title: Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.
abstract: Lipophilic compounds structurally based on caffeic, hydrocaffeic, ferulic and hydroferulic acids were synthesized. Subsequently, their antioxidant activity was evaluated as well as their partition coefficients and redox potentials. The structure-property-activity relationship (SPAR) results revealed the existence of a clear correlation between the redox potentials and the antioxidant activity. In addition, some compounds showed a proper lipophilicity to cross the blood-brain barrier. Their predicted ADME properties are also in accordance with the general requirements for potential CNS drugs. Accordingly, one can propose these phenolic compounds as potential antioxidants for tackling the oxidative status linked to the neurodegenerative processes.
authors.affiliation: CEF/Laboratório de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, Portugal. froleira@ff.uc.pt
authors.forename: Fernanda M F
authors.initials: FM
authors.lastname: Roleira
authors.forename: Christophe
authors.initials: C
authors.lastname: Siquet
authors.forename: Elizabeta
authors.initials: E
authors.lastname: Orrù
authors.forename: E Manuela
authors.initials: EM
authors.lastname: Garrido
authors.forename: Jorge
authors.initials: J
authors.lastname: Garrido
authors.forename: Nuno
authors.initials: N
authors.lastname: Milhazes
authors.forename: Gianni
authors.initials: G
authors.lastname: Podda
authors.forename: Fátima
authors.initials: F
authors.lastname: Paiva-Martins
authors.forename: Salette
authors.initials: S
authors.lastname: Reis
authors.forename: Rui A
authors.initials: RA
authors.lastname: Carvalho
authors.forename: Elisiário J Tavares da
authors.initials: EJ
authors.lastname: Silva
authors.forename: Fernanda
authors.initials: F
authors.lastname: Borges
mesh_terms: D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D002934:Cinnamates / Q000737:chemistry / Q000494:pharmacology; D015227:Lipid Peroxidation / Q000187:drug effects; D008055:Lipids / Q000737:chemistry* / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry* / Q000494:pharmacology*; D010666:Phenylpropionates / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D002934:Cinnamates; D008055:Lipids; D010636:Phenols; D010666:Phenylpropionates; C029010:cinnamic acid; C035253:3-phenylpropionic acid