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

Molecules

Natalia Quiñones Sobarzo¹  Iván Montenegro Venegas¹  Cristian Salas Sánchez¹  Luis Espinoza Catalán¹  Cristóbal Carrasco Rojas¹  Valentina Ulloa Valdivia¹  Joan Villena García¹ 

[1] ¹Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N° 1093, Valparaíso, Chile

关键词: sesquiterpenequinone;    ent-cyclozonarone;    cancer cells;    cytotoxicity;    apoptosis;    caspase 3;    mitochondrial membrane permeability;   

DOI  :  10.3390/molecules18055517

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.