Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens

Shinichi Nishimura; Shigeki Matsunaga; Satoru Yoshida; Yoichi Nakao; Hiroshi Hirota; Nobuhiro Fusetani

doi:10.1016/j.bmc.2004.10.014

Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens

Shinichi Nishimura, Shigeki Matsunaga, Satoru Yoshida, Yoichi Nakao, Hiroshi Hirota, Nobuhiro Fusetani

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

32 Citations (Scopus)

Abstract

Structure-activity relationship of 13-deoxytedanolide showed that the southern and northern hemispheres play independent roles to exhibit potent biological activity. To obtain information of structure-activity relationships (SARs) of 13-deoxytedanolide, its chemical transformation has been carried out, targeting on such functional groups as an epoxide, hydroxyls, ketones, and olefins. A total of 10 derivatives have been prepared and their cytotoxicity against P388 murine leukemia cells and inhibitory activity of polypeptide elongation in yeast cell lysate provided some important SARs; the southern hemisphere comprises the pharmacophore, while the epoxide-bearing side chain is essential for the activity.

Original language	English
Pages (from-to)	455-462
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	13
Issue number	2
DOIs	https://doi.org/10.1016/j.bmc.2004.10.014
Publication status	Published - 2005 Jan 17
Externally published	Yes

Keywords

13-Deoxytedanolide
Antitumor
Cytotoxicity
Marine sponge-derived macrolide
Protein synthesis inhibition
SAR

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)

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10.1016/j.bmc.2004.10.014

Cite this

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title = "Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens",

abstract = "Structure-activity relationship of 13-deoxytedanolide showed that the southern and northern hemispheres play independent roles to exhibit potent biological activity. To obtain information of structure-activity relationships (SARs) of 13-deoxytedanolide, its chemical transformation has been carried out, targeting on such functional groups as an epoxide, hydroxyls, ketones, and olefins. A total of 10 derivatives have been prepared and their cytotoxicity against P388 murine leukemia cells and inhibitory activity of polypeptide elongation in yeast cell lysate provided some important SARs; the southern hemisphere comprises the pharmacophore, while the epoxide-bearing side chain is essential for the activity.",

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AU - Nishimura, Shinichi

AU - Matsunaga, Shigeki

AU - Yoshida, Satoru

AU - Nakao, Yoichi

AU - Hirota, Hiroshi

AU - Fusetani, Nobuhiro

PY - 2005/1/17

Y1 - 2005/1/17

N2 - Structure-activity relationship of 13-deoxytedanolide showed that the southern and northern hemispheres play independent roles to exhibit potent biological activity. To obtain information of structure-activity relationships (SARs) of 13-deoxytedanolide, its chemical transformation has been carried out, targeting on such functional groups as an epoxide, hydroxyls, ketones, and olefins. A total of 10 derivatives have been prepared and their cytotoxicity against P388 murine leukemia cells and inhibitory activity of polypeptide elongation in yeast cell lysate provided some important SARs; the southern hemisphere comprises the pharmacophore, while the epoxide-bearing side chain is essential for the activity.

AB - Structure-activity relationship of 13-deoxytedanolide showed that the southern and northern hemispheres play independent roles to exhibit potent biological activity. To obtain information of structure-activity relationships (SARs) of 13-deoxytedanolide, its chemical transformation has been carried out, targeting on such functional groups as an epoxide, hydroxyls, ketones, and olefins. A total of 10 derivatives have been prepared and their cytotoxicity against P388 murine leukemia cells and inhibitory activity of polypeptide elongation in yeast cell lysate provided some important SARs; the southern hemisphere comprises the pharmacophore, while the epoxide-bearing side chain is essential for the activity.

KW - 13-Deoxytedanolide

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KW - Cytotoxicity

KW - Marine sponge-derived macrolide

KW - Protein synthesis inhibition

KW - SAR

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Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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