Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential
Aлкиламино и аралкиламино деривати аварона и његовог миметика као селективни агенси према ћелијама неситноћелијског карцинома плућа, њихов антибактеријски и антифунгални потенцијал

2018
Authors
Jeremić, Marko
Dinić, Jelena

Pešić, Milica

Stepanovic, Marija
Novaković, Irena

Šegan, Dejan

Sladić, Dušan

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, inclu...ding 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, 1193-1207Publisher:
- Serbian Chemical Society
Funding / projects:
- Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-172055)
- Identification of predictive molecular markers for cancer progression, response to therapy and disease outcome (RS-41031)
Note:
- Supplementary material: https://cer.ihtm.bg.ac.rs/handle/123456789/4521
Related info:
- Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4521
DOI: 10.2298/JSC180627062J
ISSN: 0352-5139
WoS: 000452167500001
Scopus: 2-s2.0-85053920097
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2361https://www.shd-pub.org.rs/index.php/JSCS/article/view/7014
Collections
Institution/Community
IHTMTY - JOUR AU - Jeremić, Marko AU - Dinić, Jelena AU - Pešić, Milica AU - Stepanovic, Marija AU - Novaković, Irena AU - Šegan, Dejan AU - Sladić, Dušan PY - 2018 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2361 UR - https://www.shd-pub.org.rs/index.php/JSCS/article/view/7014 AB - 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. PB - Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential T1 - Aлкиламино и аралкиламино деривати аварона и његовог миметика као селективни агенси према ћелијама неситноћелијског карцинома плућа, њихов антибактеријски и антифунгални потенцијал VL - 83 IS - 11 SP - 1193 EP - 1207 DO - 10.2298/JSC180627062J ER -
@article{ author = "Jeremić, Marko and Dinić, Jelena and Pešić, Milica and Stepanovic, Marija and Novaković, Irena and Šegan, Dejan and Sladić, Dušan", year = "2018", 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.", publisher = "Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society", title = "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential, Aлкиламино и аралкиламино деривати аварона и његовог миметика као селективни агенси према ћелијама неситноћелијског карцинома плућа, њихов антибактеријски и антифунгални потенцијал", volume = "83", number = "11", pages = "1193-1207", doi = "10.2298/JSC180627062J" }
Jeremić, M., Dinić, J., Pešić, M., Stepanovic, M., Novaković, I., Šegan, D.,& Sladić, D.. (2018). Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential. in Journal of the Serbian Chemical Society Serbian Chemical Society., 83(11), 1193-1207. https://doi.org/10.2298/JSC180627062J
Jeremić M, Dinić J, Pešić M, Stepanovic M, Novaković I, Šegan D, Sladić D. Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential. in Journal of the Serbian Chemical Society. 2018;83(11):1193-1207. doi:10.2298/JSC180627062J .
Jeremić, Marko, Dinić, Jelena, Pešić, Milica, Stepanovic, Marija, Novaković, Irena, Šegan, Dejan, Sladić, Dušan, "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential" in Journal of the Serbian Chemical Society, 83, no. 11 (2018):1193-1207, https://doi.org/10.2298/JSC180627062J . .