Anionic fullerenes, calixarenes, coronenes, and pyrenes as activators of oligo/polyarginines in model membranes and live cells
Anionic fullerenes, calixarenes, coronenes, and pyrenes as activators of oligo/polyarginines in model membranes and live cells
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DOI：
10.1021/ja043633c
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发表时间：
2005-02-02
影响因子：
15
通讯作者：
Matile, S
中科院分区：
文献类型：
--
作者：
Perret, F;Nishihara, M;Matile, S
我们报告，流出的5（6）-羧基荧光素阴离子从中性蛋黄磷脂酰胆碱囊泡介导的寡/聚精氨酸只有在激活两性阴离子的存在下。阴离子活化剂的筛选揭示了两亲性羧酸盐（富勒烯-杯[4]芳烃-晕苯>芘>杯[6]芳烃-烷基）的最佳协同作用，而两亲性硫酸盐显示出不太令人满意的活化，尽管通常较低的有效浓度。类似的醇和一种杯[4]芳烃二磷酸是无活性的。这些结果进行了讨论的背景下，一个试探性的阴离子载体机制，其中与双层（界面定向易位）和载体（芳烃模板羧酸盐-胍配对）的相互作用有助于激活剂的效率。应用于HeLa细胞，芘丁酸显着增加吸收的荧光标记的octarginine在浓度依赖性的方式。
We report that the efflux of 5(6)-carboxyfluorescein anions from neutral egg yolk phosphatidylcholine vesicles is mediated by oligo/polyarginines only in the presence of activating amphiphilic anions. Screening of anion activators reveals best synergism for amphiphilic carboxylates (fullerene ≫ calix[4]arene ≈ coronene > pyrene > calix[6]arene ≫ alkyl), whereas amphiphilic sulfates show less satisfactory activation despite often lower effective concentrations. The analogous alcohols and one calix[4]arene diphosphate were inactive. These results are discussed in the context of a tentative anion carrier mechanism, where interactions with bilayer (interface-directed translocation) and carrier (arene-templated carboxylate−guanidinium pairing) contribute to activator efficiencies. Applied to HeLa cells, pyrenebutyrate is shown to significantly increase the uptake of a fluorescently labeled octaarginine in a concentration-dependent manner.