Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports

Nakada, Kazuaki; Yoshikawa, Mamie; Ide, Soichiro; Suemasa, Akihiro; Kawamura, Shuhei; Kobayashi, Takaaki; Masuda, Eiji; Ito, Yoshihiko; Hayakawa, Wataru; Katayama, Takahiro; Yamada, Shizuo; Arisawa, Mitsuhiro; Minami, Masabumi; Shuto, Satoshi

Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports

Nakada, Kazuaki; Yoshikawa, Mamie; Ide, Soichiro et al.

Bioorganic & medicinal chemistry, 2013, 21(17), 4938-4950

Permalink : https://hdl.handle.net/2115/54095

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アクセス権	open access
URI	https://hdl.handle.net/2115/54095
タイトル	Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports
著者	Nakada, Kazuaki ; Yoshikawa, Mamie ; Ide, Soichiro ; Suemasa, Akihiro ; Kawamura, Shuhei ; Kobayashi, Takaaki ; Masuda, Eiji ; Ito, Yoshihiko ; Hayakawa, Wataru ; Katayama, Takahiro ; Yamada, Shizuo ; Arisawa, Mitsuhiro ; Minami, Masabumi ; Shuto, Satoshi
著者名 Nakada, Kazuaki
著者名 Yoshikawa, Mamie
e-Rad_Researcher 30389118 著者名 Ide, Soichiro
著者名 Suemasa, Akihiro
著者名 Kawamura, Shuhei
著者名 Kobayashi, Takaaki
著者名 Masuda, Eiji
著者名 Ito, Yoshihiko
著者名 Hayakawa, Wataru
e-Rad_Researcher 90399957 著者名 Katayama, Takahiro
著者名 Yamada, Shizuo
e-Rad_Researcher 40312962 著者名 Arisawa, Mitsuhiro
e-Rad_Researcher 20243040 著者名 Minami, Masabumi
e-Rad_Researcher 70241346 著者名 Shuto, Satoshi
言語	英語
キーワード	GABA transporter
	GAT3
	BGT1
	Cyclopropane
	Conformational restriction
発行日	2013-09-01
出版者	Pergamon-elsevier science ltd
収録物名	Bioorganic & medicinal chemistry
巻(号)	21(17)
ページ	4938-4950
抄録	A series of cyclopropane-based conformationally restricted gamma-aminobutyric acid (GABA) analogs with stereochemical diversity, that is, the trans- and cis-2,3-methano analogs Ia and Ib and their enantiomers ent-Ia and ent-Ib, and also the trans- and cis-3,4-methano analogs IIa and IIb and their enantiomers ent-IIa and ent-Iib, were synthesized from the chiral cyclopropane units Type-a and Type-b that we developed. These analogs were systematically evaluated with four GABA transporter (GAT) subtypes. The trans-3,4-methano analog IIa had inhibitory effects on GAT3 (IC50 = 23.9 mu M) and betaine-GABA transporter1 (5.48 mu M), indicating its potential as an effective lead compound for the development of potent GAT inhibitors due to its hydrophilic and low molecular weight properties and excellent ligand efficiency. (C) 2013 Elsevier Ltd. All rights reserved.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
PISSN	0968-0896
NCID	AA10938083
関連情報	PMID 23886812
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1016/j.bmc.2013.06.063