Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, Tempe, Arizona, United States of America.
PLoS One. 2011;6(9):e24425. doi: 10.1371/journal.pone.0024425. Epub 2011 Sep 6.
With the successful development of organic/polymeric light emitting diodes, many organic and polymeric fluorophores with high quantum efficiencies and optical stability were synthesized. However, most of these materials which have excellent optical properties are insoluble in water, limiting their applications in biological fields. Herein, we used micelles formed from an amino-group-containing poly(ε-caprolactone)-block-poly(ethylene glycol) (PCL-b-PEG-NH(2)) to incorporate a hydrophobic blue emitter oligofluorene (OF) to enable its application in biological conditions. Although OF is completely insoluble in water, it was successfully transferred into aqueous solutions with a good retention of its photophysical properties. OF exhibited a high quantum efficiency of 0.84 in a typical organic solvent of tetrahydrofuran (THF). In addition, OF also showed a good quantum efficiency of 0.46 after being encapsulated into micelles. Two cells lines, human glioblastoma (U87MG) and esophagus premalignant (CP-A), were used to study the cellular internalization of the OF incorporated micelles. Results showed that the hydrophobic OF was located in the cytoplasm, which was confirmed by co-staining the cells with nucleic acid specific SYTO 9, lysosome specific LysoTracker Red®, and mitochondria specific MitoTracker Red. MTT assay indicated non-toxicity of the OF-incorporated micelles. This study will broaden the application of hydrophobic functional organic compounds, oligomers, and polymers with good optical properties to enable their applications in biological research fields.
随着有机/聚合物发光二极管的成功开发，许多具有高量子效率和光学稳定性的有机和聚合物荧光团被合成。然而，这些具有优异光学性能的大多数材料都不溶于水，限制了它们在生物领域的应用。在这里，我们使用含有氨基的聚（ε-己内酯）-嵌段-聚（乙二醇）（PCL-b-PEG-NH2）形成的胶束来包埋疏水性蓝色荧光团低聚物芴（OF），使其能够在生物条件下应用。尽管 OF 完全不溶于水，但它成功地转移到水溶液中，保留了其光物理性质。OF 在典型的有机溶剂四氢呋喃（THF）中表现出 0.84 的高量子效率。此外，OF 被包封到胶束中后也表现出 0.46 的良好量子效率。两种细胞系，人胶质母细胞瘤（U87MG）和食管前病变（CP-A），被用于研究包埋 OF 的胶束的细胞内摄取。结果表明，疏水性 OF 位于细胞质中，这通过与核酸特异性 SYTO 9、溶酶体特异性 LysoTracker Red®和线粒体特异性 MitoTracker Red 共染色来证实。MTT 测定表明，包埋 OF 的胶束没有毒性。这项研究将拓宽具有良好光学性能的疏水性功能有机化合物、低聚物和聚合物的应用范围，使其能够应用于生物研究领域。
