Polyfluorinated bis-styrylbenzenes as amyloid-beta plaque binding ligands

Publication Type:

Journal Article


Bioorganic & medicinal chemistry, Volume 22, Issue 8, pp. 2469–2481 (2014)


1464-3391 (Electronic)09

DOI Name (links to online publication)



Detection of cerebral beta-amyloid (Abeta) by targeted contrast agents remains of great interest to aid the in vivo diagnosis of Alzheimer's disease (AD). Bis-styrylbenzenes have been previously reported as potential Abeta imaging agents. To further explore their potency as 19F MRI contrast agents we synthetized several novel fluorinated bis-styrylbenzenes and studied their fluorescent properties and amyloid-beta binding characteristics. The compounds showed a high affinity for Abeta plaques on murine and human brain sections. Interestingly, competitive binding experiments demonstrated that they bound to a different binding site than chrysamine G. Despite their high logP values, many bis-styrylbenzenes were able to enter the brain and label murine amyloid in vivo. Unfortunately initial post-mortem 19F NMR studies showed that these compounds as yet do not warrant further MRI studies due to the reduction of the 19F signal in the environment of the brain.