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Study of local anaesthetics: Part 206*
Micellization of selected of quaternary ammonium salt derived from heptacaine


Authors: Jana Gališinová;  Jozef Čižmárik;  Eva Salanci;  Andrea Gálusová;  Lenka Stopková;  Fils Andriamainty
Published in: Čes. slov. Farm., 2015; 64, 144-148
Category: Original Articles

Overview

Micellization of selected quaternary ammonium compounds derived from heptacaine have been studied by absorption spectroscopy in the UV/VIS spectral region with the use of a pyrene probe. The compounds studied in the aqueous solution have been marked as H22, H26, H27, H29, H34, H + Al and H + B and the derivative marked as H34 was studied in a 3 mol/l ethanol solution at the temperature of 25 °C. In the homologous series of the studied bromides H22, H26, H27 and H29, cmc was observed to be dependent on the number of carbon atoms nc in the hydrophobic chain: ln (cmc) = –3.131–0.421nC. The Free Gibbs energy necessary for the transfer of a methyl group of the alkyl chain from the water phase to the inner part of the micelle at the temperature of 25 °C is (–0.421 ± 0.034)RT.

Key words:
heptacaine • quaternary ammonium compounds • critical micelle concentration • pyrene • Boltzmann-sigmoidal equation • alcohol


Sources

1. Pokorná M. Vztah struktury a lokálně anestetického účinku ve skupině esterů alkoxysubstituované kyseliny fenylkarbámové. Čes. slov. Farm. 1998; 47, 14–20.

2. Čižmárik J., Mazáň Š., Švec P., Borovanský A. Štúdium lokálnych anestetík LXVIII: Kvartérne amóniové soli heptakaínu a jeho pentyloxyanalógu. Čes. slov. Farm. 1978; 27(10), 427–431.

3. Čižmárik J., Mazáň Š., Švec P., Borovanský A. Quarternary Ammonium Salts of Heptacaine. Die Pharmazie 1978; 33(11), 762–763.

4. Basu Ray G., Chakraborty I., Moulik S. P. Pyrene absorption can be a convenient method for probing critical micellar concentration (cmc) and indexing micellar polarity. J. Coll. Interf. Sci. 2006; 294, 248–254.

5. Aguiar J., Carpena P., Molina-Bolívar J. A., Carnero Ruiz C. J. On the determination of the critical micelle concentration by the pyrene 1 : 3 ratio method. J. Coll. Interf. Sci. 2003; 258, 116–122.

6. Holmberg K., et al. Surfactants and Polymers in Aqueous Solution, 2nd edition. Chichester: John Wiley & Sons, Ltd. 2002.

7. Rosen M. J. Surfactants and Interfacial Phenomena, 3nd edition. Hoboken: John Wiley & Sons, Inc. 2004.

8. Andriamainty F., Čižmárik J. Thermodynamic study of local anaesthetics based on heptacainium chloride derivates. Part 163: Study of local anaesthetics. Die Pharmazie 2003; 58(6), 440–441.

9. Andriamainty F., Čižmárik J., Malík I. Štúdium lokálnych anestetík: Časť 185. Termodynamické parametre heptakaíniumchloridu v prostredí roztoku NaBr. Čes. slov. Farm. 2008; 57(6), 260–264.

10. Hiemenz, P. C., Rajagopalan, R. Principles of Colloid and Surface Chemistry, 3nd edition. New York: Marcel Dekker, Inc. 1997.

11. Andriamainty F., Čižmárik J., Uhríková D., Balgavý P. Study of local anesthetics. Part 168. Critical micelle concentration of alkoxy homologs of local anesthetic heptacainium chloride determined by ion selective electrode. Sci. Pharm. 2005; 73(1), 17–25.

12. Blažej A., Hodul P., Markušová E., Novák L., Paulovič M., Vyskočil I. Tenzidy. Bratislava: Alfa 1977.

13. Carpena P., Aguiar J., Bernaola-Galván P., Carnero Ruiz C. Problems associated with the treatment of conductivity-concentration data in surfactant solutions: simulations and experiments. Langmuir. 2002; 18, 6054–6058.

14. Healy T. W., Drummond C. J., Grieser F., Murray B. S. Electrostatic surface potential and critical micelle concentration relationship for ionic micelles. Langmuir1990; 6, 506.

15. Gališinová J., Čižmárik J., Andriamainty F., Malík I. Štúdium lokálnych anestetík: Časť 195. Štúdium micelizácie pentakaíniumchloridu v metanolových a etanolových roztokoch. Čes. slov. Farm. 2011; 60(6), 290–295.

16. Andriamainty F., Čižmárik J., Mariščáková Z. Štúdium lokálnych anestetík: Časť 160. Stanovenie kritickej micelovej koncentrácie série piperidínoetylesterov 3-alkoxyfenylkarbámovej kyseliny. Čes. slov. Farm. 2002; 51(3), 154–156.

17. Chalabala M., a kol. Technologie léků. Praha: Galén 1997.

18. Akhter M. S. Effect of solubilization of alcohols on critical micelle concentration of non-aqueous micellar solutions. Coll. Surf. 1999; 157, 203–210.

19. Akhter M. S., Al-Alawi S. M. Influence of alcohols on the critical micelle concentration of non–aqueous micellar solutions. Colloids and Surfaces 2000; 164, 247–255.

20. Akhter M. S., Al-Alawi S. M. Micellar behaviour of cetyltrimethyl-ammonium bromide in N-methyl acetamide – alkanol and N,N-dimethyl acetamide – alkanol mixtures. Coll. Surf. 2002; 196, 163–174.

21. Tomi T., Maeda T., Satake I., Hayakawa K. Micelle formation of a cationic surfactant in the presence of 1,n-alkanediol and the miscibility of alcohols in micelles. Coll. Surf. 2009; 346, 28–33.

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Pharmacy Clinical pharmacology
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