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Electrochemical Flash Fluorination and Radiofluorination.

ABSTRACT: A new method for rapid late-stage fluorination using the cation pool technique is presented. Fluorination and no-carrier-added radiofluorination of methyl (phenylthio) acetate, methyl 2-(methylthio) acetate, and methyl 2-(ethylthio) acetate were performed. The carbocations formed through electrochemical oxidation were stabilized by using a divided electrochemical cell and 2,2,2-trifluoroethanol (TFE) as the solvent at -20 °C. At the end of electrolysis, either stable-isotope [19F]fluoride or no-carrier-added radioactive [18F]fluoride was added to the reaction mixture to form the fluorinated or radiofluorinated product.

SUBMITTER: Balandeh M

PROVIDER: S-EPMC6716519 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Electrochemical Flash Fluorination and Radiofluorination.

Balandeh Mehrdad M Rios Alejandra A Allison Nathanael N Shirazi Daniela D Gomez Adrian A Rambaran Laura L Holloway Travis T Sadeghi Saman S

ChemElectroChem 20180830 22

A new method for rapid late-stage fluorination using the cation pool technique is presented. Fluorination and no-carrier-added radiofluorination of methyl (phenylthio) acetate, methyl 2-(methylthio) acetate, and methyl 2-(ethylthio) acetate were performed. The carbocations formed through electrochemical oxidation were stabilized by using a divided electrochemical cell and 2,2,2-trifluoroethanol (TFE) as the solvent at -20 °C. At the end of electrolysis, either stable-isotope [<sup>19</sup>F]fluo ...[more]

PMID: 31475090

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Project description:Radiolabeling compounds with positron-emitting radionuclides often involves a time-consuming, customized process. Herein, we report a simple lyophilized kit formulation for labeling peptides with (18)F, based on the aluminum-fluoride procedure. The prototype kit contains IMP485, a NODA (1,4,7-triazacyclononane-1,4-diacetate)-MPAA (methyl phenylacetic acid)-di-HSG (histamine-succinyl-glycine) hapten-peptide, [NODA-MPAA-D-Lys(HSG)-D-Tyr-D-Lys(HSG)-NH(2)], used for pretargeting, but we also examined a similar kit formulation for a somatostatin-binding peptide [IMP466, NOTA-D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Throl] bearing a NOTA ligand to determine if the benefits of using a kit can be extended to other AlF-binding peptides. The NODA-MPAA ligand forms a single stable complex with (AlF)(2+) in high yields. In order to establish suitable conditions for a facile kit, the formulation was optimized for pH, peptide to Al(3+) ratio, bulking agent, radioprotectant, and the buffer. For optimal labeling, the kit was reconstituted with an aqueous solution of (18)F(-) and ethanol (1:1), heated at 100-110 °C for 15 min, and then simply and rapidly purified using one of two equally effective solid-phase extraction (SPE) methods. Al(18)F-IMP485 was isolated as a single isomer complex, in high yield (45-97%) and high specific activity (up to 223 GBq/?mol), within 20 min. The labeled product was stable in human serum at 37 °C for 4 h and in vivo, urine samples showed the intact product was eliminated. Tumor targeting of the Al(18)F-IMP485 in nude mice bearing human colon cancer xenografts pretargeted with an anti-CEACAM5 bispecific antibody showed very low uptake (0.06% ± 0.02 ID/g) in bone, further illustrating its stability. At 1 h, pretargeted animals had high Al(18)F-IMP485 tumor uptake (28.1% ± 4.5 ID/g), with ratios of 9 ± 4, 123 ± 38, 110 ± 43, and 120 ± 108 for kidney, liver, blood and bone, respectively. Tumor uptake remained high at 3 h postinjection, with increased tumor/nontumor ratios. The NOTA-somatostatin-binding peptide also was fluorinated with good yield and high specific activity in the same kit formulation. However, yields were somewhat lower than those achieved with IMP485 containing the NODA-MPAA ligand, likely reflecting this ligand's superior binding properties over the simple NOTA. These studies indicate that (18)F-labeled peptides can be reproducibly prepared as stable Al-F complexes with good radiochemical yield and high specific activity using a simple, one-step, lyophilized kit followed by a rapid purification by SPE that provides the (18)F-peptide ready for patient injection within 30 min.

Dataset Information

Electrochemical Flash Fluorination and Radiofluorination.

Publications

Electrochemical Flash Fluorination and Radiofluorination.

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