cyclo-[Nal-Gly-(D-Tyr)-Orn(PEG2-O-N=CH-4-NMe2-Ph)-Arg], Nal = 3-(naphthalen-2-yl)alaninoyl | 1361405-55-1

• 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: cyclo-[Nal-Gly-(D-Tyr)-Orn(PEG2-O-N=CH-4-NMe2-Ph)-Arg], Nal = 3-(naphthalen-2-yl)alaninoyl
• CAS: 1361405-55-1
• 化学式: C₅₂H₆₈N₁₂O₁₁
• 分子量: 1037.19
• InChiKey: WUAFSCXYBZYILS-LNYMGSRYSA-N

反应信息

• 作为产物：
  描述：

  cyclo-[Nal-Gly-(D-Tyr)-Orn(PEG2-O-NH2)-Arg], Nal = 3-(naphthalen-2-yl)alaninoyl 、 4-trimethylammoniumbenzaldehyde triflate 在 potassium [¹⁸F]fluoride 、 potassium hydrogencarbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 甲酸铵 作用下， 以 二甲基亚砜 、 甲醇 为溶剂， 反应 0.33h， 生成 cyclo-[Nal-Gly-(D-Tyr)-Orn(PEG2-O-N=CH-4-NMe2-Ph)-Arg], Nal = 3-(naphthalen-2-yl)alaninoyl 、 cyclo-[Nal-Gly-(D-Tyr)-Orn(PEG2-O-N=CH-4-(18)F-Ph)-Arg], Nal = 3-(naphthalen-2-yl)alaninoyl
  参考文献：
  名称：

  18F-labelling of a cyclic pentapeptide inhibitor of the chemokine receptor CXCR4

  摘要：

  The chemokine receptor CXCR4 is overexpressed in a variety of cancers including breast, prostate and lung cancer. Expression is also associated with invasion and metastasis. The possibility to image and quantify CXCR4 expression in vivo would be a valuable tool in the clinic to aid treatment regimens and to potentially understand the underlying biology of metastasis. Herein we describe the synthesis and the radiolabelling of an F-18-labelled cyclic pentapeptide, [F-18]CCIC-0007 designed to bind to the extracellular domains of CXCR4. Radiolabelling was performed via conjugation of [F-18]fluorobenzaldehyde with an aminooxy functionalised cyclopentapeptide. Typically, starting with 1.10 GBq (30 mCi) of aqueous [F-18]fluoride, 105 MBq (2.85 mCi) of the formulated tracer was obtained within 2.5 h (23 +/- 8% dc rcy, 8% EOS yield). Tissue pharmacokinetic studies in mice demonstrated rapid blood clearance, together with biliary and renal elimination. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.11.003