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이광자 형광 표지자인 Laurdan 유도체의 개발

이광자 형광 표지자인 Laurdan 유도체의 개발
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The cell membrane surrounds all cells and it is semi-permeable, controlling the movement of substances in and out of cells. It contains a wide variety of biological molecules, primarily proteins and lipids. Among them, a lipid raft is the most important part of cell biology. A lipid raft is a cholesterol and sphingolipid-enriched microdomain or platform found in cell membranes. Plasma membrane has rigid compartments (lipid rafts) enriched with glycosphingolipids and cholesterol floating in the sea of glycerophospholipids (non-rafts). Lipid rafts are more ordered and tightly packed than the surrounding bilayer, but float freely in the membrane bilayer. The rigid compartments, also called rafts, are believed to be involved in many cellular processes such as signal transduction, pathogen invasion, cholesterol homeostasis, neurodegenerative diseases, and angiogenesis. To understand their roles in biology, it is crucial to visualize such domains in living cells and tissues. An ideal tool for that purpose is two-photon microscopy (TPM). TPM employs two near-infrared photons for excitation and offers a number of advantages over OPM, including increased penetration depth (greater than 500 μm), localized excitation, and prolonged observation time. The extra penetration depth that TPM affords is of particular interest in tissue imaging, because surface preparation artifacts such as damaged cells extend over 70 μm into the tissue interior. 2-Dimethylamimo-6-propionylnaphthalene (prodan) and 2-dimethylamino-6-lauroylnapththalene (laurdan), membrane probes that are sensitive to the polarity of the membrane, have often been used for cell membrane imaging. We have synthesized 1-(2-(dimethylamino)naphthalene-6-yl)butane-1,3-dione which is a prodan derivative and 1-(2-[N-methyl-N(carboxylethyl) amino]naphthalene-6-yl)tetradecane-1,3-dione which is a laurdan derivative. These two compounds possessing diketone group instead of a acetyl group in prodan or laurdan to extend the conjugation length and to increase the sensitivity of the fluorescence intensity relative to its environment polarity for the selective detection of the lipid rafts in live cells and tissues. These compounds are a turn-on probe that emits fluorescence exclusively in the nonpolar domains.
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