Synthesis and characterization of nido-carborane-cobalamin conjugates

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• 作者：Hogenkamp ; Harry P.C. ; Collins ; Douglas A. ; Live ; David ; Benson ; Linda M. ; Naylor ; Stephen
• 关键词：Boron neutron capture therapy (BNCT) ; Vitamin B₁₂ ; Cyanocobalamin-nido-carborane conjugates ; Boronated vitamin B₁₂
• 刊名：Nuclear Medicine and Biology
• 出版年：2000
• 期刊代码：43_09698051
• 类别：ph
• 出版时间：January, 2000
• 卷：27
• 期：1
• 页码：89-92
• 文件大小：283 K

摘要

Three vitamin B₁₂ (cyanocobalamin) conjugates bearing one nido-carborane molecule or two nido-carborane molecules linked to the propionamide side chains via a four carbon linker have been synthesized. Reaction of o-carboranoylchloride with 1,4-diaminobutane in pyridine produced nido-carboranoyl(4-amidobutyl)amine, which was linked to the b- and d-monocarboxylic acids and the b,d-dicarboxylic acid of cyanocobalamin. Mass spectrometry analysis as well as ¹¹B nuclear magnetic resonance demonstrated that during the reaction of o-carboranonylchloride with diaminobutane one of the boron atoms was eliminated. In vitro biological activity of the cyanocobalamin-nido-carborane conjugates was assessed by the unsaturated vitamin B₁₂ binding capacity assay. When compared with ⁵⁷Co cyanocobalamin, the biological activity of cyanocobalamin-b-nido-carborane, cyanocobalamin-d-nido-carborane, and cyanocobalamin-b-d-bis-nido-carborane conjugates were 92.93%, 35.75%, and 37.02%, respectively. These findings suggest that the ¹⁰B cobalamin conjugates might be useful agents in treating malignant tumors via neutron capture therapy.