Genistein derivatives decrease liposome membrane integrity--calcein release and molecular modeling study.
The ability of newly synthesized genistein benzyl and glycosylated derivatives to permeabilize the liposome membrane was studied by calcein-leakage method. All studied derivatives appeared to be more effective than their parent compound--genistein. Comparing the experimental results with theoretical calculations we found that in the case of benzyl derivatives the dipole moment of added benzene ring (with its substitutions) might be important for the strength of flavonoids-lipid interactions. This conclusion may have some implications for QSAR studies in which mostly the dipole moments of entire molecules are considered.
Sroda
Kamila
K
Department of Biophysics, Wrocław Medical University, ul. Chałubińskiego 10, 50-368 Wrocław, Poland.
Michalak
Krystyna
K
Maniewska
Jadwiga
J
Grynkiewicz
Grzegorz
G
Szeja
Wiesław
W
Zawisza
Jadwiga
J
Hendrich
Andrzej B
AB
D002463:Cell Membrane Permeability; D005452:Fluoresceins / Q000032:analysis*; D016166:Free Radical Scavengers / Q000737:chemistry*; D019833:Genistein / Q000737:chemistry*; D008051:Lipid Bilayers / Q000737:chemistry*; D008081:Liposomes / Q000737:chemistry*; D008954:Models, Biological; D008958:Models, Molecular
D005452:Fluoresceins; D016166:Free Radical Scavengers; D008051:Lipid Bilayers; D008081:Liposomes; D019833:Genistein; C007740:fluorexon