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

2014
Authors
Pantelić, Nebojša
Zmejkovski, Bojana B.
Stanojković, Tatjana P.

Jevtić, Verica V.

Radić, Gordana P.
Trifunović, Srecko R.

Kaludjerović, Goran N.

Sabo, Tibor J.

Article (Published version)
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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:
- Srpsko hemijsko društvo, Beograd
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
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Poljoprivredni fakultetTY - JOUR AU - Pantelić, Nebojša AU - Zmejkovski, Bojana B. AU - Stanojković, Tatjana P. AU - Jevtić, Verica V. AU - Radić, Gordana P. AU - Trifunović, Srecko R. AU - Kaludjerović, Goran N. AU - Sabo, Tibor J. PY - 2014 UR - http://aspace.agrif.bg.ac.rs/handle/123456789/3417 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 - Srpsko hemijsko društvo, Beograd 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 EP - 658 IS - 6 SP - 649 VL - 79 DO - 10.2298/JSC130512022P ER -
@article{ author = "Pantelić, Nebojša and Zmejkovski, Bojana B. and Stanojković, Tatjana P. and Jevtić, Verica V. and Radić, Gordana P. and Trifunović, Srecko R. and Kaludjerović, Goran N. and Sabo, Tibor J.", 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 = "Srpsko hemijsko društvo, Beograd", 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", pages = "658-649", number = "6", volume = "79", doi = "10.2298/JSC130512022P" }
Pantelić, N., Zmejkovski, B. B., Stanojković, T. P., Jevtić, V. V., Radić, G. P., Trifunović, S. R., Kaludjerović, G. N.,& Sabo, T. J.. (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 Srpsko hemijsko društvo, Beograd., 79(6), 649-658. https://doi.org/10.2298/JSC130512022P
Pantelić N, Zmejkovski BB, Stanojković TP, Jevtić VV, Radić GP, Trifunović SR, Kaludjerović GN, Sabo TJ. 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, Zmejkovski, Bojana B., Stanojković, Tatjana P., Jevtić, Verica V., Radić, Gordana P., Trifunović, Srecko R., Kaludjerović, Goran N., Sabo, Tibor J., "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 . .