J-aggregates of Meso-[2.2]paracyclophanyl-BODIPY Dye for NIR-II Imaging

Overview

Journal Nat Commun

Specialty Biology

Date 2021 Apr 23

PMID 33888714

Citations 27

Authors

Kang Li

Xingchen Duan

Zhiyong Jiang

Dan Ding

Yuncong Chen

Guo-Qiang Zhang

Zhipeng Liu

Affiliations

Soon will be listed here.

Abstract

J-aggregation is an efficient strategy for the development of fluorescent imaging agents in the second near-infrared window. However, the design of the second near-infrared fluorescent J-aggregates is challenging due to the lack of suitable J-aggregation dyes. Herein, we report meso-[2.2]paracyclophanyl-3,5-bis-N,N-dimethylaminostyrl BODIPY (PCP-BDP2) as an example of BODIPY dye with J-aggregation induced the second near-infrared fluorescence. PCP-BDP2 shows an emission maximum at 1010 nm in the J-aggregation state. Mechanism studies reveal that the steric and conjugation effect of the PCP group on the BODIPY play key roles in the J-aggregation behavior and photophysical properties tuning. Notably, PCP-BDP2 J-aggregates can be utilized for lymph node imaging and fluorescence-guided surgery in the nude mouse, which demonstrates their potential clinical application. This study demonstrates BODIPY dye as an alternate J-aggregation platform for developing the second near-infrared imaging agents.

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References

Fang Y, Shang J, Liu D, Shi W, Li X, Ma H . Design, Synthesis, and Application of a Small Molecular NIR-II Fluorophore with Maximal Emission beyond 1200 nm. J Am Chem Soc. 2020; 142(36):15271-15275. DOI: 10.1021/jacs.0c08187. View

Su M, Li S, Zhang H, Zhang J, Chen H, Li C . Nano-Assemblies from J-Aggregated Dyes: A Stimuli-Responsive Tool Applicable To Living Systems. J Am Chem Soc. 2018; 141(1):402-413. DOI: 10.1021/jacs.8b10396. View

Philp L, Chan H, Rouzbahman M, Overchuk M, Chen J, Zheng G . Use of Porphysomes to detect primary tumour, lymph node metastases, intra-abdominal metastases and as a tool for image-guided lymphadenectomy: proof of concept in endometrial cancer. Theranostics. 2019; 9(9):2727-2738. PMC: 6525988. DOI: 10.7150/thno.31225. View

Wurthner F, Kaiser T, Saha-Moller C . J-aggregates: from serendipitous discovery to supramolecular engineering of functional dye materials. Angew Chem Int Ed Engl. 2011; 50(15):3376-410. DOI: 10.1002/anie.201002307. View

Chen Z, Lohr A, Saha-Moller C, Wurthner F . Self-assembled pi-stacks of functional dyes in solution: structural and thermodynamic features. Chem Soc Rev. 2009; 38(2):564-84. DOI: 10.1039/b809359h. View

Sun Y, Qu C, Chen H, He M, Tang C, Shou K . Novel benzo-bis(1,2,5-thiadiazole) fluorophores for NIR-II imaging of cancer. Chem Sci. 2018; 7(9):6203-6207. PMC: 6024204. DOI: 10.1039/c6sc01561a. View

Cheng M, Harmatys K, Charron D, Chen J, Zheng G . Stable J-Aggregation of an aza-BODIPY-Lipid in a Liposome for Optical Cancer Imaging. Angew Chem Int Ed Engl. 2019; 58(38):13394-13399. DOI: 10.1002/anie.201907754. View

Wang X, Wu Y, Liu Q, Li Z, Yan H, Ji C . Aggregation-induced emission (AIE) of pyridyl-enamido-based organoboron luminophores. Chem Commun (Camb). 2014; 51(4):784-7. DOI: 10.1039/c4cc07451c. View

Wan H, Yue J, Zhu S, Uno T, Zhang X, Yang Q . A bright organic NIR-II nanofluorophore for three-dimensional imaging into biological tissues. Nat Commun. 2018; 9(1):1171. PMC: 5862886. DOI: 10.1038/s41467-018-03505-4. View

10.

Kaiser T, Stepanenko V, Wurthner F . Fluorescent J-aggregates of core-substituted perylene bisimides: studies on structure-property relationship, nucleation-elongation mechanism, and sergeants-and-soldiers principle. J Am Chem Soc. 2009; 131(19):6719-32. DOI: 10.1021/ja900684h. View

11.

Kaiser T, Wang H, Stepanenko V, Wurthner F . Supramolecular construction of fluorescent J-aggregates based on hydrogen-bonded perylene dyes. Angew Chem Int Ed Engl. 2007; 46(29):5541-4. DOI: 10.1002/anie.200701139. View

12.

Li B, Lu L, Zhao M, Lei Z, Zhang F . An Efficient 1064 nm NIR-II Excitation Fluorescent Molecular Dye for Deep-Tissue High-Resolution Dynamic Bioimaging. Angew Chem Int Ed Engl. 2018; 57(25):7483-7487. DOI: 10.1002/anie.201801226. View

13.

Cai K, Xie J, Zhang D, Shi W, Yan Q, Zhao D . Concurrent Cooperative J-Aggregates and Anticooperative H-Aggregates. J Am Chem Soc. 2018; 140(17):5764-5773. DOI: 10.1021/jacs.8b01463. View

14.

Antaris A, Chen H, Cheng K, Sun Y, Hong G, Qu C . A small-molecule dye for NIR-II imaging. Nat Mater. 2015; 15(2):235-42. DOI: 10.1038/nmat4476. View

15.

Yang L, Fan G, Ren X, Zhao L, Wang J, Chen Z . Aqueous self-assembly of a charged BODIPY amphiphile via nucleation-growth mechanism. Phys Chem Chem Phys. 2015; 17(14):9167-72. DOI: 10.1039/c5cp00207a. View

16.

Lei Z, Sun C, Pei P, Wang S, Li D, Zhang X . Stable, Wavelength-Tunable Fluorescent Dyes in the NIR-II Region for In Vivo High-Contrast Bioimaging and Multiplexed Biosensing. Angew Chem Int Ed Engl. 2019; 58(24):8166-8171. DOI: 10.1002/anie.201904182. View

17.

Sun P, Wu Q, Sun X, Miao H, Deng W, Zhang W . J-Aggregate squaraine nanoparticles with bright NIR-II fluorescence for imaging guided photothermal therapy. Chem Commun (Camb). 2018; 54(95):13395-13398. DOI: 10.1039/c8cc08096h. View

18.

Kim S, Bouffard J, Kim Y . Tailoring the Solid-State Fluorescence Emission of BODIPY Dyes by meso Substitution. Chemistry. 2015; 21(48):17459-65. DOI: 10.1002/chem.201503040. View

19.

Welsher K, Liu Z, Sherlock S, Robinson J, Chen Z, Daranciang D . A route to brightly fluorescent carbon nanotubes for near-infrared imaging in mice. Nat Nanotechnol. 2009; 4(11):773-80. PMC: 2834239. DOI: 10.1038/nnano.2009.294. View

20.

Zhang J, Wang N, Ji X, Tao Y, Wang J, Zhao W . BODIPY-Based Fluorescent Probes for Biothiols. Chemistry. 2019; 26(19):4172-4192. DOI: 10.1002/chem.201904470. View