A curcumin-based molecular probe for near-infrared fluorescence imaging of tau fibrils in
- A curcumin-based molecular probe for near-infrared fluorescence imaging of tau fibrils in
- 박광수; 서유진; 김미경; 김경도; 김윤경; 추현아; 정유훈
- Alzheimer’s disease; tau fibrils; curcumin; near-infrared fluorescence imaging; molecular probe
- Issue Date
- Organic & biomolecular chemistry
- VOL 13, 11194-11199
- In recent years, there has been growing interest in the near-infrared (NIR) fluorescence imaging of tau fibrils for the early diagnosis of Alzheimer’s disease (AD). In order to develop a curcumin-based NIR fluorescent probe for tau fibrils, structural modification of the curcumin scaffold was attempted by combining the following rationales: the curcumin derivative should preserve its binding affinity to tau fibrils, and, upon binding to tau fibrils, the probe should show favorable fluorescence properties. To meet these requirements, we designed a novel curcumin scaffold with various
aromatic substituents. Among the series, the curcumin derivative 1c with a (4-dimethylamino-2,6-dimethoxy)phenyl moiety showed a significant change in its fluorescence properties (22.9-fold
increase in quantum yield; Kd, 0.77 μM; λem, 620 nm; Φ, 0.32) after binding to tau fibrils. In addition, fluorescence imaging of taugreen fluorescent protein-transfected SHSY-5Y cells with 1c confirmed that 1c detected tau fibrils in live cells.
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