Molecular engineering and bioimaging applications of C2-alkenyl indole dyes with tunable emission wavelengths covering visible to NIR light

Yan Liu; Bingya Wang; Ji-Ting Hou; Peng Xie; Weiyi Li; Shan Wang

doi:10.1016/j.bioorg.2023.106905

Molecular engineering and bioimaging applications of C2-alkenyl indole dyes with tunable emission wavelengths covering visible to NIR light

Bioorg Chem. 2023 Dec:141:106905. doi: 10.1016/j.bioorg.2023.106905. Epub 2023 Oct 5.

Authors

Yan Liu¹, Bingya Wang², Ji-Ting Hou³, Peng Xie⁴, Weiyi Li⁵, Shan Wang⁶

Affiliations

¹ School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China; Key Laboratory of Intelligent Treatment and Life Support for Critical Diseases of Zhejiang Province, the First Affiliated Hospital of Wenzhou Medical University, Wenzhou 325000, China.
² Key Laboratory of Intelligent Treatment and Life Support for Critical Diseases of Zhejiang Province, the First Affiliated Hospital of Wenzhou Medical University, Wenzhou 325000, China.
³ National Engineering Research Center of Ophthalmology and Optometry, Eye Hospital, Wenzhou Medical University, Wenzhou 325027, China.
⁴ School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China; Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, Guangxi University, Nanning 530004, China. Electronic address: [email protected].
⁵ School of Science, Research Center for Advanced Computation, Xihua University, Chengdu 610039, China. Electronic address: [email protected].
⁶ Key Laboratory of Intelligent Treatment and Life Support for Critical Diseases of Zhejiang Province, the First Affiliated Hospital of Wenzhou Medical University, Wenzhou 325000, China; Hubei Key Laboratory of Quality Control of Characteristic Fruits and Vegetables, Hubei Engineering University, Xiaogan 432000, China. Electronic address: [email protected].

PMID: 37832222
DOI: 10.1016/j.bioorg.2023.106905

Abstract

As an important member of dyes, small-molecule fluorescent dyes show indispensable value in biomedical fields. Although various molecular dyes have been developed, full-color dyes covering blue to red region derived from a single chromophore are still in urgent demand. In this work, a series of dyes based on C2-alkenyl indole skeleton were synthesized, namely AI dyes, and their photophysical properties, cytotoxicity, and imaging capacity were verified to be satisfactory. Particularly, the maximal emission wavelengths of these dyes could cover a wide range from visible to NIR light with large Stokes shifts. Besides, the optical and structural discrepancies between the C2- and C3- alkenyl AI dyes were discussed in detail, and the theoretical calculations were conducted to provide insights on such structure-activity relationship. Finally, as a proof-of-concept, a fluorescent probe AI-Py-B capable of imaging endogenous ONOO^- was presented, demonstrating the bioimaging potentials of these alkenyl indole dyes. This work is anticipated to open up new possibilities for developing dye engineering and bio-applications of natural indole framework.

Keywords: Alkenyl indole; Bioimaging; Fluorescent dyes; Peroxynitrite; Tunable emission.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Fluorescent Dyes*
Indoles*
Optical Imaging / methods
Radiopharmaceuticals

Substances

Fluorescent Dyes
Indoles
Radiopharmaceuticals