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Molecules 2013, 18(5), 5517-5530; doi:10.3390/molecules18055517
Article

Synthesis of a New ent-Cyclozonarone Angular Analog, and Comparison of Its Cytotoxicity and Apoptotic Effects with ent-Cyclozonarone

1, 1, 2, 3, 4, 4, 4 and 1,*
1 Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N° 1093, Valparaíso, Chile 2 Facultad de Química, Pontificia Universidad Católica de Chile, Vicuña Mackenna N° 4860, Santiago, Chile 3 Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, Chile 4 Centro de Investigaciones Biomédicas, Escuela de Medicina, Universidad de Valparaíso, Av. Hontaneda N° 2664, Valparaíso, Chile
* Author to whom correspondence should be addressed.
Received: 9 April 2013 / Revised: 4 May 2013 / Accepted: 6 May 2013 / Published: 13 May 2013
(This article belongs to the Section Medicinal Chemistry)
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Abstract

The synthesis of a newangular analog 11 of cyclozonarone was achieved via Diels-Alder reaction between a sesquiterpene-1,3-diene and 1,4-benzoquinone. The cytotoxic activity of ent-cyclozonarone [(+)-10] and the angular (−)-cyclozonarone analog 11 has been determined in three human cancer cell lines and in normal fibroblasts using the sulforhodamine B assay. The analyzed isomers induce cell death in different cancer cell lines by eliciting nuclear condensation and fragmentation, decreasing mitochondrial membrane permeability and increasing caspase-3 activity, all traits indicating apoptosis, with the effects of (+)-10 being stronger than those of 11 in all cases.
Keywords: sesquiterpenequinone; ent-cyclozonarone; cancer cells; cytotoxicity; apoptosis; caspase 3; mitochondrial membrane permeability sesquiterpenequinone; ent-cyclozonarone; cancer cells; cytotoxicity; apoptosis; caspase 3; mitochondrial membrane permeability
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Sobarzo, N.Q.; Venegas, I.M.; Sánchez, C.S.; Catalán, L.E.; Rojas, C.C.; Valdivia, V.U.; García, J.V.; Fritis, M.C. Synthesis of a New ent-Cyclozonarone Angular Analog, and Comparison of Its Cytotoxicity and Apoptotic Effects with ent-Cyclozonarone. Molecules 2013, 18, 5517-5530.

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