Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential
2018
Authors:
Jeremić, MarkoDinić, Jelena
Pešić, Milica
Nešović, Marija
Novaković, Irena
Šegan, Dejan
Sladić, Dušan
Document Type:
Article (Published version)
Metadata
Show full item recordAbstract:
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.
Keywords:
Quinones; Anticancer activity; Multidrug resistant; Apoptosis; Antimicrobial activity; Cyclic voltammetrySource:
Journal of the Serbian Chemical Society, 2018, 83, 11, 1193-1207Funding / projects:
- Identification of predictive molecular markers for cancer progression, response to therapy and disease outcome (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-41031)
- Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-MESTD-Basic Research (BR or ON)-172055)
DOI: 10.2298/JSC180627062J
ISSN: 0352-5139
WoS: 000452167500001
Scopus: 2-s2.0-85053920097
URI
http://www.doiserbia.nb.rs/Article.aspx?ID=0352-51391800062Jhttps://radar.ibiss.bg.ac.rs/123456789/3866