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

Wenbin Zeng, University of Tennessee - Knoxville
Min-liang Yao, University of Tennessee - Knoxville
David Townsend, University of Tennessee - Knoxville
George Kabalka, University of Tennessee - Knoxville
Jonathan Wall, University of Tennessee - Knoxville
Michael Le Puil, University of Tennessee - Knoxville
John Biggerstaff, University of Tennessee - Knoxville
Weimin Miao, University of Tennessee - Knoxville

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. [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. DOI: http://dx.doi.org/10.1016/j.bmcl.2008.05.002.