Development of Cholinesterase Inhibitors using 1-Benzyl Piperidin-4-yl (α)-Lipoic Amide Molecules 


Vol. 35,  No. 6, pp. 1681-1686, Jun.  2014
10.5012/bkcs.2014.35.6.1681


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  Abstract

A series of hybrid molecules between (α)-lipoic acid (ALA) and 4-amino-1-benzyl piperidines were synthesized and their in vitro cholinesterase (acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE)) inhibitory activities were evaluated. Even though the parent compounds did not exhibit any inhibitory activity against cholinesterase (ChE) with the exception of compound 14 (IC50 = 255.26 ± 4.41 against BuChE), all hybrid molecules demonstrated BuChE inhibitory activity. Some hybrid compounds also displayed AChE inhibitory activity. Specifically, compound 17 was shown to be an effective inhibitor against both AChE (IC50 = 1.75 ± 0.30 μM) and BuChE (IC50 = 5.61 ± 1.25 μM) comparable to galantamine (IC50 = 1.7 ± 0.9 μM against AChE and IC50 = 9.4 ± 2.5 μM against BuChE). Inhibition kinetic studies using compound 17 indicated a mixed inhibition type for AChE and a noncompetitive inhibition type for BuChE. Its binding affinity (Ki) values to AChE and BuChE were 3.8 ± 0.005 μM and 7.0 ± 0.04 μM, respectively.

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  Cite this article

[IEEE Style]

S. Lee, B. Kim, J. Kim, H. S. Lee, M. Y. Shon, J. H. Park, "Development of Cholinesterase Inhibitors using 1-Benzyl Piperidin-4-yl (α)-Lipoic Amide Molecules," Bulletin of the Korean Chemical Society, vol. 35, no. 6, pp. 1681-1686, 2014. DOI: 10.5012/bkcs.2014.35.6.1681.

[ACM Style]

Seung-hwan Lee, Beom-cheol Kim, Jae-kwan Kim, Hye Sook Lee, Min Young Shon, and Jeong Ho Park. 2014. Development of Cholinesterase Inhibitors using 1-Benzyl Piperidin-4-yl (α)-Lipoic Amide Molecules. Bulletin of the Korean Chemical Society, 35, 6, (2014), 1681-1686. DOI: 10.5012/bkcs.2014.35.6.1681.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949