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

SCI - Chemistry

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

17 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

Keywords

Cytotoxin
Depsipeptide
Marine metabolite
Marine sponge

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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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

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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