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Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters

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2014
1798.pdf (305.1Kb)
Authors
Pantelić, Nebojša Đ.
Zmejkovski, Bojana B.
Stanojković, Tatjana
Jevtic, Verica V.
Radic, Gordana P.
Trifunović, Srećko R.
Kaluđerović, Goran N.
Sabo, Tibor
Article (Published version)
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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.
Keywords:
R(2)edda-type esters / characterization / cytotoxicity / selectivity
Source:
Journal of the Serbian Chemical Society, 2014, 79, 6, 649-658
Publisher:
  • Serbian Chemical Soc, Belgrade
Funding / projects:
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Biological response modifiers in physiological and pathological conditions (RS-175011)

DOI: 10.2298/JSC130512022P

ISSN: 0352-5139

WoS: 000338268800003

Scopus: 2-s2.0-84903140555
[ Google Scholar ]
6
6
URI
https://cherry.chem.bg.ac.rs/handle/123456789/1800
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Pantelić, Nebojša Đ.
AU  - Zmejkovski, Bojana B.
AU  - Stanojković, Tatjana
AU  - Jevtic, Verica V.
AU  - Radic, Gordana P.
AU  - Trifunović, Srećko R.
AU  - Kaluđerović, Goran N.
AU  - Sabo, Tibor
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1800
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
UR  - Kon_2683
ER  - 
@article{
author = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana B. and Stanojković, Tatjana and Jevtic, Verica V. and Radic, Gordana P. and Trifunović, Srećko 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",
url = "Kon_2683"
}
Pantelić, N. Đ., Zmejkovski, B. B., Stanojković, T., Jevtic, V. V., Radic, G. P., Trifunović, 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
Kon_2683
Pantelić NĐ, Zmejkovski BB, Stanojković T, Jevtic VV, Radic GP, Trifunović 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
Kon_2683 .
Pantelić, Nebojša Đ., Zmejkovski, Bojana B., Stanojković, Tatjana, Jevtic, Verica V., Radic, Gordana P., Trifunović, Srećko 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 .,
Kon_2683 .

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