title: Pyridinium Boranephosphonate Modified DNA Oligonucleotides.
abstract: The synthesis of previously unknown derivatives of boranephosphonate that contain amine substitutions at boron and the incorporation of these derivatives into the backbone of DNA oligonucleotides is described. These derivatives result from iodine-mediated replacement of one BH3hydride of a boranephosphonate linkage by pyridine, various substituted pyridines, other aromatic amines, and certain unsaturated amines. Oligonucleotides containing these backbone modifications show enhanced uptake, relative to unmodified DNA, in mammalian cells. The redox behavior of the boranephosphonate and pyridinium boranephosphonate conjugated linkages has also been studied.
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80303, United States.
authors.forename: Subhadeep
authors.identifier: 0000-0002-8297-8541
authors.initials: S
authors.lastname: Roy
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80303, United States.
authors.forename: Sibasish
authors.initials: S
authors.lastname: Paul
authors.affiliation: Department of Basic Sciences and Humanities, National Institute of Technology, Manipur , Langol, Imphal, 795004 Manipur, India.
authors.forename: Mithun
authors.initials: M
authors.lastname: Roy
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80303, United States.
authors.forename: Rajen
authors.initials: R
authors.lastname: Kundu
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80303, United States.
authors.forename: Luca
authors.initials: L
authors.lastname: Monfregola
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80303, United States.
authors.forename: Marvin H
authors.initials: MH
authors.lastname: Caruthers
mesh_terms: D001880:Boranes / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics; D004273:DNA, Neoplasm / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D009841:Oligonucleotides / Q000737:chemistry*; D010710:Phosphates / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics; D011726:Pyridinium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics
chemical_list: D001880:Boranes; D004273:DNA, Neoplasm; D009841:Oligonucleotides; D010710:Phosphates; D011726:Pyridinium Compounds; C510710:boranophosphate