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Synthesis and Application of 1-[18F]Fluoro-4-isothiocyanatobenzene for Radiofluorination of Peptides in Aqueous Medium
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-12-12 , DOI: 10.1021/acs.joc.4c02370
Surendra Reddy Gundam, Mathew R. Callstrom, Mukesh K. Pandey

Conjugation of radiofluorinated prosthetic groups to primary amines of peptides in an aqueous medium is still considerably challenging. Herein, we report a one-pot cascade synthesis of 1-[18F]fluoro-4-isothiocyanatobenzene ([18F]2d), an isothiocyanate-functionalized prosthetic group for radiolabeling of various peptides in aqueous medium. The developed compound [18F]2d was synthesized in >99% radiochemical purity with 22.9 ± 3.8% (n = 12) decay-corrected yield having molar activity of 0.65 ± 0.19 (n = 12) GBq/μmol. Various clinically important peptides including prostate-specific membrane antigen vector, octreotide acetate, biotin analogue, Arg-Gly-Asp analogue, and bradykinin were successfully conjugated with [18F]2d in an aqueous medium in a good to moderate radiochemical yield. The overall synthesis of [18F]2d and its conjugation with a peptide take around 155 min, including purification.

中文翻译:


1-[18F]氟-4-异硫氰基苯的合成及应用在水性介质中对肽进行放射性氟化反应



在水性介质中,放射性氟化辅基与肽的伯胺偶联仍然具有相当大的挑战性。在此,我们报道了 1-[18F] 氟-4-异硫氰基苯 ([18F]2d) 的一锅级联合成,这是一种异硫氰酸酯官能化辅基,用于在水性介质中放射性标记各种肽。开发的化合物 [18F]2d 以 >99% 放射化学纯度合成,具有 22.9 ± 3.8% (n = 12) 衰变校正产率,摩尔活性为 0.65 ± 0.19 (n = 12) GBq/μmol。各种临床上重要的肽,包括前列腺特异性膜抗原载体、乙酸奥曲肽、生物素类似物、Arg-Gly-Asp 类似物和缓激肽,在水性介质中以良好至中等的放射化学产率与 [18F]2d 成功偶联。[18F]2d 的总合成及其与肽的偶联大约需要 155 分钟,包括纯化。
更新日期:2024-12-12
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