Citation: Mengxing Liu, Jing Liu, Hongxing Zhang, Jianan Tao, Peiwen Fan, Xin Lv, Wei Guo. One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor[J]. Chinese Chemical Letters, ;2025, 36(4): 109994. doi: 10.1016/j.cclet.2024.109994 shu

One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor

School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China

liujing4203@sxu.edu.cn

guow@sxu.edu.cn

Received Date: 20 February 2024
Revised Date: 6 May 2024
Accepted Date: 10 May 2024
Available Online: 11 May 2024

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In this work, we put forward a new and universal approach, i.e., cyanine ketone method, for fabricating meso–aryl heptamethine indocyanines, which is so simple that the treatment of the easy-to-get cyanine ketones with various aromatic lithium (ArLi), followed by acidification, could straightforwardly give rise to the products in one-pot way. Importantly, due to the strong nucleophilicity of ArLi, a series of bulky hydrophilic aromatic groups can be facilely integrated into the meso–position of heptamethine indocyanines, not only effectively inhibiting the undesired dye self-aggregation but also largely improving the water-solubility. Using one of anti-aggregation meso–aryl heptamethine indocyanines, we fabricated a dye-antibody conjugate for in vivo imaging tumor in a mouse model and achieved a high tumor-to-normal tissue ratio. The work laid a chemical foundation for constructing various meso–aryl heptamethine indocyanines, facilitating the advanced imaging and therapeutic applications in future.
- Heptamethine indocyanines,
- Aryl substituents,
- Aromatic lithium reagents,
- Protein labeling,
- Imaging tumor
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