Biomimetic approach to biomembrane models studies: medium influence on the interaction kinetics of some phenylurea derivatives herbicides.
The ability of herbicides to interact with cell membranes outer lipid layer and subsequently to penetrate inside cells can be a prerequisite for exhibiting a toxic activity for both the directly exposed workers and the end consumers as the herbicides are present in the soil and water. The effect exerted by fenuron, chlorotoluron, metobromuron, monolinuron, and chlorbromuron, five structurally similar phenylurea herbicides, on the thermotropic behavior of model membranes, represented by dimyristoylphosphatidylcholine (DMPC) vesicles, was investigated by differential scanning calorimetry. The examined compounds, when dispersed in liposomes during their preparation, exerted a different action on the gel-to-liquid crystal phase transition of DMPC multilamellar vesicles. The ability of phenylurea herbicides, as a finely powdered solid, to migrate through an aqueous medium and interact with biomembrane models was also studied. This transfer process was compared with these compounds intermembrane transfer from herbicide-loaded liposomes to empty ones. These processes can mimic absorption kinetics mediated by hydrophilic or lipophilic media. Different rate and entity of interaction occurred between model membranes and solid phenylurea herbicides. Different behavior was observed by considering the time-dependent studies carried out by contacting, for increasing times, equivalent amounts of empty DMPC vesicles with phenylurea herbicide-loaded ones; all compounds were able to migrate from loaded to empty DMPC vesicles. Thus, phenylurea herbicides are able to reach and penetrate biological membranes when dispersed in a lipophilic or hydrophilic medium; these processes are related to the substituents present on the compounds backbone. The obtained experimental results seem to validate the employed strategy to study the ability of bioactive compounds to both interact with biological membranes and be adsorbed inside a membrane mimicking a biological cell when dispersed in a lipophilic or hydrophilic medium.