Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential

Abstract

In this paper, the synthesis of fourteen alkylamino and arylamino derivatives of sesquiterpene quinone avarone and its model compound tert-but­ylquinone is described. Branched, cyclic, allylic and benzylic alkylamino/aryl­amino groups were introduced into the quinone moiety. For all the obtained derivatives, their biological activity and redox properties were studied. The cyto­toxic activity of the synthesized derivatives towards multidrug resistant (MDR) human non-small cell lung carcinoma NCI-H460/R cells, their sensitive counter­part NCI-H460 and human normal keratinocytes (HaCaT) was inves­tigated. The antimicrobial activity towards Gram-positive and Gram-negative bacteria, and fungal cultures was determined. Some of the synthesized deri­vat­ives showed selectivity for cancer cells, including MDR cells. Regarding their cell death ind­uction potential, the most promising compounds were allylamino derivatives, preferentially triggering apoptosis, with high selectivity for cancer cells, inc­luding MDR cells. Several compounds showed promising antimic­ro­bial activity, comparable to those of commercial antibiotic and antimycotic agents.