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    New Lyophilized Kit for Rapid Radiofluorination of Peptides
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    Immunomedics, Inc., Morris Plains, New Jersey
    Center for Molecular Medicine and Immunology and the Garden State Cancer Center, Morris Plains, New Jersey
    *(W.J.M.) Immunomedics, Inc., 300 The American Road, Morris Plains, NJ 07950. Tel: 973-605-8200 ext. 233. Fax: 973-605-1340. E-mail: [email protected]. (D.M.G.) Center for Molecular Medicine and Immunology, 300 The American Road, Morris Plains, NJ 07950. E-mail: [email protected]
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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2012, 23, 3, 538–547
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    https://doi.org/10.1021/bc200608e
    Published January 25, 2012
    Copyright © 2012 American Chemical Society

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    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 18F, 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)-NH2], 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 Al3+ ratio, bulking agent, radioprotectant, and the buffer. For optimal labeling, the kit was reconstituted with an aqueous solution of 18F 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. Al18F-IMP485 was isolated as a single isomer complex, in high yield (45–97%) and high specific activity (up to 223 GBq/μmol), 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 Al18F-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 Al18F-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 18F-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 18F-peptide ready for patient injection within 30 min.

    Copyright © 2012 American Chemical Society

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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2012, 23, 3, 538–547
    Click to copy citationCitation copied!
    https://doi.org/10.1021/bc200608e
    Published January 25, 2012
    Copyright © 2012 American Chemical Society

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