Antioxidant versus cytotoxic properties of hydroxycinnamic acid derivatives - a new paradigm in phenolic research.
Trihydroxycinnamic derivatives were synthesized and evaluated for their antioxidant and cytotoxic activities. The ester derivatives exhibited a higher radical-scavenging activity, when liposomes were used as target systems, a fact which may be related to their lipophilicity and conformational preferences. These compounds were found to display significant growth inhibition and cytotoxic effects towards a human cervix adenocarcinoma cell line (HeLa). The partition coefficients presently obtained for the trihydroxycinnamic derivatives correlate well both with their structural characteristics and with their antioxidant/cytotoxic activities. A positive structure-activity-property relationship between cytotoxic and antioxidant activities, which is intrinsically related with physico-chemical and conformational properties, is anticipated, as a noteworthy study that must be done for phenolic systems. As damage events are frequently correlated with oxidative stress, the prevalence of both properties in a single compound could be beneficial in terms of rationale preventive or therapeutic purposes.
Esteves
Mário
M
Unidade Química-Física Molecular, Departamento de Química Orgânica, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal.
Siquet
Christophe
C
Gaspar
Alexandra
A
Rio
Vitor
V
Sousa
Joana B
JB
Reis
Salette
S
Marques
Maria P M
MP
Borges
Fernanda
F
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D003373:Coumaric Acids / Q000138:chemical synthesis / Q000494:pharmacology*; D005260:Female; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000494:pharmacology*; D005609:Free Radicals / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008081:Liposomes; D018384:Oxidative Stress / Q000187:drug effects; D013329:Structure-Activity Relationship; D002583:Uterine Cervical Neoplasms / Q000188:drug therapy
D000970:Antineoplastic Agents; D003373:Coumaric Acids; D016166:Free Radical Scavengers; D005609:Free Radicals; D008081:Liposomes