Citation: Xu-Rong Liu, Xu Xu, Jian-Feng Ge, Ru Sun. Fluorescence enhancement in cells via host-guest complexation of azabicycloheptane-modified naphthalimide dyes with methyl-β-cyclodextrin[J]. Chinese Chemical Letters, ;2026, 37(10): 112262. doi: 10.1016/j.cclet.2025.112262 shu

Fluorescence enhancement in cells via host-guest complexation of azabicycloheptane-modified naphthalimide dyes with methyl-β-cyclodextrin

Xu-Rong Liu ^a ,
Xu Xu ^{b, *,} ,
Jian-Feng Ge ^{a, c} ,
Ru Sun ^{a, *,}

a.
College of Chemistry, Chemical Engineering and Material Science, Soochow University, Suzhou 215123, China
b.
The Fourth Affiliated Hospital of Soochow University, Suzhou 215000, China
c.
Jiangsu Key Laboratory of Medical Optics, Suzhou Institute of Biomedical Engineering and Technology, Chinese Academy of Science, Suzhou 215163, China

13062122@qq.com

sunru924@hotmail.com

Received Date: 15 September 2025
Revised Date: 18 November 2025
Accepted Date: 9 December 2025
Available Online: 10 December 2025

Figures(7)

Aqueous fluorescence quenching poses a significant challenge for organic fluorophores in biological applications. This study demonstrates an effective supramolecular strategy to overcome this limitation through host-guest complexation with methyl-β-cyclodextrin (M-β-CD). Three naphthalimide-based dyes (1a-1c) were obtained by incorporating an azabicycloheptane auxochrome and various targeting groups. Upon M-β-CD complexation, these dyes exhibited 2.3- to 3.4-fold enhancements in fluorescence quantum yields, with binding constants (K_a) of 1.32 × 10⁴ (1a) and 7.09 × 10³ L/mol (1b), confirming stable complex formation by ¹H NMR spectra. Most remarkably, cellular imaging revealed an 18.7-fold fluorescence intensity increase for dye 1a (0.40 µmol/L) when complexed with M-β-CD. This work establishes a dual design strategy of using an azabicycloheptane as the auxochrome and supramolecular complexes to enhance the aqueous performance of naphthalimide fluorophores while maintaining their targeting capabilities, offering broad potential for biological imaging applications.
- Azabicycloheptane,
- Naphthalimide,
- Aqueous solution,
- Host-guest chemistry,
- M-β-CD
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