2-cyano-6-(2-[(18)F-fluoro]ethoxy)benzothiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-cyano-6-(2-[(18)F-fluoro]ethoxy)benzothiazole
• 英文别名: 6-(2-(18F)fluoranylethoxy)-1,3-benzothiazole-2-carbonitrile
• 化学式: C₁₀H₇FN₂OS
• 分子量: 221.244
• InChiKey: YNWJVSLTHNDOEJ-KXMUYVCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-半胱氨酸 、 2-cyano-6-(2-[(18)F-fluoro]ethoxy)benzothiazole 在 水 、 三(2-羰基乙基)磷盐酸盐 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 0.02h， 以95%的产率得到
  参考文献：
  名称：

  Efficient Method for Site-Specific ¹⁸F-Labeling of Biomolecules Using the Rapid Condensation Reaction between 2-Cyanobenzothiazole and Cysteine

  摘要：

  An efficient method based on a rapid condensation reaction between 2-cyanobenzothiazole (CBT) and cysteine has been developed for F-18-labeling of N-terminal cysteine-bearing peptides and proteins. An F-18-labeled dimeric cRGD ([F-18]CBTRGD(2)) has been synthesized with an excellent radiochemical yield (92% based on radio-HPLC conversion, 80% decay-corrected, and isolated yield) and radiochemical purity (> 99%) under mild conditions using F-18-CBT, and shown good in vivo tumor targeting efficiency for PET imaging. The labeling strategy was also applied to the site-specific F-18-labeling of a protein, Renilla lucifierase (RLuc8) with a cysteine residue at its N-terminus. The protein labeling was achieved with 12% of decay-corrected radiochemical yield and more than 99% radiochemical purity. This strategy should provide a general approach for efficient and site-specific F-18-labeling of various peptides and proteins for in vivo molecular imaging applications.

  DOI：

  10.1021/bc300273m
• 作为产物：
  描述：

  2-氰基-6-甲氧基苯并噻唑 在 盐酸 、 18-冠醚-6 、 K(18-F)F 、 吡啶盐酸盐 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 10.17h， 生成 2-cyano-6-(2-[(18)F-fluoro]ethoxy)benzothiazole
  参考文献：
  名称：

  Efficient Method for Site-Specific ¹⁸F-Labeling of Biomolecules Using the Rapid Condensation Reaction between 2-Cyanobenzothiazole and Cysteine

  摘要：

  An efficient method based on a rapid condensation reaction between 2-cyanobenzothiazole (CBT) and cysteine has been developed for F-18-labeling of N-terminal cysteine-bearing peptides and proteins. An F-18-labeled dimeric cRGD ([F-18]CBTRGD(2)) has been synthesized with an excellent radiochemical yield (92% based on radio-HPLC conversion, 80% decay-corrected, and isolated yield) and radiochemical purity (> 99%) under mild conditions using F-18-CBT, and shown good in vivo tumor targeting efficiency for PET imaging. The labeling strategy was also applied to the site-specific F-18-labeling of a protein, Renilla lucifierase (RLuc8) with a cysteine residue at its N-terminus. The protein labeling was achieved with 12% of decay-corrected radiochemical yield and more than 99% radiochemical purity. This strategy should provide a general approach for efficient and site-specific F-18-labeling of various peptides and proteins for in vivo molecular imaging applications.

  DOI：

  10.1021/bc300273m

文献信息

• Efficient Method for Site-Specific ¹⁸F-Labeling of Biomolecules Using the Rapid Condensation Reaction between 2-Cyanobenzothiazole and Cysteine
  作者：Jongho Jeon、Bin Shen、Liqin Xiong、Zheng Miao、Kyung Hyun Lee、Jianghong Rao、Frederick T. Chin

  DOI：10.1021/bc300273m

  日期：2012.9.19

  An efficient method based on a rapid condensation reaction between 2-cyanobenzothiazole (CBT) and cysteine has been developed for F-18-labeling of N-terminal cysteine-bearing peptides and proteins. An F-18-labeled dimeric cRGD ([F-18]CBTRGD(2)) has been synthesized with an excellent radiochemical yield (92% based on radio-HPLC conversion, 80% decay-corrected, and isolated yield) and radiochemical purity (> 99%) under mild conditions using F-18-CBT, and shown good in vivo tumor targeting efficiency for PET imaging. The labeling strategy was also applied to the site-specific F-18-labeling of a protein, Renilla lucifierase (RLuc8) with a cysteine residue at its N-terminus. The protein labeling was achieved with 12% of decay-corrected radiochemical yield and more than 99% radiochemical purity. This strategy should provide a general approach for efficient and site-specific F-18-labeling of various peptides and proteins for in vivo molecular imaging applications.