N-(m-[125I]iodophenyl)maleimide: an agent for high yield radiolabeling of antibodies

International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology Pub Date : 1992-04-01 DOI:10.1016/0883-2897(92)90113-D

Leslie A. Khawli , Annick D. Van Den Abbeele, Amin I. Kassis

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引用次数: 15

Abstract

In an effort to radiolabel antibodies, N-(m-[¹²⁵I]iodophenyl)maleimide (m-[¹²⁵I]IPM) was prepared by the demetallation of an N-[m-tri-(n-butyl)stannylphenyl]maleimide intermediate. The unlabeled intermediate was synthesized in ⩾ 75% yield using a palladium catalyzed reaction of hexabutylditin with m-bromoaniline, followed by reaction with maleic anhydride and ring annulation. All products were confirmed by NMR and elemental analysis. Labeling with ¹²⁵I was carried out in a biphasic mixture containing chloramine-T (radiochemical yield ⩾ 70%). Rabbit IgG modified with the heterobifunctional crosslinking agent N-succinimidyl-3-(2-pyridyldithio)propionate (SPDP) and bovine serum albumin were conjugated with m-[¹²⁵I]IPM (yield: 40 and 80%, respectively). In addition, m-[¹²⁵I]IPM was conjugated to rabbit IgG subunits (HL) in 70% yield. The in vitro stability of the radiolabeled proteins in serum showed < 1% deiodination over 24 h.

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N-(m-[125I]碘苯基)马来酰亚胺:一种高效抗体放射性标记剂

为了对抗体进行放射性标记，将N-[m- [125I]碘苯基]马来酰亚胺中间体脱金属制备了N-(m-[125I]碘苯基)马来酰亚胺。使用钯催化的六丁基二丁与间溴苯胺的反应，以小于75%的产量合成未标记的中间体，随后与马来酸酐和环环化反应。所有产物经核磁共振和元素分析证实。在含有氯胺- t的双相混合物中进行125I标记(放射化学产率大于或等于70%)。用异双功能交联剂n -琥珀酰酰-3-(2-吡啶二硫代)丙酸(SPDP)修饰兔IgG和牛血清白蛋白，用m-[125I]IPM偶联，收率分别为40%和80%。此外，m-[125I]IPM以70%的产率与兔IgG亚单位(HL)偶联。血清中放射性标记蛋白的体外稳定性显示<1%脱碘超过24小时。

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International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology

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