Study of Micellization and Partition Balances of Acyl Stobadine Derivatives: Effect of Temperature and Length of Alkyl Chain

Ž. Bezáková; J. Oremusová; M. Stankovičová; Z. Vitková

doi:10.3139/113.110092

Published by De Gruyter April 5, 2013

Study of Micellization and Partition Balances of Acyl Stobadine Derivatives

Effect of Temperature and Length of Alkyl Chain

Untersuchung der Mizellenbildung und des Verteilungsgleichgewichts von Acylstobadindertivaten

Effekt der Temperatur und der Alkylkettenlänge

Ž. Bezáková , J. Oremusová , M. Stankovičová and Z. Vitková

From the journal Tenside Surfactants Detergents

https://doi.org/10.3139/113.110092

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Abstract

Important physicochemical characteristics for drugs, namely micellar properties and experimental partition coefficient of the series of five acyl stobadine derivatives in aqueous solutions were studied. The aim was to find out whether the studied compounds prepared as oxalates form associates. For measurements conductometry was used. The critical micelle concentrations (CMC) and thermodynamic parameters of micellization (standard molar Gibbs energy, enthalpy and entropy of micellization) were calculated from conductivity curves within the temperature range 25°C–50°C. The spectrophotometrically determined partition coefficients in the system octyl alcohol-water increased in parallel with increasing molar mass of studied substances. The dependences between values of common logarithm of CMC and partition coefficients of studied compounds were compared.

Kurzfassung

An einer Reihe von fünf Acylstobadinderivaten wurden für Wirkstoffe wichtige physikochemische Merkmale, nämlich die Mizelleigenschaften und der experimentelle Verteilungskoeffizient in wässriger Lösung untersucht. Ziel war, herauszufinden, ob die untersuchten Komponenten als Oxalate Assoziate bilden. Als Messmethode wurde die Konduktometrie eingesetzt. Die kritische Mizellbildungskonzentration (CMC) und die thermodynamischen Parameter der Mizellenbildung (Standard-Gibbsenergie, Enthalpie und Entropie der Mizellenbildung) wurden anhand der Leitfähigkeitskurven zwischen 25°C und 50°C berechnet. Die spektrophotometrisch bestimmten Verteilungskoeffizienten im System Oktylalkohol-Wasser stiegen mit zunehmender Molmasse der untersuchten Substanzen an. Die Abhängigkeiten zwischen den Werten des Logarithmus der CMC und der Verteilungskoeffizienten der untersuchten Substanzen wurde miteinander verglichen.

Key words:: Acyl stobadine derivatives; association; critical micelle concentration; partition coefficient; conductometry; UV VIS spectrophotometry

Stichwörter:: Acylstobadinderivate; Assoziation; kritische Mizellbildungskonzentration; Verteilungskoeffizient; Konduktometrie; UV-Vis-Spektrophotometrie

^∗ J. Oremusová, Department of Physical Chemistry of Drugs, Faculty of Pharmacy Comenius University, Odbojárov 10, 83232 Bratislava, Slovak Republic. E-Mail: oremusova@fpharm.uniba.sk

Dr. Jarmila Oremusová, PhD. graduated from the Faculty of Chemical Technology, Slovak University of Technology in Bratislava, Slovakia, in 1983. She obtained PhD degree in 1990. Since 1989 she has been acting at the Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University in Bratislava.

Assoc. Prof. Mária Stankovičová, PhD. graduated from the Faculty of Pharmacy, Comenius University in Bratislava, Slovakia, in 1969. She obtained PhD degree in 1987. Since 1995 she has been acting as associate professor at the Department of Pharmaceutical Chemistry. Research: Study of physico-chemical properties of drugs acting on cardiovascular system and local anaesthetics. She is author of numerous journal and conference papers related to these topics.

Assoc. Prof. Želmíra Bezáková, CSc. (PhD.) graduated from the Faculty of Pharmacy, Comenius University in Bratislava, Slovakia, in 1970. She obtained CSc. (PhD.) degree in 1985. Since 1991 she has been acting as associate professor at the Department of Pharmaceutical Chemistry. Research: study of analytical, physical and physicochemical properties and stability of new synthesized potential drugs especially with effect on cardiovascular system. She is author of numerous journal and conference papers related to these topics and also she is author of 3 monographs related to drug analysis and control.

Assoc. Prof. Zuzana Vitková, PhD. graduated from the Faculty of Pharmacy, Comenius University in Bratislava, Slovakia, in 1967. She obtained PhD degree in 1972. Since 1993 she has been acting as associate professor at the Department of Galenic Pharmacy. Research: Modern drug delivery systems and biopharmacy. She is author of numerous journal and conference papers and two monographs related to these topics.

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Received: 2010-02-11

Published Online: 2013-04-05

Published in Print: 2010-11-01