Interactions of pyrethroids with phosphatidylcholine liposomal membranes.
Interactions of several pyrethroids with membrane lipids in the form of dipalmitoylphosphatidylcholine (DPPC) liposomes have been studied using fluorescent membrane probes. Fluorescence anisotropy values and lifetimes (determined by phase-shift and demodulation techniques) of the fluorescent probe, 1,6-diphenyl-1,3,5-hexatriene, were decreased in gel phase liposomes by pyrethroids at concentrations on the order of 10 microM. The pyrethroids containing a cyano substituent were also observed to cause collisional quenching of diphenylhexatriene fluorescence. Pyrethroids differed in their effectiveness at lowering the phase transition temperature of DPPC, and in their ability to broaden the temperature range of this transition. The fluorescence intensity of DPPC-incorporated chlorophyll a was used to monitor the pretransition of DPPC and the lateral diffusion of a membrane component located in the polar headgroup region. Permethrin did not affect chlorophyll a fluorescence intensity at any temperature. It may be concluded from these results that pyrethroids are preferentially located in the interior hydrophobic regions of the lipid bilayer, and that these compounds can disorder hydrocarbon packing in the bilayer core. However, polar headgroups were not disordered, and diffusion of membrane components in the polar headgroup region was not altered.
D000487:Allethrins / Q000378:metabolism; D002734:Chlorophyll / Q000378:metabolism; D004161:Diphenylhexatriene / Q000378:metabolism; D005454:Fluorescence Polarization; D005456:Fluorescent Dyes; D008081:Liposomes / Q000378:metabolism*; D009570:Nitriles; D026023:Permethrin; D010713:Phosphatidylcholines; D011722:Pyrethrins / Q000378:metabolism*; D013696:Temperature
D000487:Allethrins; D005456:Fluorescent Dyes; D008081:Liposomes; D009570:Nitriles; D010713:Phosphatidylcholines; D011722:Pyrethrins; D002734:Chlorophyll; D004161:Diphenylhexatriene; C017160:cypermethrin; C034227:fluvalinate; D026023:Permethrin; C044267:fenpropathrin