title: Nucleoside-metallacarborane conjugates for base-specific metal labeling of DNA.
abstract: A general approach to the synthesis of nucleoside conjugates between derivatives of thymidine (T), 2'-O-deoxycytidine (dC), 2'-O-deoxyadenosine (dA), and 2'-O-deoxyguanosine (dG), and metallacarborane complexes is described. Metallacarborane-nucleoside derivatives are prepared by reaction of the dioxane-metallacarborane adduct with a base-activated 3',5'-protected nucleoside. In the case of T and dG a mixture of regioisomers, which is easily separable by chromatographic methods, is obtained, thus yielding a series of modifications containing metallacarborane groups at the 2-O, 3-N, 4-O and 1-N, 2-N, 6-O locations, respectively; dC and dA are alkylated at the exo-amino function. The proposed methodology provides a route for the synthesis and study of nucleic acids modified with metallacarboranes at designated locations and a versatile approach to the incorporation of metals into DNA.
authors.affiliation: Center of Medical Biology, Laboratory of Molecular Virology and Biological Chemistry, Polish Academy of Sciences, 106 Lodowa St., 93-232 Lodz, Poland.
authors.forename: Agnieszka B
authors.initials: AB
authors.lastname: Olejniczak
authors.forename: Jaromir
authors.initials: J
authors.lastname: Plesek
authors.forename: Zbigniew J
authors.initials: ZJ
authors.lastname: Leśnikowski
mesh_terms: D000478:Alkylation; D001896:Boron Compounds / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D013057:Spectrum Analysis
chemical_list: D001896:Boron Compounds; D009705:Nucleosides; D004247:DNA