Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca2+ pump inhibitor from marine cyanobacteria

Eisuke Sato; Maho Morita; Haruo Ogawa; Masato Iwatsuki; Rei Hokari; Aki Ishiyama; Satoshi Ōmura; Arihiro Iwasaki; Kiyotake Suenaga

doi:10.1016/j.bmcl.2017.12.050

Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca²⁺ pump inhibitor from marine cyanobacteria

Eisuke Sato, Maho Morita, Haruo Ogawa, Masato Iwatsuki, Rei Hokari, Aki Ishiyama, Satoshi Ōmura, Arihiro Iwasaki, Kiyotake Suenaga

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

4 Citations (Scopus)

Abstract

Biselyngbyaside, an 18-membered macrolide glycoside from marine cyanobacteria, and its derivatives are known to be sarco/endoplasmic reticulum Ca²⁺ ATPase (SERCA) inhibitors. Recently, a SERCA orthologue of the malaria parasite, PfATP6, has attracted attention as a malarial drug target. To provide a novel drug lead, we designed new synthetic analogs of biselyngbyolide B, the aglycone of biselyngbyaside, based on the co-crystal structure of SERCA with biselyngbyolide B, and synthesized them using the established synthetic route for biselyngbyolide B. Their biological activities against malarial parasites were evaluated.

Original language	English
Pages (from-to)	298-301
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	28
Issue number	3
DOIs	https://doi.org/10.1016/j.bmcl.2017.12.050
Publication status	Published - Feb 1 2018
Externally published	Yes

Keywords

Biselyngbyaside
Biselyngbyolide
PfATP6
SERCA
Structure–activity relationships

ASJC Scopus subject areas

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

UN SDGs

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

Access to Document

10.1016/j.bmcl.2017.12.050

Cite this

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title = "Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca2+ pump inhibitor from marine cyanobacteria",

abstract = "Biselyngbyaside, an 18-membered macrolide glycoside from marine cyanobacteria, and its derivatives are known to be sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitors. Recently, a SERCA orthologue of the malaria parasite, PfATP6, has attracted attention as a malarial drug target. To provide a novel drug lead, we designed new synthetic analogs of biselyngbyolide B, the aglycone of biselyngbyaside, based on the co-crystal structure of SERCA with biselyngbyolide B, and synthesized them using the established synthetic route for biselyngbyolide B. Their biological activities against malarial parasites were evaluated.",

keywords = "Biselyngbyaside, Biselyngbyolide, PfATP6, SERCA, Structure–activity relationships",

author = "Eisuke Sato and Maho Morita and Haruo Ogawa and Masato Iwatsuki and Rei Hokari and Aki Ishiyama and Satoshi Ōmura and Arihiro Iwasaki and Kiyotake Suenaga",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Nos. 16H03285 (K. S.) and 17J03602 (E. S.). We thank Sanyo Fine Co., Ltd. for their gift of chiral trityl glycidyl ether. We thank Prof. Dr. Chikashi Toyoshima (Tokyo University) for the suggestion about SERCA and PfATP6. Funding Information: This work was supported by JSPS KAKENHI Grant Nos. 16H03285 (K. S.) and 17J03602 (E. S.). We thank Sanyo Fine Co., Ltd. for their gift of chiral trityl glycidyl ether. We thank Prof. Dr. Chikashi Toyoshima (Tokyo University) for the suggestion about SERCA and PfATP6. Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

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AU - Sato, Eisuke

AU - Morita, Maho

AU - Ogawa, Haruo

AU - Iwatsuki, Masato

AU - Hokari, Rei

AU - Ishiyama, Aki

AU - Ōmura, Satoshi

AU - Iwasaki, Arihiro

AU - Suenaga, Kiyotake

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