Ortho-Stabilized (18) F-Azido Click Agents and their Application in PET Imaging with Single-Stranded DNA Aptamers.

Abstract

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.

• Authors: Lu Wang, Orit Jacobson, Din Avdic, Benjamin H Rotstein, Ido D Weiss, Lee Collier, Xiaoyuan Chen, Neil Vasdev, Steven H Liang
• Journal: Angewandte Chemie (International ed. in English) (Angew Chem Int Ed Engl) Vol. 54 Issue 43 Pg. 12777-81 (Oct 19 2015) ISSN: 1521-3773 [Electronic] Germany
• PMID: 26308650 (Publication Type: Journal Article, Research Support, N.I.H., Intramural, Research Support, Non-U.S. Gov't)
• Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• 18F-Tr-Sgc8
• Aptamers, Nucleotide
• Azides
• Cell Adhesion Molecules
• DNA, Single-Stranded
• Fluorine Radioisotopes
• Radiopharmaceuticals
• PTK7 protein, human
• Receptor Protein-Tyrosine Kinases

Topics

• Animals
• Aptamers, Nucleotide (chemistry)
• Azides (chemistry)
• Cell Adhesion Molecules (analysis)
• Click Chemistry
• Colon (pathology)
• Colonic Neoplasms (diagnosis)
• DNA, Single-Stranded (chemistry)
• Female
• Fluorine Radioisotopes (chemistry)
• HCT116 Cells
• Humans
• Mice
• Positron-Emission Tomography (methods)
• Radiopharmaceuticals (chemistry)
• Receptor Protein-Tyrosine Kinases (analysis)