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 Omura, Arihiro Iwasaki, Kiyotake Suenaga

Research output: Contribution to journalArticle

2 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 languageEnglish
JournalBioorganic and Medicinal Chemistry Letters
DOIs
Publication statusAccepted/In press - 2017 Jan 1

Fingerprint

Sarcoplasmic Reticulum Calcium-Transporting ATPases
Antimalarials
Cyanobacteria
Pumps
Parasites
Macrolides
Glycosides
Bioactivity
Pharmaceutical Preparations
Malaria
Crystal structure
Derivatives
biselyngbyolide B
biselyngbyaside

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

Cite this

Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca2+ pump inhibitor from marine cyanobacteria. / Sato, Eisuke; Morita, Maho; Ogawa, Haruo; Iwatsuki, Masato; Hokari, Rei; Ishiyama, Aki; Omura, Satoshi; Iwasaki, Arihiro; Suenaga, Kiyotake.

In: Bioorganic and Medicinal Chemistry Letters, 01.01.2017.

Research output: Contribution to journalArticle

@article{bd33b070ea0042ec955fd3f54853c2d9,
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 Omura and Arihiro Iwasaki and Kiyotake Suenaga",
year = "2017",
month = "1",
day = "1",
doi = "10.1016/j.bmcl.2017.12.050",
language = "English",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Limited",

}

TY - JOUR

T1 - Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca2+ pump inhibitor from marine cyanobacteria

AU - Sato, Eisuke

AU - Morita, Maho

AU - Ogawa, Haruo

AU - Iwatsuki, Masato

AU - Hokari, Rei

AU - Ishiyama, Aki

AU - Omura, Satoshi

AU - Iwasaki, Arihiro

AU - Suenaga, Kiyotake

PY - 2017/1/1

Y1 - 2017/1/1

N2 - 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.

AB - 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.

KW - Biselyngbyaside

KW - Biselyngbyolide

KW - PfATP6

KW - SERCA

KW - Structure-activity relationships

UR - http://www.scopus.com/inward/record.url?scp=85039552818&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85039552818&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2017.12.050

DO - 10.1016/j.bmcl.2017.12.050

M3 - Article

C2 - 29292225

AN - SCOPUS:85039552818

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

ER -