Synthesis and properties of radioiodinated phospholipid analogues that spontaneously undergo vesicle-vesicle and vesicle-cell transfer.
Synthesis and properties of radioiodinated phospholipid analogues that spontaneously undergo vesicle-vesicle and vesicle-cell transfer.
复制标题
自发进行囊泡-囊泡和囊泡-细胞转移的放射性碘化磷脂类似物的合成和性质。
DOI：
10.1021/bi00284a012
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发表时间：
1983
期刊：
影响因子：
2.9
通讯作者：
Madsen,JW
中科院分区：
文献类型：
--
作者：
Schroit,AJ;Madsen,JW
1-酰基-2-（氨基己酰基）磷脂酰胆碱与单碘化Bolton-Hunter试剂发生烷基化反应，制得1-酰基-2-[3-（3-[125 I]碘-4-羟基苯基）丙酰基]氨基]己酰基]磷脂酰胆碱（125 I-PC）。在乙醇胺或L-丝氨酸存在下，磷脂酶D催化125 I-PC进行碱交换，生成125 I-PC标记的磷脂酸、磷脂酰乙醇胺和磷脂酰丝氨酸。所有这些脂质类似物容易从供体囊泡转移到受体膜。当过量的受体囊泡与一群脂质囊泡混合时，一些生物化学和生物学研究表明，某些磷脂分子可以在脂质囊泡群体之间以及囊泡与细胞之间交换/转移。尽管这种现象已经显示在未修饰的磷脂中发生（Pagano和Huang，1975; Papahadjopoulos等人，1976; Martin & MacDonald，1976; Duckwitz-Peterlein等人，1977; Kremer等人，1977 a; Sandra & Pagano，1979; De Cuyper等人，1980），通过使用荧光脂质类似物已经获得了对该过程中涉及的机制的另外的了解（Monti等人，1977; Roseman & Thompson，1980）。Pagano及其同事使用各种囊泡-囊泡的优雅研究（Pagano等人，1981 a）和囊泡细胞（Struck & Pagano，1980; Pagano et al.，1982）系统已经证明某些酰基链标记的磷脂类似物可以容易地从合成磷脂囊泡转移。这已被证明发生在1-酰基-2-[6-[（7-硝基-2，1，3-苯并恶二唑-4-基）氨基]己酰基]磷脂酰胆碱（NBD-PC），* 1
1-Acyl-2-[[[3-(3-[125I] iodo-4-hydroxyphenyl)-propionyl] amino] caproyl] phosphatidylcholine (125I-PC) was prepared by alkylation of l-acyl-2-(aminocaproyl) phospha-tidylcholine with monoiodinated Bolton-Hunter reagent. 125I-Labeled phosphatidic acid, phosphatidylethanolamine, and phosphatidylserine were produced from 125I-PC by phospholipase D catalyzed base exchange in thepresence of ethanolamine or L-serine. All of these lipid analogues transferred readily from donorvesicles into recipient membranes. When an excess of acceptor vesicles was mixed with a population ofSeveral biochemical and biological studieshave demon-strated that certain phospholipid molecules can exchange/transfer between populations of lipid vesicles and between vesicles and cells. Although this phenomenon has been shown to occur with unmodifiedphospholipids (Pagano & Huang, 1975; Papahadjopoulos et al., 1976; Martin & MacDonald, 1976; Duckwitz-Peterlein et al., 1977; Kremer et al., 1977a; Sandra & Pagano, 1979; De Cuyper et al., 1980), additional insight into the mechanism involved in this process has been obtained through the use of fluorescent lipid analogues (Monti et al., 1977; Roseman & Thompson, 1980). The elegant studies of Pagano and co-workers using a variety of vesicle-vesicle (Pagano et al., 1981a) and vesicle-cell (Struck & Pagano, 1980; Pagano et al., 1982) systems have demonstrated that certain acyl chain labeled phospholipid analogues can readily transfer from synthetic phospholipid vesicles. This has been shown to occur with 1-acyl-2-[6-[(7-nitro-2, 1, 3-benzoxadiazol-4-yl) amino] caproyl] phosphatidylcholine (NBD-PC),* 1