衍生于咔唑的双氰基二苯代乙烯型双光子荧光脂筏探针

制备了一个衍生于咔唑的双氰基二苯代乙烯型双光子荧光脂筏探针——(E)-2-甲基-5-{2-[9-正辛基(3-咔唑基)]乙烯基}对苯二甲腈(DLR), 并对其结构进行了表征. 结果表明, DLR属于推-拉电子结构(供体-桥-受体, D-π-A), 其最大发射波长随介质极性递增, 而其荧光强度却随极性递减. DLR在二棕榈酰磷脂酰胆碱 (DPPC)中的发射强度是在二油酰磷脂酰胆碱(DOPC)中的20倍, 其对DPPC, 模拟脂筏[n(DOPC)∶n(鞘磷脂)∶n(胆固醇)=1∶1∶1]和DOPC的荧光强度比为20∶12.8∶1, 在DPPC中的荧光寿命是在DOPC中的2.2倍以上, 表明DLR能很好地区分DPPC与DOPC. DLR在DPPC和DOPC中的双光子发射截面(Φδ)分别为1350和67 GM, 表明DLR能够很好地识别脂筏, 成像脂筏在细胞与组织中的分布动态.

Carbazole-derived Dicyanostilbene Two-photon Fluorescence Probe for Lipid Raft

Lipid raft is a microdomain which is rich in cholesterol and sphingolipid（sphingomyelin and glycosphingolipid） in the cytoplasmic membrane. They are involved in cellular processes such as cell transduction and protein transport， and are closely related to neurodegenerative diseases such as Alzheimer's disease and prion disease. Therefore， the studies on the dynamic physiological processes and the action mechanism of lipid raft are helpful to reveal its life mystery and its correlations with some diseases. The two-photon fluorescence probe for lipid raft became an indispensable sharp tool to achieve this goal. A carbazole-derived two-photon fluorescence probe for lipid raft（DLR） was developed and characterized. DLR belonged to push-pull electronic architecture（donor-bridge-receptor， D-π-A）. The maximum emission wavelength of the probe increased with the medium polarity and its fluorescence intensity decreased with the polarity. The emission intensity of DLR in dipalmitoylphosphatidylcholine（DPPC） was 20 times higher than that in dioleoylphosphatidylcholine（DOPC）， and the fluorescence intensity ratio of DLR in DPPC， Raft mix［n（DOPC）∶n（sphingomyelin）∶ n（cholesterol）=1∶1∶1］ and DOPC was 20∶12.8∶1， and its fluorescence lifetime in DPPC was more than 2.2 times that in DOPC， which indicated that DLR could distinguish DPPC from DOPC. The two-photon action cross sections（Φδ） of DLR in DPPC and DOPC were 1350 and 67 GM， respectively. DLR was able to image lipid raft distribution in cells and tissues.