Synthesis of novel phosphoramidite reagents for the attachment of antisense oligonucleotides to various regions of the benzophenanthridine ring system.
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.
Chen
J K
JK
Department of Medicinal Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Weith
H L
HL
Grewal
R S
RS
Wang
G
G
Cushman
M
M
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
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