Structural, biological and computational study of oxamide derivative: Scientific paper

Ignjat P. Filipović; Emina M. Mrkalić; Giorgio Pelosi; Vesna Kojić; Dimitar Jakimov; Dejan Baskić; Zoran D. Matović

doi:10.2298/JSC211204114F

PDF (2,421 kB) Supplementary Material (3.26 MB)

Published: Feb 18, 2022

Updated: 18.02.2022

DOI: https://doi.org/10.2298/JSC211204114F

Keywords:

oxamides crystal structure apoptosis docking molecular dynamics

Ignjat P. Filipović

University of Kragujevac, Faculty of Science, Department of Chemistry, Radoja Domanovića 12, 34000 Kragujevac, Serbia

https://orcid.org/0000-0003-1307-6242

Emina M. Mrkalić

University of Kragujevac, Institute for Information Technologies, Department of Science, Jovana Cvijića bb, Kragujevac 34000, Serbia

https://orcid.org/0000-0002-9708-2326

Giorgio Pelosi

Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica Chimica Fisica, Universita` di Parma, 43100 Parma, Italy

https://orcid.org/0000-0002-7946-0602

Vesna Kojić

lnstitute of Oncology Sremska Kamenica, Novi Sad, lnstitutski put 4, 21204 Sremska Kamenica, Serbia

https://orcid.org/0000-0002-2399-0807

Dimitar Jakimov

lnstitute of Oncology Sremska Kamenica, Novi Sad, lnstitutski put 4, 21204 Sremska Kamenica, Serbia

https://orcid.org/0000-0002-1747-4718

Dejan Baskić

University of Kragujevac, Faculty of Medicinal Science, S. Markovića 69, 34000 Kragujevac, Serbia

https://orcid.org/0000-0002-6152-0742

Zoran D. Matović

Department of Chemistry, Faculty of Science, University of Kragujevac, Serbia

https://orcid.org/0000-0002-5937-4424

Abstract

A dicarboxylato-diamide-type compound 2,2'-[(1,2-dioxoethane-1,2-diyl)diimino]dibenzoic acid (H₄obbz) (1) was synthesized and characterized. The crystal structure of K₂H₂obbz·2H₂O (2) was determined by X-ray diffracttion analysis. The cytotoxic activities of the compounds were tested against four different cancer cell lines MCF-7, A549, HT-29, HeLa and a human normal cell line MRC-5. The results indicate reasonable dose-dependent cytotoxicity of the ligands that show selectivity against the tested carcinoma and healthy cell lines. Flow cytometric analysis and fluorescence microscopy showed that the most active compound, H₄obbz, induced apoptosis and G0/G1 cell cycle arrest, indicating blockage of DNA synthesis as a possible mechanism that triggers apoptosis. Docking and molecular dynamics simulations gave similar responses regarding interactions (binding) between their ligands and chaperon Grp78. The MMGBSA determined ΔG binding energies were in the range from –104 to –140 kJ mol^-1.

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How to Cite

[1]

I. P. Filipović, “Structural, biological and computational study of oxamide derivative: Scientific paper”, J. Serb. Chem. Soc., vol. 87, no. 5, pp. 545–559, Feb. 2022.

Issue

Vol. 87 No. 5 (2022)

Section

Organic Chemistry

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

Funding data

Ministarstvo Prosvete, Nauke i Tehnološkog Razvoja
Grant numbers 451-03-9/2021-14/200122

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Structural, biological and computational study of oxamide derivative Scientific paper