Molecular Engineering of Sulfone-Xanthone Chromophore for Enhanced Fluorescence Navigation.

Autor:	Zhang H; Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu 610064, P. R. China.; Department of Radiology, West China Hospital, Sichuan University, No. 37, Guoxue Street, Chengdu 610041, P. R. China., Xiang FF; Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu 610064, P. R. China., Liu YZ; Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu 610064, P. R. China., Chen YJ; Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu 610064, P. R. China., Zhou DH; Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu 610064, P. R. China., Liu YH; Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu 610064, P. R. China., Chen SY; Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu 610064, P. R. China., Yu XQ; Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu 610064, P. R. China.; Asymmetric Synthesis and Chiral Technology Key Laboratory of Sichuan Province, Department of Chemistry, Xihua University, Chengdu 610039, P. R. China., Li K; Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu 610064, P. R. China.
Jazyk:	angličtina
Zdroj:	JACS Au [JACS Au] 2023 Dec 08; Vol. 3 (12), pp. 3462-3472. Date of Electronic Publication: 2023 Dec 08 (Print Publication: 2023).
DOI:	10.1021/jacsau.3c00613
Abstrakt:	Enriching the palette of high-performance fluorescent dyes is vital to support the frontier of biomedical imaging. Although various rhodamine skeletons remain the premier type of small-molecule fluorophores due to the apparent high brightness and flexible modifiability, they still suffer from the inherent defect of small Stokes shift due to the nonideal fluorescence imaging signal-to-background ratio. Especially, the rising class of fluorescent dyes, sulfone-substituted xanthone, exhibits great potential, but low chemical stability is also pointed out as the problem. Molecular engineering of sulfone-xanthone to obtain a large Stokes shift and high stability is highly desired, but it is still scarce. Herein, we present the combination modification method for optimizing the performance of sulfone-xanthone. These redesigned fluorescent skeletons owned greatly improved stability and Stokes shift compared with the parent sulfone-rhodamine. To the proof of bioimaging capacity, annexin protein-targeted peptide LS301 was introduced to the most promising dyes, J-S-ARh, to form the tumor-targeted fluorescent probe, J-S-LS301. The resulting probe, J-S-LS301, can be an outstanding fluorescence tool for the orthotopic transplantation tumor model of hepatocellular carcinoma imaging and on-site pathological analysis. In summary, the combination method could serve as a basis for rational optimization of sulfone-xanthone. Overall, the chemistry reported here broadens the scope of accessible sulfone-xanthone functionality and, in turn, enables to facilitate the translation of biomedical research toward the clinical domain. Competing Interests: The authors declare no competing financial interest. (© 2023 The Authors. Published by American Chemical Society.)
Databáze:	MEDLINE
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