Synthesis of nucleotide analogues, EFdA, EdA and EdAP, and the effect of EdAP on hepatitis B virus replication

Mai Kamata, Toshifumi Takeuchi, Ei Hayashi, Kazane Nishioka, Mizuki Oshima, Masashi Iwamoto, Kota Nishiuchi, Shogo Kamo, Shusuke Tomoshige, Koichi Watashi, Shinji Kamisuki, Hiroshi Ohrui, Fumio Sugawara, Kouji Kuramochi

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

4′-Ethynyl-2-fluoro-2′-deoxyadenosine (EFdA) and 4′-ethynyl-2′-deoxyadenosine (EdA) are nucleoside analogues which inhibit human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. EdAP, a cyclosaligenyl (cycloSal) phosphate derivative of EdA, inhibits the replication of the influenza A virus. The common structural feature of these compounds is the ethynyl group at the 4′-position. In this study, these nucleoside analogues were prepared by a common synthetic strategy starting from the known 1,2-di-O-acetyl-D-ribofuranose. Biological evaluation of EdAP revealed that this compound reduced hepatitis B virus (HBV) replication dose-dependently without cytotoxicity against host cells tested in this study.

Original languageEnglish
Pages (from-to)217-227
Number of pages11
JournalBioscience, Biotechnology and Biochemistry
Volume84
Issue number2
DOIs
Publication statusPublished - 2020 Feb 1
Externally publishedYes

Keywords

  • EdAP
  • hepatitis B virus
  • Nucleotide analogue
  • synthesis

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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  • Cite this

    Kamata, M., Takeuchi, T., Hayashi, E., Nishioka, K., Oshima, M., Iwamoto, M., Nishiuchi, K., Kamo, S., Tomoshige, S., Watashi, K., Kamisuki, S., Ohrui, H., Sugawara, F., & Kuramochi, K. (2020). Synthesis of nucleotide analogues, EFdA, EdA and EdAP, and the effect of EdAP on hepatitis B virus replication. Bioscience, Biotechnology and Biochemistry, 84(2), 217-227. https://doi.org/10.1080/09168451.2019.1673696