Quinoxaline-Based Polymer Dots with Ultrabright Red to Near-Infrared Fluorescence for In Vivo Biological Imaging

This article describes the design and synthesis of quinoxaline-based semiconducting polymer dots (Pdots) that exhibit near-infrared fluorescence, ultrahigh brightness, large Stokes shifts, and excellent cellular targeting capability. We also introduced fluorine atoms and long alkyl chains into polym...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-08, Vol.137 (32), p.10420-10429
Main Authors: Liu, Hong-Yi, Wu, Pei-Jing, Kuo, Shih-Yu, Chen, Chuan-Pin, Chang, En-Hao, Wu, Chang-Yi, Chan, Yang-Hsiang
Format: Article
Language:English
Subjects:
Animals
Chemistry Techniques, Synthetic
Embryo, Nonmammalian - blood supply
Embryo, Nonmammalian - diagnostic imaging
Fluorescein Angiography - methods
Fluorescence
Fluorine - chemistry
HeLa Cells
Humans
MCF-7 Cells
Optical Imaging - methods
Photochemistry - methods
Quantum Dots - chemistry
Quinoxalines - chemistry
Semiconductors
Streptavidin - chemistry
Thiophenes - chemistry
Zebrafish - embryology
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Summary:This article describes the design and synthesis of quinoxaline-based semiconducting polymer dots (Pdots) that exhibit near-infrared fluorescence, ultrahigh brightness, large Stokes shifts, and excellent cellular targeting capability. We also introduced fluorine atoms and long alkyl chains into polymer backbones and systematically investigated their effect on the fluorescence quantum yields of Pdots. These new series of quinoxaline-based Pdots have a fluorescence quantum yield as high as 47% with a Stokes shift larger than 150 nm. Single-particle analysis reveals that the average per-particle brightness of the Pdots is at least 6 times higher than that of the commercially available quantum dots. We further demonstrated the use of this new class of quinoxaline-based Pdots for effective and specific cellular and subcellular labeling without any noticeable nonspecific binding. Moreover, the cytotoxicity of Pdots were evaluated on HeLa cells and zebrafish embryos to demonstrate their great biocompatibility. By taking advantage of their extreme brightness and minimal cytotoxicity, we performed, for the first time, in vivo microangiography imaging on living zebrafish embryos using Pdots. These quinoxaline-based NIR-fluorescent Pdots are anticipated to find broad use in a variety of in vitro and in vivo biological research.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b06710