(11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.
The positron-emitting radionuclide carbon-11 ((11)C, t1/2 = 20.3 min) possesses the unique potential for radiolabeling of any biological, naturally occurring, or synthetic organic molecule for in vivo positron emission tomography (PET) imaging. Carbon-11 is most often incorporated into small molecules by methylation of alcohol, thiol, amine or carboxylic acid precursors using [(11)C]methyl iodide or [(11)C]methyl triflate (generated from [(11)C]carbon dioxide or [(11)C]methane). Consequently, small molecules that lack an easily substituted (11)C-methyl group are often considered to have non-obvious strategies for radiolabeling and require a more customized approach. [(11)C]Carbon dioxide itself, [(11)C]carbon monoxide, [(11)C]cyanide, and [(11)C]phosgene represent alternative reactants to enable (11)C-carbonylation. Methodologies developed for preparation of (11)C-carbonyl groups have had a tremendous impact on the development of novel PET tracers and provided key tools for clinical research. (11)C-Carbonyl radiopharmaceuticals based on labeled carboxylic acids, amides, carbamates and ureas now account for a substantial number of important imaging agents that have seen translation to higher species and clinical research of previously inaccessible targets, which is a testament to the creativity, utility and practicality of the underlying radiochemistry.
Massachusetts General Hospital, Harvard Medical School, Boston, USA. vasdev.neil@mgh.harvard.edu.
Benjamin H
BH
Rotstein
Massachusetts General Hospital, Harvard Medical School, Boston, USA. vasdev.neil@mgh.harvard.edu.
Steven H
SH
Liang
Athinoula A. Martinos Center for Biomedical Imaging, MGH, HMS, Charlestown, USA and McLean Hospital, Belmont, USA.
Michael S
MS
Placzek
Athinoula A. Martinos Center for Biomedical Imaging, MGH, HMS, Charlestown, USA.
Jacob M
JM
Hooker
King's College London, London, UK.
Antony D
AD
Gee
CEA - Institut d'imagerie biomédicale, Service hospitalier Frédéric Joliot, Université Paris-Saclay, Orsay, France.
Frédéric
F
Dollé
Centre for Addiction and Mental Health, Toronto, Canada.
Alan A
AA
Wilson
Massachusetts General Hospital, Harvard Medical School, Boston, USA. vasdev.neil@mgh.harvard.edu.
Neil
N
Vasdev
D002250:Carbon Radioisotopes / Q000737:chemistry*; D003606:Dacarbazine / Q000031:analogs & derivatives / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D049268:Positron-Emission Tomography / Q000295:instrumentation*; D019275:Radiopharmaceuticals / Q000737:chemistry*; D000077204:Temozolomide
D002250:Carbon Radioisotopes; C000615233:Carbon-11; D019275:Radiopharmaceuticals; D003606:Dacarbazine; D010100:Oxygen; D000077204:Temozolomide