Synthesis of 18 F-radiolabeled organophosphine fluorides for thiol-chemoselective peptide conjugation.,Journal of Labelled Compounds and Radiopharmaceuticals

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Synthesis of 18 F-radiolabeled organophosphine fluorides for thiol-chemoselective peptide conjugation.
Journal of Labelled Compounds and Radiopharmaceuticals ( IF 0.9 ) Pub Date : 2020-09-19 , DOI: 10.1002/jlcr.3882
Huanglan Zhuang ₁ , Zhide Guo ₁ , Rongqiang Zhuang ₁ , Xianzhong Zhang ₂

Affiliation

Two ¹⁸F‐radiolabeled organofluorophosphine fluorides ([¹⁸F]4 and [¹⁸F]7) for chemoselective thiol‐conjugation were designed and synthesized via ¹⁸F–¹⁹F isotopic exchange reaction. This simple and rapid radiofluorination produced both ¹⁸F‐radiolabeled fluorides in excellent radiochemical yields (>94%) and radiochemical purity. The optimal reaction conditions are 0.05‐mg substrate, 0.69 mg of potassium carbonate, and dried [¹⁸F]F⁻ were mixed in 100‐μl anhydrous acetonitrile at room temperature for 5 min. Both of [¹⁸F]4 and [¹⁸F]7 showed specificity for thiol‐conjugation with cysteine and have been used in the radiosynthesis of c (RGDfC). The [¹⁸F]7 with an adamantanyl‐hindered substituent displayed superior in vitro and in vivo stability.

中文翻译：

用于硫醇-化学选择性肽缀合的 18 F-放射性标记有机膦氟化物的合成。

通过¹⁸ F- ¹⁹ F 同位素交换反应设计并合成了两种用于化学选择性硫醇缀合的¹⁸ F放射性标记有机氟氟化膦（[ ¹⁸ F] 4和 [ ¹⁸ F] 7 ）。这种简单而快速的放射性氟化反应产生了¹⁸ F 放射性标记的氟化物，具有优异的放射化学收率 (>94%) 和放射化学纯度。最佳反应条件为0.05 mg底物、0.69 mg碳酸钾和干燥的[ ¹⁸ F]F ^-在100 μl无水乙腈中室温混合5 min。 [ ¹⁸ F] 4和 [ ¹⁸ F] 7均表现出硫醇与半胱氨酸缀合的特异性，并已用于 c (RGDfC) 的放射合成。具有金刚烷基位阻取代基的[ ¹⁸ F] 7显示出优异的体外和体内稳定性。

更新日期：2020-09-19

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