Browning J L, Nelson D L
J Membr Biol. 1979 Aug;49(1):75-103. doi: 10.1007/BF01871040.
We have synthesized three sets of fluorescent probes which we believe will be useful in studies of asymmetric membranes and have studied their interactions with model lipid bilayers and erythrocyte membranes. The probes were designed to partition preferentially into one face of a lipid bilayer with asymmetrically disposed phospholipids and to report lipid transitions in that monolayer. We synthesized more than twenty probes containing anthroyl-, dansyl-, or pyrene rings with acidic, basic, and neutral functional groups and alkyl "spacers" of various lengths. The interactions of these probes with liposomes of phosphatidyl choline and with erythrocyte membranes were characterized to determine whether probe insertion was asymmetric, how deeply the probe penetrated the bilayer, and whether the probe reflected thermotropic phase transitions in model membranes. The set of variously charged anthroyl esters, analogs of local anaesthetics, appears to be promising for studies of asymmetric membranes. Fluorescent probes have been used extensively to provide information on the lipid regions of biological membranes. Membrane fluidity, a composite of molecular packing and motion of acyl chains in lipid bilayers, has been assessed with a variety of fluorescent probes, the fluorescence of which undergoes some measurable change at the temperature of the membrane's thermotropic phase transition. A large number of fluorescent probes have been used for this purpose. Bashford, Morgan and Radda (Bashford, C.L., Morgan, C.G., Radda, G.K. 1976; Biochim. Biophys. Acta 426:157) and Thulborn and Sawyer (Thulborn, K.R., Sawyer, W. H. 1978; Biochim. Biophys. Acta 511:125) synthesized several fatty acid derivatives in which an anthracene group is attached (in ester linkage) along the acyl chain at various positions, and have shown that this set of probes may be useful in probing membrane fluidity at different depths within the bilayer. This report describes the synthesis and properties of several sets of amphipathic fluorescent probes, which may partition unequally into the two faces of an asymmetric lipid bilayer, and may therefore provide information about membranes complementary to that obtainable with existing probes.
我们合成了三组荧光探针，我们认为这些探针将有助于非对称膜的研究，并研究了它们与模型脂质双层和红细胞膜的相互作用。这些探针被设计用于优先分配到具有不对称分布磷脂的脂质双层的一个面中，并报告该单层中的脂质转变。我们合成了二十多种含有蒽基、丹磺酰基或芘环以及酸性、碱性和中性官能团以及不同长度烷基“间隔基”的探针。对这些探针与磷脂酰胆碱脂质体和红细胞膜的相互作用进行了表征，以确定探针插入是否不对称、探针穿透双层的深度以及探针是否反映了模型膜中的热致相变。一组带不同电荷的蒽酯，即局部麻醉剂的类似物，似乎在非对称膜研究中很有前景。荧光探针已被广泛用于提供有关生物膜脂质区域的信息。膜流动性是脂质双层中酰基链分子堆积和运动的综合体现，已经用多种荧光探针进行了评估，这些探针的荧光在膜的热致相变温度下会发生一些可测量的变化。大量荧光探针已用于此目的。巴什福德、摩根和拉达（巴什福德，C.L.，摩根，C.G.，拉达，G.K. 1976；生物化学与生物物理学报426:157）以及图尔伯恩和索耶（图尔伯恩，K.R.，索耶，W.H. 1978；生物化学与生物物理学报511:125）合成了几种脂肪酸衍生物，其中蒽基团（以酯键形式）沿着酰基链连接在不同位置，并表明这组探针可用于探测双层内不同深度的膜流动性。本报告描述了几组两亲性荧光探针的合成和性质，这些探针可能会不平等地分配到不对称脂质双层的两个面中，因此可能提供与现有探针互补的膜相关信息。
