Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies
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2015
Authors
Marković, VioletaDebeljak, Nevena
Stanojković, Tatjana
Kolundžija, Branka
Sladić, Dušan
Vujčić, Miroslava
Janović, Barbara
Tanić, Nikola
Perović, Milka
Tešić, Vesna
Antić, Jadranka
Joksović, Milan D.
Article (Published version)
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Novel anthraquinone based chalcone compounds were synthesized starting from 1-acetylanthraquinone in a Claisen-Schmidt reaction and evaluated for their anticancer potential against three human cancer cell lines. Compounds 4a, 4b and 4j showed promising activity in inhibition of HeLa cells with IC50 values ranging from 2.36 to 2.73 mu M and low cytotoxicity against healthy MRC-5 cell lines. The effects that compounds produces on the cell cycle were investigated by flow cytometry. It was found that 4a, 4b and 4j cause the accumulation of cells in the S and G2/M phases in a dose-dependent manner and induce caspase-dependent apoptosis. All of three compounds exhibit calf thymus DNA-binding activity. The determined binding constants by absorption titrations (2.65 x 10(3) M-1, 1.36 x 10(3) M(-1)and 2.51 x 10(3) M-1 of 4a/CT-DNA, 4b/CT-DNA and 4j/CT-DNA, respectively) together with fluorescence displacement analysis designate 4a, 4b and 4j as strong minor groove binders, but no cleavage of pl...asmid DNA was observed. (C) 2014 Elsevier Masson SAS. All rights reserved.
Keywords:
Chalcone / Anthraquinone / Cytotoxicity / Apoptosis / DNA studySource:
European Journal of Medicinal Chemistry, 2015, 89, 401-410Publisher:
- Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
Funding / projects:
- Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes (RS-MESTD-Basic Research (BR or ON)-172016)
- Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-MESTD-Basic Research (BR or ON)-172055)
- Brain plasticity in aging: effect of dietary restriction and anesthesia (RS-MESTD-Basic Research (BR or ON)-173056)
- Biological response modifiers in physiological and pathological conditions (RS-MESTD-Basic Research (BR or ON)-175011)
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3338
DOI: 10.1016/j.ejmech.2014.10.055
ISSN: 0223-5234
PubMed: 25462255
WoS: 000348003500036
Scopus: 2-s2.0-84908368917
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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, Violeta AU - Debeljak, Nevena AU - Stanojković, Tatjana AU - Kolundžija, Branka AU - Sladić, Dušan AU - Vujčić, Miroslava AU - Janović, Barbara AU - Tanić, Nikola AU - Perović, Milka AU - Tešić, Vesna AU - Antić, Jadranka AU - Joksović, Milan D. PY - 2015 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1903 AB - Novel anthraquinone based chalcone compounds were synthesized starting from 1-acetylanthraquinone in a Claisen-Schmidt reaction and evaluated for their anticancer potential against three human cancer cell lines. Compounds 4a, 4b and 4j showed promising activity in inhibition of HeLa cells with IC50 values ranging from 2.36 to 2.73 mu M and low cytotoxicity against healthy MRC-5 cell lines. The effects that compounds produces on the cell cycle were investigated by flow cytometry. It was found that 4a, 4b and 4j cause the accumulation of cells in the S and G2/M phases in a dose-dependent manner and induce caspase-dependent apoptosis. All of three compounds exhibit calf thymus DNA-binding activity. The determined binding constants by absorption titrations (2.65 x 10(3) M-1, 1.36 x 10(3) M(-1)and 2.51 x 10(3) M-1 of 4a/CT-DNA, 4b/CT-DNA and 4j/CT-DNA, respectively) together with fluorescence displacement analysis designate 4a, 4b and 4j as strong minor groove binders, but no cleavage of plasmid DNA was observed. (C) 2014 Elsevier Masson SAS. All rights reserved. PB - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris T2 - European Journal of Medicinal Chemistry T1 - Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies VL - 89 SP - 401 EP - 410 DO - 10.1016/j.ejmech.2014.10.055 ER -
@article{ author = "Marković, Violeta and Debeljak, Nevena and Stanojković, Tatjana and Kolundžija, Branka and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Tanić, Nikola and Perović, Milka and Tešić, Vesna and Antić, Jadranka and Joksović, Milan D.", year = "2015", abstract = "Novel anthraquinone based chalcone compounds were synthesized starting from 1-acetylanthraquinone in a Claisen-Schmidt reaction and evaluated for their anticancer potential against three human cancer cell lines. Compounds 4a, 4b and 4j showed promising activity in inhibition of HeLa cells with IC50 values ranging from 2.36 to 2.73 mu M and low cytotoxicity against healthy MRC-5 cell lines. The effects that compounds produces on the cell cycle were investigated by flow cytometry. It was found that 4a, 4b and 4j cause the accumulation of cells in the S and G2/M phases in a dose-dependent manner and induce caspase-dependent apoptosis. All of three compounds exhibit calf thymus DNA-binding activity. The determined binding constants by absorption titrations (2.65 x 10(3) M-1, 1.36 x 10(3) M(-1)and 2.51 x 10(3) M-1 of 4a/CT-DNA, 4b/CT-DNA and 4j/CT-DNA, respectively) together with fluorescence displacement analysis designate 4a, 4b and 4j as strong minor groove binders, but no cleavage of plasmid DNA was observed. (C) 2014 Elsevier Masson SAS. All rights reserved.", publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris", journal = "European Journal of Medicinal Chemistry", title = "Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies", volume = "89", pages = "401-410", doi = "10.1016/j.ejmech.2014.10.055" }
Marković, V., Debeljak, N., Stanojković, T., Kolundžija, B., Sladić, D., Vujčić, M., Janović, B., Tanić, N., Perović, M., Tešić, V., Antić, J.,& Joksović, M. D.. (2015). Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies. in European Journal of Medicinal Chemistry Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 89, 401-410. https://doi.org/10.1016/j.ejmech.2014.10.055
Marković V, Debeljak N, Stanojković T, Kolundžija B, Sladić D, Vujčić M, Janović B, Tanić N, Perović M, Tešić V, Antić J, Joksović MD. Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies. in European Journal of Medicinal Chemistry. 2015;89:401-410. doi:10.1016/j.ejmech.2014.10.055 .
Marković, Violeta, Debeljak, Nevena, Stanojković, Tatjana, Kolundžija, Branka, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Tanić, Nikola, Perović, Milka, Tešić, Vesna, Antić, Jadranka, Joksović, Milan D., "Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies" in European Journal of Medicinal Chemistry, 89 (2015):401-410, https://doi.org/10.1016/j.ejmech.2014.10.055 . .