Influence of some quaternised 1,4-dihydropyridine derivatives on liposomes and erythrocyte membranes.
1,4-Dihydropyridine derivatives possess various physiological activities but their mechanism of membranotropic action is not completely investigated yet. We have examined the membranotropic effects of 4-beta-pyridyl-1,4-Dihydropyridine derivatives containing different length alkyl chain substituent at N-quaternised 4-beta-pyridyl moiety. The results show the relation between incorporation of 1,4-dihydropyridine derivatives in the liposomal membranes and influence on bilayer fluidity. The compound with hexadecyl (C16H33) substituent in the 4-beta-pyridyl moiety possess the most pronounced incorporation ability and fluidizing effect. This compound causes the remarkable release of fluorescent probe calcein from liposomes and induces the hemolysis of human erythrocytes as well. The obtained results suggest that the length of alkyl chain at quaternized 4-beta-pyridyl moiety is significant for the expression of membranotropic effects of tested compounds.
Latvian Institute of Organic Synthesis, Riga, Latvia. diana@osi.lanet.lv
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D015060:1,2-Dipalmitoylphosphatidylcholine; D004095:Dihydropyridines / Q000737:chemistry / Q000494:pharmacology*; D004910:Erythrocyte Membrane / Q000187:drug effects* / Q000502:physiology; D005452:Fluoresceins / Q000378:metabolism; D005456:Fluorescent Dyes / Q000378:metabolism; D006461:Hemolysis; D006801:Humans; D008051:Lipid Bilayers; D008081:Liposomes; D008560:Membrane Fluidity / Q000187:drug effects*; D013050:Spectrometry, Fluorescence; D013329:Structure-Activity Relationship
D004095:Dihydropyridines; D005452:Fluoresceins; D005456:Fluorescent Dyes; D008051:Lipid Bilayers; D008081:Liposomes; D015060:1,2-Dipalmitoylphosphatidylcholine; C007740:fluorexon