Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction

2015
Authors
Filipovic, Nenad R.Bjelogrlić, Snežana K.

Marinković, Aleksandar D.

Verbić, Tatjana

Cvijetić, Ilija

Senćanski, Milan

Rodić, Marko V.

Vujčić, Miroslava

Sladić, Dušan

Strikovic, Zlatko
Todorović, Tamara

Muller, Christian D.
Article (Published version)
Metadata
Show full item recordAbstract
A new Zn(II)-based potential chemotherapeutic agent was synthesized from the ligand 2-quinolinecarboxaldehyde selenosemicarbazone (Hqasesc). Single crystal X-ray diffraction analysis showed that the Zn(II) complex consists of a cation [Zn(Hqasesc)(2)](2+), two perchlorate anions and one ethanol solvent molecule. The interaction of calf thymus (CT) DNA and human serum albumin (HSA) with the Zn(II) complex was explored using absorption and emission spectral methods, and also has been supported by molecular docking studies. The complex has more affinity to minor DNA groove than major, with no significant intercalation. The HSA interaction studies of the complex revealed the quenching of the intrinsic fluorescence of the HSA through a static quenching mechanism. The antitumor activity of the ligand and the complex against pancreatic adenocarcinoma cell line (AsPC-1) and acute monocytic leukemia (THP-1) cells was evaluated. Both compounds are strong concentration-dependent apoptosis inducer...s in THP-1 cells. While Hqasesc in AsPC-1 cells induces apoptosis only at the highest concentration, treatment with the Zn complex shows a concentration-dependent apoptotic response, where the treated cells are arrested in the G1-to-S phase accompanied with extensive activation of caspase-8 and -9. These results indicate that the ligand and Zn(II) complex display cell phenotype specific activity.
Source:
RSC Advances, 2015, 5, 115, 95191-95211Publisher:
- Royal Soc Chemistry, Cambridge
Funding / projects:
- Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-172055)
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
- European Commission
- COST Action CM1106 StemChem - "Chemical Approaches to Targeting Drug Resistance in Cancer Stem Cells"
DOI: 10.1039/c5ra19849f
ISSN: 2046-2069
WoS: 000364906600078
Scopus: 2-s2.0-84946944475
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Institution/Community
IHTMTY - JOUR AU - Filipovic, Nenad R. AU - Bjelogrlić, Snežana K. AU - Marinković, Aleksandar D. AU - Verbić, Tatjana AU - Cvijetić, Ilija AU - Senćanski, Milan AU - Rodić, Marko V. AU - Vujčić, Miroslava AU - Sladić, Dušan AU - Strikovic, Zlatko AU - Todorović, Tamara AU - Muller, Christian D. PY - 2015 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1830 AB - A new Zn(II)-based potential chemotherapeutic agent was synthesized from the ligand 2-quinolinecarboxaldehyde selenosemicarbazone (Hqasesc). Single crystal X-ray diffraction analysis showed that the Zn(II) complex consists of a cation [Zn(Hqasesc)(2)](2+), two perchlorate anions and one ethanol solvent molecule. The interaction of calf thymus (CT) DNA and human serum albumin (HSA) with the Zn(II) complex was explored using absorption and emission spectral methods, and also has been supported by molecular docking studies. The complex has more affinity to minor DNA groove than major, with no significant intercalation. The HSA interaction studies of the complex revealed the quenching of the intrinsic fluorescence of the HSA through a static quenching mechanism. The antitumor activity of the ligand and the complex against pancreatic adenocarcinoma cell line (AsPC-1) and acute monocytic leukemia (THP-1) cells was evaluated. Both compounds are strong concentration-dependent apoptosis inducers in THP-1 cells. While Hqasesc in AsPC-1 cells induces apoptosis only at the highest concentration, treatment with the Zn complex shows a concentration-dependent apoptotic response, where the treated cells are arrested in the G1-to-S phase accompanied with extensive activation of caspase-8 and -9. These results indicate that the ligand and Zn(II) complex display cell phenotype specific activity. PB - Royal Soc Chemistry, Cambridge T2 - RSC Advances T1 - Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction VL - 5 IS - 115 SP - 95191 EP - 95211 DO - 10.1039/c5ra19849f ER -
@article{ author = "Filipovic, Nenad R. and Bjelogrlić, Snežana K. and Marinković, Aleksandar D. and Verbić, Tatjana and Cvijetić, Ilija and Senćanski, Milan and Rodić, Marko V. and Vujčić, Miroslava and Sladić, Dušan and Strikovic, Zlatko and Todorović, Tamara and Muller, Christian D.", year = "2015", abstract = "A new Zn(II)-based potential chemotherapeutic agent was synthesized from the ligand 2-quinolinecarboxaldehyde selenosemicarbazone (Hqasesc). Single crystal X-ray diffraction analysis showed that the Zn(II) complex consists of a cation [Zn(Hqasesc)(2)](2+), two perchlorate anions and one ethanol solvent molecule. The interaction of calf thymus (CT) DNA and human serum albumin (HSA) with the Zn(II) complex was explored using absorption and emission spectral methods, and also has been supported by molecular docking studies. The complex has more affinity to minor DNA groove than major, with no significant intercalation. The HSA interaction studies of the complex revealed the quenching of the intrinsic fluorescence of the HSA through a static quenching mechanism. The antitumor activity of the ligand and the complex against pancreatic adenocarcinoma cell line (AsPC-1) and acute monocytic leukemia (THP-1) cells was evaluated. Both compounds are strong concentration-dependent apoptosis inducers in THP-1 cells. While Hqasesc in AsPC-1 cells induces apoptosis only at the highest concentration, treatment with the Zn complex shows a concentration-dependent apoptotic response, where the treated cells are arrested in the G1-to-S phase accompanied with extensive activation of caspase-8 and -9. These results indicate that the ligand and Zn(II) complex display cell phenotype specific activity.", publisher = "Royal Soc Chemistry, Cambridge", journal = "RSC Advances", title = "Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction", volume = "5", number = "115", pages = "95191-95211", doi = "10.1039/c5ra19849f" }
Filipovic, N. R., Bjelogrlić, S. K., Marinković, A. D., Verbić, T., Cvijetić, I., Senćanski, M., Rodić, M. V., Vujčić, M., Sladić, D., Strikovic, Z., Todorović, T.,& Muller, C. D.. (2015). Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction. in RSC Advances Royal Soc Chemistry, Cambridge., 5(115), 95191-95211. https://doi.org/10.1039/c5ra19849f
Filipovic NR, Bjelogrlić SK, Marinković AD, Verbić T, Cvijetić I, Senćanski M, Rodić MV, Vujčić M, Sladić D, Strikovic Z, Todorović T, Muller CD. Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction. in RSC Advances. 2015;5(115):95191-95211. doi:10.1039/c5ra19849f .
Filipovic, Nenad R., Bjelogrlić, Snežana K., Marinković, Aleksandar D., Verbić, Tatjana, Cvijetić, Ilija, Senćanski, Milan, Rodić, Marko V., Vujčić, Miroslava, Sladić, Dušan, Strikovic, Zlatko, Todorović, Tamara, Muller, Christian D., "Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction" in RSC Advances, 5, no. 115 (2015):95191-95211, https://doi.org/10.1039/c5ra19849f . .