Surfactant-chaperoned donor–acceptor–donor NIR-II dye strategy efficiently circumvents intermolecular aggregation to afford enhanced bioimaging contrast

Tianyang Han; Yajun Wang; Jiajun Xu; Ningning Zhu; Lang Bai; Xiangping Liu; Bin Sun; Chenlong Yu; Qinglun Meng; Jiaqi Wang; Qi Su; Qing Cai; Kenneth S. Hettie; Yuewei Zhang; Shoujun Zhu; Bai Yang

doi:10.1039/D2SC05651H

Surfactant-chaperoned donor–acceptor–donor NIR-II dye strategy efficiently circumvents intermolecular aggregation to afford enhanced bioimaging contrast†

Tianyang Han,^ab Yajun Wang,^ab Jiajun Xu,^ab Ningning Zhu,^ab Lang Bai,^ab Xiangping Liu,^ab Bin Sun,^ab Chenlong Yu,

^ab Qinglun Meng,^a Jiaqi Wang,^a Qi Su,^a Qing Cai,^c Kenneth S. Hettie,

^d Yuewei Zhang,

^e Shoujun Zhu*^ab and Bai Yang

^ab

Author affiliations

* Corresponding authors

^a State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, P. R. China
E-mail: sjzhu@jlu.edu.cn

^b Joint Laboratory of Opto-Functional Theranostics in Medicine and Chemistry, First Hospital of Jilin University, Changchun, P. R. China

^c Hospital of Stomatology, Jilin University, Changchun, P. R. China

^d Molecular Imaging Program at Stanford (MIPS), Department of Radiology, Stanford University School of Medicine, Stanford, California, USA

^e School of Chemistry and Pharmaceutical Engineering, Jilin Institute of Chemical Technology, Jilin, P. R. China

Abstract

Fluorescence emission in the near-infrared-II (NIR-II) optical window affords reduced autofluorescence and light scattering, enabling deep-tissue visualization for both disease detection and surgical navigation. Small-molecule NIR-II dyes are preferable for clinical bioimaging applications, as the flexibility in their molecular synthesis allows for precise control of their optical and pharmacokinetic properties. Among the various types of dye, donor–acceptor–donor-based (D–A–D) dyes demonstrate exceptional photostability, whereas the frequently used PEGylation approach does not keep their intrinsic brightness enough in water environments due to their inherent effect of self-assembly. Here, we demonstrate that the commercially-available surfactants can serve as a dispersant to prevent molecular aggregation of PEGylated D–A–D dyes. Due to the favorable energetics for co-assembly between D–A–D dyes and surfactants, the formed surfactant-chaperoned dye strategy dramatically increases dye brightness. Accordingly, this effect provides remarkably improved performance for in vivo bioimaging applications. In parallel, we also investigate the D–A–D dye uptake and signal enhancement properties in the liver of murine models and demonstrate that the lumen-lining Kupffer cells can potentially disassemble PEGylated D–A–D aggregates such that their inherent brightness is restored. This phenomenon is similar to the surfactant-chaperoned dye strategy and our investigations provide a positive addition to better use of the current NIR-II fluorophores, especially for visualizing high-brightness required events.

This article is part of the themed collection: In celebration of Chinese New Year

Chemical Science

Surfactant-chaperoned donor–acceptor–donor NIR-II dye strategy efficiently circumvents intermolecular aggregation to afford enhanced bioimaging contrast†

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Surfactant-chaperoned donor–acceptor–donor NIR-II dye strategy efficiently circumvents intermolecular aggregation to afford enhanced bioimaging contrast

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