Document Detail


Design, synthesis and anticholinesterase activity of some new α-aminobisphosphonates.
MedLine Citation:
PMID:  20353344     Owner:  NLM     Status:  In-Process    
Abstract/OtherAbstract:
Some new α-aminomethylenephosphonic acids 1-11 were synthesised and characterised by (1)H, (13)C, (31)P NMR, IR spectroscopy and elemental analysis. The potencies of these compounds to inhibit human erythrocyte acetylcholinesterase (hAChE, EC 3.1.1.7) were studied by a modified Ellman's method. In addition, the log P values were computed by Hyperchem software. Here, alendronate was used as a reference inhibitor. Results showed that the IC(50) values ranged from 9.11 to 28.72 mM. The half maximal inhibitory concentration (IC(50)) value decreased with an increasing number of carbon atoms of the amine group in compounds 1-5. Also, in most cases, increasing the number of carbon atoms led to enhancement of the toxicity as predicted by the log P values. Using Lineweaver-Burk and Dixon analysis, it was indicated that compounds 1-10 are mixed inhibitors while compound 11 is a coupling or uncompetitive inhibitor. The results showed that the electronic changes have ignorable effects, steric influence is important in some cases, but the lipophilicity parameter is the most significant factor in hAChE inhibition by bisphosphonates.
Authors:
Khodayar Gholivand; Fatemeh Ghaziani; Rouhollah Yaghoubi; Zahra Hosseini; Zahra Shariatinia
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-03-30
Journal Detail:
Title:  Journal of enzyme inhibition and medicinal chemistry     Volume:  25     ISSN:  1475-6374     ISO Abbreviation:  J Enzyme Inhib Med Chem     Publication Date:  2010 Dec 
Date Detail:
Created Date:  2010-11-08     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101150203     Medline TA:  J Enzyme Inhib Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  827-35     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Faculty of Basic Sciences, Tarbiat Modares University, Tehran, Iran. gholi_kh@modares.ac.ir
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