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(11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

ABSTRACT: 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.

SUBMITTER: Rotstein BH

PROVIDER: S-EPMC5000859 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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(11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

Rotstein Benjamin H BH Liang Steven H SH Placzek Michael S MS Hooker Jacob M JM Gee Antony D AD Dollé Frédéric F Wilson Alan A AA Vasdev Neil N

Chemical Society reviews 20160801 17

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, sm ...[more]

PMID: 27276357

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Dataset Information

(11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

Publications

(11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

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