Interactions of Schiff base compounds and their coordination complexes with the drug cisplatin

József Magyari, Berta Barta Holló, Ljiljana S. Vojinović-Ješić, Mirjana M. Radanović, Stevan Armaković, Sanja J. Armaković, J. Molnár, Annamária Kincses, Márió Gajdács, G. Spengler, Katalin Meszaros Szecsenyi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

There is a complex interplay between the structural and other physicochemical properties of new compounds and the molecules in living organisms. To understand the mechanism of the interactions at the molecular level, the correlations between the selected properties and their biological responses have to be examined. With this aim, in this paper, density functional theory (DFT) and LMP2 calculations were carried out for the 2-acetylpyridine-aminoguanidine ligand, L, and its copper(ii) complexes containing different monoanionic ligands. In addition, several parameters, most frequently used for the prediction of drug-likeness of new compounds, were calculated. The influence of the compounds on the effectiveness of the reference chemotherapeutic drug cisplatin was determined in vitro, by comparison of their combination indices (CIs). The drug interactions between cisplatin and the earlier synthesized ligands L1 (bis(3-chloropyridazine-6-hydrazone)-2,6-diacetylpyridine) and L2 (bis(phthalazine-1-hydrazone)-2,6-diacetylpyridine) and their Co(iii), Ni(ii), Cu(ii) and Zn(ii) complexes, respectively, were also measured. The ligands L, L2, and L3, as well as their complexes, showed different interactions in combination with cisplatin from strong antagonism of L to strong synergism of 4-L1 and 4-L2. The experimental results and the calculated parameters were analyzed to evaluate their correlation with the measured interactions. The thermal stability of the L·2HCl ligand and its four copper(ii) complexes was determined and the thermal stability data were correlated to selected calculated molecular descriptors.

Original languageEnglish
Pages (from-to)5834-5843
Number of pages10
JournalNew Journal of Chemistry
Volume42
Issue number8
DOIs
Publication statusPublished - Jan 1 2018

Fingerprint

Schiff Bases
Coordination Complexes
Cisplatin
Ligands
Hydrazones
Pharmaceutical Preparations
Copper
Thermodynamic stability
Drug interactions
Density functional theory
Molecules

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

Cite this

Magyari, J., Barta Holló, B., Vojinović-Ješić, L. S., Radanović, M. M., Armaković, S., Armaković, S. J., ... Meszaros Szecsenyi, K. (2018). Interactions of Schiff base compounds and their coordination complexes with the drug cisplatin. New Journal of Chemistry, 42(8), 5834-5843. https://doi.org/10.1039/c8nj00357b

Interactions of Schiff base compounds and their coordination complexes with the drug cisplatin. / Magyari, József; Barta Holló, Berta; Vojinović-Ješić, Ljiljana S.; Radanović, Mirjana M.; Armaković, Stevan; Armaković, Sanja J.; Molnár, J.; Kincses, Annamária; Gajdács, Márió; Spengler, G.; Meszaros Szecsenyi, Katalin.

In: New Journal of Chemistry, Vol. 42, No. 8, 01.01.2018, p. 5834-5843.

Research output: Contribution to journalArticle

Magyari, J, Barta Holló, B, Vojinović-Ješić, LS, Radanović, MM, Armaković, S, Armaković, SJ, Molnár, J, Kincses, A, Gajdács, M, Spengler, G & Meszaros Szecsenyi, K 2018, 'Interactions of Schiff base compounds and their coordination complexes with the drug cisplatin', New Journal of Chemistry, vol. 42, no. 8, pp. 5834-5843. https://doi.org/10.1039/c8nj00357b
Magyari J, Barta Holló B, Vojinović-Ješić LS, Radanović MM, Armaković S, Armaković SJ et al. Interactions of Schiff base compounds and their coordination complexes with the drug cisplatin. New Journal of Chemistry. 2018 Jan 1;42(8):5834-5843. https://doi.org/10.1039/c8nj00357b
Magyari, József ; Barta Holló, Berta ; Vojinović-Ješić, Ljiljana S. ; Radanović, Mirjana M. ; Armaković, Stevan ; Armaković, Sanja J. ; Molnár, J. ; Kincses, Annamária ; Gajdács, Márió ; Spengler, G. ; Meszaros Szecsenyi, Katalin. / Interactions of Schiff base compounds and their coordination complexes with the drug cisplatin. In: New Journal of Chemistry. 2018 ; Vol. 42, No. 8. pp. 5834-5843.
@article{db78faa6fa85472bb3a8a2186d39429d,
title = "Interactions of Schiff base compounds and their coordination complexes with the drug cisplatin",
abstract = "There is a complex interplay between the structural and other physicochemical properties of new compounds and the molecules in living organisms. To understand the mechanism of the interactions at the molecular level, the correlations between the selected properties and their biological responses have to be examined. With this aim, in this paper, density functional theory (DFT) and LMP2 calculations were carried out for the 2-acetylpyridine-aminoguanidine ligand, L, and its copper(ii) complexes containing different monoanionic ligands. In addition, several parameters, most frequently used for the prediction of drug-likeness of new compounds, were calculated. The influence of the compounds on the effectiveness of the reference chemotherapeutic drug cisplatin was determined in vitro, by comparison of their combination indices (CIs). The drug interactions between cisplatin and the earlier synthesized ligands L1 (bis(3-chloropyridazine-6-hydrazone)-2,6-diacetylpyridine) and L2 (bis(phthalazine-1-hydrazone)-2,6-diacetylpyridine) and their Co(iii), Ni(ii), Cu(ii) and Zn(ii) complexes, respectively, were also measured. The ligands L, L2, and L3, as well as their complexes, showed different interactions in combination with cisplatin from strong antagonism of L to strong synergism of 4-L1 and 4-L2. The experimental results and the calculated parameters were analyzed to evaluate their correlation with the measured interactions. The thermal stability of the L·2HCl ligand and its four copper(ii) complexes was determined and the thermal stability data were correlated to selected calculated molecular descriptors.",
author = "J{\'o}zsef Magyari and {Barta Holl{\'o}}, Berta and Vojinović-Ješić, {Ljiljana S.} and Radanović, {Mirjana M.} and Stevan Armaković and Armaković, {Sanja J.} and J. Moln{\'a}r and Annam{\'a}ria Kincses and M{\'a}ri{\'o} Gajd{\'a}cs and G. Spengler and {Meszaros Szecsenyi}, Katalin",
year = "2018",
month = "1",
day = "1",
doi = "10.1039/c8nj00357b",
language = "English",
volume = "42",
pages = "5834--5843",
journal = "New Journal of Chemistry",
issn = "1144-0546",
publisher = "Royal Society of Chemistry",
number = "8",

