title: Synthesis of antisense oligonucleotides containing 2'-O-psoralenylmethoxyalkyl adenosine for photodynamic regulation of point mutations in RNA.
abstract: 2'-O-psoralen-conjugated antisense oligonucleotide was able to recognize a point mutation of mRNA. It had outstanding ability to photo-cross-link only to oligoribonucleotides (ORN) having a point mutation. This type of antisense molecule is the only one of its kind so far. To give high photo-cross-linking efficiency and sequence selectivity to antisense molecules, we synthesized novel photo-reactive oligonucleotides (2'-Ps-xom) containing psoralen at the 2'-O-position adenosine via an ethoxymethylene (2'-Ps-eom), propoxymethylene (2'-Ps-pom) and butoxymethylene (2'-Ps-bom) linker, respectively. We evaluated the photo-cross-linking efficiency and sequence selectivity in photo-cross-linking of 2'-Ps-xom to the complementary ORN and to an ORN having a mismatch base. Among them, 2'-Ps-eom exhibited superior photo-cross-linking efficiency with high sequence selectivity.
authors.affiliation: Department of Biomolecular Engineering, Kyoto Institute of Technology, Matsugasaki, Kyoto 606-8585, Japan.
authors.forename: Maiko
authors.initials: M
authors.lastname: Higuchi
authors.forename: Akio
authors.initials: A
authors.lastname: Kobori
authors.forename: Asako
authors.initials: A
authors.lastname: Yamayoshi
authors.forename: Akira
authors.initials: A
authors.lastname: Murakami
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives*; D001665:Binding Sites; D003432:Cross-Linking Reagents; D011564:Furocoumarins / Q000737:chemistry*; D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis* / Q000494:pharmacology; D010777:Photochemistry; D017354:Point Mutation; D012333:RNA, Messenger / Q000235:genetics* / Q000378:metabolism
chemical_list: D003432:Cross-Linking Reagents; D011564:Furocoumarins; D016376:Oligonucleotides, Antisense; D012333:RNA, Messenger; D000241:Adenosine