Department of Chemistry & Pharmacy, Chair of Organic Chemistry II, Friedrich-Alexander University of Erlangen-Nuremberg, Nikolaus-Fiebiger-Straße 10, 91058, Erlangen, Germany.
Department Chemistry and Pharmacy, Physical Chemistry I and ICMM, Friedrich-Alexander University of Erlangen-Nuremberg, Egerlandstraße 3, 91058, Erlangen, Germany.
Chemistry. 2021 Jan 21;27(5):1655-1669. doi: 10.1002/chem.202003232. Epub 2020 Nov 30.
A new series of shell-by-shell (SbS)-functionalized Al O nanoparticles (NPs) containing a perylene core in the organic interlayer as a fluorescence marker is introduced. Initially, the NPs were functionalized with both, a fluorescent perylene phosphonic acid derivative, together with the lipophilic hexadecylphosphonic acid or the fluorophilic (1 H,1 H,2 H,2H-perfluorodecyl)phosphonic acid. The lipophilic first-shell functionalized NPs were further implemented with amphiphiles built of aliphatic chains and polar head-groups. However, the fluorophilic NPs were combined with amphiphiles consisting of fluorocarbon tails and polar head-groups. Depending on the nature of the combined phosphonic acids and the amphiphiles, tuning of the perylene fluorescence can be accomplished due variations of supramolecular organization with the shell interface. Because the SbS-functionalized NPs dispose excellent dispersibility in water and in biological media, two sorts of NPs with different surface properties were tested with respect to biological fluorescent imaging applications. Depending on the agglomeration of the NPs, the cellular uptake differs. The uptake of larger agglomerates is facilitated by endocytosis, whereas individualized NPs cross directly the cellular membrane. Also, the larger agglomerates were preferentially incorporated by all tested cells.
引入了一系列新的壳层（SbS）功能化 Al O 纳米粒子（NPs），其中有机层间含有作为荧光标记的苝核。最初，NPs 同时被荧光苝膦酸衍生物以及亲脂性十六烷基膦酸或亲氟性（1H,1H,2H,2H-全氟癸基）膦酸功能化。亲脂性的第一壳层功能化 NPs 进一步与由脂肪链和极性头基团组成的两亲分子结合。然而，亲氟性 NPs 与由氟碳尾和极性头基团组成的两亲分子结合。根据所结合的膦酸和两亲分子的性质，可以通过壳层界面的超分子组织变化来实现对苝荧光的调谐。由于 SbS 功能化 NPs 在水和生物介质中具有优异的分散性，因此对具有不同表面性质的两种 NPs 进行了生物荧光成像应用测试。根据 NPs 的聚集程度，细胞摄取情况不同。较大聚集体的摄取通过内吞作用促进，而单个 NPs 则直接穿过细胞膜。此外，较大的聚集体优先被所有测试的细胞吸收。
