Unprecedented NES non-antagonistic inhibitor for nuclear export of Rev from Sida cordifolia

Satoru Tamura; Masafumi Kaneko; Atsushi Shiomi; Guang Ming Yang; Toshiaki Yamaura; Nobutoshi Murakami

doi:10.1016/j.bmcl.2010.01.165

Unprecedented NES non-antagonistic inhibitor for nuclear export of Rev from Sida cordifolia

Satoru Tamura, Masafumi Kaneko, Atsushi Shiomi, Guang Ming Yang, Toshiaki Yamaura, Nobutoshi Murakami

SCI - Chemistry

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

12 Citations (Scopus)

Abstract

Bioassay-guided separation from the MeOH extract of the South American medicinal plant Sida cordifolia resulted in isolation of (10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid (1) as an unprecedented NES non-antagonistic inhibitor for nuclear export of Rev. This mechanism of action was established by competitive experiment by the biotinylated probe derived from leptomycin B, the known NES antagonistic inhibitor. Additionally, structure-activity relationship analysis by use of the synthesized analogs clarified cooperation of several functionalities in the Rev-export inhibitory activity of 1.

Original language	English
Pages (from-to)	1837-1839
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2010.01.165
Publication status	Published - 2010 Mar 15

Keywords

(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
Anti-HIV
NES non-antagonistic inhibitor
Rev-export inhibitor
Sida cordifolia

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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@article{a657bcd4890247379ce40c30d61ede63,

title = "Unprecedented NES non-antagonistic inhibitor for nuclear export of Rev from Sida cordifolia",

abstract = "Bioassay-guided separation from the MeOH extract of the South American medicinal plant Sida cordifolia resulted in isolation of (10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid (1) as an unprecedented NES non-antagonistic inhibitor for nuclear export of Rev. This mechanism of action was established by competitive experiment by the biotinylated probe derived from leptomycin B, the known NES antagonistic inhibitor. Additionally, structure-activity relationship analysis by use of the synthesized analogs clarified cooperation of several functionalities in the Rev-export inhibitory activity of 1.",

keywords = "(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid, Anti-HIV, NES non-antagonistic inhibitor, Rev-export inhibitor, Sida cordifolia",

author = "Satoru Tamura and Masafumi Kaneko and Atsushi Shiomi and Yang, {Guang Ming} and Toshiaki Yamaura and Nobutoshi Murakami",

note = "Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (Grant No. 19590100 ) from the Ministry of Education, Science, Culture and Sports . The authors are grateful to the Shorai Foundation for Science and Technology for financial support.",

year = "2010",

month = mar,

day = "15",

doi = "10.1016/j.bmcl.2010.01.165",

language = "English",

volume = "20",

pages = "1837--1839",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "6",

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TY - JOUR

T1 - Unprecedented NES non-antagonistic inhibitor for nuclear export of Rev from Sida cordifolia

AU - Tamura, Satoru

AU - Kaneko, Masafumi

AU - Shiomi, Atsushi

AU - Yang, Guang Ming

AU - Yamaura, Toshiaki

AU - Murakami, Nobutoshi

N1 - Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (Grant No. 19590100 ) from the Ministry of Education, Science, Culture and Sports . The authors are grateful to the Shorai Foundation for Science and Technology for financial support.

PY - 2010/3/15

Y1 - 2010/3/15

N2 - Bioassay-guided separation from the MeOH extract of the South American medicinal plant Sida cordifolia resulted in isolation of (10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid (1) as an unprecedented NES non-antagonistic inhibitor for nuclear export of Rev. This mechanism of action was established by competitive experiment by the biotinylated probe derived from leptomycin B, the known NES antagonistic inhibitor. Additionally, structure-activity relationship analysis by use of the synthesized analogs clarified cooperation of several functionalities in the Rev-export inhibitory activity of 1.

AB - Bioassay-guided separation from the MeOH extract of the South American medicinal plant Sida cordifolia resulted in isolation of (10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid (1) as an unprecedented NES non-antagonistic inhibitor for nuclear export of Rev. This mechanism of action was established by competitive experiment by the biotinylated probe derived from leptomycin B, the known NES antagonistic inhibitor. Additionally, structure-activity relationship analysis by use of the synthesized analogs clarified cooperation of several functionalities in the Rev-export inhibitory activity of 1.

KW - (10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

KW - Anti-HIV

KW - NES non-antagonistic inhibitor

KW - Rev-export inhibitor

KW - Sida cordifolia

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