4.6 Article

Synthesis, duplex-forming ability, enzymatic stability, and in vitro antisense potency of oligonucleotides including 2'-C,4'-C-ethyleneoxy-bridged thymidine derivatives

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 18, Pages 3955-3963

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00698e

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, MEXT (Japan) [22136006]
  2. Japan Society for the Promotion of Science (JSPS)
  3. Takeda Science Foundation

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We synthesized thymidine derivatives of 2'-C,4-C-ethyleneoxy-bridged 2'-deoxyribonucleic acids with an 8'-methyl group ((R)-Me-EoDNA and (S)-Me-EoDNA) and without any substituent (EoDNA). Oligonucleotides including these EoDNAs showed high hybridization abilities with complementary RNA and excellent enzymatic stabilities compared with natural DNA. Moreover, the in vitro antisense potency of oligonucleotides with these EoDNAs and our recently reported methylene-EoDNAs was investigated and compared with that of LNA, which is a practical chemical modification for oligonucleotide-therapeutic agents. The results showed that EoDNAs and methylene-EoDNAs could be promising candidates for antisense technology.

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