Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents

A series of 23 novel anthraquinone-chalcone hybrids containing amide function was synthesized and structurally characterized. Sixteen compounds exerted strong cytotoxic activities against K562, Jurkat and HL-60 leukemia cell lines and significantly lower cytotoxic effects against normal MRC-5 cells, indicating very high selectivity in their anticancer action. The compounds 6g, 6u and 6v activate apoptosis in K562 cells through the extrinsic and intrinsic apoptotic pathway. The compound 6e triggered apoptosis in K562 cells only through the extrinsic apoptotic pathway. Treatment of K562 cells with each of these four compounds caused decrease in the expression levels of MMP2, MMP9, and VEGF, suggesting their anti-invasive, antimetastatic and antiangiogenic properties. The compounds 6g and 6v downregulated expression levels of miR-155 in K562 cells, while compounds 6e and 6u upregulated miR-155 levels in treated cells, in comparison with control cells. The structure-based 3-D QSAR models f...

Keywords:

anthraquinone-chalcone / leukemia / gene expression / miR-155 / 3-D QSAR

Source:
Bioorganic and Medicinal Chemistry Letters, 2018, 28, 15, 2593-2598

Funding / projects:

DOI: 10.1016/j.bmcl.2018.06.048

ISSN: 0960-894X; 1464-3405

PubMed: 29970309

WoS: 000440568900003

Scopus: 2-s2.0-85049322460

[ Google Scholar ]


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TY  - JOUR
AU  - Stanojković, Tatjana P.
AU  - Marković, Violeta
AU  - Matić, Ivana Z.
AU  - Mladenović, Milan P.
AU  - Petrović, Nina
AU  - Krivokuća, Ana M.
AU  - Petković, Miloš R.
AU  - Joksović, Milan D.
PY  - 2018
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0960894X18305493
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7815
AB  - A series of 23 novel anthraquinone-chalcone hybrids containing amide function was synthesized and structurally characterized. Sixteen compounds exerted strong cytotoxic activities against K562, Jurkat and HL-60 leukemia cell lines and significantly lower cytotoxic effects against normal MRC-5 cells, indicating very high selectivity in their anticancer action. The compounds 6g, 6u and 6v activate apoptosis in K562 cells through the extrinsic and intrinsic apoptotic pathway. The compound 6e triggered apoptosis in K562 cells only through the extrinsic apoptotic pathway. Treatment of K562 cells with each of these four compounds caused decrease in the expression levels of MMP2, MMP9, and VEGF, suggesting their anti-invasive, antimetastatic and antiangiogenic properties. The compounds 6g and 6v downregulated expression levels of miR-155 in K562 cells, while compounds 6e and 6u upregulated miR-155 levels in treated cells, in comparison with control cells. The structure-based 3-D QSAR models for 6f, 6e, 6i and 6l describe pro-apoptotic activity against caspase-3. © 2018 Elsevier Ltd
T2  - Bioorganic and Medicinal Chemistry Letters
T1  - Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents
VL  - 28
IS  - 15
SP  - 2593
EP  - 2598
DO  - 10.1016/j.bmcl.2018.06.048
ER  -

@article{
author = "Stanojković, Tatjana P. and Marković, Violeta and Matić, Ivana Z. and Mladenović, Milan P. and Petrović, Nina and Krivokuća, Ana M. and Petković, Miloš R. and Joksović, Milan D.",
year = "2018",
abstract = "A series of 23 novel anthraquinone-chalcone hybrids containing amide function was synthesized and structurally characterized. Sixteen compounds exerted strong cytotoxic activities against K562, Jurkat and HL-60 leukemia cell lines and significantly lower cytotoxic effects against normal MRC-5 cells, indicating very high selectivity in their anticancer action. The compounds 6g, 6u and 6v activate apoptosis in K562 cells through the extrinsic and intrinsic apoptotic pathway. The compound 6e triggered apoptosis in K562 cells only through the extrinsic apoptotic pathway. Treatment of K562 cells with each of these four compounds caused decrease in the expression levels of MMP2, MMP9, and VEGF, suggesting their anti-invasive, antimetastatic and antiangiogenic properties. The compounds 6g and 6v downregulated expression levels of miR-155 in K562 cells, while compounds 6e and 6u upregulated miR-155 levels in treated cells, in comparison with control cells. The structure-based 3-D QSAR models for 6f, 6e, 6i and 6l describe pro-apoptotic activity against caspase-3. © 2018 Elsevier Ltd",
journal = "Bioorganic and Medicinal Chemistry Letters",
title = "Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents",
volume = "28",
number = "15",
pages = "2593-2598",
doi = "10.1016/j.bmcl.2018.06.048"
}

Stanojković, T. P., Marković, V., Matić, I. Z., Mladenović, M. P., Petrović, N., Krivokuća, A. M., Petković, M. R.,& Joksović, M. D.. (2018). Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents. in Bioorganic and Medicinal Chemistry Letters, 28(15), 2593-2598.
https://doi.org/10.1016/j.bmcl.2018.06.048

Stanojković TP, Marković V, Matić IZ, Mladenović MP, Petrović N, Krivokuća AM, Petković MR, Joksović MD. Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents. in Bioorganic and Medicinal Chemistry Letters. 2018;28(15):2593-2598.
doi:10.1016/j.bmcl.2018.06.048 .

Stanojković, Tatjana P., Marković, Violeta, Matić, Ivana Z., Mladenović, Milan P., Petrović, Nina, Krivokuća, Ana M., Petković, Miloš R., Joksović, Milan D., "Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents" in Bioorganic and Medicinal Chemistry Letters, 28, no. 15 (2018):2593-2598,
https://doi.org/10.1016/j.bmcl.2018.06.048 . .