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• W1996057100 abstract "Curcumin is a yellow-orange pigment derived from the turmeric, which was found to bind β-amyloid (Aβ) protein. Chemically, curcumin possesses a 1,6-heptadiene-3,5-dione (α,β-unsaturated β-diketone) moiety, which implies that it can exist in two tautomers, a keto form and an enol. The aim of this study was to assess the involvement of keto-enol tautomerism in the binding activity to Aβ fibrils/aggregates. We synthesized curcumin derivatives F-H-Cur and F-Mecar-Cur. Further, we synthesized a keto form analogue of curcumin derivatives F-diMe-Cur. UV-visible spectrophotometric analysis performed between 250 and 750 nm. Distinction between the keto and the enol forms was assessed in 19F- and 13C-NMR analysis. The binding affinity of curcumin derivatives to Aβ aggregates was measured and expressed in the half maximal inhibitory concentration (IC50) in thioflavin T fluorescence assay. F-H-Cur and F-Mecar-Cur consist of four forms, that is, keto form with phenolic hydroxy group, keto form with phenolic anion, enol form with phenolic hydroxy group, and enol form with phenolic anion. On the other hand, F-diMe-Cur possesses only keto forms. Each form displayed a unique UV-visible absorption spectrum, color and fluorescence. The thioflavin T fluorescence assay for the binding affinity of chemicals to Aβ aggregates demonstrated that IC50 values of F-H-Cur and F-Mecar-Cur were 0.26 μM and 0.44 μM, respectively. While, the IC50 value of F-diMe-Cur was 23 μM, indicating that a keto form of curcumin derivatives little binds to Aβ aggregates. F-Mecar-Cur in phosphate buffer (pH 7.5) showed yellow color that was resulted from the keto forms. When Aβ aggregates were added into the solution, the color of the solution containing F-Mecar-Cur turned into reddish orange from yellow. NMR analysis and UV-visible spectrophotometry showed that reddish color was resulted from enol forms of F-Mecar-Cur. Although F-Mecar-Cur in phosphate buffer (pH 7.5) showed little fluorescence, F-Mecar-Cur bound to Aβ aggregates exhibited strong fluorescence that was resulted from enole forms. The results suggest that enol-shift of curcumin is crucially involved in its amyloid binding. The compounds with keto-enol tautomerism have the potential to be a novel indicator for amyloid detection." @default.
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• W1996057100 date "2009-07-01" @default.
• W1996057100 modified "2023-10-16" @default.
• W1996057100 title "P3-007: Binding form of curcumin derivatives to β -amyloid aggregates" @default.
• W1996057100 doi "https://doi.org/10.1016/j.jalz.2009.04.1184" @default.
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