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

Autor:	Edyta Paradowska, Irina A. Lobanova, Agnieszka Jabłońska, Anna Ilinova, Vladimir I. Bregadze, Zbigniew J. Lesnikowski, Andrey Semioshkin, Mirosława Studzińska
Rok vydání:	2013
Předmět:	inorganic chemicals Chemistry Stereochemistry Organic Chemistry Dodecaborate chemistry.chemical_element Biochemistry Medicinal chemistry Adduct Drug Discovery Alkoxy group Reactivity (chemistry) Oxonium ion Boron Cobalt Conjugate
Zdroj:	Tetrahedron. 69:8034-8041
ISSN:	0040-4020
DOI:	10.1016/j.tet.2013.06.100
Popis:	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.
Databáze:	OpenAIRE
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