Synthesis and Biological Activities of Indolactone-V, the Lactone Analogue of the Tumor Promoter (–)-Indolactam-V

Yu Nakagawa; Kazuhiro Irie; Yoshimasa Nakamura; Hajime Ohigashi; Hideo Hayashi

doi:10.1271/bbb.61.1415

Synthesis and Biological Activities of Indolactone-V, the Lactone Analogue of the Tumor Promoter (–)-Indolactam-V

Yu Nakagawa, Kazuhiro Irie, Yoshimasa Nakamura, Hajime Ohigashi, Hideo Hayashi

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

6 Citations (Scopus)

Abstract

The tumor promoter (–)-indolactam-V (1) exists in two stable conformers (twist and sofa) due to isomerization of the amide group. Indolactone-V (2), the lactone analogue of 1, has been synthesized to investigate the effects of the amide group on its conformation and biological activities. Indolactone-V (2) existed only as the inactive sofa-like conformer, indicating that the amide group of 1 plays a critical role in formation of the active twist conformation.

Original language	English
Pages (from-to)	1415-1417
Number of pages	3
Journal	Bioscience, Biotechnology and Biochemistry
Volume	61
Issue number	8
DOIs	https://doi.org/10.1271/bbb.61.1415
Publication status	Published - Jan 1997
Externally published	Yes

Keywords

(–)-indolactam-V
Conformation
Indolactone-V
Protein kinase C
Teleocidin
Tumor promoter

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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title = "Synthesis and Biological Activities of Indolactone-V, the Lactone Analogue of the Tumor Promoter (–)-Indolactam-V",

abstract = "The tumor promoter (–)-indolactam-V (1) exists in two stable conformers (twist and sofa) due to isomerization of the amide group. Indolactone-V (2), the lactone analogue of 1, has been synthesized to investigate the effects of the amide group on its conformation and biological activities. Indolactone-V (2) existed only as the inactive sofa-like conformer, indicating that the amide group of 1 plays a critical role in formation of the active twist conformation.",

keywords = "(–)-indolactam-V, Conformation, Indolactone-V, Protein kinase C, Teleocidin, Tumor promoter",

author = "Yu Nakagawa and Kazuhiro Irie and Yoshimasa Nakamura and Hajime Ohigashi and Hideo Hayashi",

note = "Funding Information: Acknowledgments. This work was supported in part by a Grantin-Aid for Scientific Research (C) (No. 08660137) from the Ministry of Education, Science. and Culture of Japan.",

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AU - Nakagawa, Yu

AU - Irie, Kazuhiro

AU - Nakamura, Yoshimasa

AU - Ohigashi, Hajime

AU - Hayashi, Hideo

N1 - Funding Information: Acknowledgments. This work was supported in part by a Grantin-Aid for Scientific Research (C) (No. 08660137) from the Ministry of Education, Science. and Culture of Japan.

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AB - The tumor promoter (–)-indolactam-V (1) exists in two stable conformers (twist and sofa) due to isomerization of the amide group. Indolactone-V (2), the lactone analogue of 1, has been synthesized to investigate the effects of the amide group on its conformation and biological activities. Indolactone-V (2) existed only as the inactive sofa-like conformer, indicating that the amide group of 1 plays a critical role in formation of the active twist conformation.

KW - (–)-indolactam-V

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KW - Indolactone-V

KW - Protein kinase C

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KW - Tumor promoter

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Synthesis and Biological Activities of Indolactone-V, the Lactone Analogue of the Tumor Promoter (–)-Indolactam-V

Abstract

Keywords

ASJC Scopus subject areas

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