Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group
Само за регистроване кориснике
2013
Аутори
Marković, VioletaJanićijević, Ana
Stanojković, Tatjana
Kolundžija, Branka
Sladić, Dušan
Vujčić, Miroslava
Janović, Barbara
Joksović, Ljubinka
Đurđević, Predrag T.
Todorović, Nina
Trifunović, Snežana S.
Joksović, Milan D.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed.
Кључне речи:
Anthraquinone / Thiosemicarbazone / Tautomerism / Cytotoxicity / DNA-binding studiesИзвор:
European Journal of Medicinal Chemistry, 2013, 64, 228-238Издавач:
- Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
Финансирање / пројекти:
- Синтеза, моделовање, физичко-хемијске и биолошке особине органских једињења и одговарајућих комплекса метала (RS-MESTD-Basic Research (BR or ON)-172016)
- Модификатори биолошког одговора у физиолошким и патолошким стањима (RS-MESTD-Basic Research (BR or ON)-175011)
Напомена:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3548
DOI: 10.1016/j.ejmech.2013.03.071
ISSN: 0223-5234
PubMed: 23644206
WoS: 000321230300024
Scopus: 2-s2.0-84877040246
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, Violeta AU - Janićijević, Ana AU - Stanojković, Tatjana AU - Kolundžija, Branka AU - Sladić, Dušan AU - Vujčić, Miroslava AU - Janović, Barbara AU - Joksović, Ljubinka AU - Đurđević, Predrag T. AU - Todorović, Nina AU - Trifunović, Snežana S. AU - Joksović, Milan D. PY - 2013 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1370 AB - A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed. PB - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris T2 - European Journal of Medicinal Chemistry T1 - Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group VL - 64 SP - 228 EP - 238 DO - 10.1016/j.ejmech.2013.03.071 ER -
@article{ author = "Marković, Violeta and Janićijević, Ana and Stanojković, Tatjana and Kolundžija, Branka and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksović, Ljubinka and Đurđević, Predrag T. and Todorović, Nina and Trifunović, Snežana S. and Joksović, Milan D.", year = "2013", abstract = "A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed.", publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris", journal = "European Journal of Medicinal Chemistry", title = "Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group", volume = "64", pages = "228-238", doi = "10.1016/j.ejmech.2013.03.071" }
Marković, V., Janićijević, A., Stanojković, T., Kolundžija, B., Sladić, D., Vujčić, M., Janović, B., Joksović, L., Đurđević, P. T., Todorović, N., Trifunović, S. S.,& Joksović, M. D.. (2013). Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group. in European Journal of Medicinal Chemistry Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 64, 228-238. https://doi.org/10.1016/j.ejmech.2013.03.071
Marković V, Janićijević A, Stanojković T, Kolundžija B, Sladić D, Vujčić M, Janović B, Joksović L, Đurđević PT, Todorović N, Trifunović SS, Joksović MD. Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group. in European Journal of Medicinal Chemistry. 2013;64:228-238. doi:10.1016/j.ejmech.2013.03.071 .
Marković, Violeta, Janićijević, Ana, Stanojković, Tatjana, Kolundžija, Branka, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksović, Ljubinka, Đurđević, Predrag T., Todorović, Nina, Trifunović, Snežana S., Joksović, Milan D., "Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group" in European Journal of Medicinal Chemistry, 64 (2013):228-238, https://doi.org/10.1016/j.ejmech.2013.03.071 . .