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Synthesis of a 2-nitroimidazole derivative N-(4-[F]fluorobenzyl)-2-(2-nitro-1H-imidazol-1-yl)-acetamide ([ F]FBNA) as PET radiotracer for imaging tumor hypoxia. | LitMetric
Background : Tissue hypoxia is a pathological condition characterized by reducing oxygen supply. Hypoxia is a hallmark of tumor environment and is commonly observed in many solid tumors. Non-invasive imaging techniques like positron emission tomography (PET) are at the forefront of detecting and monitoring tissue hypoxia changes in vivo.Results : We have developed a novel F-labeled radiotracer for hypoxia PET imaging based on cytotoxic agent benznidazole. Radiotracer N-(4-[F]fluorobenzyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide ([F]FBNA) was synthesized through acylation chemistry with readily available 4-[F]fluorobenzyl amine. Radiotracer [F]FBNA was obtained in good radiochemical yields (47.4 ± 5.3%) and high radiochemical purity (> 95%). The total synthesis time was 100 min, including HPLC purification and the molar activity was greater than 40 GBq/µmol. Radiotracer [F]FBNA was stable in saline and mouse serum for 6 h. [F]FBNA partition coefficient (logP = 1.05) was found to be more lipophilic than [F]EF-5 (logP = 0.75), [F]FMISO (logP = 0.4) and [F]FAZA (logP = - 0.4). In vitro studies showed that [F]FBNA accumulates in gastric cancer cell lines AGS and MKN45 under hypoxic conditions.Conclusions : Hence, [F]FBNA represents a novel and easy-to-prepare PET radioligand for imaging hypoxia.
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