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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 34, Number 4
BKCSDE 34(4)
April 20, 2013 

Synthesis of Selective Butyrylcholinesterase Inhibitors Coupled between α-Lipoic Acid and Polyphenols by Using 2-(Piperazin-1-yl)ethanol Linker
Go Heum Yeun, Seung Hwan Lee, Yong Bae Lim, Hye Sook Lee, Moo-Ho Won, Bong Ho Lee, Jeong Ho Park*
Molecular hybridization, α-Lipoic acid (ALA), Polyphenols (PPs), Butyrylcholinesterase inhibitor, 2-(Piperazin-1-yl)ethanol linker
In the previous paper (Bull. Korean Chem. Soc., 2011, 32, 2997), the hybrid molecules between α-lipoic acid (ALA) and polyphenols (PPs) connected with neutral 2-(2-aminoethoxy)ethanol linker (linker-1) showed new biological activity such as butyrylcholinesterase (BuChE) inhibition. In order to increase the binding affinity of the hybrid compounds to cholinesterase (ChE), the neutral 2-(2-aminoethoxy)ethanol (linker 1) was switched to the cationic 2-(piperazin-1-yl)ethanol linker (linker 2). The IC50 values of the linker-2 hybrid molecules for BuChE inhibition were lower than those of linker-1 hybrid molecules (except 9-2) and they also had the same great selectivity for BuChE over AChE (> 800 fold) as linker-1 hybrid molecules. ALA-acetyl caffeic acid (10- 2, ALA-AcCA) was shown as an effective inhibitor of BuChE (IC50 = 0.44 ± 0.24 μM). A kinetic study using 7- 2 showed that it is the same mixed type inhibition as 7-1. Its inhibition constant (Ki) to BuChE is 4.3 ± 0.09 μM.
1025 - 1029
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