NMR study of the interaction of beta-blockers with sonicated dimyristoylphosphatidylcholine liposomes in the presence of praseodymium cation

Membr Biochem. 1989;8(4):197-206. doi: 10.3109/09687688909026814.

Abstract

The interaction of a series of beta-adrenoreceptor blocking agents with unilamellar dimyristoylphosphatidylcholine (DMPC) liposomes has been studied by proton nuclear magnetic resonance (1H-NMR) in the presence of praseodymium cation (Pr3+) at 30 degrees C. Addition of Pr3+ increased the splitting of the trimethylammonium group signals arising from the phospholipid molecules located at the internal and external surfaces of the bilayers. Adding Pr3+ caused a considerable downfield shift of the external peak but only a slight upfield shift of the internal peak (approximately 3%). The difference in chemical shift of the external and internal peaks (delta Hz) increased linearly as a function of Pr3+ concentration up to 10 mM. The addition of beta-blockers reversed the effect of Pr3+, and propranolol exerted the most pronounced effect, causing complete reversal of the splitting at a concentration of 5 mM. Much higher concentrations of other beta-blockers were required to displace Pr3+. A linear correlation between Pr3+ displacement (P) and logarithm of the apparent partition coefficient (K'm) in DMPC liposomes was obtained for hydrophobic beta-blockers, but hydrophilic beta-blockers did not fit this correlation. It appears that beta-blockers that have ortho or meta substitution require penetration of the liposome bilayers before significant polar group interaction can occur. On the other hand, beta-blockers that have para substitution and low K'm values are able to interact with the polar surfaces of the liposomes without penetration to cause displacement of Pr3+.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adrenergic beta-Antagonists / chemistry
  • Adrenergic beta-Antagonists / pharmacology*
  • Cations
  • Chemical Phenomena
  • Chemistry, Physical
  • Dimyristoylphosphatidylcholine / chemistry*
  • Dimyristoylphosphatidylcholine / metabolism
  • Lipid Bilayers / chemistry
  • Lipid Bilayers / metabolism
  • Liposomes / chemistry*
  • Liposomes / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Praseodymium / metabolism
  • Praseodymium / pharmacology*
  • Propranolol / pharmacology
  • Sonication
  • Structure-Activity Relationship

Substances

  • Adrenergic beta-Antagonists
  • Cations
  • Lipid Bilayers
  • Liposomes
  • Propranolol
  • Praseodymium
  • Dimyristoylphosphatidylcholine