title: 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: Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, Boston, MA 02114 (USA).
authors: Lu
authors: L
authors: Wang
authors: Laboratory of Molecular Imaging and Nanomedicine, National Institute of Biomedical Imaging and Bioengineering, National Institutes of Health, Bethesda, MD 20892 (USA).
authors: Orit
authors: O
authors: Jacobson
authors: Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, Boston, MA 02114 (USA).
authors: Din
authors: D
authors: Avdic
authors: Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, Boston, MA 02114 (USA).
authors: Benjamin H
authors: BH
authors: Rotstein
authors: Laboratory of Molecular Immunology, National Institute of Allergy and Infectious Diseases, National Institutes of Health, Bethesda, MD 20892 (USA).
authors: Ido D
authors: ID
authors: Weiss
authors: Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, Boston, MA 02114 (USA).
authors: Lee
authors: L
authors: Collier
authors: Laboratory of Molecular Imaging and Nanomedicine, National Institute of Biomedical Imaging and Bioengineering, National Institutes of Health, Bethesda, MD 20892 (USA). shawn.chen@nih.gov.
authors: Xiaoyuan
authors: X
authors: Chen
authors: Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, Boston, MA 02114 (USA). vasdev.neil@mgh.harvard.edu.
authors: Neil
authors: N
authors: Vasdev
authors: Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, Boston, MA 02114 (USA). liang.steven@mgh.harvard.edu.
authors: Steven H
authors: SH
authors: Liang
mesh_terms: D000818:Animals; D052157:Aptamers, Nucleotide / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D015815:Cell Adhesion Molecules / Q000032:analysis*; D057930:Click Chemistry; D003106:Colon / Q000473:pathology*; D003110:Colonic Neoplasms / Q000175:diagnosis*; D004277:DNA, Single-Stranded / Q000737:chemistry*; D005260:Female; D005462:Fluorine Radioisotopes / Q000737:chemistry; D045325:HCT116 Cells; D006801:Humans; D051379:Mice; D049268:Positron-Emission Tomography / Q000379:methods*; D019275:Radiopharmaceuticals / Q000737:chemistry; D020794:Receptor Protein-Tyrosine Kinases / Q000032:analysis*
chemical_list: C000604953:18F-Tr-Sgc8; D052157:Aptamers, Nucleotide; D001386:Azides; D015815:Cell Adhesion Molecules; D004277:DNA, Single-Stranded; D005462:Fluorine Radioisotopes; D019275:Radiopharmaceuticals; C096905:PTK7 protein, human; D020794:Receptor Protein-Tyrosine Kinases
keywords: PET imaging; aptamers; bioconjugation; fluorine; radiopharmaceuticals