Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide

Nobutoshi Murakami; Satoru Tamura; Weiqi Wang; Tatsuya Takagi; Motomasa Kobayashi

doi:10.1016/S0040-4020(01)00339-8

Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide

Nobutoshi Murakami, Satoru Tamura, Weiqi Wang, Tatsuya Takagi, Motomasa Kobayashi

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

16 Citations (Scopus)

Abstract

In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A.

Original language	English
Pages (from-to)	4323-4336
Number of pages	14
Journal	Tetrahedron
Volume	57
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4020(01)00339-8
Publication status	Published - 2001 May 14
Externally published	Yes

Keywords

Arenastatin A
Depsipeptide
Marine metabolite
Restrained molecular dynamics

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

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

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10.1016/S0040-4020(01)00339-8

Cite this

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abstract = "In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A.",

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T1 - Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide

AU - Murakami, Nobutoshi

AU - Tamura, Satoru

AU - Wang, Weiqi

AU - Takagi, Tatsuya

AU - Kobayashi, Motomasa

PY - 2001/5/14

Y1 - 2001/5/14

N2 - In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A.

AB - In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A.

KW - Arenastatin A

KW - Depsipeptide

KW - Marine metabolite

KW - Restrained molecular dynamics

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DO - 10.1016/S0040-4020(01)00339-8

M3 - Article

AN - SCOPUS:0035858729

VL - 57

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EP - 4336

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 20

ER -

Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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