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

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Marko Jeremić
http://orcid.org/0000-0003-0205-948X
Jelena Dinić
http://orcid.org/0000-0003-3371-2381
Milica Pešić
http://orcid.org/0000-0002-9045-8239
Marija Stepanović
Irena Novaković
http://orcid.org/0000-0001-9881-1204
Dejan Šegan
http://orcid.org/0000-0003-1541-9106
Dušan Sladić
http://orcid.org/0000-0002-1000-9813

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.

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How to Cite
[1]
M. Jeremić, “Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential”, J. Serb. Chem. Soc., vol. 83, no. 11, pp. 1193–1207, Dec. 2018.
Section
Organic Chemistry

References

GBD 2015 Mortality and Causes of Death Collaborators, Lancet 388 (2016) 1459

L. H. Kushi, C. Doyle, M. McCullough, C. L. Rock, W. Demark-Wahnefried, E. V. Bandera, S. Gapstur, A. V. Patel, K. Andrews, T. Gansler, Ca ̶ Cancer J. Clin. 62 (2012) 30

K. Mross, F. Kratz ,in Drug Delivery in Oncology: From Basic Research to Cancer Therapy, Vol. 1, F. Kratz, P. Senter, H. Steinhagen, Eds., Wiley–VCH, Weinheim, Germany, 2011, p. 3

K. Nooter, G. Stoter, Pathol., Res. Pract. 192 (1996) 768

M. González-Ibarra, N. Farfán, C. Trejo, S. Uribe, B. Lotina-Hennsen, J. Agric. Food Chem. 53 (2005) 3415

T.-S. Lin, L.-Y. Zhu, S.-P. Xu, A. A. Divo, A. C. Sartorelli, J. Med. Chem. 34 (1991) 1634

P. S. Sarin, D. Sun, A. Thornton, W. E. G. Müller, J. Natl. Cancer Inst. 78 (1987) 663

K. Müller, A. Sellmer, W. Wiergrebe, J. Nat. Prod. 62 (1999) 1134

A. J. M. da Silva, C. D. Netto, W. Pacienza-Lima, E. C. Torres-Santos, B. Rossi-Berg-man, S. Maurel, A. Valentin, P. R. R. Costa, J. Braz. Chem. Soc. 20 (2009) 176

L.-Y. Tao, J.-Y. Zhang, Y.-J. Liang, L.-M. Chen, L.-S. Zheng, F. Wang, Y.-J. Mi, Z.-G. She, K. K. W. To, Y.-C. Lin, L.-W. Fu, Mar. Drugs 8 (2010) 1094

V. Kuete, L. K. Omosa, V. R. Sipowo Tala, J. O. Midio, A. T. Mbaveng, S. Swaleh, O. Karaosmanoğlu, H. Sivas, BMC Pharmacol. Toxicol. 17 (2016) 60

R. R. Kitagawa, W. Vilegas, I. Z. Carlos, M. S. G. Raddi, Braz. J. Pharmacogn. 21 (2011) 1084

X. Wang, B. Thomas, R. Sachdeva, L. Arteburn, L. Frye, P. G. Hatcher, D. G. Cornwell, J. Ma, Proc. Natl. Acad. Sci. U. S. A. 103 (2006) 3604

C. S. Coates, J. Ziegler, K. Manz, J. Good, B. Kang, S. Milikisiyants, R. Chatterjee, S. Hao, J. H. Golbeck, K. V. Lakshmi, J. Phys. Chem. B 117 (2013) 7210

G. Lenaz, M. L. Genova, Biochim. Biophys. Acta, Bioenerg. 1787 (2009) 563

M. G. Traber, J. F. Stevens, Free Radical Biol. Med. 51 (2011) 1000

A. Kijjoa, P. Sawangwong, Mar. Drugs 2 (2004) 73

T. F. Molinski, D. S. Dalisay, S. L. Lievens, J. P. Saludes, Nat. Rev. Drug Discovery 8 (2009) 69

M. Gordaliza, Mar. Drugs 8 (2010) 2849

M. Jeremić, M. Pešić, J. Dinić, J. Banković, I. Novaković, D. Šegan, D. Sladić, Eur. J. Med. Chem. 118 (2016) 107

J. Vilipić, I. Novaković, T. Stanojković, I. Matić, D. Šegan, Z. Kljajić, D. Sladić, Bioorg. Med. Chem. 23 (2015) 6930

National Cancer Institute (NCI). Available from: https://www.cancer.gov/about-cancer/treatment/drugs/lung (last accessed 2018/04/10).

E. White, D. R. Green, in The molecular basis of cancer, 4th ed., J. Mendelsohn, J. W. Gray, P. M. Howley, M. A. Israel, C. B. Thompson, Eds., Elsevier Saunders, Philadelphia, PA, USA, 2015, pp. 209

G. Kroemer, L. Galluzzi, P. Vandenabeele, J. Abrams, E. S. Alnemri, E. H. Baehrecke, M. V. Blagosklonny, W. S. El-Deiry, P. Goldstein, D. R. Green. M. Hengartner, R. A. Knight, S. Kumar, S. A. Lipton, W. Malorni, G. Nuñez, M. E. Peter, J. Tschopp, J. Yuan, M. Piacentini, B. Zhivotovsky, G. Melino, Cell Death Differ. 16 (2009) 3

S. Elmore, Toxicol. Pathol. 35 (2007) 495

K. L. Rock, H. Kono, Annu. Rev. Pathol. 3 (2008) 99

L. M. Coussens, Z. Werb, Nature 420 (2002) 860

P. J. Boor, R. M. Hysmith, Toxicology 44 (1987) 129

S. Toyokuni, K. Okamoto, J. Yodoi, H. Hiai, FEBS Lett. 358 (1995) 1.

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