Synthesis of amide analogs of arenastatin A

Nobutoshi Murakami; Weiqi Wang; Naoki Ohyabu; Takeshi Ito; Satoru Tamura; Shunji Aoki; Motomasa Kobayashi; Isao Kitagawa

doi:10.1016/S0040-4020(00)00766-3

Synthesis of amide analogs of arenastatin A

Nobutoshi Murakami, Weiqi Wang, Naoki Ohyabu, Takeshi Ito, Satoru Tamura, Shunji Aoki, Motomasa Kobayashi, Isao Kitagawa

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

19 Citations (Scopus)

Abstract

In order to probe the metabolism of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized three analogs in which the ester linkages were replaced by amide bonds. Triamide analog-II and tetraamide analog, both of which contained a 15,20-amide linkage, showed stability in serum. However, arenastatin A and triamide analog-I, which both contained a 15,20-ester moiety, were readily metabolized in serum. Among the three amide analogs, only triamide analog-II exhibited potent cytotoxic activity against KB cells.

Original language	English
Pages (from-to)	9121-9128
Number of pages	8
Journal	Tetrahedron
Volume	56
Issue number	46
DOIs	https://doi.org/10.1016/S0040-4020(00)00766-3
Publication status	Published - 2000 Nov 10
Externally published	Yes

Keywords

Cytotoxin
Depsipeptide
Marine metabolite
Marine sponge

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(00)00766-3

Cite this

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title = "Synthesis of amide analogs of arenastatin A",

abstract = "In order to probe the metabolism of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized three analogs in which the ester linkages were replaced by amide bonds. Triamide analog-II and tetraamide analog, both of which contained a 15,20-amide linkage, showed stability in serum. However, arenastatin A and triamide analog-I, which both contained a 15,20-ester moiety, were readily metabolized in serum. Among the three amide analogs, only triamide analog-II exhibited potent cytotoxic activity against KB cells.",

keywords = "Cytotoxin, Depsipeptide, Marine metabolite, Marine sponge",

author = "Nobutoshi Murakami and Weiqi Wang and Naoki Ohyabu and Takeshi Ito and Satoru Tamura and Shunji Aoki and Motomasa Kobayashi and Isao Kitagawa",

note = "Funding Information: The authors are grateful to Dr K. Sugita, the Research Laboratory of Shionogi Pharmaceutical Co., Ltd., for in vivo anti-tumor test. The authors are also grateful to the Naito Foundation, the Houansha Foundation, and the Ministry of Education, Sciences, Sports, and Culture of Japan for financial support.",

year = "2000",

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doi = "10.1016/S0040-4020(00)00766-3",

language = "English",

volume = "56",

pages = "9121--9128",

journal = "Tetrahedron",

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number = "46",

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TY - JOUR

T1 - Synthesis of amide analogs of arenastatin A

AU - Murakami, Nobutoshi

AU - Wang, Weiqi

AU - Ohyabu, Naoki

AU - Ito, Takeshi

AU - Tamura, Satoru

AU - Aoki, Shunji

AU - Kobayashi, Motomasa

AU - Kitagawa, Isao

N1 - Funding Information: The authors are grateful to Dr K. Sugita, the Research Laboratory of Shionogi Pharmaceutical Co., Ltd., for in vivo anti-tumor test. The authors are also grateful to the Naito Foundation, the Houansha Foundation, and the Ministry of Education, Sciences, Sports, and Culture of Japan for financial support.

PY - 2000/11/10

Y1 - 2000/11/10

N2 - In order to probe the metabolism of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized three analogs in which the ester linkages were replaced by amide bonds. Triamide analog-II and tetraamide analog, both of which contained a 15,20-amide linkage, showed stability in serum. However, arenastatin A and triamide analog-I, which both contained a 15,20-ester moiety, were readily metabolized in serum. Among the three amide analogs, only triamide analog-II exhibited potent cytotoxic activity against KB cells.

AB - In order to probe the metabolism of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized three analogs in which the ester linkages were replaced by amide bonds. Triamide analog-II and tetraamide analog, both of which contained a 15,20-amide linkage, showed stability in serum. However, arenastatin A and triamide analog-I, which both contained a 15,20-ester moiety, were readily metabolized in serum. Among the three amide analogs, only triamide analog-II exhibited potent cytotoxic activity against KB cells.

KW - Cytotoxin

KW - Depsipeptide

KW - Marine metabolite

KW - Marine sponge

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U2 - 10.1016/S0040-4020(00)00766-3

DO - 10.1016/S0040-4020(00)00766-3

M3 - Article

AN - SCOPUS:0034634668

VL - 56

SP - 9121

EP - 9128

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 46

ER -

Synthesis of amide analogs of arenastatin A

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

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