Synthesis of the first conjugates of 5-ethynyl-2¡ä-deoxyuridine with closo-dodecaborate and cobalt-bis-dicarbollide boron clusters

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• 作者：Andrey Semioshkin ; Anna Ilinova ; Irina Lobanova ; Vladimir Bregadze ; Edyta Paradowska ; Miros?awa Studzi¨½ska ; Agnieszka Jab?o¨½ska ; Zbigniew J. Lesnikowski
• 关键词：5-Ethynyl-2&prime ; -deoxyuridine ; Boron cluster conjugates ; Closo-dodecaborate ; Cobalt-bis-dicarbollide ; Oxonium derivatives ; Cytotoxicity
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：16 September, 2013
• 年：2013
• 卷：69
• 期：37
• 页码：8034-8041
• 全文大小：446 K

文摘

A new 2¡ä-deoxyuridine modification, 3¡ä,5¡ä-bis-(dimethyl-tert-butylsilyl)-5-(3-(2-(dimethylamino)ethoxy)-3-methylbutyn-1-yl)-2¡ä-deoxyuridine was effectively synthesized in four easy steps. Its reactivity toward a range of cyclic oxonium adducts of closo-dodecaborate and cobalt-bis-dicarbollide boron clusters was studied. The cleavage reactions of cluster oxonium rings by the N,N-dimethylamino group of the modified nucleoside led to 5-ethynyl-2¡ä-deoxyuridine conjugates with [B₁₂H₁₂]^2? and [Co(C₂B₉H₁₁)₂]^?, respectively. Cytotoxicity of these new conjugates in several cell lines was examined. Closo-dodecaborate conjugates showed low cytotoxicity in all examined cell lines, an advantageous and preferred property for potential boron delivering drugs for the boron neutron capture therapy (BNCT) of tumors.