Synthesis and Properties of 2′-OMe-RNAs Modified with Cross-Linkable 7-Deazaguanosine Derivatives

Ken Yamada, Yusuke Abe, Hirotaka Murase, Yuta Ida, Shinya Hagihara, Fumi Nagatsugi

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Cross-linkable 7-deaza-6-vinylguanosine (ADVP) and 7-propynyl-7-deaza-6-vinylguanosine (ADpVP) derivatives were synthesized and successfully incorporated into 2′-OMe-RNA oligonucleotides by solid-phase oligonucleotide synthesis. Analysis of their cross-link properties revealed that the 7-propynyl substituent on ADpVP induces a significant enhancement of the cross-link kinetics of the proximal 6-vinyl group to the complementary uracil base in the target RNA compared to that of ADVP. In addition, the 2′-OMe-RNA oligonucleotide containing ADpVP exhibited a higher antisense effect on luciferase production in the cell lysate than that of ADVP. These results suggested that the 7-substituted 7-deaza-6-vinylguanosine derivatives can be used as potent cross-linkers to target mRNA inside of cells.

Original languageEnglish
Pages (from-to)8851-8862
Number of pages12
JournalJournal of Organic Chemistry
Volume83
Issue number16
DOIs
Publication statusPublished - 2018 Aug 17

ASJC Scopus subject areas

  • Organic Chemistry

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