Purpose. To improve the bioavailability of the ocular drug timolol by
facilitating its transport through the cornea, an amphiphilic prodrug
was synthesized via the addition of a palmitic chain by esterification
. The present study was undertaken to investigate the physicochemical
and tensioactive properties of the prodrug. Methods. The amphiphilic p
roperties of the prodrug were firstly investigated by the Wilhelmy pla
te method. The textures generated by the supramolecular organizations
of the ester were visualized by optical microscopy. Results. The prodr
ug clearly decreased the surface tension. Optical microscopy provided
excellent evidence for the existence of lyotropic liquid crystalline p
hases: two isotropic but organized phases and a birefringent lamellar
phase.Conclusions. The results from the ensemble of studies undertaken
to determine the amphiphilic properties of the prodrug were all in ac
cord with its ability to form liquid crystalline phases. The liquid cr
ystalline state of the prodrug is believed to introduce a delay in the
drug pharmacological effect.