title: Synthesis of novel phosphoramidite reagents for the attachment of antisense oligonucleotides to various regions of the benzophenanthridine ring system.
abstract: Four benzophenanthridine phosphoramidite reagents have been prepared in which the linker chain between the benzophenanthridine and the phosphoramidite moiety is attached to C-2, C-6, C-9, and C-12 of the benzophenanthridine ring system. These benzophenanthridine phosphoramidites should prove to be useful in the syntheses of antisense oligonucleotide-intercalator conjugates in which the linker chain is attached to various regions of the benzophenanthridine intercalator. One of the new benzophenanthridine phosphoramidite reagents was used to prepare an antisense oligonucleotide-intercalator conjugate in which the oligonucleotide TCAGTGGTp was connected at its 5'-hydroxyl group through a linker chain to the C-2 hydroxyl group of a benzophenanthridine.
authors.affiliation: Department of Medicinal Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
authors.forename: J K
authors.initials: JK
authors.lastname: Chen
authors.forename: H L
authors.initials: HL
authors.lastname: Weith
authors.forename: R S
authors.initials: RS
authors.lastname: Grewal
authors.forename: G
authors.initials: G
authors.lastname: Wang
authors.forename: M
authors.initials: M
authors.lastname: Cushman
mesh_terms: D000577:Amides; D000588:Amines / Q000138:chemical synthesis*; D000818:Animals; D001483:Base Sequence; D001665:Binding Sites; D005914:Globins / Q000096:biosynthesis; D007202:Indicators and Reagents; D007364:Intercalating Agents / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis / Q000737:chemistry*; D010617:Phenanthridines; D010756:Phosphoric Acids / Q000138:chemical synthesis*; D012333:RNA, Messenger; D011817:Rabbits; D013053:Spectrophotometry; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000588:Amines; D007202:Indicators and Reagents; D007364:Intercalating Agents; D016376:Oligonucleotides, Antisense; D010617:Phenanthridines; D010756:Phosphoric Acids; D012333:RNA, Messenger; D005914:Globins; C011067:phosphoramidic acid