title: Synthesis and properties of cholesteryl-modified triple-helix forming oligonucleotides containing a triglycyl linker.
abstract: In order to enhance the nuclear uptake of triple-helix forming oligonucleotides (TFOs), a triglycylcholesterol group was attached to the 3' end. The peptide unit was introduced as a "labile" linker with the aim of releasing the oligonucleotide from the endosomes by the action of peptidases after crossing the cell membrane. Cholesteryl-CPG (8) and -TentaGel (9) supports containing 2-[N-(glycylglycylglycyl)amino]propane-1,3-diol (GAP-3) linker were prepared and used for automated oligonucleotide synthesis. The synthesis, characterization, and stability of these compounds are described.
authors.affiliation: Triplex Pharmaceutical Corporation, Woodlands, Texas 77380.
authors.forename: H
authors.initials: H
authors.lastname: Vu
authors.forename: T S
authors.initials: TS
authors.lastname: Hill
authors.forename: K
authors.initials: K
authors.lastname: Jayaraman
mesh_terms: D001483:Base Sequence; D002784:Cholesterol / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004355:Drug Stability; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009842:Oligopeptides / Q000737:chemistry*
chemical_list: D009841:Oligonucleotides; D009842:Oligopeptides; D002784:Cholesterol; C035647:glycyl-glycyl-glycine