Bulletin of the Korean Chemical Society

대한화학회 (Korean Chemical Society)
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Development of Selective Butyrylcholinesterase Inhibitors Using (R)-Lipoic Acid-Polyphenol Hybrid Molecules

  • Woo, Yeun-Ji (Division of Applied Chemistry and Biotechnology, Hanbat National University) ;
  • Lee, Bo-Hyun (Division of Applied Chemistry and Biotechnology, Hanbat National University) ;
  • Yeun, Go-Heum (Division of Applied Chemistry and Biotechnology, Hanbat National University) ;
  • Kim, Hyun-Ju (Division of Applied Chemistry and Biotechnology, Hanbat National University) ;
  • Ko, Jang-Myoun (Division of Applied Chemistry and Biotechnology, Hanbat National University) ;
  • Won, Moo-Ho (Department of Neuroscience, Institute of Medical Sciences, School of Medicine, Kangwon National University) ;
  • Lee, Bong-Ho (Division of Applied Chemistry and Biotechnology, Hanbat National University) ;
  • Park, Jeong-Ho (Division of Applied Chemistry and Biotechnology, Hanbat National University)
  • 투고 : 2011.02.25
  • 심사 : 2011.04.17
  • 발행 : 2011.08.20
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초록

A series of hybrid molecules between (R)-lipoic acid (ALA) and the acetylated or methylated polyphenol compounds were synthesized and their in vitro cholinesterase [acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE)] inhibition activities were checked. The $IC_{50}$ values of all hybrid molecules for a BuChE inhibition were lower than those of the single parent compounds. Specifically, ALA-acetyl protected caffeic acid (11, ALA-AcCA) was shown as an effective inhibitor of BuChE ($IC_{50}=0.5{\pm}0.2\;{\mu}M$) and also had a great selectivity for BuChE over AChE (more than 800 fold). Inhibition kinetic study indicated that 11 is a mixed inhibition type. Its binding affinity ($K_i$) value to BuChE is $1.52{\pm}0.18\;{\mu}M$.

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