Skip to main content
SpringerLink
Log in

The effect of dimyristoylphosphatidylethanol on the lateral and rotational mobilities of liposome lipid bilayers

  • Articles
  • Drug Efficacy
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

The aim of this study was to provide the basis to further examine the mode of action of ethanol. Fluorescent probes reported to have different membrane mobilities were used to evaluate the effect of dimyristoylphosphatidylethanol (DMPEt) on the lateral and rotational mobilities of liposome lipid bilayers. An experimental procedure, based on the selective quenching of 1,6-diphenyl-1,3,5-hexatriene (DPH) and 1,3-di(1-pyrenyl)propane (Py-3-Py) by trinitrophenyl groups, was used. DMPEt increased the bulk lateral and rotational mobilities, and had a greater fluidizing effect on the outer than the inner monolayer. These effects of DMPEt on liposomes may be responsible for some, but not all, of the general anesthetic actions of ethanol.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Alling, C., Gustavsson, L., Månsson, J.-E., Benthin, G., and Anggård, E., Phosphatidylethanol formation in rat organs after ethanol treatment.Biochim. Biophys. Acta, 793, 119–122 (1984).

    PubMed  CAS  Google Scholar 

  • Angelova, M. L. and Dimitrov, D. S., Liposome electroformation.Faraday Discuss. Chem. Soc., 81, 303–311 (1986).

    Article  CAS  Google Scholar 

  • Angelova, M. L., Soléau, S., Meléard, P. H., Faucon, J. F., and Bothorel, P., Preparation of giant vesicles by external AC fields, kinetics and application.Prog. Colloid. Polym. Sci., 89, 127–131 (1992).

    Article  CAS  Google Scholar 

  • Armbrecht, H. J., Wood, W. G., Wise, R. W., Walsh, J. B., Thomas B. N., and Strong, R., Ethanol-induced disordering of membranes from different age groups of C57BL/6NNIA mice.J. Pharmacol. Exp. Ther., 226, 387–391 (1983).

    PubMed  CAS  Google Scholar 

  • Bae, M. K., Huh, M. H., Lee, S. W., Kang, H. G., Pyun, J. H., Kwak, M. H., Jang, H. O., and Yun, I., Effects of dopamine·Hcl on structural parameters of bovine brain membranes.Arch. Pharm. Res., 27, 653–661 (2004).

    Article  PubMed  CAS  Google Scholar 

  • Bae, M. K., Jeong, D. K., Park, N. S., Lee, C. H., Cho, B. H., Jang, H. O., and Yun, I., Effects of ethanol on the physical properties of Neuronal Membranes.Mol. Cells, 19, 356–364 (2005).

    PubMed  CAS  Google Scholar 

  • Bagatolli, L. A. and Gratton, E., Two photon fluorescence microscopy observation of shape change at the phase transition in phospholipid giant unilamellar vesicles.Biophys. J., 77, 2090–2101 (1999).

    PubMed  CAS  Google Scholar 

  • Bagatolli, L. A. and Gratton, E., Two photon fluorescence microscopy of coexisiting lipid domains in giant unilamellar vesicles of binary phospholipid mixtures.Biophys. J., 78, 290–305 (2000).

    Article  PubMed  CAS  Google Scholar 

  • Bangham, A. D. and Mason, W., The effect of some general anesthetics on the surface potential of lipid monolayers.Br. J. Pharmacol., 66, 259–265 (1979).

    PubMed  CAS  Google Scholar 

  • Bartlett, G. R., Phosphorous assay in column chromatography.J. Biol. Chem., 234, 466–468 (1959).

    PubMed  CAS  Google Scholar 

  • Chin, J. H. and Goldstein, D. B., Effects of low concentrations of ethanol on the fluidity of spin-labeled erythrocyte and brain membranes.Mol. Pharmacol., 13, 435–441 (1977a).

    PubMed  CAS  Google Scholar 

  • Chin, J. H. and Goldstein, D. B., Drug tolerance in biomembranes: a spin label study of the effects of ethanol.Science, 196, 684–685 (1977b).

    Article  PubMed  CAS  Google Scholar 

  • Chin, J. H. and Goldstein, D. B., Membrane-disordering action of ethanol: variation with membrane cholesterol content and depth of the spin label probe.Mol. Pharmacol., 19, 425–431 (1981).

    PubMed  CAS  Google Scholar 

  • Chin, J. H. and Goldstein, D. B., Cholesterol blocks the disordering effects of ethanol in biomembranes.Lipids, 19, 929–935 (1984).

