Compounds > 1-2-dielaidoylphosphatidylethanolamine

1-2-dielaidoylphosphatidylethanolamine and 2-hydroxy-1-naphthaldehyde

1-2-dielaidoylphosphatidylethanolamine has been researched along with 2-hydroxy-1-naphthaldehyde* in 1 studies

Other Studies

1 other study(ies) available for 1-2-dielaidoylphosphatidylethanolamine and 2-hydroxy-1-naphthaldehyde

Article	Year
The chemical synthesis of N-[1-(2-naphthol)]-phosphatidylethanolamine, a fluorescent phospholipid for excited-state proton transfer studies. Chemistry and physics of lipids, 1992, Volume: 61, Issue:3 A procedure for the preparation of N-[1-(2-naphthol)]-phosphatidylethanolamine (NAPH-PE) has been developed. The synthesis is based on the Schiff base formation between the NH2 of the phospholipid and the aldehyde moiety of 2-hydroxy-1-naphthaldehyde. Then selective reduction of the imine is used to obtain the stable secondary amine, NAPH-PE. Formation of the intermediate Schiff base and the final product is confirmed by 13C- and 1H-NMR. Similar to free 2-naphthol, the excited-state pKa (pKa*) of its phospholipid derivative appears to be significantly lower than the ground-state pKa. At pH 7.4, the excitation spectrum of NAPH-PE shows no deprotonated species in the ground-state, while the emission spectrum presents a significant contribution of this species. Thus the fluorescent phospholipid exhibits the typical behavior of excited-state proton-transfer probes. NAPH-PE is found to incorporate in dimyristoyllecithin (DML) vesicles. The emission spectrum of the probe inserted in the liposomes is affected by acetate used as a proton acceptor. These properties should also be manifest in other lipid bilayers (e.g., plasma membranes of cells) and used for excited-state proton transfer studies. Topics: Fluorescence; Fluorescent Dyes; Hydrogen-Ion Concentration; Kinetics; Lipids; Magnetic Resonance Spectroscopy; Membranes; Naphthalenes; Optics and Photonics; Phosphatidylethanolamines; Protons; Spectrum Analysis	1992

Article

Year

The chemical synthesis of N-[1-(2-naphthol)]-phosphatidylethanolamine, a fluorescent phospholipid for excited-state proton transfer studies.

Chemistry and physics of lipids, 1992, Volume: 61, Issue:3

A procedure for the preparation of N-[1-(2-naphthol)]-phosphatidylethanolamine (NAPH-PE) has been developed. The synthesis is based on the Schiff base formation between the NH2 of the phospholipid and the aldehyde moiety of 2-hydroxy-1-naphthaldehyde. Then selective reduction of the imine is used to obtain the stable secondary amine, NAPH-PE. Formation of the intermediate Schiff base and the final product is confirmed by 13C- and 1H-NMR. Similar to free 2-naphthol, the excited-state pKa (pKa*) of its phospholipid derivative appears to be significantly lower than the ground-state pKa. At pH 7.4, the excitation spectrum of NAPH-PE shows no deprotonated species in the ground-state, while the emission spectrum presents a significant contribution of this species. Thus the fluorescent phospholipid exhibits the typical behavior of excited-state proton-transfer probes. NAPH-PE is found to incorporate in dimyristoyllecithin (DML) vesicles. The emission spectrum of the probe inserted in the liposomes is affected by acetate used as a proton acceptor. These properties should also be manifest in other lipid bilayers (e.g., plasma membranes of cells) and used for excited-state proton transfer studies.

Topics: Fluorescence; Fluorescent Dyes; Hydrogen-Ion Concentration; Kinetics; Lipids; Magnetic Resonance Spectroscopy; Membranes; Naphthalenes; Optics and Photonics; Phosphatidylethanolamines; Protons; Spectrum Analysis

1992