New analogue of arenastatin A, a potent cytotoxic spongean depsipeptide, with anti-tumor activity

Nobutoshi Murakami; Satoru Tamura; Kouhei Koyama; Masanori Sugimoto; Ryuji Maekawa; Motomasa Kobayashi

doi:10.1016/j.bmcl.2004.02.080

New analogue of arenastatin A, a potent cytotoxic spongean depsipeptide, with anti-tumor activity

Nobutoshi Murakami, Satoru Tamura, Kouhei Koyama, Masanori Sugimoto, Ryuji Maekawa, Motomasa Kobayashi

研究成果: Article › 査読

9 被引用数 (Scopus)

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Two analogues possessing steric hindered substituents on C-15 of arenastatin A (1), a potent cytotoxic spongean depsipeptide, were synthesized and shown to enhance stability in mouse serum. Notably, 15-tert-butylanalogue (6) with higher cytotoxicity exhibited in vivo anti-tumor activity through iv administration different from 1. Additionally, conformation analysis among the two analogues and arenastatin A (1) indicated that the torsion angle from C-14 to C-20 is a conclusive factor for the potent cytotoxicity of 1.

本文言語	English
ページ（範囲）	2597-2601
ページ数	5
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	14
号	10
DOI	https://doi.org/10.1016/j.bmcl.2004.02.080
出版ステータス	Published - 2004 5月 17
外部発表	はい

ASJC Scopus subject areas

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

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10.1016/j.bmcl.2004.02.080

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title = "New analogue of arenastatin A, a potent cytotoxic spongean depsipeptide, with anti-tumor activity",

abstract = "Two analogues possessing steric hindered substituents on C-15 of arenastatin A (1), a potent cytotoxic spongean depsipeptide, were synthesized and shown to enhance stability in mouse serum. Notably, 15-tert-butylanalogue (6) with higher cytotoxicity exhibited in vivo anti-tumor activity through iv administration different from 1. Additionally, conformation analysis among the two analogues and arenastatin A (1) indicated that the torsion angle from C-14 to C-20 is a conclusive factor for the potent cytotoxicity of 1.",

author = "Nobutoshi Murakami and Satoru Tamura and Kouhei Koyama and Masanori Sugimoto and Ryuji Maekawa and Motomasa Kobayashi",

note = "Funding Information: The authors are grateful to Messrs Naomi Uchida and Tohru Wada, Shionogi Research Laboratories, for in vivo experiment. This study was financially supported by Grants-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture of Japan. The authors are also grateful to the Naito Foundation and the Hoh-ansha Foundation for financial support.",

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AU - Murakami, Nobutoshi

AU - Tamura, Satoru

AU - Koyama, Kouhei

AU - Sugimoto, Masanori

AU - Maekawa, Ryuji

AU - Kobayashi, Motomasa

N1 - Funding Information: The authors are grateful to Messrs Naomi Uchida and Tohru Wada, Shionogi Research Laboratories, for in vivo experiment. This study was financially supported by Grants-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture of Japan. The authors are also grateful to the Naito Foundation and the Hoh-ansha Foundation for financial support.

PY - 2004/5/17

Y1 - 2004/5/17

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AB - Two analogues possessing steric hindered substituents on C-15 of arenastatin A (1), a potent cytotoxic spongean depsipeptide, were synthesized and shown to enhance stability in mouse serum. Notably, 15-tert-butylanalogue (6) with higher cytotoxicity exhibited in vivo anti-tumor activity through iv administration different from 1. Additionally, conformation analysis among the two analogues and arenastatin A (1) indicated that the torsion angle from C-14 to C-20 is a conclusive factor for the potent cytotoxicity of 1.

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New analogue of arenastatin A, a potent cytotoxic spongean depsipeptide, with anti-tumor activity

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