title: Synthesis, reactivity and biological activity of N(4)-boronated derivatives of 2'-deoxycytidine.
abstract: By seeking new stable boron-containing nucleoside derivatives, potential BNCT boron delivery agents, a novel synthetic approach was tested, aimed at a boron attachment via a single bond to an aliphatic carbon of sp(3) hybridization. The latter allowed successful modification of deoxycytidine in the reaction with 2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane of the deoxynucleoside amino group. For new compounds, detailed NMR, LDI HRMS (Laser Desorption/Ionization High-Resolution Mass Spectrometry) analyses along with in vivo phosphorylation studies, toxicity assays and DFT modelling are presented.
authors.affiliation: Rzeszów University of Technology, Faculty of Chemistry, Bioorganic Chemistry Laboratory, 6 Powstańców Warszawy Ave., 35-959 Rzeszów, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Nizioł
authors.affiliation: Nencki Institute of Experimental Biology, 3 Pasteur Street, 02-093 Warsaw, Poland.
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Zieliński
authors.affiliation: University of Warsaw, Faculty of Chemistry, Quantum Chemistry Laboratory, 1 Pasteur Street, Warsaw 02-093, Poland; Pharmaceutical Research Institute, Rydygier Street 8, Warsaw 01-793, Poland.
authors.forename: Andrzej
authors.initials: A
authors.lastname: Leś
authors.affiliation: Nencki Institute of Experimental Biology, 3 Pasteur Street, 02-093 Warsaw, Poland.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Dąbrowska
authors.affiliation: Nencki Institute of Experimental Biology, 3 Pasteur Street, 02-093 Warsaw, Poland.
authors.forename: Wojciech
authors.initials: W
authors.lastname: Rode
authors.affiliation: Rzeszów University of Technology, Faculty of Chemistry, Bioorganic Chemistry Laboratory, 6 Powstańców Warszawy Ave., 35-959 Rzeszów, Poland. Electronic address: tomruman@prz.edu.pl.
authors.forename: Tomasz
authors.initials: T
authors.lastname: Ruman
mesh_terms: D001895:Boron / Q000737:chemistry*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003841:Deoxycytidine / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010766:Phosphorylation / Q000187:drug effects; D011725:Pyridines / Q000737:chemistry; D011789:Quantum Theory
chemical_list: D011725:Pyridines; D003841:Deoxycytidine; D001895:Boron; C023666:pyridine
keywords: Boron nucleoside; Boron nucleotide; In vivo phosphorylation; NMR; Solvolysis