Leslie A. Khawli , Annick D. Van Den Abbeele, Amin I. Kassis
{"title":"N-(m-[125I]碘苯基)马来酰亚胺:一种高效抗体放射性标记剂","authors":"Leslie A. Khawli , Annick D. Van Den Abbeele, Amin I. Kassis","doi":"10.1016/0883-2897(92)90113-D","DOIUrl":null,"url":null,"abstract":"<div><p>In an effort to radiolabel antibodies, <em>N</em>-(<em>m</em>-[<sup>125</sup>I]iodophenyl)maleimide (<em>m</em>-[<sup>125</sup>I]IPM) was prepared by the demetallation of an <em>N</em>-[<em>m</em>-tri-(<em>n</em>-butyl)stannylphenyl]maleimide intermediate. The unlabeled intermediate was synthesized in ⩾ 75% yield using a palladium catalyzed reaction of hexabutylditin with <em>m</em>-bromoaniline, followed by reaction with maleic anhydride and ring annulation. All products were confirmed by NMR and elemental analysis. Labeling with <sup>125</sup>I was carried out in a biphasic mixture containing chloramine-T (radiochemical yield ⩾ 70%). Rabbit IgG modified with the heterobifunctional crosslinking agent <em>N</em>-succinimidyl-3-(2-pyridyldithio)propionate (SPDP) and bovine serum albumin were conjugated with <em>m</em>-[<sup>125</sup>I]IPM (yield: 40 and 80%, respectively). In addition, <em>m</em>-[<sup>125</sup>I]IPM was conjugated to rabbit IgG subunits (HL) in 70% yield. The <em>in vitro</em> stability of the radiolabeled proteins in serum showed < 1% deiodination over 24 h.</p></div>","PeriodicalId":14328,"journal":{"name":"International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology","volume":"19 3","pages":"Pages 289-295"},"PeriodicalIF":0.0000,"publicationDate":"1992-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/0883-2897(92)90113-D","citationCount":"15","resultStr":"{\"title\":\"N-(m-[125I]iodophenyl)maleimide: an agent for high yield radiolabeling of antibodies\",\"authors\":\"Leslie A. Khawli , Annick D. Van Den Abbeele, Amin I. Kassis\",\"doi\":\"10.1016/0883-2897(92)90113-D\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>In an effort to radiolabel antibodies, <em>N</em>-(<em>m</em>-[<sup>125</sup>I]iodophenyl)maleimide (<em>m</em>-[<sup>125</sup>I]IPM) was prepared by the demetallation of an <em>N</em>-[<em>m</em>-tri-(<em>n</em>-butyl)stannylphenyl]maleimide intermediate. The unlabeled intermediate was synthesized in ⩾ 75% yield using a palladium catalyzed reaction of hexabutylditin with <em>m</em>-bromoaniline, followed by reaction with maleic anhydride and ring annulation. All products were confirmed by NMR and elemental analysis. Labeling with <sup>125</sup>I was carried out in a biphasic mixture containing chloramine-T (radiochemical yield ⩾ 70%). Rabbit IgG modified with the heterobifunctional crosslinking agent <em>N</em>-succinimidyl-3-(2-pyridyldithio)propionate (SPDP) and bovine serum albumin were conjugated with <em>m</em>-[<sup>125</sup>I]IPM (yield: 40 and 80%, respectively). In addition, <em>m</em>-[<sup>125</sup>I]IPM was conjugated to rabbit IgG subunits (HL) in 70% yield. The <em>in vitro</em> stability of the radiolabeled proteins in serum showed < 1% deiodination over 24 h.</p></div>\",\"PeriodicalId\":14328,\"journal\":{\"name\":\"International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology\",\"volume\":\"19 3\",\"pages\":\"Pages 289-295\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1992-04-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/0883-2897(92)90113-D\",\"citationCount\":\"15\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/088328979290113D\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/088328979290113D","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
N-(m-[125I]iodophenyl)maleimide: an agent for high yield radiolabeling of antibodies
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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