Specific inhibitor of puromycin-sensitive aminopeptidase with a homophthalimide skeleton: Identification of the target molecule and a structure-activity relationship study

Masato Komoda; Hiroki Kakuta; Hiroyasu Takahashi; Yasuyuki Fujimoto; Shizuo Kadoya; Fuminori Kato; Yuichi Hashimoto

doi:10.1016/S0968-0896(00)00231-5

Specific inhibitor of puromycin-sensitive aminopeptidase with a homophthalimide skeleton: Identification of the target molecule and a structure-activity relationship study

Masato Komoda, Hiroki Kakuta, Hiroyasu Takahashi, Yasuyuki Fujimoto, Shizuo Kadoya, Fuminori Kato, Yuichi Hashimoto

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

61 Citations (Scopus)

Abstract

2-(2,6-Diethylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione (2: PIQ-22) was found to be a potent and specific inhibitor of puromycin-sensitive aminopeptidase (PSA). Lineweaver-Burk plot analysis showed that PSA is inhibited by PIQ-22 in a non-competitive manner. Structure-activity relationship studies indicated that tautomerism of the imidobenzoylketone group in the cyclic imide moiety of the PIQ-22 skeleton is important for the inhibitory activity.

Original language	English
Pages (from-to)	121-131
Number of pages	11
Journal	Bioorganic and Medicinal Chemistry
Volume	9
Issue number	1
DOIs	https://doi.org/10.1016/S0968-0896(00)00231-5
Publication status	Published - 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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Specific inhibitor of puromycin-sensitive aminopeptidase with a homophthalimide skeleton : Identification of the target molecule and a structure-activity relationship study. / Komoda, Masato; Kakuta, Hiroki; Takahashi, Hiroyasu; Fujimoto, Yasuyuki; Kadoya, Shizuo; Kato, Fuminori; Hashimoto, Yuichi.

In: Bioorganic and Medicinal Chemistry, Vol. 9, No. 1, 2001, p. 121-131.

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

Komoda, M, Kakuta, H, Takahashi, H, Fujimoto, Y, Kadoya, S, Kato, F & Hashimoto, Y 2001, 'Specific inhibitor of puromycin-sensitive aminopeptidase with a homophthalimide skeleton: Identification of the target molecule and a structure-activity relationship study', Bioorganic and Medicinal Chemistry, vol. 9, no. 1, pp. 121-131. https://doi.org/10.1016/S0968-0896(00)00231-5

Komoda, Masato ; Kakuta, Hiroki ; Takahashi, Hiroyasu ; Fujimoto, Yasuyuki ; Kadoya, Shizuo ; Kato, Fuminori ; Hashimoto, Yuichi. / Specific inhibitor of puromycin-sensitive aminopeptidase with a homophthalimide skeleton : Identification of the target molecule and a structure-activity relationship study. In: Bioorganic and Medicinal Chemistry. 2001 ; Vol. 9, No. 1. pp. 121-131.

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title = "Specific inhibitor of puromycin-sensitive aminopeptidase with a homophthalimide skeleton: Identification of the target molecule and a structure-activity relationship study",

abstract = "2-(2,6-Diethylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione (2: PIQ-22) was found to be a potent and specific inhibitor of puromycin-sensitive aminopeptidase (PSA). Lineweaver-Burk plot analysis showed that PSA is inhibited by PIQ-22 in a non-competitive manner. Structure-activity relationship studies indicated that tautomerism of the imidobenzoylketone group in the cyclic imide moiety of the PIQ-22 skeleton is important for the inhibitory activity.",

author = "Masato Komoda and Hiroki Kakuta and Hiroyasu Takahashi and Yasuyuki Fujimoto and Shizuo Kadoya and Fuminori Kato and Yuichi Hashimoto",

note = "Funding Information: The work described in this paper was partially supported by funds for the Promotion of Fundamental Studies in Health Science from the Organization for Pharmaceutical Safety Research, and Grants-in-Aid from the Ministry of Education, Science, Sports, and Culture of Japan. The authors are grateful to Dr. Naoko Morisaki and Dr. Hisayoshi Kobayashi (IMCB, University of Tokyo) for their assistance.",

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AU - Fujimoto, Yasuyuki

AU - Kadoya, Shizuo

AU - Kato, Fuminori

AU - Hashimoto, Yuichi

N1 - Funding Information: The work described in this paper was partially supported by funds for the Promotion of Fundamental Studies in Health Science from the Organization for Pharmaceutical Safety Research, and Grants-in-Aid from the Ministry of Education, Science, Sports, and Culture of Japan. The authors are grateful to Dr. Naoko Morisaki and Dr. Hisayoshi Kobayashi (IMCB, University of Tokyo) for their assistance.

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AB - 2-(2,6-Diethylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione (2: PIQ-22) was found to be a potent and specific inhibitor of puromycin-sensitive aminopeptidase (PSA). Lineweaver-Burk plot analysis showed that PSA is inhibited by PIQ-22 in a non-competitive manner. Structure-activity relationship studies indicated that tautomerism of the imidobenzoylketone group in the cyclic imide moiety of the PIQ-22 skeleton is important for the inhibitory activity.

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Specific inhibitor of puromycin-sensitive aminopeptidase with a homophthalimide skeleton: Identification of the target molecule and a structure-activity relationship study

Abstract

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