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Rapid one-pot radiosynthesis of [carbonyl-11C]formamides from primary amines and [11C]CO2.


ABSTRACT:

Background

Formamides are common motifs of biologically-active compounds (e.g. formylated peptides) and are frequently employed as intermediates to yield a number of other functional groups. A rapid, simple and reliable route to [carbonyl-11C]formamides would enable access to this important class of compounds as in vivo PET imaging agents.

Results

A novel radiolabelling strategy for the synthesis of carbon-11 radiolabelled formamides ([11C]formamides) is presented. The reaction proceeded with the conversion of a primary amine to the corresponding [11C]isocyanate using cyclotron-produced [11C]CO2, a phosphazene base (2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine, BEMP) and phosphoryl chloride (POCl3). The [11C]isocyanate was subsequently reduced to [11C]formamide using sodium borohydride (NaBH4). [11C]Benzyl formamide was obtained with a radiochemical yield (RCY) of 80% in 15?min from end of cyclotron target bombardment and with an activity yield of 12%. This novel method was applied to the radiolabeling of aromatic and aliphatic formamides and the chemotactic amino acid [11C]formyl methionine (RCY?=?48%).

Conclusions

This study demonstrates the feasibility of 11C-formylation of primary amines with the primary synthon [11C]CO2. The reactivity is proportional to the nucleophilicity of the precursor amine. This novel method can be used for the production of biomolecules containing a radiolabelled formyl group.

SUBMITTER: Luzi F 

PROVIDER: S-EPMC7462944 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Publications

Rapid one-pot radiosynthesis of [carbonyl-<sup>11</sup>C]formamides from primary amines and [<sup>11</sup>C]CO<sub>2</sub>.

Luzi Federico F   Gee Antony D AD   Bongarzone Salvatore S  

EJNMMI radiopharmacy and chemistry 20200901 1


<h4>Background</h4>Formamides are common motifs of biologically-active compounds (e.g. formylated peptides) and are frequently employed as intermediates to yield a number of other functional groups. A rapid, simple and reliable route to [carbonyl-<sup>11</sup>C]formamides would enable access to this important class of compounds as in vivo PET imaging agents.<h4>Results</h4>A novel radiolabelling strategy for the synthesis of carbon-11 radiolabelled formamides ([<sup>11</sup>C]formamides) is pres  ...[more]

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