Dataset Information

Radiofluorination of a NHC-PF5 adduct: toward new probes for 18F PET imaging.

ABSTRACT: The radiofluorination of N-heterocyclic carbene (NHC) phosphorus(v) fluoride adducts has been investigated. The results show that the IMe-PF5 derivative (IMe = 1,3-dimethylimidazol-2-ylidene) undergoes a Lewis acid promoted 18F-19F isotopic exchange. The resulting radiofluorinated probe is remarkably resistant to hydrolysis both in vitro as well as in vivo.

SUBMITTER: Vabre B

PROVIDER: S-EPMC5615223 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Radiofluorination of a NHC-PF5 adduct: toward new probes for 18F PET imaging.

Vabre Boris B Chansaenpak Kantapat K Wang Mengzhe M Wang Hui H Li Zibo Z Li Zibo Z Gabbaï François P FP

Chemical communications (Cambridge, England) 20170721 62

The radiofluorination of N-heterocyclic carbene (NHC) phosphorus(v) fluoride adducts has been investigated. The results show that the IMe-PF5 derivative (IMe = 1,3-dimethylimidazol-2-ylidene) undergoes a Lewis acid promoted 18F-19F isotopic exchange. The resulting radiofluorinated probe is remarkably resistant to hydrolysis both in vitro as well as in vivo. ...[more]

PMID: 28731482

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Project description:IntroductionOur previous work demonstrated that the 99mTc renal tracer, 99mTc(CO)3(FEDA) (99mTc-1), has a rapid clearance comparable in rats to that of 131I-OIH, the radioactive gold standard for the measurement of effective renal plasma flow. The uncharged fluoroethyl pendant group of 99mTc-1 provides a route to the synthesis of a structurally analogous rhenium-tricarbonyl 18F renal imaging agent, Re(CO)3([18F]FEDA) (18F-1). Our goal was to develop an efficient one-step method for the preparation of 18F-1 and to compare its pharmacokinetic properties with those of 131I-OIH in rats.Methods18F-1 was prepared by the nucleophilic 18F-fluorination of its tosyl precursor. The labeled compound was isolated by HPLC and subsequently evaluated in Sprague-Dawley rats using 131I-OIH as an internal control and by dynamic PET/CT imaging. Plasma protein binding (PPB) and erythrocyte uptake (RCB) were determined and the urine was analyzed for metabolites.Results18F-1 was efficiently prepared as a single species with high radiochemical purity (>99%) and it displayed high radiochemical stability in vitro and in vivo. PPB was 87% and RCB was 21%. Biodistribution studies confirmed rapid renal extraction and high specificity for renal excretion, comparable to that of 131I-OIH, with minimal hepatic/gastrointestinal elimination. The activity in the urine, as a percentage of 131I-OIH, was 92% and 95% at 10 and 60 min, respectively. All other organs (heart, spleen, lungs) showed a negligible tracer uptake (<0.4% ID). Dynamic microPET/CT imaging demonstrated rapid transit of 18F-1 through the kidneys and into the bladder; there was no demonstrable activity in bone verifying the absence of free [18F]fluoride.Conclusions18F-1 exhibited a high specificity for the kidney, rapid renal excretion comparable to that of 131I-OIH and high in vivo radiochemical stability. Not only is 18F-1 a promising PET renal tracer, but it provides a route to the development of a pair of analogous 18F/99mTc renal imaging agents with almost identical structures and comparable pharmacokinetic properties. These promising in vivo results warrant subsequent evaluation in humans.

Dataset Information

Radiofluorination of a NHC-PF5 adduct: toward new probes for 18F PET imaging.

Publications

Radiofluorination of a NHC-PF<sub>5</sub> adduct: toward new probes for <sup>18</sup>F PET imaging.

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