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Pure Appl. Chem., 2013, Vol. 85, No. 9, pp. 1813-1823

Published online 2013-06-06

Fluorescent amyloid β-peptide ligand derivatives as potential diagnostic tools for Alzheimer’s disease

Cristina Airoldi1, Francisco Cardona1,2, Erika Sironi1, Laura Colombo3, Mario Salmona3, Ilaria Cambianica4, Francesca Ornaghi4, Giulio Sancini4, Francesco Nicotra1 and Barbara La Ferla1*

1 Department of Biotechnology and Biosciences, University of Milano – Bicocca, Piazza della Scienza 2, 20126 Milano, Italy
2 Department of Chemistry, University of Aveiro, Campus Universitario de Santiago, 3810-193 Aveiro, Portugal
3 Department of Molecular Biochemistry and Pharmacology, Mario Negri Institute for Pharmacological Research, Via La Masa 19, 20156 Milan, Italy
4 Department of Experimental Medicine, University of Milano – Bicocca, via Cadore 48, 20052 Monza, MB, Italy

Abstract: Aβ-peptide ligands based on a cis-glycofused benzopyran structure have been fluorescently labeled using coumarine derivatives. Among the synthesized compounds, two conserved their binding ability to β-amyloid peptides, as shown by NMR experiments. Moreover, exploiting its fluorescent property, it was demonstrated that one of such compounds was able to cross an in vitro model of blood–brain barrier (BBB) and to stain Aβ‑deposits.