[18F]Fluoromisonidazole ([18F]FMISO) and 1-[18F]fluoro-3-((2-((1E,3E)-4-(6-(methylamino)pyridine-3-yl)buta-1,3-dien-1-yl)benzo[d]thiazol-6-yl)oxy)propan-2-ol ([18F]PM-PBB3 or [18F]APN-1607) are clinically used radiotracers for imaging hypoxia and tau pathology, respectively. Both radiotracers were produced by direct 18F-fluorination using the corresponding tosylate precursors 1 or 2 and [18F]F−, followed by the removal of protecting groups. In this study, we synthesized [18F]FMISO and [18F]PM-PBB3 by 18F-fluoroalkylation using [18F]epifluorohydrin ([18F]5) for clinical applications. First, [18F]5 was synthesized by the reaction of 1,2-epoxypropyl tosylate (8) with [18F]F− and was purified by distillation. Subsequently, [18F]5 was reacted with 2-nitroimidazole (6) or PBB3 (7) as a precursor for 18F-labeling, and each reaction mixture was purified by preparative high-performance liquid chromatography and formulated to obtain the [18F]FMISO or [18F]PM-PBB3 injection. All synthetic sequences were performed using an automated 18F-labeling synthesizer. The obtained [18F]FMISO showed sufficient radioactivity (0.83 ± 0.20 GBq at the end of synthesis (EOS); n = 8) with appropriate radiochemical yield based on [18F]F− (26 ± 7.5 % at EOS, decay-corrected; n = 8). The obtained [18F]PM-PBB3 also showed sufficient radioactivity (0.79 ± 0.10 GBq at EOS; n = 11) with appropriate radiochemical yield based on [18F]F− (16 ± 3.2 % at EOS, decay-corrected; n = 11). Both [18F]FMISO and [18F]PM-PBB3 injections were successfully synthesized with sufficient radioactivity by 18F-fluoroalkylation using [18F]5.

中文翻译：

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两种含有 3-氟-2-羟丙基部分、[ ¹⁸ F]FMISO 和 [ ¹⁸ F]PM-PBB3 的¹⁸ F 标记示踪剂的自动放射合成，通过 [ ¹⁸ F] 表氟醇

[18F]Fluoromisonidazole ([18F]FMISO) 和 1-[18F]fluoro-3-((2-((1E,3E)-4-(6-(methylamino)pyridine-3-yl)buta-1,3) -dien-1-yl)benzo[d]thiazol-6-yl)oxy)propan-2-ol ([18F]PM-PBB3 或 [18F]APN-1607) 是临床上用于成像缺氧和 tau 病理学的放射性示踪剂，分别。两种放射性示踪剂都是通过使用相应的甲苯磺酸盐前体 1 或 2 和 [18F]F- 直接 18F-氟化，然后去除保护基团而产生的。在这项研究中，我们使用 [18F] 表氟醇 ([18F]5) 通过 18F-氟烷基化合成了 [18F]FMISO 和 [18F]PM-PBB3，用于临床应用。首先，[18F]5 是通过甲苯磺酸 1,2-环氧丙酯 (8) 与 [18F]F- 反应合成的，并通过蒸馏纯化。随后，[18F]5 与作为 18F 标记前体的 2-硝基咪唑 (6) 或 PBB3 (7) 反应，各反应混合物经制备型高效液相色谱纯化，配制成[18F]FMISO或[18F]PM-PBB3注射液。所有合成序列均使用自动 18F 标记合成仪进行。获得的 [18F]FMISO 显示出足够的放射性（合成结束时 (EOS) 为 0.83 ± 0.20 GBq；n = 8），具有基于 [18F]F− 的适当放射化学产率（EOS 处为 26 ± 7.5 %，衰减校正； n = 8）。获得的 [18F]PM-PBB3 还显示出足够的放射性（EOS 处为 0.79 ± 0.10 GBq；n = 11）以及基于 [18F]F− 的适当放射化学产率（EOS 处为 16 ± 3.2 %，衰减校正；n = 11 ）。[18F]FMISO 和 [18F]PM-PBB3 注射液均通过使用 [18F]5 的 18F-氟烷基化成功合成，具有足够的放射性。