(7S)-Kaitocephalin as a potent NMDA receptor selective ligand

Yoko Yasuno; Makoto Hamada; Masanori Kawasaki; Keiko Shimamoto; Yasushi Shigeri; Toshifumi Akizawa; Motomi Konishi; Yasufumi Ohfune; Tetsuro Shinada

doi:10.1039/c5ob02301g

(7S)-Kaitocephalin as a potent NMDA receptor selective ligand

Yoko Yasuno, Makoto Hamada, Masanori Kawasaki, Keiko Shimamoto, Yasushi Shigeri, Toshifumi Akizawa, Motomi Konishi, Yasufumi Ohfune, Tetsuro Shinada

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

6 Citations (Scopus)

Abstract

A structure-activity relationship (SAR) study of kaitocephalin (KCP), known to be a potent naturally occurring NMDA receptor ligand, was performed. This study led us to the discovery of (7S)-kaitocephalin as a highly selective NMDA receptor ligand. It displayed a 22-fold higher degree of selectivity for the NMDA receptor over KCP, though the binding affinity of (7S)-KCP [K_i = 29 nM] was 3.7-fold less potent than that of KCP [K_i = 7.8 nM].

Original language	English
Pages (from-to)	1206-1210
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	4
DOIs	https://doi.org/10.1039/c5ob02301g
Publication status	Published - 2016
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "(7S)-Kaitocephalin as a potent NMDA receptor selective ligand",

abstract = "A structure-activity relationship (SAR) study of kaitocephalin (KCP), known to be a potent naturally occurring NMDA receptor ligand, was performed. This study led us to the discovery of (7S)-kaitocephalin as a highly selective NMDA receptor ligand. It displayed a 22-fold higher degree of selectivity for the NMDA receptor over KCP, though the binding affinity of (7S)-KCP [Ki = 29 nM] was 3.7-fold less potent than that of KCP [Ki = 7.8 nM].",

author = "Yoko Yasuno and Makoto Hamada and Masanori Kawasaki and Keiko Shimamoto and Yasushi Shigeri and Toshifumi Akizawa and Motomi Konishi and Yasufumi Ohfune and Tetsuro Shinada",

note = "Funding Information: TS gratefully acknowledges financial support from Scientific Research of Innovative Areas, Chemical Biology of Natural Products, the Ministry of Education, Culture, Sports, Science and Technology (No. 23102009) and the Japan Society for the Promotion of Science (KAKENHI No. 23228001, 25282233). YY gratefully acknowledges financial support by the Sasagawa Scientific Research Grant from The Japan Science Society. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

doi = "10.1039/c5ob02301g",

language = "English",

volume = "14",

pages = "1206--1210",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "4",

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TY - JOUR

T1 - (7S)-Kaitocephalin as a potent NMDA receptor selective ligand

AU - Yasuno, Yoko

AU - Hamada, Makoto

AU - Kawasaki, Masanori

AU - Shimamoto, Keiko

AU - Shigeri, Yasushi

AU - Akizawa, Toshifumi

AU - Konishi, Motomi

AU - Ohfune, Yasufumi

AU - Shinada, Tetsuro

N1 - Funding Information: TS gratefully acknowledges financial support from Scientific Research of Innovative Areas, Chemical Biology of Natural Products, the Ministry of Education, Culture, Sports, Science and Technology (No. 23102009) and the Japan Society for the Promotion of Science (KAKENHI No. 23228001, 25282233). YY gratefully acknowledges financial support by the Sasagawa Scientific Research Grant from The Japan Science Society. Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016

Y1 - 2016

N2 - A structure-activity relationship (SAR) study of kaitocephalin (KCP), known to be a potent naturally occurring NMDA receptor ligand, was performed. This study led us to the discovery of (7S)-kaitocephalin as a highly selective NMDA receptor ligand. It displayed a 22-fold higher degree of selectivity for the NMDA receptor over KCP, though the binding affinity of (7S)-KCP [Ki = 29 nM] was 3.7-fold less potent than that of KCP [Ki = 7.8 nM].

AB - A structure-activity relationship (SAR) study of kaitocephalin (KCP), known to be a potent naturally occurring NMDA receptor ligand, was performed. This study led us to the discovery of (7S)-kaitocephalin as a highly selective NMDA receptor ligand. It displayed a 22-fold higher degree of selectivity for the NMDA receptor over KCP, though the binding affinity of (7S)-KCP [Ki = 29 nM] was 3.7-fold less potent than that of KCP [Ki = 7.8 nM].

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DO - 10.1039/c5ob02301g

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AN - SCOPUS:84983122800

SN - 1477-0520

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SP - 1206

EP - 1210

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 4

ER -

(7S)-Kaitocephalin as a potent NMDA receptor selective ligand

Abstract

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