title: Structural Modifications of cis-Glycofused Benzopyran Compounds and Their Influence on the Binding to Amyloid-β Peptide.
abstract: A small library of glycofused tricyclic compounds with a central pyran ring chemically modified in the position para to the ring oxygen has been synthesised. The influence of the chemical modification on the structural conformation of the compounds and on their ability to bind Aβ peptide has been evaluated respectively using molecular mechanics (MM) and molecular dynamics (MD) simulations, and STD NMR spectroscopy. The introduction of particularly polar/charged groups leads to the loss of binding ability, without a significant change in the conformation, whilst other substitutions does not significantly affect either the structural conformation or the binding.
authors.affiliation: Department of Biotecnology and Bioscience (Btbs), University of Milano-Bicocca, Piazza della Scienza 2, I-20126, Milan, Italy. cristina.airoldi@unimib.it.
authors.forename: Cristina
authors.identifier: http://orcid.org/0000-0002-3670-6262
authors.initials: C
authors.lastname: Airoldi
authors.affiliation: Department of Biotecnology and Bioscience (Btbs), University of Milano-Bicocca, Piazza della Scienza 2, I-20126, Milan, Italy.
authors.forename: Giuseppe
authors.initials: G
authors.lastname: D'Orazio
authors.affiliation: Department of Chemistry "Ugo Schiff", University of Florence, Via della Lastruccia 3-13, I-50019, Sesto Fiorentino (FI), Italy.
authors.forename: Barbara
authors.identifier: http://orcid.org/0000-0001-7093-9513
authors.initials: B
authors.lastname: Richichi
authors.affiliation: Department of Biotecnology and Bioscience (Btbs), University of Milano-Bicocca, Piazza della Scienza 2, I-20126, Milan, Italy.
authors.forename: Cinzia
authors.initials: C
authors.lastname: Guzzi
authors.affiliation: Department of Chemistry "Ugo Schiff", University of Florence, Via della Lastruccia 3-13, I-50019, Sesto Fiorentino (FI), Italy.
authors.forename: Veronica
authors.identifier: http://orcid.org/0000-0002-5460-7479
authors.initials: V
authors.lastname: Baldoneschi
authors.affiliation: Department Biochemistry and Molecular Pharmacology, IRCCS-Istituto di Ricerche Farmacologiche "Mario Negri", Via Giuseppe La Masa, 19, 20156, Milano, Italy.
authors.forename: Laura
authors.initials: L
authors.lastname: Colombo
authors.affiliation: Department Biochemistry and Molecular Pharmacology, IRCCS-Istituto di Ricerche Farmacologiche "Mario Negri", Via Giuseppe La Masa, 19, 20156, Milano, Italy.
authors.forename: Mario
authors.initials: M
authors.lastname: Salmona
authors.affiliation: Department of Chemistry "Ugo Schiff", University of Florence, Via della Lastruccia 3-13, I-50019, Sesto Fiorentino (FI), Italy.
authors.forename: Cristina
authors.identifier: http://orcid.org/0000-0002-6312-3230
authors.initials: C
authors.lastname: Nativi
authors.affiliation: Department of Biotecnology and Bioscience (Btbs), University of Milano-Bicocca, Piazza della Scienza 2, I-20126, Milan, Italy.
authors.forename: Francesco
authors.identifier: http://orcid.org/0000-0003-1008-196X
authors.initials: F
authors.lastname: Nicotra
authors.affiliation: Department of Biotecnology and Bioscience (Btbs), University of Milano-Bicocca, Piazza della Scienza 2, I-20126, Milan, Italy. barbara.laferla@unimib.it.
authors.forename: Barbara
authors.identifier: http://orcid.org/0000-0002-4340-9717
authors.initials: B
authors.lastname: La Ferla
mesh_terms: D016229:Amyloid beta-Peptides / Q000737:chemistry*; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011485:Protein Binding
chemical_list: D016229:Amyloid beta-Peptides; D001578:Benzopyrans
keywords: Alzheimer's disease; Aβ ligands; Aβ peptides; NMR binding studies; glycofused compounds