Synthon for Preparing Iodine-Based Molecular Imaging and Radiotherapy Agents
  作者：Alla Darwish、Megan Blacker、Nancy Janzen、Stephanie M. Rathmann、Shannon Czorny、Shawn M. Hillier、John L. Joyal、John W. Babich、John F. Valliant

  DOI：10.1021/ml300003v

  日期：2012.4.12

  A new prosthetic group referred to as the triazole appending agent (TAAG) was developed as a means to prepare targeted radioiodine-based molecular imaging and therapy agents. Tributyltin-TAAG and the fluorous analogue were synthesized in high yield using simple click chemistry and the products labeled in greater than 95% RCY with I-123. A TAAG derivative of an inhibitor of prostate-specific membrane antigen was prepared and radiolabeled with I-123 in 85% yield where biodistribution studies in LNCap prostate cancer tumor models showed rapid clearance of the agent from nontarget tissues and tumor accumulation of 20% injected dose g(-1) at 1 h. The results presented demonstrate that the TAAG group promotes minimal nonspecific binding and that labeled conjugates can achieve high tumor uptake and exquisite target-to-nontarget ratios.