6-deoxy-6-fluoro-α-D-fructose | 1186468-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-6-fluoro-α-D-fructose
• 英文别名: (2S,3S,4S,5S)-5-(fluoromethyl)-2-(hydroxymethyl)oxolane-2,3,4-triol
• CAS: 1186468-88-1
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: ODWGBJLPHMOVNK-ZXXMMSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 1,3,4-tri-O-acetyl-6-deoxy-6-fluoro-D-fructofuranoside 在 sodium methylate 、 盐酸 作用下， 以 甲醇 、 1,4-二氧六环 、 水 为溶剂， 生成 6-deoxy-6-fluoro-α-D-fructose 、 6-deoxy-6-fluoro-β-D-fructose
  参考文献：
  名称：

  Synthesis and characterization of 6-deoxy-6-fluoro-d-fructose as a potential compound for imaging breast cancer with PET

  摘要：

  FDG-based imaging with positron emission tomography (PET) has been widely used in the detection of cancer, but has not reached its full potential. In breast cancer, the glucose/fructose transporter GLUT2 and the fructose transporter GLUT5 are known to be overexpressed in transformed tissues, implicating that a fructose-based analogue would be a useful target for the improved imaging of breast cancer. We have successfully synthesized the fluorinated fructose compound, 6-deoxy-6-fluoro-D-fructose (6FDF) and examined its potential for transport and accumulation in breast cancer cells. Expression analysis of GLUT isoforms was performed on two GLUT5 expressing breast cancer cell lines using western blotting and immunocytochemistry. Uptake and inhibition studies were undertaken using [14C]- labelled hexoses. Transport inhibition studies showed dose dependent inhibition of fructose transport in both cell lines by the newly synthesized 6-deoxy-6-fluoro-D-fructose (6FDF). Also, near linear uptake over time of [14C]labelled 6FDF was observed in both cell lines. It appears that 6FDF may have great promise for use in in vivo PET imaging of breast cancer. Ongoing work will confirm the efficacy of this compound in imaging in mouse models. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.034