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• Sanmartín, C
• Plano, D
• Domínguez, E
• Font, M
• Calvo, A
• Prior, C
• Encío, I
• Palop, JAntonio
• [+] on Google Scholar
• Sanmartín, C
• Plano, D
• Domínguez, E
• Font, M
• Calvo, A
• Prior, C
• Encío, I
• Palop, JAntonio
• [+] on PubMed
• Sanmartín, C
• Plano, D
• Domínguez, E
• Font, M
• Calvo, A
• Prior, C
• Encío, I
• Palop, JAntonio

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Molecules 2009, 14(9), 3313-3338; doi:10.3390/molecules14093313

Article

Synthesis and Pharmacological Screening of Several Aroyl and Heteroaroyl Selenylacetic Acid Derivatives as Cytotoxic and Antiproliferative Agents

Carmen Sanmartín ^1,* , Daniel Plano ¹ , Enrique Domínguez ¹ , María Font ² , Alfonso Calvo ³ , Celia Prior ³ , Ignacio Encío ⁴  and Juan Antonio Palop ^1,*

¹ Synthesis Section, Department of Organic and Pharmaceutical Chemistry, University of Navarra, Irunlarrea, 1, E-31008 Pamplona, Spain ² Molecular Modeling Section, Department of Organic and Pharmaceutical Chemistry, University of Navarra, Irunlarrea, 1, E-31008 Pamplona, Spain ³ Oncology Division, Center for Applied Medical Research, CIMA, University of Navarra, Pío XII, 53, E-31008 Pamplona, Spain ⁴ Department of Health Science, Public University of Navarra, Avda. Barañain, s/n, E-31008 Pamplona, Spain

* Authors to whom correspondence should be addressed.

Received: 1 July 2009; in revised form: 4 August 2009 / Accepted: 27 August 2009 / Published: 1 September 2009

(This article belongs to the Special Issue Selenium and Tellurium Chemistry)

Download PDF Full-Text [825 KB, uploaded 31 August 2009 15:30 CEST]

Abstract: The synthesis and cytotoxic activity of a series of twenty six aroyl and heteroaroyl selenylacetic acid derivatives of general formula Ar-CO-Se-CH₂-COOH or Heterar-CO-Se-CH₂-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 α-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 μM. On the other hand, in PC-3 these compounds showed values of 6.8, 4.0 and 2.9 μM. Furthermore, benzoylselenylacetic acid did not provoke apoptosis nor did it perturb the cell cycle in MCF-7.

Keywords: selenylacetic acid; cytotoxicity; apoptosis

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