Dihydropyridopyrazine Functionalized Xanthene: Generating Stable NIR Dyes with Small-Molecular Weight by Enhanced Charge Separation.

Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: MEDLINE

Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-

Fluorescent Dyes*/chemistry ; Molecular Weight* ; Xanthenes*/chemistry; Pyrazines/chemistry ; Animals ; Mice ; Molecular Structure ; Infrared Rays ; Humans ; Optical Imaging

Near-infrared region (NIR; 650-1700 nm) dyes offer many advantages over traditional dyes with absorption and emission in the visible region. However, developing new NIR dyes, especially organic dyes with long wavelengths, small molecular weight, and excellent stability and biocompatibility, is still quite challenging. Herein, we present a general method to enhance the absorption and emission wavelengths of traditional fluorophores by simply appending a charge separation structure, dihydropyridopyrazine. These novel NIR dyes not only exhibited greatly redshifted wavelengths compared to their parent dyes, but also displayed a small molecular weight increase together with retained stability and biocompatibility. Specifically, dye NIR-OX, a dihydropyridopyra-zine derivative of oxazine with a molecular mass of 386.2 Da, exhibited an absorption at 822 nm and an emission extending to 1200 nm, making it one of the smallest molecular-weight NIR-II emitting dyes. Thanks to its rapid metabolism and long wave-length, NIR-OX enabled high-contrast bioimaging and assessment of cholestatic liver injury in vivo and also facilitated the evalua-tion of the efficacy of liver protection medicines against cholestatic liver injury.
(© 2024 Wiley-VCH GmbH.)

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22325401, 22374039, 22074036 National Natural Science Foundation of China; 2023JJ20004 Natural Science Foundation of Hunan Province

Keywords: Enhanced Charge Separation; NIR Dyes; Stable and Small Molecular Weight; Xanthene

0 (Fluorescent Dyes)
0 (Xanthenes)
0 (Pyrazines)

Date Created: 20240715 Date Completed: 20241007 Latest Revision: 20241007

20241007

10.1002/anie.202410666

39007416