Eugenol and its Synthetic Analogues Inhibit Cell Growth of Human Cancer Cells (Part I)

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dc.contributor.authorCarrasco, H.
dc.contributor.authorEspinoza, L.
dc.contributor.authorCardile, V.
dc.contributor.authorGallardo, C.
dc.contributor.authorCardona, W.
dc.contributor.authorLombardo, L.
dc.contributor.authorCatálan, K.
dc.contributor.authorCuellar, M.
dc.contributor.authorRusso, A.
dc.date.accessioned2014-01-29T14:20:14Z
dc.date.accessioned2016-05-24T20:28:47Z
dc.date.available2014-01-29T14:20:14Z
dc.date.available2016-05-24T20:28:47Z
dc.date.issued2008
dc.descriptionhttp://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000300024&nrm=isoes
dc.description.abstractEugenol (4-allyl-2-methoxyphenol) (1) has been reported to possess antioxidant and anticancer properties. In an attempt to enhance intrinsic activity of this natural compound, some derivatives were synthesized. Eugenol was extracted from cloves oil and further, the eugenol analogues (2-6) were obtained through acetylation and nitration reactions. Eugenol (1) and its analogues (2-6) were examined by in vitro model of cancer using two human cancer cell lines: DU-145 (androgen-insensitive prostate cancer cells) and KB (oral squamous carcinoma cells). Cell viability, by tetrazolium salts assay, was measured. Lactic dehydrogenase (LDH) release was also investigated to evaluate the presence of cell toxicity as a result of cell disruption, subsequent to membrane rupture. In the examined cancer cells, all compounds showed cell-growth inhibition activity. The obtained results demonstrate that the compounds 5-allyl-3-nitrobenzene-1,2-diol (3) and 4-allyl-2-methoxy-5-nitrophenyl acetate (5) were significantly (p < 0,001) more active than eugenol, with IC50 values in DU-145 cells of 19.02 x 10-6 and 21.5 × 10-6 mol L-1, respectively, and in KB cells of 18.11 × 10-6 and 21.26 × 10-6 mol L-1, respectively, suggesting that the presence of nitro and hydroxyl groups could be important in the activity of these compounds. In addition, our results seem to indicate that apoptotic cell demise appears to be induced in KB and DU-145 cells. In fact, in our experimental conditions, no statistically significant increase in LDH release was observed in cancer cells treated with eugenol and its analogues.es
dc.description.sponsorshipUniversidad Andrés Bello (Chile)es
dc.identifier.citationJournal of the Brazilian Chemical Society, Vol. 19 N° 3, pp. 543-548, 2008.es
dc.identifier.issn0103-5053
dc.identifier.otherDOI:http: //dx.doi.org/10.1590/S0103-50532008000300024
dc.identifier.urihttp://repositorio.unab.cl/xmlui/handle/ria/2349
dc.language.isoeses
dc.publisherSociedad Brasilera de Químicaes
dc.subjectEugenoles
dc.subjectSynthesises
dc.subjectDU-145 cancer cellses
dc.subjectKB cancer cellses
dc.subjectCell viabilityes
dc.subjectLactic dehydrogenasees
dc.titleEugenol and its Synthetic Analogues Inhibit Cell Growth of Human Cancer Cells (Part I)es
dc.typeArtículoes
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