Synthesis and evaluation of stilbenylbenzoxazole and stilbenylbenzothiazole derivatives for detecting β-amyloid fibrils

This paper describes a novel series of stilbenylbenzoxazole (SBO) and stilbenylbenzothiazole (SBT) derivatives for β-amyloid specific binding probes. These 24 compounds were synthesized and evaluated by competitive binding assay against β-amyloid 1–42 (Aβ42) aggregates using [125I]TZDM. All the derivatives displayed higher binding affinities with Ki value in the subnanomolar range (0.10–0.74 nM) than Pittsburgh Compound-B (PIB) (0.77 nM). Among these derivatives, SBT-2, 5-fluoroethoxy-2-{4-[2-(4-methylaminophenyl)vinyl]phenyl}benzothiazole, showed lowest Ki value (0.10 nM). In conclusion, the preliminary results suggest that these compounds are implying a possibility as a probe for detection of Aβ fibrils in Alzheimer’s disease (AD) patients.

Graphical abstractNovel series of stilbenylbenzoxazole (SBO) and stilbenylbenzothiazole (SBT) derivatives were synthesized and evaluated by competitive binding assay against β-amyloid 1–42 (Aβ42) aggregates using [125I]TZDM. All the derivatives displayed higher binding affinities with Ki values in the subnanomolar range (0.10–0.74 nM) than PIB (0.77 nM). In conclusion, the preliminary results suggest that these compounds are implying a possibility as a probe for detection of Aβ fibrils in Alzheimer’s disease (AD) patients.Figure optionsDownload full-size imageDownload as PowerPoint slide