2-[(1R,4S,10R,13S,16R,19S,25S)-10-[2-[2-[2-[2-[[2-(2-amino-2-oxoethoxy)acetyl]amino]ethoxy]ethoxy]ethoxy]ethylcarbamoyl]-13-benzyl-25-[3-(diaminomethylideneamino)propyl]-4-[4-[(6-(18F)fluoranylpyridine-3-carbonyl)amino]butyl]-3,6,12,15,18,21,24,27-octaoxo-8,29,30-trithia-2,5,11,14,17,20,23,26-octazabicyclo[14.11.4]hentriacontan-19-yl]acetic acid | 1207955-08-5

• 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-[(1R,4S,10R,13S,16R,19S,25S)-10-[2-[2-[2-[2-[[2-(2-amino-2-oxoethoxy)acetyl]amino]ethoxy]ethoxy]ethoxy]ethylcarbamoyl]-13-benzyl-25-[3-(diaminomethylideneamino)propyl]-4-[4-[(6-(18F)fluoranylpyridine-3-carbonyl)amino]butyl]-3,6,12,15,18,21,24,27-octaoxo-8,29,30-trithia-2,5,11,14,17,20,23,26-octazabicyclo[14.11.4]hentriacontan-19-yl]acetic acid
• CAS: 1207955-08-5
• 化学式: C₅₆H₈₁FN₁₆O₁₈S₃
• 分子量: 1380.55
• InChiKey: PAXQWIPHGQQBNM-NTGMVHMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  94
• 可旋转键数：
  31
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  591
• 氢给体数：
  15
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  NC-100717 、 6-[18F]fluoronicotinic acid 2,3,5,6-tetrafluorophenyl ester 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 1.42h， 以22.5%的产率得到2-[(1R,4S,10R,13S,16R,19S,25S)-10-[2-[2-[2-[2-[[2-(2-amino-2-oxoethoxy)acetyl]amino]ethoxy]ethoxy]ethoxy]ethylcarbamoyl]-13-benzyl-25-[3-(diaminomethylideneamino)propyl]-4-[4-[(6-(18F)fluoranylpyridine-3-carbonyl)amino]butyl]-3,6,12,15,18,21,24,27-octaoxo-8,29,30-trithia-2,5,11,14,17,20,23,26-octazabicyclo[14.11.4]hentriacontan-19-yl]acetic acid
  参考文献：
  名称：

  One Step Radiosynthesis of 6-[¹⁸F]Fluoronicotinic Acid 2,3,5,6-Tetrafluorophenyl Ester ([¹⁸F]F-Py-TFP): A New Prosthetic Group for Efficient Labeling of Biomolecules with Fluorine-18

  摘要：

  The labeling of biomolecules for positron emission tomography (PET) with no-carrier-added fluorine-18 is almost exclusively accomplished using prosthetic groups in a two step procedure. The inherent complexity of the process renders full automation a challenge and leads to protracted synthesis times. Here we describe a new F-18-labeled prosthetic group based on nicotinic acid tetrafluorophenyl ester. Reaction of [F-18]fluoride at 40 degrees C with the trimethylammonium precursor afforded 6-[F-18]fluoronicotinic acid tetrafluorophenyl ester ([F-18]F-Py-TFP) directly in 60-70% yield. [F-18]F-Py-TFP was conveniently purified by Sep-Pak cartridge prior to incubation with a peptide containing the RGD sequence. The desired conjugate was formed rapidly and in good yields. An in vitro receptor-binding assay for the integrin alpha(v)beta(3) was established to explore competition with peptide and peptidomimetic prepared from F-Py-TFP with I-125-echistatin. The nonradioactive conjugates were found to possess high binding affinities with calculated K-i values in the low nanomolar range.

  DOI：

  10.1021/jm9015813

文献信息

• One Step Radiosynthesis of 6-[¹⁸F]Fluoronicotinic Acid 2,3,5,6-Tetrafluorophenyl Ester ([¹⁸F]F-Py-TFP): A New Prosthetic Group for Efficient Labeling of Biomolecules with Fluorine-18
  作者：Dag E. Olberg、Joseph M. Arukwe、David Grace、Ole K. Hjelstuen、Magne Solbakken、Grete M. Kindberg、Alan Cuthbertson

  DOI：10.1021/jm9015813

  日期：2010.2.25

  The labeling of biomolecules for positron emission tomography (PET) with no-carrier-added fluorine-18 is almost exclusively accomplished using prosthetic groups in a two step procedure. The inherent complexity of the process renders full automation a challenge and leads to protracted synthesis times. Here we describe a new F-18-labeled prosthetic group based on nicotinic acid tetrafluorophenyl ester. Reaction of [F-18]fluoride at 40 degrees C with the trimethylammonium precursor afforded 6-[F-18]fluoronicotinic acid tetrafluorophenyl ester ([F-18]F-Py-TFP) directly in 60-70% yield. [F-18]F-Py-TFP was conveniently purified by Sep-Pak cartridge prior to incubation with a peptide containing the RGD sequence. The desired conjugate was formed rapidly and in good yields. An in vitro receptor-binding assay for the integrin alpha(v)beta(3) was established to explore competition with peptide and peptidomimetic prepared from F-Py-TFP with I-125-echistatin. The nonradioactive conjugates were found to possess high binding affinities with calculated K-i values in the low nanomolar range.