The interaction of two 6-fluoroquinolones, ciprofloxacin and its penty
l derivative, with model membranes was studied as a function of drug h
ydrophobicity as reflected in the pentyl side chain at position 4 in t
he piperazinyl group, by epifluorescence surface balance technique and
differencial scanning calorimetry. In the first part of this study dr
ug incorporation in dipalmitoylphosphatidylcholine monolayers was inve
stigated using epifluorescence microscopy, In the second part, the inf
luence of the presence of the hydrophobic chain and fluoroquinolone co
ntent on the thermotropic behavior of liposomes was investigated. Both
monolayer and calorimetric studies demonstrated that hydrophobicity o
f the drug had a role in determining the nature of drug-membrane inter
action as seen in greater perturbations of the lipid packing by pentyl
ciprofloxacin.