Highly efficient method for ¹²⁵I-radiolabeling of biomolecules using inverse-electron-demand Diels-Alder reaction

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• 作者：Mi Hee Choi^a ; Ha Eun Shim^a ; Seong-Jae Yun^a ; Hye Rim Kim^a ; Sajid Mushtaq^a ; ^b ; Chang Heon Lee^a ; Sang Hyun Park^a ; ^b ; Dae Seong Choi^a ; Dong-Eun Lee^a ; Eui-Baek Byun^a ; ^b ; Beom-Su Jang^a ; ^b ; ^{jangbs@kaeri.re.kr" class="auth_mail" title="E-mail the corresponding author} ; Jongho Jeon^a ; ^b ; ^{jeonj@kaeri.re.kr" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Bioorthogonal reaction ; Radiolabeling ; Radioactive iodine ; Radiotracer ; Inverse-electron-demand Diels&ndash ; Alder reaction
• 刊名：Bioorganic & Medicinal Chemistry
• 出版年：2016
• 出版时间：1 June 2016
• 年：2016
• 卷：24
• 期：11
• 页码：2589-2594
• 全文大小：626 K

文摘

In this report, we present a rapid and highly efficient method for radioactive iodine labeling of trans-cyclooctene group conjugated biomolecules using inverse-electron-demand Diels–Alder reaction. Radioiodination reaction of the tetrazine structure was carried out using the stannylated precursor 2 to give ¹²⁵I-labeled product ([¹²⁵I]1) with high radiochemical yield (65 ± 8%) and radiochemical purity (>99%). For radiolabeling application of [¹²⁵I]1, trans-cyclooctene derived cRGD peptide and human serum albumin were prepared. These substrates were reacted with [¹²⁵I]1 under mild condition to provide the radiolabeled products [¹²⁵I]6 and [¹²⁵I]8, respectively, with excellent radiochemical yields. The biodistribution study of [¹²⁵I]8 in normal ICR mice showed significantly lower thyroid uptake values than that of ¹²⁵I-labeled human serum albumin prepared by a traditional radiolabeling method. Therefore [¹²⁵I]8 will be a useful radiolabeled tracer in various molecular imaging and biological studies. Those results clearly demonstrate that [¹²⁵I]1 will be used as a valuable prosthetic group for radiolabeling of biomolecules.