    Article  PubMed  CAS  Google Scholar 

  • Davidson, F. M. and Long, C., The structure of the naturally occurring phosphoglycerides. 4. Action of cabbage-leaf phospholipase D on ovolecithin and related substances.Biochem. J., 69, 458–466 (1958).

    PubMed  CAS  Google Scholar 

  • Dimitrov, D. S. and Angelova, M. L., Lipid swelling and liposome formation on solid surfaces in external electric fields.Prog. Colloid. Polym. Sci., 73, 48–56 (1987).

    Article  CAS  Google Scholar 

  • Franks, N. P. and Lieb, W. R., Mapping of general anesthetic target sites provides a molecular basis for cutoff effects.Nature, 316, 349–351 (1985).

    Article  PubMed  CAS  Google Scholar 

  • Franks, N. P. and Lieb, W. R., Neuron membranes: anesthetics on the mind.Nature, 328, 113–114 (1987).

    Article  PubMed  CAS  Google Scholar 

  • Franks, N. P. and Lieb, W. R., Do general anesthetics act by competitive binding to specific receptors?Nature, 310, 599–601 (1993).

    Article  Google Scholar 

  • Franks, N. P. and Lieb, W. R., Molecular and cellular mechanisms of general anesthesia.Nature, 367, 607–614 (1994).

    Article  PubMed  CAS  Google Scholar 

  • Gonzales, R. A. and Hoffman, P. L., Receptor-gated ion channels may be selective CNS targets for ethanol.Trends Pharmacol. Sci., 12, 1–3 (1991).

    Article  PubMed  CAS  Google Scholar 

  • Huang, N.-N., Florine-Casteel, K., Feigenson, G. W., and Spink, C., Effect of fluorophore linkage position ofn-(9-anthroyloxy) fatty acids on probe distribution between coexisting gel and fluid phospholipid phases.Biochim. Biophys. Acta, 939, 124–130 (1988).

    Article  PubMed  CAS  Google Scholar 

  • Jacobs, R. E. and White, S. H., The nature of the hydrophobic binding of small peptides at the bilayer interface. Implications for the insertion of transbilayer helices.Biochemistry, 28, 3421–3437 (1989).

    Article  PubMed  CAS  Google Scholar 

  • Jang, H. O., Jeong, D. K., Ahn, S. H., Yoon, C. D., Jeong, S. C., Jin, S. D., and Yun, I., Effects of chlorpromazine·Hcl on the structural parameters of bovine brain membranes.J. Biochem. Mol. Biol., 37, 603–611 (2004b).

    PubMed  CAS  Google Scholar 

  • Jang, H. O., Shin, H. G., and Yun, I., Effects of dimyristoylphosphatidylethanol on the structural parameters of neuronal membrane.Mol. Cells, 17, 485–491 (2004a).

    PubMed  CAS  Google Scholar 

  • Kang, J.-S., Choi, Ch.-M., and Yun, I., Effects of ethanol on lateral and rotational mobility of plasma membrane vesicles isolated from cultured mouse myeloma cell line, Sp2/0-Ag14.Biochim. Biophys. Acta, 1281, 157–163 (1996).

    Article  PubMed  Google Scholar 

  • Lasic, D. D., The mechanism of vesicle formation.Biochem. J., 256, 1–11 (1988).

    PubMed  CAS  Google Scholar 

  • Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J., Protein measurement with the Folin phenol reagent.J. Biol. Chem., 193, 265–275 (1951).

    PubMed  CAS  Google Scholar 

  • Madeira, V. M. C. and Antunes-Madeira, M. C., Lipid composition of biomembranes: a complete analysis of sarcoplasmic reticulum phospholipids.Cienc. Biol., (Coimbra), 2, 265–291 (1976).

    CAS  Google Scholar 

  • Menger, F. M. and Keiper, J. S., Chemistry and physics of giant vesicles as biomembrane models.Curr. Opin. Chem. Biol., 2, 726–732 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Omodeo-Salê, M. F., Cestaro, B., Mascherpa, A., Monti, D., and Masserini, M., Enzymatic synthesis and thermotropic behavior of phosphatidylethanol.Chem. Phys. Lipids, 50, 135–142 (1989).

    Article  Google Scholar 

  • Omodeo-Salê, M. F., Lindi, C., Palestini, P., and Masserini, M., Role of phosphatidylethanol in membranes. Effects on membrane fluidity, tolerance to ethanol, and activity of membrane-bound enzymes.Biochemistry, 30, 2477–2482 (1991).