}

TY - JOUR

T1 - Interactions of Schiff base compounds and their coordination complexes with the drug cisplatin

AU - Magyari, József

AU - Barta Holló, Berta

AU - Vojinović-Ješić, Ljiljana S.

AU - Radanović, Mirjana M.

AU - Armaković, Stevan

AU - Armaković, Sanja J.

AU - Molnár, J.

AU - Kincses, Annamária

AU - Gajdács, Márió

AU - Spengler, G.

AU - Meszaros Szecsenyi, Katalin

PY - 2018/1/1

Y1 - 2018/1/1

N2 - There is a complex interplay between the structural and other physicochemical properties of new compounds and the molecules in living organisms. To understand the mechanism of the interactions at the molecular level, the correlations between the selected properties and their biological responses have to be examined. With this aim, in this paper, density functional theory (DFT) and LMP2 calculations were carried out for the 2-acetylpyridine-aminoguanidine ligand, L, and its copper(ii) complexes containing different monoanionic ligands. In addition, several parameters, most frequently used for the prediction of drug-likeness of new compounds, were calculated. The influence of the compounds on the effectiveness of the reference chemotherapeutic drug cisplatin was determined in vitro, by comparison of their combination indices (CIs). The drug interactions between cisplatin and the earlier synthesized ligands L1 (bis(3-chloropyridazine-6-hydrazone)-2,6-diacetylpyridine) and L2 (bis(phthalazine-1-hydrazone)-2,6-diacetylpyridine) and their Co(iii), Ni(ii), Cu(ii) and Zn(ii) complexes, respectively, were also measured. The ligands L, L2, and L3, as well as their complexes, showed different interactions in combination with cisplatin from strong antagonism of L to strong synergism of 4-L1 and 4-L2. The experimental results and the calculated parameters were analyzed to evaluate their correlation with the measured interactions. The thermal stability of the L·2HCl ligand and its four copper(ii) complexes was determined and the thermal stability data were correlated to selected calculated molecular descriptors.

AB - There is a complex interplay between the structural and other physicochemical properties of new compounds and the molecules in living organisms. To understand the mechanism of the interactions at the molecular level, the correlations between the selected properties and their biological responses have to be examined. With this aim, in this paper, density functional theory (DFT) and LMP2 calculations were carried out for the 2-acetylpyridine-aminoguanidine ligand, L, and its copper(ii) complexes containing different monoanionic ligands. In addition, several parameters, most frequently used for the prediction of drug-likeness of new compounds, were calculated. The influence of the compounds on the effectiveness of the reference chemotherapeutic drug cisplatin was determined in vitro, by comparison of their combination indices (CIs). The drug interactions between cisplatin and the earlier synthesized ligands L1 (bis(3-chloropyridazine-6-hydrazone)-2,6-diacetylpyridine) and L2 (bis(phthalazine-1-hydrazone)-2,6-diacetylpyridine) and their Co(iii), Ni(ii), Cu(ii) and Zn(ii) complexes, respectively, were also measured. The ligands L, L2, and L3, as well as their complexes, showed different interactions in combination with cisplatin from strong antagonism of L to strong synergism of 4-L1 and 4-L2. The experimental results and the calculated parameters were analyzed to evaluate their correlation with the measured interactions. The thermal stability of the L·2HCl ligand and its four copper(ii) complexes was determined and the thermal stability data were correlated to selected calculated molecular descriptors.

UR - http://www.scopus.com/inward/record.url?scp=85045584102&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85045584102&partnerID=8YFLogxK

U2 - 10.1039/c8nj00357b

DO - 10.1039/c8nj00357b

M3 - Article

VL - 42

SP - 5834

EP - 5843

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 8

ER -