Bioorganic & Medicinal Chemistry Letters 2008-06-15

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

Wenbin Zeng, Min-Liang Yao, David Townsend, George Kabalka, Jonathan Wall, Michael Le Puil, John Biggerstaff, Weimin Miao

Index: Bioorg. Med. Chem. Lett. 18(12) , 3573-7, (2008)

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Abstract

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. [(18)F]-DFNSH ([(18)F]-3) was synthesized and isolated in 50-60% radiochemical yields, based on [K/K(222)](18)F, 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.