香豆素衍生物的合成及其作为荧光探针在膜和细胞动态研究中的应用。
Synthesis of coumarin derivatives as fluorescent probes for membrane and cell dynamics studies.
机构信息
Department of Chemistry, Faculty of Sciences, University of Chile, Santiago, Chile; Facultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 Calle 67, Ibagué, Colombia.
Centro de Bioinformática y Simulación Molecular, Facultad de Ingeniería, Universidad de Talca, 2 Norte 685, Casilla 721, Talca, Chile.
出版信息
Eur J Med Chem. 2014 Apr 9;76:79-86. doi: 10.1016/j.ejmech.2014.02.016. Epub 2014 Feb 11.
Three coumarin-derived fluorescent probes, 3-acetyl-7-[(6-bromohexyl)oxy]-2H-chromen-2-one (FM1), 7-[(6-bromohexyl)oxy]-4-methyl-2H-chromen-2-one (FM2) and ethyl 2-{7-[(6-bromohexyl)oxy]-2-oxo-2H-chromen-4-yl}acetate (FM3), are described, with their photophysical constants. The compounds were tested in preliminary studies employing epifluorescence microscopy demonstrating that they allow the imaging of human neuroblastoma SH-SY5Y cell membranes. The structure of FM3 was confirmed by X-ray crystallographic analysis. Molecular dynamics (MD) simulations were used to characterize the localization and interactions of the studied compounds with a lipid bilayer model of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC).
描述了三种香豆素衍生的荧光探针，3-乙酰基-7-[(6-溴己基)氧基]-2H-色烯-2-酮（FM1）、7-[(6-溴己基)氧基]-4-甲基-2H-色烯-2-酮（FM2）和乙酯 2-{7-[(6-溴己基)氧基]-2-氧代-2H-色烯-4-基}乙酸酯（FM3），并给出了它们的光物理常数。这些化合物在初步研究中通过荧光显微镜测试，证明它们可以对人神经母细胞瘤 SH-SY5Y 细胞膜进行成像。FM3 的结构通过 X 射线晶体学分析得到证实。分子动力学（MD）模拟用于表征研究化合物与 1-棕榈酰基-2-油酰基-sn-甘油-3-磷酸胆碱（POPC）的脂质双层模型的定位和相互作用。
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