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通过一锅多组分反应合成具有聚集诱导发射特性的荧光树状大分子及其在生物成像中的应用。

Synthesis of fluorescent dendrimers with aggregation-induced emission features through a one-pot multi-component reaction and their utilization for biological imaging.

机构信息

Shaanxi Key Laboratory of Degradable Biomedical Materials, Shaanxi R&D Center of Biomaterials and Fermentation Engineering, School of Chemical and Engineering, Northwest University, Xi'an 710069, PR China; Department of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China.

Department of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China.

出版信息

J Colloid Interface Sci. 2018 Jan 1;509:327-333. doi: 10.1016/j.jcis.2017.09.039. Epub 2017 Sep 9.

DOI:10.1016/j.jcis.2017.09.039
PMID:28918375
Abstract

Hyperbranched polymers have attracted wide research attention owing to their unique topological structure, physicochemical properties and great potential for applications such asadditives, drug delivery, catalysts and nanotechnology. Among these, the polyamidoamine(PAMAM) dendrimers are some of the most important dendrimers. However, the synthesis and biomedical applications of fluorescent PAMAM dendrimers have received only limited attention. In this work, we present a rather effective and convenient approach for synthesis of fluorescent PAMAM dendrimers with aggregation-induced emission (AIE) properties through a one-pot catalyst-free Mannich reaction under rather mild experimental conditions (e.g., low reaction temperature, air atmosphere in the presence of water). The obtained AIE-active amphiphiles (PhE-PAD) could self-assemble into fluorescent organic nanoparticles (FONs). The obtained AIE-active FONs (PhE-PAD FONs) were fully characterized, and their successful construction was confirmed by H NMR spectroscopy, FT-IR spectroscopy and transmission electron microscopy. Fluorescence and UV-Visible absorption spectroscopy results demonstrated that the final PhE-PAD FONs showed strong yellow fluorescence, desirable photostability and good water dispersity. The cell viability evaluation and confocal laser scanning microscope imaging results suggested that PhE-PAD FONs possessed low cytotoxicity and excellent biocompatibility. Taken together, these results demonstrate that we have developed a facile and efficient strategy for the fabrication of AIE-active FONs, which possess many desirable features for biomedical applications.

摘要

超支化聚合物因其独特的拓扑结构、物理化学性质以及在添加剂、药物传递、催化剂和纳米技术等领域的巨大应用潜力而引起了广泛的研究关注。在这些聚合物中,聚酰胺-胺(PAMAM)树枝状大分子是最重要的树枝状大分子之一。然而,荧光 PAMAM 树枝状大分子的合成及其在生物医学中的应用仅受到有限的关注。在这项工作中,我们提出了一种在温和实验条件下(例如,低反应温度、在水存在下的空气气氛)通过一锅无催化剂的曼尼希反应合成具有聚集诱导发射(AIE)性质的荧光 PAMAM 树枝状大分子的相当有效和方便的方法。得到的具有 AIE 活性的两亲物(PhE-PAD)可以自组装成荧光有机纳米粒子(FONs)。所得的具有 AIE 活性的 FONs(PhE-PAD FONs)进行了全面的表征,并通过 1H NMR 光谱、FT-IR 光谱和透射电子显微镜确认了其成功构建。荧光和紫外-可见吸收光谱结果表明,最终的 PhE-PAD FONs 表现出强的黄色荧光、理想的光稳定性和良好的水分散性。细胞活力评估和共聚焦激光扫描显微镜成像结果表明,PhE-PAD FONs 具有低细胞毒性和优异的生物相容性。综上所述,这些结果表明我们已经开发出一种用于制备具有 AIE 活性的 FONs 的简便有效的策略,该策略具有许多用于生物医学应用的理想特性。

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