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

Research output: Contribution to journalArticle

28 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)3573-3577
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume18
Issue number12
DOIs
StatePublished - Jun 15 2008
Externally publishedYes

Fingerprint

Labeling
Apoptosis
Derivatives
Imaging techniques
Fluorine
Annexin A5
Cell membranes
Paclitaxel
Cytoplasm
Cells
Cell Membrane
Molecules
Neoplasms

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Synthesis, biological evaluation and radiochemical labeling of a dansylhydrazone derivative as a potential imaging agent for apoptosis. / Zeng, Wenbin; Yao, Min liang; Townsend, David; Kabalka, George; Wall, Jonathan; Le Puil, Michael; Biggerstaff, John; Miao, Weimin.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 18, No. 12, 15.06.2008, p. 3573-3577.

Research output: Contribution to journalArticle

Zeng, Wenbin ; Yao, Min liang ; Townsend, David ; Kabalka, George ; Wall, Jonathan ; Le Puil, Michael ; Biggerstaff, John ; Miao, Weimin. / Synthesis, biological evaluation and radiochemical labeling of a dansylhydrazone derivative as a potential imaging agent for apoptosis. In: Bioorganic and Medicinal Chemistry Letters. 2008 ; Vol. 18, No. 12. pp. 3573-3577.
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