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Ortho ‐Stabilized 18 F‐Azido Click Agents and their Application in PET Imaging with Single‐Stranded DNA Aptamers
Author(s) -
Wang Lu,
Jacobson Orit,
Avdic Din,
Rotstein Benjamin H.,
Weiss Ido D.,
Collier Lee,
Chen Xiaoyuan,
Vasdev Neil,
Liang Steven H.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505927
Subject(s) - bioconjugation , click chemistry , aptamer , cycloaddition , biomolecule , chemistry , combinatorial chemistry , bioorthogonal chemistry , positron emission tomography , dna , biodistribution , nanotechnology , organic chemistry , biochemistry , materials science , catalysis , in vitro , medicine , genetics , radiology , biology
Azido 18 F‐arenes are important and versatile building blocks for the radiolabeling of biomolecules via Huisgen cycloaddition (“click chemistry”) for positron emission tomography (PET). However, routine access to such clickable agents is challenged by inefficient and/or poorly defined multistep radiochemical approaches. A high‐yielding direct radiofluorination for azido 18 F‐arenes was achieved through the development of an ortho ‐oxygen‐stabilized iodonium derivative (OID). This OID strategy addresses an unmet need for a reliable azido 18 F‐arene clickable agent for bioconjugation reactions. A ssDNA aptamer was radiolabeled with this agent and visualized in a xenograft mouse model of human colon cancer by PET, which demonstrates that this OID approach is a convenient and highly efficient way of labeling and tracking biomolecules.