doiSerbia

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

Pantelić Nebojša (Faculty of Agriculture, Belgrade)
Zmejkovski Bojana B. (Institute of Chemistry, Tehnology and Metallurgy, Department of Chemistry, Belgrade)
Stanojković Tatjana P. (Institute of Oncology and Radiology, Belgrade)
Jeftić Verica V. (Faculty of Science, Institute of Chemistry, Kragujevac)
Radić Gordana P. (Faculty of Science, Institute of Chemistry, Kragujevac)
Trifunović Srećko R. (Faculty of Science, Institute of Chemistry, Kragujevac)
Kaluđerović Goran N. (Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Halle (Saale), Germany)
Sabo Tibor J. (Faculty of Chemistry, Belgrade)

Novel (S,S)-R2eddip ester, O,O’-diisoamyl-(S,S)-ethylenediamine-N,N’-di-2-propanoate dihydrochloride, 1, was synthesized and characterized by IR, 1H and 13C NMR spectroscopy, mass spectroscopy and elemental analysis.In vitro antitumor action of 1, and two more R2eddip esters, O,O’-dialkyl-(S,S)-ethylenediamine-N,N’-di-2-propanoate dihydrochlorides, obtained before, (alkyl = n-Bu, 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 MTT assay. Esters 1-3 showed higher cytotoxicity and better selectivity in comparison to cisplatin, used as reference compound. The highest activityis expressed by1,with IC50(Fem-x)value1.51 ± 0.09 µM.

Keywords: R2edda-type esters, characterization, cytotoxicity, selectivity

Projekat Ministarstva nauke republike Srbije, br. 172035 i br. 175011