Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.
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.
Roleira
Fernanda M F
FM
CEF/Laboratório de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, Portugal. froleira@ff.uc.pt
Siquet
Christophe
C
Orrù
Elizabeta
E
Garrido
E Manuela
EM
Garrido
Jorge
J
Milhazes
Nuno
N
Podda
Gianni
G
Paiva-Martins
Fátima
F
Reis
Salette
S
Carvalho
Rui A
RA
Silva
Elisiário J Tavares da
EJ
Borges
Fernanda
F
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
D000975:Antioxidants; D002934:Cinnamates; D008055:Lipids; D010636:Phenols; D010666:Phenylpropionates; C029010:cinnamic acid; C035253:3-phenylpropionic acid