In order to investigate the interaction of hydrophilic molecules with liposomal membranes, we employed 1-(4-(trimethylamino)phenyl)-6-phenyl-1,3,5-hexatriene and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(5-dimethylamino-1-naphthalenesulfonyl) as fluorescent probes to monitor the surface regions of the membrane, and the results for various liposomes were plotted in correlation diagrams. According to the formation of a variety of phase states, different tendencies of decreasing surface hydrophobicity were observed in the liposomes that were modified with high concentrations of cholesterol or in the liposomes that were composed of ternary components. These liposomes, with hydrophobic surfaces, also showed preferential adsorption of l-histidine (l-His), and the hydrophobicity of the liposomal membrane at the surface changed during l-His adsorption regardless of the initial liposomal properties. Furthermore, we revealed that accelerated adsorption of l-His and preferential binding was induced in ternary liposomes forming boundaries between two separate phases.
Carbonic anhydrase (CA) is a hydrolase enzyme possessing an active center composed of three histidines (His), zinc(II) (Zn 2+ ), and a hydration water. Here we report the hydrolase-like catalytic activity provided by the oleoyl-histidine (O-His) modified on liposome membranes. O-His was synthesized by the amide bond between oleic acid and His, and was incorporated into 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) liposomes. The hydrolysis of p-nitrophenylacetate was promoted by O-His modified DOPC liposomes in the presence of Zn 2+ . The formation of the active center was revealed by UV resonance Raman spectra. We conclude that the liposome membrane surface can be utilized as a platform for artificial hydrolysis reactions by modifying essential ligands inspired from natural enzymes.
We investigated the effect of organic acids such as mandelic acid (MA) and tartaric acid (TA) on the adsorption behavior of both histidine (His) and propranolol (PPL) onto liposomes. A cationic and heterogeneous liposome prepared using 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC)/sphingomyelin (SM)/3β-[N-(N',N'-dimethylaminoethane)carbamoyl]cholesterol (DC-Ch) in a ratio of (4/3/3) showed the highest adsorption efficiency of MA and TA independent of chirality, while neutral liposome DOPC/SM/cholesterol = (4/3/3) showed low efficiency. As expected, electrostatic interactions were dominant in MA or TA adsorption onto DOPC/SM/DC-Ch = (4/3/3) liposomes, suggesting that organic acids had adsorbed onto SM/DC-Ch-enriched domains. The adsorption behaviors of organic acids onto DOPC/SM/DC-Ch = (4/3/3) were governed by Langmuir adsorption isotherms. For adsorption, the membrane polarities slightly decreased (i.e., membrane surface was hydrophilic), but no alterations in membrane fluidity were observed. In the presence of organic acids that had been preincubated with DOPC/SM/DC-Ch = (4/3/3), the adsorption of l- and d-His onto those liposomes was examined. Preferential l-His adsorption was dramatically prevented only in the presence of l-MA, suggesting that the adsorption sites for l-His and l-MA on DOPC/SM/DC-Ch = (4/3/3) liposomes are competitive, while those for l-His and d-MA, l-TA, and d-TA are isolated.
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