Document Detail

Study of physico-chemical properties of novel highly sulfated, aromatic, mimetics of heparin and heparan sulfate.
MedLine Citation:
PMID:  19711446     Owner:  NLM     Status:  MEDLINE    
Heparin (H) and heparan sulfate (HS) play major roles in a number of biological processes. Yet, H/HS-based pharmaceutical agents are also associated with multiple adverse effects. This has led to the concept of designing noncarbohydrate, aromatic mimetics that modulate H/HS function. In this work, we study a library of synthetic, aromatic H/HS mimetics for their capillary electrophoretic profiles, the acid and base stability, and aqueous-organic partitioning property. The nonsugar H/HS mimetics exhibit electrophoretic properties similar to sulfated oligosaccharides suggesting that the mimetics can be rapidly and quantitatively analyzed. Stability studies show that the mimetics are essentially stable under neutral and basic conditions in a manner similar to the heparins, but are considerably unstable under acidic conditions in contrast to heparins. The measurement of partition coefficients show major differences within the sulfated mimetics as well as between the measured and calculated log P values. Understanding these physico-chemical properties is expected to have significant implications in the pharmaceutical development of this growing class of molecules.
Aiye Liang; Jay N Thakkar; Umesh R Desai
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of pharmaceutical sciences     Volume:  99     ISSN:  1520-6017     ISO Abbreviation:  J Pharm Sci     Publication Date:  2010 Mar 
Date Detail:
Created Date:  2010-01-19     Completed Date:  2010-04-02     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985195R     Medline TA:  J Pharm Sci     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1207-16     Citation Subset:  IM    
Copyright Information:
2009 Wiley-Liss, Inc. and the American Pharmacists Association
Department of Medicinal Chemistry, Institute for Structural Biology and Drug Discovery, Virginia Commonwealth University, Richmond, Virginia 23219, USA.
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MeSH Terms
Anticoagulants / chemical synthesis,  chemistry*
Chemistry, Pharmaceutical / methods
Drug Design*
Drug Stability
Electrophoresis, Capillary / methods
Heparin / analogs & derivatives,  chemistry*
Heparitin Sulfate / chemistry*
Molecular Structure
Physicochemical Processes*
Polycyclic Hydrocarbons, Aromatic / chemical synthesis,  chemistry*
Grant Support
Reg. No./Substance:
0/Anticoagulants; 0/Polycyclic Hydrocarbons, Aromatic; 9005-49-6/Heparin; 9050-30-0/Heparitin Sulfate

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