Calorimetric Study of the Interaction of Local Anesthetics [2-(Alkyloxy)phenyl]-2-(1-piperidinyl)ethyl Carbamates with Model Dipalmitoylphosphatidylcholine Membranes

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Title:Calorimetric Study of the Interaction of Local Anesthetics [2-(Alkyloxy)phenyl]-2-(1-piperidinyl)ethyl Carbamates with Model Dipalmitoylphosphatidylcholine Membranes
Creators:
Gallová, Jana
Bágeľová, Jaroslava
Čižmárik, Jozef
Balgavý, Pavol
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 60, 5, pp. 763-780

Abstract

<p>Local anesthetics of the homologous series of monohydrochlorides of [2-(alkoxy)phenyl]-2-(1-piperidinyl)ethyl esters of carbamic acid decrease the temperature of phase transitions L<sub>β'</sub> → P<sub>β</sub> (pretransition) and P<sub>β</sub> → L<sub>α</sub> (main transition) of 1,2-dipalmitoyl-<i>sn</i>-phosphatidylcholine in aqueous phase at pH 6.2. The efficiency of the anesthetics in decreasing the pretransition temperature increases with the number of carbon atoms <i>n</i> of the alkoxy substituent up to <i>n</i> = 6. For <i>n</i> &gt; 6 no pretransition could be detected. The efficiency in decreasing the temperature of the main transition increases up to <i>n</i> = 8 - 9 while it starts decreasing at <i>n</i> = 10. Computer simulation of the thermograms has shown that the decrease of efficiency at <i>n</i> = 10 is caused by the dependence of the partition coefficients of the anesthetics <i>K</i><sub>P,G</sub> and <i>K</i><sub>P,LC</sub> between the aqueous phase and the P<sub>β</sub> and L<sub>α</sub> phases, respectively, on the length of the alkoxy substituent, thus: log <i>K</i><sub>P,LC</sub> = <i>A</i><sub>LC</sub> + <i>B</i><sub>LC</sub> <i>n</i> and log <i>K</i><sub>P,G</sub> = <i>A</i><sub>G</sub> + <i>B</i><sub>G</sub> <i>n</i>, where <i>B</i><sub>LC</sub> &lt; <i>B</i><sub>G</sub>.

Title:Calorimetric Study of the Interaction of Local Anesthetics [2-(Alkyloxy)phenyl]-2-(1-piperidinyl)ethyl Carbamates with Model Dipalmitoylphosphatidylcholine Membranes
Creators:
Gallová, Jana
Bágeľová, Jaroslava
Čižmárik, Jozef
Balgavý, Pavol
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:60
Number:5
Page Range:pp. 763-780
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19950763UNSPECIFIED
ID Code:766
Item Type:Article
Deposited On:06 Feb 2009 17:03
Last Modified:06 Feb 2009 16:03

Citation

Gallová, Jana; Bágeľová, Jaroslava; Čižmárik, Jozef; Balgavý, Pavol (1995) Calorimetric Study of the Interaction of Local Anesthetics [2-(Alkyloxy)phenyl]-2-(1-piperidinyl)ethyl Carbamates with Model Dipalmitoylphosphatidylcholine Membranes. Collection of Czechoslovak Chemical Communications, 60 (5). pp. 763-780. ISSN 0010-0765

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