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

Sanmartín, Carmen; Plano, Daniel; Domínguez, Enrique; Font, María; Calvo, Alfonso; Prior, Celia; Encío, Ignacio; Palop, Juan Antonio

doi:10.3390/molecules14093313

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

Carmen Sanmartín

^1,*, Daniel Plano¹, Enrique Domínguez¹, María Font², Alfonso Calvo³, Celia Prior³, Ignacio Encío⁴ and

Juan Antonio Palop

^1,*

Synthesis Section, Department of Organic and Pharmaceutical Chemistry, University of Navarra, Irunlarrea, 1, E-31008 Pamplona, Spain

Molecular Modeling Section, Department of Organic and Pharmaceutical Chemistry, University of Navarra, Irunlarrea, 1, E-31008 Pamplona, Spain

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.

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

Received: 1 July 2009 / Revised: 4 August 2009 / Accepted: 27 August 2009 / Published: 1 September 2009

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

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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. View Full-Text

Keywords: selenylacetic acid; cytotoxicity; apoptosis

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MDPI and ACS Style

Sanmartín, C.; Plano, D.; Domínguez, E.; Font, M.; Calvo, A.; Prior, C.; Encío, I.; Palop, J.A. Synthesis and Pharmacological Screening of Several Aroyl and Heteroaroyl Selenylacetic Acid Derivatives as Cytotoxic and Antiproliferative Agents. Molecules 2009, 14, 3313-3338. https://doi.org/10.3390/molecules14093313

AMA Style

Sanmartín C, Plano D, Domínguez E, Font M, Calvo A, Prior C, Encío I, Palop JA. Synthesis and Pharmacological Screening of Several Aroyl and Heteroaroyl Selenylacetic Acid Derivatives as Cytotoxic and Antiproliferative Agents. Molecules. 2009; 14(9):3313-3338. https://doi.org/10.3390/molecules14093313

Chicago/Turabian Style

Sanmartín, Carmen, Daniel Plano, Enrique Domínguez, María Font, Alfonso Calvo, Celia Prior, Ignacio Encío, and Juan A. Palop. 2009. "Synthesis and Pharmacological Screening of Several Aroyl and Heteroaroyl Selenylacetic Acid Derivatives as Cytotoxic and Antiproliferative Agents" Molecules 14, no. 9: 3313-3338. https://doi.org/10.3390/molecules14093313

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

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