title: Synthesis, binding and cellular uptake properties of oligodeoxynucleotides containing cationic bicyclo-thymidine residues.
abstract: The synthesis and incorporation into oligodeoxynucleotides of two novel derivatives of bicyclothymidine carrying a cationic diaminopropyl or lysine unit in the C(6')-β position is described. Compared to unmodified DNA these oligonucleotides show T(m)-neutral behavior when paired against complementary DNA and are destabilizing when paired against RNA. Unaided uptake experiments of a decamer containing five lys-bcT units into HeLa and HEK293T cells showed substantial internalization with mostly cytosolic distribution which was not observed in the case of an unmodified control oligonucleotide.
authors: Department of Chemistry & Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
authors: Jory
authors: J
authors: Lietard
authors: Damian
authors: D
authors: Ittig
authors: Christian J
authors: CJ
authors: Leumann
mesh_terms: D020029:Base Pairing; D001483:Base Sequence; D002460:Cell Line; D004247:DNA / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D008239:Lysine / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D020319:Oligodeoxyribonucleotides, Antisense / Q000737:chemistry; D012313:RNA / Q000737:chemistry / Q000378:metabolism; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D044366:Transition Temperature
chemical_list: D009838:Oligodeoxyribonucleotides; D020319:Oligodeoxyribonucleotides, Antisense; D012313:RNA; D004247:DNA; D008239:Lysine; D013936:Thymidine