Synthesis, biological evaluation and radiochemical labeling of a dansylhydrazone derivative as a potential imaging agent for apoptosis.
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.
Zeng
Wenbin
W
Molecular Imaging and Translational Research Program, University of Tennessee, Graduate School of Medicine, Box 93, 1924 Alcoa Highway, Knoxville, TN 37920, USA.
Yao
Min-Liang
ML
Townsend
David
D
Kabalka
George
G
Wall
Jonathan
J
Le Puil
Michael
M
Biggerstaff
John
J
Miao
Weimin
W
D017209:Apoptosis; D001665:Binding Sites; D001943:Breast Neoplasms / Q000378:metabolism* / Q000473:pathology; D045744:Cell Line, Tumor; D003287:Contrast Media / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D003593:Cytoplasm / Q000737:chemistry / Q000378:metabolism; D003619:Dansyl Compounds / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D005260:Female; D005462:Fluorine Radioisotopes; D006801:Humans; D006834:Hydrazines / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D007553:Isotope Labeling; D015394:Molecular Structure; D008970:Molecular Weight; D049268:Positron-Emission Tomography / Q000379:methods; D019275:Radiopharmaceuticals / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
D003287:Contrast Media; D003619:Dansyl Compounds; D005462:Fluorine Radioisotopes; D006834:Hydrazines; D019275:Radiopharmaceuticals; C027913:dansyl hydrazine