Synthesis and pharmacological screening of several aroyl and heteroaroyl selenylacetic acid derivatives as cytotoxic and antiproliferative agents
Encío Martínez, Ignacio
Palop, Juan Antonio
Acceso abierto / Sarbide irekiainfo:eu-repo/semantics/openAccess
Artículo / Artikuluainfo:eu-repo/semantics/article
Versión publicada / Argitaratu den bertsioainfo:eu-repo/semantics/publishedVersion
The synthesis and cytotoxic activity of a series of twenty six aroyl and heteroaroyl selenylacetic acid derivatives of general formula Ar-CO-Se-CH(2)-COOH or Heterar-CO-Se-CH(2)-COOH are reported. The synthesis was carried out by reaction of acyl chlorides with sodium hydrogen selenide, prepared in situ, and this led to the formation of sodium aroylselenides that subsequently reacted with alpha ... [++]
The synthesis and cytotoxic activity of a series of twenty six aroyl and heteroaroyl selenylacetic acid derivatives of general formula Ar-CO-Se-CH(2)-COOH or Heterar-CO-Se-CH(2)-COOH are reported. The synthesis was carried out by reaction of acyl chlorides with sodium hydrogen selenide, prepared in situ, and this led to the formation of sodium aroylselenides that subsequently reacted with alpha-bromoacetic acid to produce the corresponding selenylacetic acid derivatives. All of the compounds were tested against a prostate cancer cell line (PC-3) and some of the more active compounds were assessed against a panel of four human cancer cell lines (CCRF-CEM, HTB-54, HT-29, MCF-7) and one mammary gland-derived non-malignant cell line (184B5). Some of the compounds exhibited remarkable cytotoxic and antiproliferative activities against MCF-7 and PC-3 that were higher than those of the reference compounds doxorubicin and etoposide, respectively. For example, in MCF-7 when Ar = phenyl, 3, 5-dimethoxyphenyl or benzyl the TGI values were 3.69, 4.18 and 6.19 mu M. On the other hand, in PC-3 these compounds showed values of 6.8, 4.0 and 2.9 mu M. Furthermore, benzoylselenylacetic acid did not provoke apoptosis nor did it perturb the cell cycle in MCF-7. [--]
Selenylacetic acid, Cytotoxicity, Apoptosis, Prostate cancer cells, Selenium compounds, Organoselenium compounds, Semiempirical methods, Methylseleninic acid, Diphenyl diselenide, Growth inhibition, Tumor cells, In vitro, Prevention, Chemistry
Molecules, 2009, 14(9). Págs. 3313-3338
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