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Interaction of hexahydro 1 benzopyranobenzodiazepine derivatives with liposomes as studied by absorption spectroscopy and fluorescence probe technique

Interaction of hexahydro 1 benzopyranobenzodiazepine derivatives with liposomes as studied by absorption spectroscopy and fluorescence probe technique

Studia Biophysica 128(1): 51-61

By means of absorption spectroscopy, steady-state fluorescence and fluorescence decay measurements it was found that the cancerostatically active compound (+)cis-3,4-dimethoxy-10,11-dimethyl-6,6aR,7,8,13,13aS-hexahydro-[1]-benzopyrano-[4,3-b]-1,5-benzodiazepine (ZIMET 54/79) and its biologically inactive (-)-enantiomer (ZIMET 55/79) interact with liposomal membranes. At pH values of 6.0 and 7.3, the longwave absorption bands of ZIMET 54/79 and 55/79 show weak bathochromic and hypochromic effects upon addition of neutral, positively and negatively charged phosphatidylcholine and phosphatidylcholine-cholesterol liposomes. Those spectral changes are interpreted as being caused by binding of both drugs to the phospholipid bilayers. Steady-state fluorescence measurements using the membrane probe 1-anilino-8-naphthalene sulfonic acid (ANS) result in a weak decrease of the fluorescence intensity in the presence of the drugs. Time-resolved measurements demonstrate that the drug effect mainly consists in a partial dislocation of the ANS molecules from the hydrophobic binding environment into regions of higher solvent accessibility. No significant differences in the binding properties of the cancerostatically active and inactive compound with liposomes could be detected on the basis of spectrophotometric and fluorescence measurements.

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