Preparation of 7-Methoxy Tacrine Dimer Analogs and Their In vitro/In silico Evaluation as Potential Cholinesterase Inhibitors

Title
Preparation of 7-Methoxy Tacrine Dimer Analogs and Their In vitro/In silico Evaluation as Potential Cholinesterase Inhibitors
Author(s)
나춘섭이상광박민균장호은이진주남기평조대원K. Musilek[K. Musilek]A. Horova[A. Horova]J. Korabecny[J. Korabecny]R. Dolezal[R. Dolezal]D. Jun[D. Jun]K. Kuca[K. Kuca]
Keywords
ALZHEIMERS-DISEASE; BIOLOGICAL EVALUATION; CONTROLLED-TRIAL; AMYLOID-BETA; ACETYLCHOLINESTERASE; THERAPY; HYBRIDS
Issue Date
201506
Publisher
WILEY-V C H VERLAG GMBH
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.36, no.6, pp.1654 - 1660
Abstract
Novel types of symmetric bis-7-methoxytacrines connected by oligoethyleneoxy chains 3-5 and nonsymmetric monomeric 7-methoxytacrines containing hydroxyl-terminated oligoethyleneoxy chains 6-8 were prepared, and their in vitro/in silico effects on human recombinant AChE (hAChE) and human plasmatic butyrylcholinesterase (hBChE) were compared, with 7-MEOTA (2) as the standard compound. The symmetric bis-7-MEOTA derivatives 3-5 showed hAChE inhibition similar to that of 2. On the other hand, their effects on hBChE revealed an increasing inhibition trend when the oligoethyleneoxy units between the two 7-MEOTA moieties became longer. Accordingly, compounds 4 and 5 showed better selectivity towards hBChE. The most effective in the inhibition hAChE and hBChE was compound 8 with the longest oligoethyleneglycol chain, whereas compounds 6 and 7 resulted in similar IC50 values. A molecular modeling study using substrates 5 and 8 showed a possible binding conformation and protein-ligand interaction between the substrates and AChE/BChE.
URI
http://hdl.handle.net/YU.REPOSITORY/32067http://dx.doi.org/10.1002/bkcs.10317
ISSN
0253-2964
Appears in Collections:
이과대학 > 화학생화학부 > Articles
문과대학 > 중국언어문화학과 > Articles
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