βAG-TOCA | 1310573-42-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: βAG-TOCA
• 英文别名: propynoyl-β-Ala-Gly-[Tyr³]-octreotate；propioloyl-bAla-Gly-D-Phe-Cys(1)-Tyr-D-Trp-Lys-Thr-Cys(1)-Thr-OH；(2S,3R)-2-[[(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-7-[(1R)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-19-[[(2R)-3-phenyl-2-[[2-[3-(prop-2-ynoylamino)propanoylamino]acetyl]amino]propanoyl]amino]-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]amino]-3-hydroxybutanoic acid
• CAS: 1310573-42-2
• 化学式: C₅₇H₇₂N₁₂O₁₅S₂
• 分子量: 1229.4
• InChiKey: WHCJBFRXKSSQHF-LGDPYURPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  86
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  481
• 氢给体数：
  16
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (19^F)2-fluoroethylazide 、 βAG-TOCA 在 铜 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以29%的产率得到
  参考文献：
  名称：

  Synthesis and in vitro evaluation of [18F]fluoroethyl triazole labelled [Tyr3]octreotate analogues using click chemistry

  摘要：

  A novel class of alkyne linked [Tyr(3)]octreotate analogues have been labelled by a copper catalysed azide-alkyne cycloaddition reaction (CuAAC) to form a 1,4-substituted triazole using the reagent [F-18]2-fluoroethyl azide. An unexpected variability in reactivity during the CuAAC reaction was observed for each alkyne analogue which has been investigated. Two lead alkyne linked [Tyr(3)]octreotate analogues, G-TOCA (3a) and beta AG-TOCA (5a) have been identified to be highly reactive in the click reaction showing complete conversion to the [F-18]2-fluoroethyl triazole linked [Tyr(3)]octreotate analogues FET-G-TOCA (3b) and FET-beta AG-TOCA (5b) under mild conditions and with short synthesis times (5 min at 20 degrees C). As well as ease of synthesis, in vitro binding to the pancreatic tumour AR42J cells showed that both FET-G-TOCA and FET-beta AG-TOCA have high affinity for the somatostatin receptor with IC50 of 4.0 +/- 1.4, and 1.6 +/- 0.2 nM, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.016
• 作为产物：
  描述：

  propynoyl-β-Ala-Gly-D-Phe-Cys-Tyr-D-Trp-Lys-Thr-Cys-Thr-OH 在 2,2'-二硫二吡啶 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以140 mg的产率得到βAG-TOCA
  参考文献：
  名称：

  Radiolabelled octreotate analogues as PET tracers

  摘要：

  描述了用于正电子发射断层扫描（PET）成像的新型放射性示踪剂。描述了用于正电子发射断层扫描（PET）成像神经内分泌肿瘤的新型放射性示踪剂。具体而言，本发明描述了新型[18F]氟乙基三唑-[Tyr3]奥曲肽类似物；特别是那些靶向胃肠胰神经内分泌肿瘤细胞表面上生长抑素受体的类似物。本发明还描述了中间体、前体、药物组合物、制备方法和新型放射性示踪剂的使用方法。

  公开号：

  US10201625B2

文献信息

• Radiolabelled octreotate analogues as PET tracers
  申请人：Luthra Sajinker Kaur

  公开号：US10201625B2

  公开（公告）日：2019-02-12

  Novel radiotracer(s) for Positron Emission Tomography (PET) imaging are described. Novel radiotracer(s) for Positron Emission Tomography (PET) imaging of neuorendocrine tumors are described. Specifically the present invention describes novel [18F]Fluoroethyltriazol-[Tyr3]Octreotate analogs; in particular those that target somatostatin receptors found on the cell surface of gastroenteropancreatic neuorendocrine tumors. The present invention also describes intermediate(s), precursor(s), pharmaceutical composition(s), methods of making, and methods of use of the novel radiotracer(s).

  描述了用于正电子发射断层扫描（PET）成像的新型放射性示踪剂。描述了用于正电子发射断层扫描（PET）成像神经内分泌肿瘤的新型放射性示踪剂。具体而言，本发明描述了新型[18F]氟乙基三唑-[Tyr3]奥曲肽类似物；特别是那些靶向胃肠胰神经内分泌肿瘤细胞表面上生长抑素受体的类似物。本发明还描述了中间体、前体、药物组合物、制备方法和新型放射性示踪剂的使用方法。
• Synthesis and in vitro evaluation of [18F]fluoroethyl triazole labelled [Tyr3]octreotate analogues using click chemistry
  作者：Lisa Iddon、Julius Leyton、Bård Indrevoll、Matthias Glaser、Edward G. Robins、Andrew J.T. George、Alan Cuthbertson、Sajinder Kaur Luthra、Eric O. Aboagye

  DOI：10.1016/j.bmcl.2011.03.016

  日期：2011.5

  A novel class of alkyne linked [Tyr(3)]octreotate analogues have been labelled by a copper catalysed azide-alkyne cycloaddition reaction (CuAAC) to form a 1,4-substituted triazole using the reagent [F-18]2-fluoroethyl azide. An unexpected variability in reactivity during the CuAAC reaction was observed for each alkyne analogue which has been investigated. Two lead alkyne linked [Tyr(3)]octreotate analogues, G-TOCA (3a) and beta AG-TOCA (5a) have been identified to be highly reactive in the click reaction showing complete conversion to the [F-18]2-fluoroethyl triazole linked [Tyr(3)]octreotate analogues FET-G-TOCA (3b) and FET-beta AG-TOCA (5b) under mild conditions and with short synthesis times (5 min at 20 degrees C). As well as ease of synthesis, in vitro binding to the pancreatic tumour AR42J cells showed that both FET-G-TOCA and FET-beta AG-TOCA have high affinity for the somatostatin receptor with IC50 of 4.0 +/- 1.4, and 1.6 +/- 0.2 nM, respectively. (C) 2011 Elsevier Ltd. All rights reserved.