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Synthesis of glycolysis inhibitor (E)-3-(pyridin-3-yl)-1-(pyridin-4-yl)prop-2-en-1-one (3PO) and its inhibition of HUVEC proliferation alone or in a combination with the multi-kinase inhibitor sunitinib

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While a treatment of tumours by anti-angiogenic kinase inhibitors has limited efficacy and is associated with resistance and side effects, also other key biological pathways should be targeted to fight cancer more effectively. Active endothelial and cancer cells acquire energy predominantly via a glycolysis (Warburg effect) in contrast to most of other somatic cells preferring an oxidative phosphorylation. Proliferation of endothelial and cancer cells may be suppressed by a glycolysis inhibitor (E)-3-(pyridin-3-yl)-1-(pyridin-4-yl)prop-2-en-1-one (3PO) that synthesis is not sufficiently described in the literature. Moreover, a synergistic effect of inhibitors with different mechanisms of action may provide further advantages in cancer treatment. A combined effect of 3PO with inhibitor of angiogenesis sunitinib l-malate (SU) was not yet investigated on HUVEC cells. We have developed a novel and efficient method for a synthesis of a glycolysis inhibitor 3PO. The activity of 3PO on HUVECs proliferation was investigated and its IC50 = 10.7 μM determined. By combination of 3PO (10 μM) with sunitinib l-malate (0.1 μM) a significant synergistic effect on HUVECs proliferation was observed. Based on the structure, chemical reactivity and biological results, we proposed that 3PO could be a multi-target inhibitor.

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VEGA1/0670/18 and 1/0557/15; Biomagi, Ltd. (novel synthesis of 3PO, proposals: mechanism of Et2NH, multi-target 3PO properties). This publication is partially also the result of the project implementation: Comenius University in Bratislava Science Park supported by the Research and Development Operational Programme funded by the ERDF. Grant number: ITMS 26240220086.

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Correspondence to Andrej Boháč.

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Electronic Supplementary Material contains physico-chemical characteristics for 3PO together with its 1D and 2D (HSQC, HMBC) spectral figures, procedure for the synthesis of 3PO in the presence of Et2NH and the proposed mechanism of this reaction.

Supplementary material 1 (DOCX 724 kb)

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Murár, M., Horvathová, J., Moravčík, R. et al. Synthesis of glycolysis inhibitor (E)-3-(pyridin-3-yl)-1-(pyridin-4-yl)prop-2-en-1-one (3PO) and its inhibition of HUVEC proliferation alone or in a combination with the multi-kinase inhibitor sunitinib. Chem. Pap. 72, 2979–2985 (2018).

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