4.6 Article

Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 38, Pages 8145-8152

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob01874f

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Funding

  1. Core Research for Evolutional Science and Technology (CREST) program of the Japan Science and Technology Agency (JST)
  2. JSPS KAKENHI [15K08024]
  3. Platform Project for Supporting Drug Discovery and Life Science Research from the Japan Agency for Medical Research and Development (AMED)
  4. Grants-in-Aid for Scientific Research [15K08024] Funding Source: KAKEN

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We designed and synthesized a novel artificial 2'-O,4'-C-methylene bridged nucleic acid (2',4'-BNA/LNA) with a phenoxazine nucleobase and named this compound BNAP. Oligodeoxynucleotide (ODN) containing BNAP showed higher binding affinities toward complementary DNA and RNA as compared to ODNs bearing 2',4'-BNA/LNA with 5-methylcytosine or 2'-deoxyribonucleoside with phenoxazine. Thermodynamic analysis revealed that BNAP exhibits properties associated with the phenoxazine moiety in DNA/DNA duplexes and characteristics associated with the 2',4'-BNA/LNA moiety in DNA/RNA duplexes.

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