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8. Synthesis of New Tyrosol‐Based Phosphodiester Derivatives: Effect on Amyloid β Aggregation and Metal Chelation Ability

Author

Sara García-Viñuales, Danilo Milardi, Armando Zarrelli, Giovanni Di Fabio, Gaetano De Tommaso, Mauro Iuliano, Valeria Romanucci, Mariangela Clemente, Roberta Bernini, Maddalena Giordano, Romanucci, V., Giordano, M., De Tommaso, G., Iuliano, M., Bernini, R., Clemente, M., Garcia-Vinuales, S., Milardi, D., Zarrelli, A., and Di Fabio, G.

Subjects
amyloid beta-peptide, amyloid aggregation, Antioxidant, medicine.medical_treatment, 01 natural sciences, Biochemistry, Protein Aggregates, Structure-Activity Relationship, chemistry.chemical_compound, Organophosphorus Compounds, Alzheimer Disease, Coordination Complexes, Drug Discovery, medicine, Humans, Moiety, Chelation, General Pharmacology, Toxicology and Pharmaceutics, Chelating Agents, Pharmacology, Phosphoramidite, Catechol, Dose-Response Relationship, Drug, Molecular Structure, 010405 organic chemistry, Chemistry, amyloid beta-peptides, Organic Chemistry, Phenylethyl Alcohol, Alzheimer's disease, Combinatorial chemistry, 0104 chemical sciences, Tyrosol, 010404 medicinal & biomolecular chemistry, dimer flavonoid, dimer flavonoids, Phosphodiester bond, Molecular Medicine, Hydroxytyrosol, hydroxytyrosol
Abstract

Alzheimer's disease (AD) is a multifactorial pathology that requires multifaceted agents able to address its peculiar nature. Increasing evidence has shown that aggregation of amyloid β (Aβ) and oxidative stress are strictly interconnected, and their modulation might have a positive and synergic effect in contrasting AD-related impairments. Herein, a new and efficient fragment-based approach towards tyrosol phosphodiester derivatives (TPDs) has been developed starting from suitable tyrosol building blocks and exploiting the well-established phosphoramidite chemistry. The antioxidant activity of new TPDs has been tested as well as their ability to inhibit Aβ protein aggregation. In addition, their metal chelating ability has been evaluated as a possible strategy to develop new natural-based entities for the prevention or therapy of AD. Interestingly, TPDs containing a catechol moiety have demonstrated highly promising activity in inhibiting the aggregation of Aβ40 and a strong ability to chelate biometals such as CuII and ZnII .

Published
2021

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