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( E )‐2‐Cyano‐3‐(5′‐piperidin‐1‐yl‐2,2′‐bithien‐5‐yl)acrylic Acid: A Fluorescent Probe for Detecting Prefibrillar Oligomers
Author(s) -
Attanasio Francesco,
Bonaccorso Carmela,
Bellia Francesco,
Cataldo Sebastiano,
Fortuna Cosimo G.,
Musumarra Giuseppe,
Pignataro Bruno,
Rizzarelli Enrico
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300241
Subject(s) - thioflavin , chemistry , fluorescence , amyloid (mycology) , biophysics , acrylic acid , dynamic light scattering , fluorescence microscope , biochemistry , combinatorial chemistry , organic chemistry , polymer , nanotechnology , monomer , medicine , inorganic chemistry , physics , disease , pathology , quantum mechanics , biology , alzheimer's disease , materials science , nanoparticle
The synthesis of ( E )‐2‐cyano‐3‐(5′‐piperidin‐1‐yl‐2,2′‐bithien‐5‐yl)acrylic acid, a novel amyloid aggregation fluorescent probe, is reported. This new probe is able to monitor soluble oligomeric aggregates after 24 h, at which time Thioflavin T emission, commonly used to monitor amyloid fibril formation, remains unchanged. Atomic force microscopy, native polyacrylamide gel electrophoresis, and dynamic light scattering confirm that the earlier stages of aggregation are prefibrillar oligomeric species not possessing the amyloid structure. This new molecular scaffold expands the toolbox of fluorescent probes for the identification of prefibrillar oligomers, which is needed in studies aimed at the early detection of the soluble toxic aggregates that characterize the so‐called protein misfolding diseases.