ABSTRACT
Two diastereomers of methylpheophorbide a 13(2)-N-n-octyl-N-(2-hydroxy-3-isobornyl-5-methylbenzyl)amide were obtained from (+)- and (-)-enantiomers of 2-isobornyl-4-methylphenol. Evaluation of membrane protective and antioxidant activity of individual diastereomers on the model of H2O2-induced hemolysis of blood erythrocytes showed that the stereochemistry of isobornyl substituent in the synthesized conjugates has no effect on their biological activity.
Subject(s)
Camphanes/chemistry , Chlorophyll/analogs & derivatives , Membranes/drug effects , Protective Agents/chemistry , Animals , Chlorophyll/chemical synthesis , Chlorophyll/chemistry , Chlorophyll/pharmacology , Chromatography, High Pressure Liquid , Cresols/chemistry , Erythrocytes/drug effects , Hydrogen Peroxide/chemistry , Mice , Molecular Structure , Protective Agents/chemical synthesis , Protective Agents/pharmacology , StereoisomerismABSTRACT
A series of terpenophenol-chlorin conjugates where terpenophenolic fragment has amide bond with macrocycle of methylpheophorbide a, formed by amidation of 13(2)-ester group were obtained by interaction of methylpheophorbide a and ortho-aminomethyl derivatives of 2-isobornyl-4-methylphenol. The substances investigated ability to interact with the cell membrane was shown in blood erythrocytes surface structure with scanning electron microscope. The conjugates studied were established to have antioxidant and membrane protective properties resulted from inhibiting H2O2-induced erythrocytes hemolysis and decrease of lipid peroxidation secondary product accumulation.
