Donor−Acceptor−Donor Fluorene Derivatives for Two-Photon Fluorescence Lysosomal Imaging
| Autor: | Jie Fu, Eric W. Van Stryland, Xuhua Wang, David J. Hagan, Sheng Yao, Kevin D. Belfield, Hyo Yang Ahn |
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| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Fluorenes Fluorophore Organic Chemistry Electron donor Fluorene Electron acceptor HCT116 Cells Photochemistry Two-photon absorption Fluorescence Acceptor Article Molecular Imaging chemistry.chemical_compound chemistry Humans Lysosomes Micelles Fluorescence anisotropy Fluorescent Dyes |
| Zdroj: | The Journal of Organic Chemistry. 75:3965-3974 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | As part of a strategy to achieve large two-photon absorptivity in fluorene-based probes, a series of donor-acceptor-donor (D-A-D) type derivatives were synthesized and their two-photon absorption (2PA) properties investigated. The synthesis of D-A-D fluorophores was achieved by efficient preparation of key intermediates for the introduction of central electron acceptor groups. To accomplish the synthesis of two of the new derivatives, a high-yield method for a one-step direct dibromomethylation of phenyl sulfide was developed. The linear and nonlinear optical properties, including UV-vis absorption, fluorescence emission, fluorescence anisotropy, and two-photon absorption (2PA), of the new D-A-D compounds were measured and compared to their D-A or D-D counterparts. Fully conjugated acceptor moieties in the center of the D-A-D fluorophore led to the greatest increase in the 2PA cross section, while weakly conjugated central acceptors exhibited only a modest increase in the 2PA cross section relative to D-A diploar analogs. Encapsulation of the new probes in Pluronic F 108NF micelles, and subsequent incubation in HCT 116 cells, resulted in very high lysosomal colocalization (0.98 colocalization coefficient) relative to commercial Lysotracker Red, making the micelle-encapsulated dyes particularly attractive as fluorescent probes for two-photon fluorescence microscopy lysosomal imaging. |
| Databáze: | OpenAIRE |
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