The amide hydrogen of (-)-indolactam-V and benzolactam-V8's plays a critical role in protein kinase C binding and tumor-promoting activities

Yu Nakagawa; Kazuhiro Irie; Yoshimasa Nakamura; Hajime Ohigashi

doi:10.1016/S0960-894X(01)00047-6

The amide hydrogen of (-)-indolactam-V and benzolactam-V8's plays a critical role in protein kinase C binding and tumor-promoting activities

Yu Nakagawa, Kazuhiro Irie, Yoshimasa Nakamura, Hajime Ohigashi

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

19 Citations (Scopus)

Abstract

To investigate the role of the amide hydrogen of (-)-indolactam-V (1) and benzolactam-V8's on protein kinase C (PKC) binding and tumor promotion. 8-decylbenzolactone-V8 (6), a new lactone analogue of 8-decylbenzolactam-V8 (4), was synthesized from 2-nitrophenylpyruvic acid (7) in 11 steps. The PKC binding ability and tumor-promoting activities in vitro of 6 were much lower than those of 1 and 4, suggesting that the amide hydrogen of 1 and benzolactam-V8's plays a critical role in tumor promotion, However, it is noteworthy that 6 showed significant selectivity in the PKC isozyme surrogate binding.

Original language	English
Pages (from-to)	723-728
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	11
Issue number	5
DOIs	https://doi.org/10.1016/S0960-894X(01)00047-6
Publication status	Published - Mar 12 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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title = "The amide hydrogen of (-)-indolactam-V and benzolactam-V8's plays a critical role in protein kinase C binding and tumor-promoting activities",

abstract = "To investigate the role of the amide hydrogen of (-)-indolactam-V (1) and benzolactam-V8's on protein kinase C (PKC) binding and tumor promotion. 8-decylbenzolactone-V8 (6), a new lactone analogue of 8-decylbenzolactam-V8 (4), was synthesized from 2-nitrophenylpyruvic acid (7) in 11 steps. The PKC binding ability and tumor-promoting activities in vitro of 6 were much lower than those of 1 and 4, suggesting that the amide hydrogen of 1 and benzolactam-V8's plays a critical role in tumor promotion, However, it is noteworthy that 6 showed significant selectivity in the PKC isozyme surrogate binding.",

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

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (C) (2) (No. 11660109) and on Priority Areas (A) (2) (No. 12045241) from the Ministry of Education, Science, Culture, and Sports of Japan (for K.I.), and from the Japan Society for the Promotion of Science for Young Scientists (Y.N.).",

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doi = "10.1016/S0960-894X(01)00047-6",

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T1 - The amide hydrogen of (-)-indolactam-V and benzolactam-V8's plays a critical role in protein kinase C binding and tumor-promoting activities

AU - Nakagawa, Yu

AU - Irie, Kazuhiro

AU - Nakamura, Yoshimasa

AU - Ohigashi, Hajime

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (C) (2) (No. 11660109) and on Priority Areas (A) (2) (No. 12045241) from the Ministry of Education, Science, Culture, and Sports of Japan (for K.I.), and from the Japan Society for the Promotion of Science for Young Scientists (Y.N.).

PY - 2001/3/12

Y1 - 2001/3/12

N2 - To investigate the role of the amide hydrogen of (-)-indolactam-V (1) and benzolactam-V8's on protein kinase C (PKC) binding and tumor promotion. 8-decylbenzolactone-V8 (6), a new lactone analogue of 8-decylbenzolactam-V8 (4), was synthesized from 2-nitrophenylpyruvic acid (7) in 11 steps. The PKC binding ability and tumor-promoting activities in vitro of 6 were much lower than those of 1 and 4, suggesting that the amide hydrogen of 1 and benzolactam-V8's plays a critical role in tumor promotion, However, it is noteworthy that 6 showed significant selectivity in the PKC isozyme surrogate binding.

AB - To investigate the role of the amide hydrogen of (-)-indolactam-V (1) and benzolactam-V8's on protein kinase C (PKC) binding and tumor promotion. 8-decylbenzolactone-V8 (6), a new lactone analogue of 8-decylbenzolactam-V8 (4), was synthesized from 2-nitrophenylpyruvic acid (7) in 11 steps. The PKC binding ability and tumor-promoting activities in vitro of 6 were much lower than those of 1 and 4, suggesting that the amide hydrogen of 1 and benzolactam-V8's plays a critical role in tumor promotion, However, it is noteworthy that 6 showed significant selectivity in the PKC isozyme surrogate binding.

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JO - Bioorganic and Medicinal Chemistry Letters

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The amide hydrogen of (-)-indolactam-V and benzolactam-V8's plays a critical role in protein kinase C binding and tumor-promoting activities

Abstract

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