Synthesis, biological evaluation and radiochemical labeling of a dansylhydrazone derivative as a potential imaging agent for apoptosis

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• 作者：Wenbin Zeng ; Min-liang Yao ; David Townsend ; George Kabalka ; Jonathan Wall ; Michael Le Puil ; John Biggerstaff ; Weimin Miao
• 关键词：Dansylhydrazone ; Apoptosis detection ; Annexin V ; Fluorescent imaging ; Fluorine-18 labelling ; Potential PET tracer
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2008
• 出版时间：15 June 2008
• 年：2008
• 卷：18
• 期：12
• 页码：3573-3577
• 全文大小：1432 K

文摘

To develop a small molecule-based tracer for in vivo apoptosis imaging, dansylhydrazone (DFNSH) was synthesized in 93 % yield in less than 30 min. The biological evaluation showed that DFNSH selectively binds to paclitaxel-induced apoptotic cancer cells. The high magnification fluorescent images demonstrate that DFNSH is localized within the cytoplasm of cells that bound Alexa^® 488 labeled annexin V on the plasma membrane. [¹⁸F]-DFNSH ([¹⁸F]-3) was synthesized and isolated in 50–60 % radiochemical yields, based on [K/K₂₂₂]¹⁸F, with a synthesis time of 50 min (EOB). The straightforward preparation of fluorine-18 labeled 3 makes it a promising tracer for PET imaging of apoptosis.