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.
Copyright © 2010 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzamides / chemical synthesis*
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Benzamides / chemistry
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Benzamides / pharmacology*
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Cell Line
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Cell Proliferation / drug effects
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Crystallography, X-Ray
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Cyclopropanes / chemical synthesis*
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Cyclopropanes / chemistry
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Cyclopropanes / pharmacology*
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology*
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Growth Inhibitors / chemical synthesis
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Growth Inhibitors / chemistry
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Growth Inhibitors / pharmacology
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HEK293 Cells
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HeLa Cells
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Histone Demethylases / antagonists & inhibitors*
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Humans
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Inhibitory Concentration 50
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Lysine / chemistry*
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Magnetic Resonance Spectroscopy
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Stereoisomerism
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Substrate Specificity
Substances
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2-(3-(3-benzamido-4-(benzylamino)-4-oxobutoxy)phenyl)cyclopropylamine
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Benzamides
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Cyclopropanes
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Enzyme Inhibitors
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Growth Inhibitors
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Histone Demethylases
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Lysine