Park, Kwang-su Seo, Yujin Kim, Mi Kyoung Kim, Kyungdo Kim, Yun Kyung Choo, Hyunah Chong, Youhoon 2024-01-20T05:31:57Z 2024-01-20T05:31:57Z 2021-09-05 2015-12 1477-0520 https://pubs.kist.re.kr/handle/201004/124672 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; K-d, 0.77 mu M; lambda(em), 620 nm; Phi, 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. English ROYAL SOC CHEMISTRY AMYLOID-BETA IN-VIVO PLAQUES AGGREGATION PATHOLOGY A curcumin-based molecular probe for near-infrared fluorescence imaging of tau fibrils in Alzheimer's disease Article 10.1039/c5ob01847a 1 ORGANIC & BIOMOLECULAR CHEMISTRY, v.13, no.46, pp.11194 - 11199 ORGANIC & BIOMOLECULAR CHEMISTRY 13 46 11194 11199 scie scopus 000365307400004 2-s2.0-84947796447 Chemistry, Organic Chemistry Article AMYLOID-BETA IN-VIVO PLAQUES AGGREGATION PATHOLOGY Alzheimer’s disease tau fibrils curcumin near-infrared fluorescence imaging molecular probe