Tunable Wavelength, High-Brightness, and NIR-II Emission Phenanthridinium-Based Heptamethine Dyes for High-Contrast Vascular and Intestinal Imaging In Vivo

He, Xiaofan; Yu, Jiaying; Hu, Jinzhong; Wei, Wanying; Sun, Kai; Chen, Jian; Cai, Zhuoer; Liu, Min; Xu, Yang; Sun, Baiwang

doi:10.1021/acsmaterialslett.3c00978

ACS Materials Lett.

2023

DOI: 10.1021/acsmaterialslett.3c00978

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Tunable Wavelength, High-Brightness, and NIR-II Emission Phenanthridinium-Based Heptamethine Dyes for High-Contrast Vascular and Intestinal Imaging In Vivo

Xiaofan He,

Jiaying Yu,

Jinzhong Hu

et al.

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Cited by 5 publications

References 57 publications

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Albumin‐Chaperoned Deep‐NIR Triarylmethane Dyes for High‐Contrast In Vivo Imaging and Photothermal Therapy

Zhang,

Liu,

et al. 2024

Advanced Materials

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Fluorophores absorbing/emitting in the deep near‐infrared (deep NIR) spectral region, that is, 800 nm and beyond, hold great promise for in vivo bioimaging, diagnosis, and phototherapy due to deeper tissue penetration. The bottleneck is the lack of bright, stable, and readily synthesized deep NIR fluorophores. Here, it is reported that the albumin‐chaperon strategy is a viable one‐for‐all strategy to address these difficulties. A focused library of deep‐NIR absorbing dyes (EA5) is easily synthesized via a two‐step cascade. They are neither very stable nor bright in phosphate buffer due to a propeller‐type flexible scaffold. Through screening, EA5_c3 is found to exhibit a high affinity toward bovine serum albumin (BSA). Binding‐associated structural rigidification resulted in a gigantic 26‐fold fluorescence enhancement. The albumin chaperone also greatly improved the stability of EA5_c3 by shielding the bisbenzannulated triarylmethane core from nucleophilic or oxidative species. The resulting EA5_c3@BSA exhibits high biocompatibility. It offered high‐resolution vasculature, lymph systems, tumors, and other tissue imaging with its bright deep NIR emission. At the same time, it exhibits prominent potential in photoacoustic imaging and photothermal treatment of subcutaneous and orthotopic breast tumors. These findings provide insights into robust and high‐performance fluorophores with deep NIR regions for theranostic against aggressive cancers.

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Albumin‐Chaperoned Deep‐NIR Triarylmethane Dyes for High‐Contrast In Vivo Imaging and Photothermal Therapy

Zhang,

Liu,

et al. 2024

Advanced Materials

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Water‐Soluble Lipophilic Near‐Infrared Region II Fluorophores for High‐Brightness Lipid Layer and Lipid Droplets Imaging Applications

Xu,

Sun,

et al. 2024

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Fluorescence imaging in the second near‐infrared region (NIR‐II, 1000–1700 nm) has garnered considerable attention for displaying the biological information of deep tissues. However, the lack of biocompatible contrast agents with bright NIR‐II emission has hampered the precise clinical application of deep tissue imaging. Here, a lipophilic enhancement strategy employing donor‐acceptor‐donor (D‐A‐D) molecules, introducing long alkoxy chains and quaternary ammonium salts for the development of highly bright water‐soluble NIR‐II fluorophores (BBTD‐2C‐N), is described. Notably, liposome‐encapsulated BBTD‐2C‐N nanoparticles (B‐2C‐N/DMPC) in aqueous solution exhibit a 1.8‐fold increase in NIR‐II fluorescence brightness compared to free BBTD‐2C‐N in methanol. Avoidance of the aggregation‐caused quenching effect and enhanced NIR‐II fluorescence are attributed to significantly attenuated π–π stacking interactions and maintained monodisperses in the hydrophobic liposome shell. Moreover, BBTD‐2C‐N demonstrates superior performance in visualizing lipid droplet‐rich HeLa cells in vitro, as well as precise monitoring of adipose tissue and fatty liver in vivo. This study reveals a new avenue for the development of bright NIR‐II fluorophores and precise in vivo imaging.

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Biomedical applications of NIR-II organic small molecule fluorescent probes in different organs

Xu,

Zhang,

Wang

et al. 2024

Coordination Chemistry Reviews

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Tunable Wavelength, High-Brightness, and NIR-II Emission Phenanthridinium-Based Heptamethine Dyes for High-Contrast Vascular and Intestinal Imaging In Vivo

Cited by 5 publications

References 57 publications

Albumin‐Chaperoned Deep‐NIR Triarylmethane Dyes for High‐Contrast In Vivo Imaging and Photothermal Therapy

Albumin‐Chaperoned Deep‐NIR Triarylmethane Dyes for High‐Contrast In Vivo Imaging and Photothermal Therapy

Water‐Soluble Lipophilic Near‐Infrared Region II Fluorophores for High‐Brightness Lipid Layer and Lipid Droplets Imaging Applications

Biomedical applications of NIR-II organic small molecule fluorescent probes in different organs

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