title: Synthesis and biological activity of optically active NCL-1, a lysine-specific demethylase 1 selective inhibitor.
abstract: Optically active (1S,2R)-NCL-1 and (1R,2S)-NCL-1 were synthesized and evaluated for their lysine-specific demethylase 1 inhibitory activity and cell growth inhibitory activity. In enzyme assays, the (1S,2R)-isomer was approximately four times more potent than the (1R,2S)-isomer. In cell growth inhibition assays, the two isomers showed similar activity in HEK293 cells and SH-SY5Y cells, whereas the (1S,2R)-isomer showed approximately four times more potent activity than the (1R,2S)-isomer in HeLa cells.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Nagoya, Aichi 467-8603, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Ogasawara
authors.forename: Takayoshi
authors.initials: T
authors.lastname: Suzuki
authors.forename: Koshiki
authors.initials: K
authors.lastname: Mino
authors.forename: Rie
authors.initials: R
authors.lastname: Ueda
authors.forename: Mohammed Naseer Ahmed
authors.initials: MN
authors.lastname: Khan
authors.forename: Takuya
authors.initials: T
authors.lastname: Matsubara
authors.forename: Koichi
authors.initials: K
authors.lastname: Koseki
authors.forename: Makoto
authors.initials: M
authors.lastname: Hasegawa
authors.forename: Ryuzo
authors.initials: R
authors.lastname: Sasaki
authors.forename: Hidehiko
authors.initials: H
authors.lastname: Nakagawa
authors.forename: Tamio
authors.initials: T
authors.lastname: Mizukami
authors.forename: Naoki
authors.initials: N
authors.lastname: Miyata
mesh_terms: D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006131:Growth Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D057809:HEK293 Cells; D006367:HeLa Cells; D056466:Histone Demethylases / Q000037:antagonists & inhibitors*; D006801:Humans; D020128:Inhibitory Concentration 50; D008239:Lysine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: C562353:2-(3-(3-benzamido-4-(benzylamino)-4-oxobutoxy)phenyl)cyclopropylamine; D001549:Benzamides; D003521:Cyclopropanes; D004791:Enzyme Inhibitors; D006131:Growth Inhibitors; D056466:Histone Demethylases; D008239:Lysine