Document Detail

Influence of local anesthetics on the phosphatidylcholine model membrane: small-angle synchrotron X-ray diffraction and neutron scattering study.
MedLine Citation:
PMID:  15110934     Owner:  NLM     Status:  MEDLINE    
The phase preferences of egg yolk phosphatidylcholine (EYPC) have been examined in the presence of tertiary amine anesthetics [2-(propyloxy)phenyl]-2-(1-piperidinyl)ethyl ester of carbamic acid (C3A) and [2-(heptyloxy)phenyl]-2-(1-piperidinyl)ethyl ester of carbamic acid (C7A, heptacaine). Using the synchrotron small-angle X-ray diffraction (SAXD), it is shown that the C3A anesthetic induces the cubic and hexagonal (H(I)) phases at 2 > or = C3A:EYPC > 0.5 and H2O:EYPC < or = 40 molar ratios. In contrast, longer alkyloxy chain homolog C7A has no effect on the bilayer arrangement of EYPC at C7A:EYPC < = 1 molar ratios as observed by SAXD in C7A + EYPC mixtures hydrated at H2O:EYPC < = 40 molar ratios, as well as in sonicated C7A + EYPC mixtures hydrated in excess water as proved by the small-angle neutron scattering (SANS). The bilayer thickness d(L) decreases and the bilayer C7A surface area SC7A increases with the increase of C7A:EYPC molar ratio. It is suggested that the ability of tertiary amine local anesthetics to influence the dL and SC7A values and EYPC polymorphism is caused by their effective molecular shape and by charge. The possibility that anesthetic molecules may exert some of their biological effects by virtue of these properties is discussed.
Daniela Uhríková; Gert Rapp; Sergej Yaradaikin; Valentin Gordeliy; Pavol Balgavý
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biophysical chemistry     Volume:  109     ISSN:  0301-4622     ISO Abbreviation:  Biophys. Chem.     Publication Date:  2004 Jun 
Date Detail:
Created Date:  2004-04-27     Completed Date:  2004-12-20     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0403171     Medline TA:  Biophys Chem     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  361-73     Citation Subset:  IM    
Copyright Information:
Copyright 2003 Elsevier B.V
Laboratory of Biophysics, Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University, Odbojárov 10, 832 32 Bratislava, Slovakia.
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MeSH Terms
Amines / chemistry*,  pharmacology
Anesthetics, Local / chemistry,  pharmacology*
Egg Yolk / metabolism
Lipid Bilayers / chemistry*
Membranes / drug effects*
Models, Biological
Phosphatidylcholines / chemistry*
Polymorphism, Genetic
Scattering, Radiation
Structure-Activity Relationship
X-Ray Diffraction / methods
Reg. No./Substance:
0/Amines; 0/Anesthetics, Local; 0/Lipid Bilayers; 0/Phosphatidylcholines

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