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
Autori
Jeremić, Marko
Dinić, Jelena

Pešić, Milica

Stepanovic, Marija
Novaković, Irena

Šegan, Dejan

Sladić, Dušan

Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
quinones / anticancer activity / multidrug resistant / apoptosis / antimicrobial activity / cyclic voltammetryIzvor:
Journal of the Serbian Chemical Society, 2018, 83, 11, 1193-1207Izdavač:
- Serbian Chemical Society
Projekti:
- Interakcije prirodnih proizvoda, njihovih derivata i kompleksnih jedinjenja sa proteinima i nukleinskim kiselinama (RS-172055)
- Identifikacija molekularnih markera za predikciju progresije tumora, odgovora na terapiju i ishoda bolesti (RS-41031)
DOI: 10.2298/JSC180627062J
ISSN: 0352-5139
WoS: 000452167500001
Scopus: 2-s2.0-85053920097
Institucija
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 - http://cer.ihtm.bg.ac.rs/handle/123456789/2361 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 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", url = "http://cer.ihtm.bg.ac.rs/handle/123456789/2361", 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", 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. Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential. Journal of the Serbian Chemical Society. 2018;83(11):1193-1207
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. Journal of the Serbian Chemical SocietySerbian Chemical Society., 83(11), 1193-1207. https://doi.org/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" 83, no. 11 (2018):1193-1207, https://doi.org/10.2298/JSC180627062J .