Novel anthraquinone based chalcone analogues containing an imine fragment: synthesis, cytotoxicity and anti-angiogenic activity

Branka Kolundžija; Violeta Marković; Tatjana Stanojković; Ljubinka Joksović; Ivana Matić; Nina Todorović; Marijana Nikolić; Milan D Joksović

doi:10.1016/j.bmcl.2013.11.075

Novel anthraquinone based chalcone analogues containing an imine fragment: synthesis, cytotoxicity and anti-angiogenic activity

Bioorg Med Chem Lett. 2014 Jan 1;24(1):65-71. doi: 10.1016/j.bmcl.2013.11.075. Epub 2013 Dec 4.

Authors

Branka Kolundžija¹, Violeta Marković², Tatjana Stanojković¹, Ljubinka Joksović², Ivana Matić¹, Nina Todorović³, Marijana Nikolić⁴, Milan D Joksović⁵

Affiliations

¹ Institute of Oncology and Radiology of Serbia, Pasterova 14, 11000 Belgrade, Serbia.
² Faculty of Science, Department of Chemistry, University of Kragujevac, R. Domanovića 12, 34000 Kragujevac, Serbia.
³ Institute for Chemistry, Technology and Metallurgy, Njegoševa 12, 11000 Belgrade, Serbia.
⁴ Faculty of Medicinal Sciences, University of Kragujevac, S. Markovića 69, 34000 Kragujevac, Serbia.
⁵ Faculty of Science, Department of Chemistry, University of Kragujevac, R. Domanovića 12, 34000 Kragujevac, Serbia. Electronic address: mjoksovic@kg.ac.rs.

PMID: 24332490
DOI: 10.1016/j.bmcl.2013.11.075

Abstract

A new class of imine derivatives of hybrid chalcone analogues containing anthraquinone scaffold was synthesized and evaluated for their in vitro cytotoxic activity against HeLa, LS174, and A549 cancer cells. The compound 5n with furan ring linked to imino group showed potent activity against all target cells with IC50 values ranging from 1.76 to 6.11μM. A mode of action study suggested that compounds induced changes typical for apoptosis in HeLa cells. The most active compounds inhibited tubulogenesis and 5h was found to exhibit a strong anti-angiogenic effect.

Keywords: Angiogenesis; Anthraquinone; Chalcone; Cytotoxicity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Angiogenesis Inhibitors / chemical synthesis
Angiogenesis Inhibitors / chemistry
Angiogenesis Inhibitors / pharmacology*
Anthraquinones / chemistry*
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Chalcone / chemical synthesis
Chalcone / chemistry
Chalcone / pharmacology*
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
HeLa Cells
Humans
Imines / chemistry*
Molecular Structure
Structure-Activity Relationship

Substances

Angiogenesis Inhibitors
Anthraquinones
Antineoplastic Agents
Imines
Chalcone