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Synthesis and Spectroscopic Analysis of Chromophoric Lipids Inducing pH-Dependent Liposome Fusion

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journal contribution
posted on 03.12.2003, 00:00 by Takenori Tomohiro, Yoshikatsu Ogawa, Hiroaki Okuno, Masato Kodaka
We design novel chromophoric amphiphiles 6ac, which lead to pH-dependent membrane fusion of egg phosphatidylcholine (eggPC) liposome containing them. Lipids 6ac comprise double alkyl chains, a single chain with a 2-nitrophenol group as a pH trigger, and dipeptide (Asp-Asp) between them. The pKa values of 2-nitrophenol groups of 6ac in liposome are larger than that of hydrophilic compound 9 in an aqueous solution. Absorption spectra indicate that the fields around 2-nitrophenol of 6ac situated in liposome membranes are more hydrophobic than that of 9 in an aqueous solution, whereas the environments around deprotonated 2-nitrophenolate of 6b and 6c are not so hydrophobic as that of 6a. This means that protonated 2-nitrophenol groups of 6ac are embedded in bilayer membranes. Deprotonated 2-nitrophenol groups of 6b and 6c must be located in less hydrophobic circumstances, while that of 6a is still embedded in bilayer membranes because of its larger hydrophobicity. Absorption spectra and 1H NMR spectra respectively suggest that protonated 2-nitrophenol groups of 6a and those of 6c might take face-to-face associations in bilayer membranes.