Document Detail

1,3-Diacylglycero-2-phosphocholines--synthesis, aggregation behaviour and properties as inhibitors of phospholipase D.
MedLine Citation:
PMID:  10660212     Owner:  NLM     Status:  MEDLINE    
A series of 1,3-diacylglycero-2-phosphocholines (1,3-PCs) with acyl chain lengths of C8-C18 were synthesised by chemical introduction of the phosphocholine moiety into the regioisomerically pure 1,3-diacylglycerols, which were obtained from glycerol and the vinyl esters of fatty acid by means of lipase from Rhizomucor mihei. The 1,3-PCs being regioisomers of the natural glycerophospholipids were studied with respect to their aggregation behaviour in the absence and in the presence of sodium dodecylsulfate (SDS) as well as their properties as substrates and inhibitors of phospholipase D (PLD) from cabbage. While the main structures of the pure 1,3-PCs were micelles (C8), liposomes (C10, C12) or planar bilayers (C14, C16, C18), the addition of SDS resulted in the formation of mixed micelles (C8, C10) and mixed liposomes (C12, C14, C16, C18). None of the 1,3-PCs was found to be hydrolysed by PLD, whereas all of them showed inhibitory properties in the standard assay for PLD. The inhibitory power was strongest with 1,3-didecanoylglycero-2-phosphocholine (IC50 = 43 microM).
R Haftendorn; G Schwarze; R Ulbrich-Hofmann
Publication Detail:
Type:  In Vitro; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  104     ISSN:  0009-3084     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  2000 Jan 
Date Detail:
Created Date:  2000-03-07     Completed Date:  2000-03-07     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  IRELAND    
Other Details:
Languages:  eng     Pagination:  57-66     Citation Subset:  IM    
Institut für Biotechnologie, Martin-Luther-Universität Halle-Wittenberg, Halle, Germany.
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MeSH Terms
Enzyme Inhibitors / chemical synthesis*,  chemistry,  pharmacology*
Lipid Bilayers
Lysophosphatidylcholines / chemical synthesis*,  chemistry,  pharmacology*
Macromolecular Substances
Magnetic Resonance Spectroscopy
Phospholipase D / antagonists & inhibitors*
Scattering, Radiation
Reg. No./Substance:
0/Enzyme Inhibitors; 0/Lipid Bilayers; 0/Liposomes; 0/Lysophosphatidylcholines; 0/Macromolecular Substances; 0/Micelles; EC D

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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