Abstract
Here we report the 18F labeling of a prostate specific membrane antigen (PSMA) ligand via a strain promoted oxa-dibenzocyclooctyne (ODIBO)- or bicyclo[6.1.0]nonyne (BCN)-azide reaction. Although ODIBO reacts with azide 20 fold faster than BCN, in vivo PET imaging suggests that 18F-BCN-azide-PSMA demonstrated much higher tumor uptake and a much higher tumor to background contrast.
MeSH terms
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Alkynes / chemistry*
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Animals
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Antigens, Surface / metabolism*
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Azides / chemistry*
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Bridged Bicyclo Compounds / chemical synthesis
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Bridged Bicyclo Compounds / chemistry
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Bridged Bicyclo Compounds / metabolism*
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Bridged Bicyclo Compounds / pharmacology
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Cyclooctanes / chemical synthesis
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Cyclooctanes / chemistry
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Cyclooctanes / metabolism*
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Cyclooctanes / pharmacology
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Dipeptides / metabolism
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Fluorine Radioisotopes
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Glutamate Carboxypeptidase II / metabolism*
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Heterocyclic Compounds, 1-Ring / metabolism
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Humans
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Hydrocarbons, Fluorinated / chemical synthesis
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Hydrocarbons, Fluorinated / chemistry
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Hydrocarbons, Fluorinated / metabolism*
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Hydrocarbons, Fluorinated / pharmacology
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Hydrophobic and Hydrophilic Interactions
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Kinetics
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Ligands
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Male
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Mice
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Positron-Emission Tomography
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Prostate-Specific Antigen
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Prostatic Neoplasms / diagnostic imaging
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Protein Binding
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Radiopharmaceuticals / chemical synthesis
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Radiopharmaceuticals / chemistry
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Radiopharmaceuticals / metabolism*
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Radiopharmaceuticals / pharmacology
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Xenograft Model Antitumor Assays
Substances
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Alkynes
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Antigens, Surface
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Azides
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Bridged Bicyclo Compounds
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Cyclooctanes
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Dipeptides
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Fluorine Radioisotopes
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Heterocyclic Compounds, 1-Ring
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Hydrocarbons, Fluorinated
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Ligands
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PSMA-617
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Radiopharmaceuticals
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bicyclo(6.1.0)nonyne
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FOLH1 protein, human
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Glutamate Carboxypeptidase II
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Prostate-Specific Antigen