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Caffeic Acid Phenethyl Ester: Consequences of Its Hydrophobicity in the Oxidative Functions and Cytokine Release by Leukocytes


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Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)

Numerous anti-inflammatory properties have been attributed to caffeic acid phenethyl ester (CAPE), an active component of propolis. NADPH oxidases are multienzymatic complexes involved in many inflammatory diseases. Here, we studied the importance of the CAPE hydrophobicity on cell-free antioxidant capacity, inhibition of the NADPH oxidase and hypochlorous acid production, and release of TNF-alpha and IL-10 by activated leukocytes. The comparison was made with the related, but less hydrophobic, caffeic and chlorogenic acids. Cell-free studies such as superoxide anion scavenging assay, triene degradation, and anodic peak potential (E-pa) measurements showed that the alterations in the hydrophobicity did not provoke significant changes in the oxidation potential and antiradical potency of the tested compounds. However, only CAPE was able to inhibit the production of superoxide anion by activated leukocytes. The inhibition of the NADPH oxidase resulted in the blockage of production of hypochlorous acid. Similarly, CAPE was the more effective inhibitor of the release of TNF-alpha and IL-10 by Staphylococcus aureus stimulated cells. In conclusion, the presence of the catechol moiety and the higher hydrophobicity were essential for the biological effects. Considering the involvement of NADPH oxidases in the genesis and progression of inflammatory diseases, CAPE should be considered as a promising anti-inflammatory drug.

Sao Paulo State Univ UNESP, Sch Pharmaceut Sci, Dept Clin Anal, BR-14801902 Araraquara, SP, Brazil

Univ Sao Paulo, Sch Med, Dept Pediat, BR-05403900 Sao Paulo, Brazil

Sao Paulo State Univ UNESP, Inst Chem, Dept Organ Chem, BR-14800900 Araraquara, SP, Brazil

Sao Paulo State Univ UNESP, Fac Sci, Dept Chem, BR-17033360 Bauru, SP, Brazil

Sao Paulo State Univ UNESP, Sch Pharmaceut Sci, Dept Clin Anal, BR-14801902 Araraquara, SP, Brazil

Sao Paulo State Univ UNESP, Inst Chem, Dept Organ Chem, BR-14800900 Araraquara, SP, Brazil

Sao Paulo State Univ UNESP, Fac Sci, Dept Chem, BR-17033360 Bauru, SP, Brazil

Tipo de Documento Artigo científico
Idioma Inglês
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