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  • Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.

Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.

Bioorganic & medicinal chemistry (2010-07-24)
Fernanda M F Roleira, Christophe Siquet, Elizabeta Orrù, E Manuela Garrido, Jorge Garrido, Nuno Milhazes, Gianni Podda, Fátima Paiva-Martins, Salette Reis, Rui A Carvalho, Elisiário J Tavares da Silva, Fernanda Borges
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
3-Phenylpropionic acid, 99%, FG
Sigma-Aldrich
trans-Ferulic acid, ≥99%
Sigma-Aldrich
3,4-Dihydroxyhydrocinnamic acid, 98%
Sigma-Aldrich
trans-Ferulic acid, 99%
Supelco
trans-Ferulic acid, suitable for matrix substance for MALDI-MS, ≥99.0% (HPLC)
Supelco
Caffeic acid, suitable for matrix substance for MALDI-MS, ≥99.0% (HPLC)
Sigma-Aldrich
Caffeic acid, ≥98.0% (HPLC)
Supelco
trans-Ferulic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Sigma-Aldrich
Hydrocinnamic acid, 99%