Nonspecific membrane effects of CH-103: Hydrophobicity, surface activity and membrane fluidity studies in comparison with propranolol and practolol

E. Varga, J. Szöllősi, K. Antal, P. Kovács, J. Szabó

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14 Citations (Scopus)

Abstract

The partition coefficient, surface activity and membrane fluidizing/disordering effects of CH-103, a β-adrenergic receptor antagonist, were compared to those of propranolol and practolol as reference compounds. Changes in membrane fluidity were followed by measuring the steady-state fluorescence anisotropy of bull sperm cells with 1-[4- (trimethylammonium)phenyl]-6-phenyl-1,3,5-hexatriene(TMA-DPH) as a fluorescence probe. The octanol/buffer (pH 7.0) partition coefficients for CH-103, propranolol and practolol were 32.9, 5.08 and 0.013, respectively; the surface activity of the compounds decreased in the same order. CH-103 and propranolol significantly increased the fluidity of the membrane in a concentration-dependent manner, whereas practolol reduced fluidity. These physicochemical parameters correlated with the effects of these drugs on rat sarcolemmal Ca2+, Mg2+-ATPase, a manifestation of their nonspecific membrane activity. Our results suggest that the physicochemical properties of CH-103, similarly to those of propranolol, are the main determinants of its nonspecific membrane activity.

Original languageEnglish
Pages (from-to)380-384
Number of pages5
JournalPharmazie
Volume54
Issue number5
Publication statusPublished - 1999

Fingerprint

Practolol
Membrane Fluidity
Fluidity
Hydrophobicity
Hydrophobic and Hydrophilic Interactions
Propranolol
Membranes
Octanols
Ca(2+) Mg(2+)-ATPase
Fluorescence Polarization
Fluorescence
Adrenergic Antagonists
Fluidization
Spermatozoa
Buffers
Rats
Anisotropy
naphthoxybutanolcyclohexylamine
Pharmaceutical Preparations

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science

Cite this

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abstract = "The partition coefficient, surface activity and membrane fluidizing/disordering effects of CH-103, a β-adrenergic receptor antagonist, were compared to those of propranolol and practolol as reference compounds. Changes in membrane fluidity were followed by measuring the steady-state fluorescence anisotropy of bull sperm cells with 1-[4- (trimethylammonium)phenyl]-6-phenyl-1,3,5-hexatriene(TMA-DPH) as a fluorescence probe. The octanol/buffer (pH 7.0) partition coefficients for CH-103, propranolol and practolol were 32.9, 5.08 and 0.013, respectively; the surface activity of the compounds decreased in the same order. CH-103 and propranolol significantly increased the fluidity of the membrane in a concentration-dependent manner, whereas practolol reduced fluidity. These physicochemical parameters correlated with the effects of these drugs on rat sarcolemmal Ca2+, Mg2+-ATPase, a manifestation of their nonspecific membrane activity. Our results suggest that the physicochemical properties of CH-103, similarly to those of propranolol, are the main determinants of its nonspecific membrane activity.",
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T2 - Hydrophobicity, surface activity and membrane fluidity studies in comparison with propranolol and practolol

AU - Varga, E.

AU - Szöllősi, J.

AU - Antal, K.

AU - Kovács, P.

AU - Szabó, J.

PY - 1999

Y1 - 1999

N2 - The partition coefficient, surface activity and membrane fluidizing/disordering effects of CH-103, a β-adrenergic receptor antagonist, were compared to those of propranolol and practolol as reference compounds. Changes in membrane fluidity were followed by measuring the steady-state fluorescence anisotropy of bull sperm cells with 1-[4- (trimethylammonium)phenyl]-6-phenyl-1,3,5-hexatriene(TMA-DPH) as a fluorescence probe. The octanol/buffer (pH 7.0) partition coefficients for CH-103, propranolol and practolol were 32.9, 5.08 and 0.013, respectively; the surface activity of the compounds decreased in the same order. CH-103 and propranolol significantly increased the fluidity of the membrane in a concentration-dependent manner, whereas practolol reduced fluidity. These physicochemical parameters correlated with the effects of these drugs on rat sarcolemmal Ca2+, Mg2+-ATPase, a manifestation of their nonspecific membrane activity. Our results suggest that the physicochemical properties of CH-103, similarly to those of propranolol, are the main determinants of its nonspecific membrane activity.

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