Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters
2014
Authors
Pantelić, Nebojša Đ.Zmejkovski, Bojana
Stanojković, Tatjana
Jevtic, Verica V.
Radic, Gordana P.
Trifunovic, Srecko R.
Kaluđerović, Goran N.
Sabo, Tibor
Article (Published version)
Metadata
Show full item recordAbstract
A novel (S,S)-R(2)eddip ester, O,O'-diisopentyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate dihydrochloride (1) was synthesized and characterized by IR, H-1- and C-13-NMR spectroscopy, mass spectroscopy and elemental analysis. In vitro antitumor action of 1, and two more R(2)eddip esters, dialkyl (S,S)-ethylenediamine-N,N'-di-2-propanoate dihydrochlorides, obtained before (alkyl = n-Bu or n-Pe, 2 and 3, respectively), was determined against cervix adenocarcinoma (HeLa), human melanoma (Fem-x), human chronic myelogenous leukemia (K562) cells, and a non-cancerous cell line human embryonic lung fibroblast (MRC-5), using the microculture tetrazolium test MTT assay. Esters 1-3 showed higher cytotoxicity and better selectivity in comparison to cisplatin, used as reference compound. The highest activity was expressed by 1, with IC50(Fem-x) value of 1.51 +/- 0.09 mu M.
Keywords:
R(2)edda-type esters / characterization / cytotoxicity / selectivitySource:
Journal of the Serbian Chemical Society, 2014, 79, 6, 649-658Publisher:
- Serbian Chemical Soc, Belgrade
Funding / projects:
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-MESTD-Basic Research (BR or ON)-172035)
- Biological response modifiers in physiological and pathological conditions (RS-MESTD-Basic Research (BR or ON)-175011)
DOI: 10.2298/JSC130512022P
ISSN: 0352-5139
WoS: 000338268800003
Scopus: 2-s2.0-84903140555
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IHTMTY - JOUR AU - Pantelić, Nebojša Đ. AU - Zmejkovski, Bojana AU - Stanojković, Tatjana AU - Jevtic, Verica V. AU - Radic, Gordana P. AU - Trifunovic, Srecko R. AU - Kaluđerović, Goran N. AU - Sabo, Tibor PY - 2014 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1574 AB - A novel (S,S)-R(2)eddip ester, O,O'-diisopentyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate dihydrochloride (1) was synthesized and characterized by IR, H-1- and C-13-NMR spectroscopy, mass spectroscopy and elemental analysis. In vitro antitumor action of 1, and two more R(2)eddip esters, dialkyl (S,S)-ethylenediamine-N,N'-di-2-propanoate dihydrochlorides, obtained before (alkyl = n-Bu or n-Pe, 2 and 3, respectively), was determined against cervix adenocarcinoma (HeLa), human melanoma (Fem-x), human chronic myelogenous leukemia (K562) cells, and a non-cancerous cell line human embryonic lung fibroblast (MRC-5), using the microculture tetrazolium test MTT assay. Esters 1-3 showed higher cytotoxicity and better selectivity in comparison to cisplatin, used as reference compound. The highest activity was expressed by 1, with IC50(Fem-x) value of 1.51 +/- 0.09 mu M. PB - Serbian Chemical Soc, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters VL - 79 IS - 6 SP - 649 EP - 658 DO - 10.2298/JSC130512022P ER -
@article{ author = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana and Stanojković, Tatjana and Jevtic, Verica V. and Radic, Gordana P. and Trifunovic, Srecko R. and Kaluđerović, Goran N. and Sabo, Tibor", year = "2014", abstract = "A novel (S,S)-R(2)eddip ester, O,O'-diisopentyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate dihydrochloride (1) was synthesized and characterized by IR, H-1- and C-13-NMR spectroscopy, mass spectroscopy and elemental analysis. In vitro antitumor action of 1, and two more R(2)eddip esters, dialkyl (S,S)-ethylenediamine-N,N'-di-2-propanoate dihydrochlorides, obtained before (alkyl = n-Bu or n-Pe, 2 and 3, respectively), was determined against cervix adenocarcinoma (HeLa), human melanoma (Fem-x), human chronic myelogenous leukemia (K562) cells, and a non-cancerous cell line human embryonic lung fibroblast (MRC-5), using the microculture tetrazolium test MTT assay. Esters 1-3 showed higher cytotoxicity and better selectivity in comparison to cisplatin, used as reference compound. The highest activity was expressed by 1, with IC50(Fem-x) value of 1.51 +/- 0.09 mu M.", publisher = "Serbian Chemical Soc, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters", volume = "79", number = "6", pages = "649-658", doi = "10.2298/JSC130512022P" }
Pantelić, N. Đ., Zmejkovski, B., Stanojković, T., Jevtic, V. V., Radic, G. P., Trifunovic, S. R., Kaluđerović, G. N.,& Sabo, T.. (2014). Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 79(6), 649-658. https://doi.org/10.2298/JSC130512022P
Pantelić NĐ, Zmejkovski B, Stanojković T, Jevtic VV, Radic GP, Trifunovic SR, Kaluđerović GN, Sabo T. Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters. in Journal of the Serbian Chemical Society. 2014;79(6):649-658. doi:10.2298/JSC130512022P .
Pantelić, Nebojša Đ., Zmejkovski, Bojana, Stanojković, Tatjana, Jevtic, Verica V., Radic, Gordana P., Trifunovic, Srecko R., Kaluđerović, Goran N., Sabo, Tibor, "Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters" in Journal of the Serbian Chemical Society, 79, no. 6 (2014):649-658, https://doi.org/10.2298/JSC130512022P . .