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

doi:10.1080/09168451.2019.1673696

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

LIF - Molecular and Chemical Life Science

Research output: Contribution to journal › Article › peer-review

2 Citations (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 language	English
Pages (from-to)	217-227
Number of pages	11
Journal	Bioscience, Biotechnology and Biochemistry
Volume	84
Issue number	2
DOIs	https://doi.org/10.1080/09168451.2019.1673696
Publication status	Published - 2020 Feb 1

Keywords

EdAP
hepatitis B virus
Nucleotide analogue
synthesis

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1080/09168451.2019.1673696

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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

@article{619cc51df10a4b04a533a3fe820cfbd0,

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

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.",

keywords = "EdAP, hepatitis B virus, Nucleotide analogue, synthesis",

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

note = "Funding Information: This work was supported by the Core Research for Evolutional Science and Technology [JPMJCR1413]; Japan Agency for Medical Research and Development [JP18fk0210036j0001, JP18fk0310101j1002, JP18fk0310103j0202, JP18fk0310114j0002, JP18fm0208019j0002]; Japan Society for the Promotion of Science [KAKENHI/JP17H04085,KAKENHI/JP66KT0111]. This study was supported by the Japan Society for the Promotion of Science KAKENHI (JP17H04085, JP66KT0111); the JST CREST program (JPMJCR1413); the Japan Agency for Medical Research and Development, AMED (JP18fk0310114j0002, JP18fk0310101j1002, JP18fk0310103j0202, JP18fm0208019j0002, JP18fk0210036j0001). Funding Information: This study was supported by the Japan Society for the Promotion of Science KAKENHI (JP17H04085, JP66KT0111); the JST CREST program (JPMJCR1413); the Japan Agency for Medical Research and Development, AMED (JP18fk0310114j0002, JP18fk0310101j1002, JP18fk0310103j0202, JP18fm0208019j0002, JP18fk0210036j0001). Publisher Copyright: {\textcopyright} 2019, {\textcopyright} 2019 Japan Society for Bioscience, Biotechnology, and Agrochemistry.",

year = "2020",

month = feb,

day = "1",

doi = "10.1080/09168451.2019.1673696",

language = "English",

volume = "84",

pages = "217--227",

journal = "Bioscience, Biotechnology and Biochemistry",

issn = "0916-8451",

publisher = "Oxford University Press",

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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, vol. 84, no. 2, pp. 217-227. https://doi.org/10.1080/09168451.2019.1673696

TY - JOUR

T1 - Synthesis of nucleotide analogues, EFdA, EdA and EdAP, and the effect of EdAP on hepatitis B virus replication

AU - Kamata, Mai

AU - Takeuchi, Toshifumi

AU - Hayashi, Ei

AU - Nishioka, Kazane

AU - Oshima, Mizuki

AU - Iwamoto, Masashi

AU - Nishiuchi, Kota

AU - Kamo, Shogo

AU - Tomoshige, Shusuke

AU - Watashi, Koichi

AU - Kamisuki, Shinji

AU - Ohrui, Hiroshi

AU - Sugawara, Fumio

AU - Kuramochi, Kouji

N1 - Funding Information: This work was supported by the Core Research for Evolutional Science and Technology [JPMJCR1413]; Japan Agency for Medical Research and Development [JP18fk0210036j0001, JP18fk0310101j1002, JP18fk0310103j0202, JP18fk0310114j0002, JP18fm0208019j0002]; Japan Society for the Promotion of Science [KAKENHI/JP17H04085,KAKENHI/JP66KT0111]. This study was supported by the Japan Society for the Promotion of Science KAKENHI (JP17H04085, JP66KT0111); the JST CREST program (JPMJCR1413); the Japan Agency for Medical Research and Development, AMED (JP18fk0310114j0002, JP18fk0310101j1002, JP18fk0310103j0202, JP18fm0208019j0002, JP18fk0210036j0001). Funding Information: This study was supported by the Japan Society for the Promotion of Science KAKENHI (JP17H04085, JP66KT0111); the JST CREST program (JPMJCR1413); the Japan Agency for Medical Research and Development, AMED (JP18fk0310114j0002, JP18fk0310101j1002, JP18fk0310103j0202, JP18fm0208019j0002, JP18fk0210036j0001). Publisher Copyright: © 2019, © 2019 Japan Society for Bioscience, Biotechnology, and Agrochemistry.

PY - 2020/2/1

Y1 - 2020/2/1

N2 - 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.

AB - 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.

KW - EdAP

KW - hepatitis B virus

KW - Nucleotide analogue

KW - synthesis

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UR - http://www.scopus.com/inward/citedby.url?scp=85077016726&partnerID=8YFLogxK

U2 - 10.1080/09168451.2019.1673696

DO - 10.1080/09168451.2019.1673696

M3 - Article

C2 - 31589093

AN - SCOPUS:85077016726

SN - 0916-8451

VL - 84

SP - 217

EP - 227

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 2

ER -

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

Abstract

Keywords

UN SDGs

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