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

被引：23

作者：

Semioshkin, Andrey ^{[1
]}

Ilinova, Anna ^{[1
]}

Lobanova, Irina ^{[1
]}

Bregadze, Vladimir ^{[1
]}

Paradowska, Edyta ^{[2
]}

Studzinska, Miroslawa ^{[2
]}

Jablonska, Agnieszka ^{[2
]}

Lesnikowski, Zbigniew J. ^{[2
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

[2] Polish Acad Sci, Inst Med Biol, Lab Mol Virol & Biol Chem, PL-93232 Lodz, Poland

来源：

TETRAHEDRON | 2013年 / 69卷 / 37期

基金：

俄罗斯基础研究基金会;

关键词：

5-Ethynyl-2 '-deoxyuridine; Boron cluster conjugates; Closo-dodecaborate; Cobalt-bis-dicarbollide; Oxonium derivatives; Cytotoxicity; NEUTRON-CAPTURE THERAPY; ACID RELATED-COMPOUNDS; OXONIUM DERIVATIVES; NUCLEOSIDE BASES; ADENOSINE; ANALOGS; CELLS; CARBORANES; 5-ALKYNYL; ANION;

D O I：

10.1016/j.tet.2013.06.100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new 2'-deoxyuridine modification, 3',5'-bis-(dimethyl-tert-butylsilyl)-5-(3-(2-(dimethylamino)ethoxy)-3-methylbutyn-1-yl)-2'-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'-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. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：8034 / 8041

页数：8

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