Oligo(p-phenyleneethynylene) embedded amphiphiles: synthesis, photophysical properties and self-assembled nanoparticles with high structural stability and photostability for cell imaging
Oligo(p-phenyleneethynylene) embedded amphiphiles: synthesis, photophysical properties and self-assembled nanoparticles with high structural stability and photostability for cell imaging
复制标题
DOI：
10.1039/c4py00376d
复制
发表时间：
2014-08
影响因子：
4.6
通讯作者：
Chao Yin;Wen-li Song;Rongcui Jiang;Xiaomei Lu;Wenbo Hu;Qingming Shen;Xiang Li;Jie Li;Quli Fan;Wei Huang
中科院分区：
文献类型：
--
作者：
Chao Yin;Wen-li Song;Rongcui Jiang;Xiaomei Lu;Wenbo Hu;Qingming Shen;Xiang Li;Jie Li;Quli Fan;Wei Huang
设计并合成了新型两亲性有机不对称低聚对苯撑乙炔（OPE）共轭分子，末端为疏水性烷基链和亲水性甲氧基聚乙二醇（MPEG）链段。由于不对称两亲性OPE共轭分子的疏水-疏水性质，单分散的荧光纳米粒子很容易在水溶液中通过自组装获得。通过调节两亲性OPE中MPEG链的长度，制备了一系列具有不同水溶性的纳米粒子。通过动态光散射（DLS）和透射电子显微镜（TEM）研究了这些染料的聚集行为，结果表明，当与两亲性OPE键合的MPEG链较长时，在10 - 5 mol L-1的相同浓度下，将形成较小尺寸的纳米颗粒。此外，以OPE-PEG 1900为例，通过DLS和TEM可以推断不同浓度下的聚集行为，紫外吸收（UV）和光致发光（PL）分析也支持了这一结论。与以往报道的无光电功能的两亲物和油溶性共轭聚合物通过非共价键包封而成的共轭聚合物纳米粒子相比，OPE生色团通过共价键连接到两亲物中有效地提高了纳米粒子的结构稳定性。紫外光激发下的光漂白测试显示这些OPE纳米粒子的高光稳定性。鉴于这些纳米颗粒良好的水溶性、生物相容性、结构稳定性、光稳定性和优异的光电特性，进行了人胰腺癌细胞（PANC-1细胞）的细胞成像。共聚焦显微镜结果表明，纳米粒子（OPE-PEG 1000和OPE-PEG 1900）特异性地位于细胞质内。我们相信，OPE纳米粒子将发挥重要作用，作为长期生物成像的荧光生物标志物，并提供了新的机会，在生物医学科学的细胞成像和传感的良好适用性。
Novel amphiphilic organic asymmetrically oligo(p-phenyleneethynylene) (OPE) conjugated molecules, ending with a hydrophobic alkyl chain and a hydrophilic methoxypolyethyleneglycol (MPEG) segment, were designed and synthesized. Due to the hydrophilic–hydrophobic nature of the asymmetrically amphiphilic OPE conjugated molecules, monodispersed fluorescent nanoparticles were obtained easily by self-assembly in aqueous solution. Through adjusting the length of MPEG chains in amphiphilic OPE, a series of nanoparticles with different water solubility were prepared. The aggregation behaviors of these dyes were investigated by dynamic light scattering (DLS) and transmission electron microscopy (TEM), which indicated that when the MPEG chains bonding with amphiphilic OPE are longer, smaller sized nanoparticles will be formed at the same concentration of 10−5 mol L−1. Besides, taking OPE–PEG1900 as an example, diversified aggregation behaviors under different concentrations can be inferred through DLS and TEM, which were also supported by ultraviolet absorption (UV) and photoluminescence (PL) analyses. Compared with previously reported conjugated-polymer nanoparticles consisting of amphiphiles without photoelectric features and oil-soluble conjugated-polymers through non-covalent encapsulation, the introduction of OPE chromophores into amphiphiles by covalent linkage efficiently enhanced the structural stability of nanoparticles. A photobleaching test under UV excitation revealed the high photostability of these OPE nanoparticles. In view of the good water solubility, biocompatibility, structural stability, photostability, and excellent photoelectric features of these nanoparticles, cellular imaging of human pancreatic cancer cells (PANC-1 cells) was conducted. Confocal microscopy results showed that the nanoparticles (OPE–PEG1000 and OPE–PEG1900) were located specifically within the cell cytoplasm. We believe that the OPE nanoparticles would play an important role as fluorescent biomarkers for long-term bioimaging, and offer new opportunities for good applicability in cell imaging and sensing in biomedical science.