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Synthesis of Fluorescent Probes based on Stilbenes and Diphenylacetylenes targeting ?-Amyloid Plaques.


ABSTRACT: Three fluorescent probes were synthesized aiming for optical imaging to detect amyloid plaques present in patients with Alzheimer's disease (AD). These compounds were prepared via Sonogashira coupling of a well-defined fluorophore (4-bora-3a, 4a-diaza s-indacene, BODIPY) with the pharmacophore possessing either a stilbene or a diphenylacetylene moiety. Different polyethylene glycol chain lengths were used as linkers between the fluorophore and the pharmacophore to adjust the lipophilicity of these probes. These compounds exhibit strong fluorescence emission between 665-680 nm and have very high extinction coefficients comparable to the parent fluorophore, BODIPY dye.

SUBMITTER: Parhi AK 

PROVIDER: S-EPMC2504756 | biostudies-literature | 2008

REPOSITORIES: biostudies-literature

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Synthesis of Fluorescent Probes based on Stilbenes and Diphenylacetylenes targeting β-Amyloid Plaques.

Parhi Ajit K AK   Kung Mei-Ping MP   Ploessl Karl K   Kung Hank F HF  

Tetrahedron letters 20080101 12


Three fluorescent probes were synthesized aiming for optical imaging to detect amyloid plaques present in patients with Alzheimer's disease (AD). These compounds were prepared via Sonogashira coupling of a well-defined fluorophore (4-bora-3a, 4a-diaza s-indacene, BODIPY) with the pharmacophore possessing either a stilbene or a diphenylacetylene moiety. Different polyethylene glycol chain lengths were used as linkers between the fluorophore and the pharmacophore to adjust the lipophilicity of the  ...[more]

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