Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine Salileptolyngbya sp. Cyanobacterium

Naoaki Kurisawa; Keisuke Otomo; Arihiro Iwasaki; Ghulam Jeelani; Tomoyoshi Nozaki; Kiyotake Suenaga

doi:10.1021/acs.joc.1c00817

Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine Salileptolyngbya sp. Cyanobacterium

Naoaki Kurisawa, Keisuke Otomo, Arihiro Iwasaki, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga

Department of Chemistry

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

5 Citations (Scopus)

Abstract

Kinenzoline (1), a new linear depsipeptide, was isolated from a marine Salileptolyngbya sp. cyanobacterium. Its structure was elucidated by spectroscopic analyses and degradation reactions. In addition, we achieved a total synthesis of 1 and confirmed its structure. Kinenzoline (1) showed highly selective antiproliferative activity against the causative organism of sleeping sickness, Trypanosoma brucei rhodesiense (IC50 4.5 μM), compared to normal human cells (WI-38, IC50 > 100 μM). Kinenzoline (1) is a promising lead compound for the development of new antitrypanosomal drugs.

Original language	English
Pages (from-to)	12528-12536
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	86
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.1c00817
Publication status	Published - 2021 Sept 17

ASJC Scopus subject areas

Organic Chemistry

UN SDGs

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

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10.1021/acs.joc.1c00817

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title = "Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine Salileptolyngbya sp. Cyanobacterium",

abstract = "Kinenzoline (1), a new linear depsipeptide, was isolated from a marine Salileptolyngbya sp. cyanobacterium. Its structure was elucidated by spectroscopic analyses and degradation reactions. In addition, we achieved a total synthesis of 1 and confirmed its structure. Kinenzoline (1) showed highly selective antiproliferative activity against the causative organism of sleeping sickness, Trypanosoma brucei rhodesiense (IC50 4.5 μM), compared to normal human cells (WI-38, IC50 > 100 μM). Kinenzoline (1) is a promising lead compound for the development of new antitrypanosomal drugs.",

author = "Naoaki Kurisawa and Keisuke Otomo and Arihiro Iwasaki and Ghulam Jeelani and Tomoyoshi Nozaki and Kiyotake Suenaga",

note = "Funding Information: This work was supported by JSPS KAKENHI (Grant Numbers 18K14346, 20H02870, and 21J13608) and Keio Gijuku Academic Development Funds. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.joc.1c00817",

language = "English",

volume = "86",

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journal = "Journal of Organic Chemistry",

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T1 - Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine Salileptolyngbya sp. Cyanobacterium

AU - Kurisawa, Naoaki

AU - Otomo, Keisuke

AU - Iwasaki, Arihiro

AU - Jeelani, Ghulam

AU - Nozaki, Tomoyoshi

AU - Suenaga, Kiyotake

N1 - Funding Information: This work was supported by JSPS KAKENHI (Grant Numbers 18K14346, 20H02870, and 21J13608) and Keio Gijuku Academic Development Funds. Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/9/17

Y1 - 2021/9/17

N2 - Kinenzoline (1), a new linear depsipeptide, was isolated from a marine Salileptolyngbya sp. cyanobacterium. Its structure was elucidated by spectroscopic analyses and degradation reactions. In addition, we achieved a total synthesis of 1 and confirmed its structure. Kinenzoline (1) showed highly selective antiproliferative activity against the causative organism of sleeping sickness, Trypanosoma brucei rhodesiense (IC50 4.5 μM), compared to normal human cells (WI-38, IC50 > 100 μM). Kinenzoline (1) is a promising lead compound for the development of new antitrypanosomal drugs.

AB - Kinenzoline (1), a new linear depsipeptide, was isolated from a marine Salileptolyngbya sp. cyanobacterium. Its structure was elucidated by spectroscopic analyses and degradation reactions. In addition, we achieved a total synthesis of 1 and confirmed its structure. Kinenzoline (1) showed highly selective antiproliferative activity against the causative organism of sleeping sickness, Trypanosoma brucei rhodesiense (IC50 4.5 μM), compared to normal human cells (WI-38, IC50 > 100 μM). Kinenzoline (1) is a promising lead compound for the development of new antitrypanosomal drugs.

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DO - 10.1021/acs.joc.1c00817

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SP - 12528

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine Salileptolyngbya sp. Cyanobacterium

Abstract

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