    Article  PubMed  Google Scholar 

  • Sanna, E., Concas, A., Serra, M., Santoro, G., and Biggio, G.,Ex vivo binding of t-[35S)butylbicyclophosphorothionate: a biochemical tool to study the pharmacology of ethanol at the gamma-aminobutyric acid-coupled chloride channel.J. Pharmacol. Exp. Ther., 256, 922–928 (1991).

    PubMed  CAS  Google Scholar 

  • Schachter, D., Fluidity and function of hepatocyte plasma membranes.Hepatology, 4, 140–151 (1984).

    Article  PubMed  CAS  Google Scholar 

  • Sheetz, M. P. and Singer, S. J., Biological membranes as bilayer couples. A molecular mechanism of drug-erythrocyte interactions.Proc. Natl. Acad. Sci. U.S.A., 71, 4457–4461 (1974).

    Article  PubMed  CAS  Google Scholar 

  • Stubbs, C. D. and Williams, B. W., Fluorescence in, membranes; in Fluorescence Spectroscopy in Biochemistry, In Lakowicz, J. R. (Ed.). Vol. III, Plenum Press, New York, pp 231–263, (1992).

    Google Scholar 

  • Teeter, M. M., Water-protein interaction: the theory and experiment.Annu. Rev. Biophys. Biophys. Chem., 20, 577–600 (1991).

    Article  PubMed  CAS  Google Scholar 

  • Yun, I., Cho, E. S., Jang, H. O., Kim, U. K., Choi, C. H., Chung, I. K., Kim, I. S., and Wood, W. G., Amphiphilic effects of local anesthetics on rotational mobility in neuronal and model membranes.Biochim. Biophys. Acta, 1564, 123–132 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Yun, I. and Kang, J.-S., The general lipid composition and aminophospholipid asymmetry of synaptosomal plasma membrane vesicles isolated from bovine cerebral cortex.Mol. Cells, 1, 15–20 (1990).

    CAS  Google Scholar 

  • Yun, I., Kim, Y.-S., Yu, S.-H., Chung, I.-K., Kim, I.-S., Baik, S.-W., Cho, G.-J., Chung, Y.-Z., Kim, S.-H., and Kang, J.-S., Comparision of several procedures for the preparation of synaptosomal plasma, membrane vesicles.Arch. Pharm. Res., 13, 325–329 (1990).

    Article  Google Scholar 

  • Yun, I., Lee, S.-H., and Kang, J.-S., Effects of ethanol on lateral and rotational mobility of plasma membrane vesicles isolated from cultured Mar 18.5 hybridoma cells.J. Membr. Biol., 138, 221–227 (1994).

    PubMed  CAS  Google Scholar 

  • Yun, I., Yang, M.-S., Kim, I.-S., and Kang, J.-S., Bulkvs. transbilayer effects of ethanol on the fluidity of the plasma membrane vesicles of cultured Chinese hamster ovary cells.Asia Pacific J. Pharmacol., 8, 9–16 (1993).

    CAS  Google Scholar 

  • Zachariasse, K. A., Vaz, W. L. C., Stomayer, C., and Kuhnle, W., Investigation of human erythrocyte ghost membranes with intramolecular excimer probes.Biochim. Biophys. Acta, 688, 323–332 (1982).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Dental Pharmacology and Biophysics, College of Dentistry and Research Institute for Oral Biotechnology, Pusan National University, 602-739, Busan, Korea

    Hye-Ock Jang, Min-Hoi Huh, Seung-Woo Lee, Young-Ho Lee, Jong-Hwa Lee, Jun-Bong Seo, Kyo-Il Koo, Seong-Deok Jin, Je-Hyung Jeong, Jang-Seop Lim, Moon-Kyung Bae & Il Yun

Authors
  1. Hye-Ock Jang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Min-Hoi Huh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Seung-Woo Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Young-Ho Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jong-Hwa Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jun-Bong Seo
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Kyo-Il Koo
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Seong-Deok Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Je-Hyung Jeong
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Jang-Seop Lim
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Moon-Kyung Bae
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Il Yun
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Il Yun.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jang, HO., Huh, MH., Lee, SW. et al. The effect of dimyristoylphosphatidylethanol on the lateral and rotational mobilities of liposome lipid bilayers. Arch Pharm Res 28, 839–847 (2005). https://doi.org/10.1007/BF02977351

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02977351

Key words

Search

Navigation