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Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib

Authorized Users Only
2017
Authors
Pavić, Aleksandar
Glišić, Biljana Đ.
Vojnović, Sandra
Warżajtis, Beata
Savić, Nada D.
Antić, Marija
Radenković, Slavko
Janjić, Goran V.
Nikodinović-Runić, Jasmina
Rychlewska, Urszula
Đuran, Miloš I.
Article (Published version)
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Abstract
Gold(III) complexes with 1,7- and 4,7-phenanthroline ligands, [AuCl3(1,7-phen-kappa N7)] (1) and [AuCl3(4,7-phen-kappa N4)] (2) were synthesized and structurally characterized by spectroscopic (NMR, IR and UV-vis) and single crystal X-ray diffraction techniques. In these complexes, 1,7- and 4,7-phenanthrolines are monodentatedly coordinated to the Au(III) ion through the N7 and N4 nitrogen atoms, respectively. In comparison to the clinically relevant anti-angiogenic compounds auranofin and sunitinib, gold(III)-phenanthroline complexes showed from 1.5- to 20-fold higher anti-angiogenic potential, and 13- and 118-fold lower toxicity. Among the tested compounds, complex 1 was the most potent and may be an excellent anti-angiogenic drug candidate, since it showed strong anti-angiogenic activity in zebrafish embryos achieving IC50 value (concentration resulting in an anti-angiogenic phenotype at 50% of embryos) of 2.89 mu M, while had low toxicity with LC50 value (the concentration inducing... the lethal effect of 50% embryos) of 128 mu M. Molecular docking study revealed that both complexes and ligands could suppress angiogenesis targeting the multiple major regulators of angiogenesis, such as the vascular endothelial growth factor receptor (VEGFR-2), the matrix metalloproteases (MMP-2 and MMP-9), and thioredoxin reductase (TrxR1), where the complexes showed higher binding affinity in comparison to ligands, and particularly to auranofin, but comparable to sunitinib, an anti-angiogenic drug of clinical relevance.

Keywords:
Gold(III) complexes / Phenanthroline / Cytotoxicity / Embryotoxicity / Angiogenesis
Source:
Journal of Inorganic Biochemistry, 2017, 174, 156-168
Publisher:
  • Elsevier Science Inc, New York
Funding / projects:
  • Synthesis of new metal complexes and investigation of their reactions with peptides (RS-172036)
  • Microbial diversity study and characterization of beneficial environmental microorganisms (RS-173048)
  • Graph theory and mathematical programming with applications in chemistry and computer science (RS-174033)
  • SupraMedChem'Balkans.Net SCOPES Institutional Partnership [IZ74Z0_160515]
Note:
  • Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/3110
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3111

DOI: 10.1016/j.jinorgbio.2017.06.009

ISSN: 0162-0134

PubMed: 28675847

WoS: 000406647700016

Scopus: 2-s2.0-85021674718
[ Google Scholar ]
21
20
URI
https://cherry.chem.bg.ac.rs/handle/123456789/2496
Collections
  • Publikacije
Institution/Community
Inovacioni centar
TY  - JOUR
AU  - Pavić, Aleksandar
AU  - Glišić, Biljana Đ.
AU  - Vojnović, Sandra
AU  - Warżajtis, Beata
AU  - Savić, Nada D.
AU  - Antić, Marija
AU  - Radenković, Slavko
AU  - Janjić, Goran V.
AU  - Nikodinović-Runić, Jasmina
AU  - Rychlewska, Urszula
AU  - Đuran, Miloš I.
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2496
AB  - Gold(III) complexes with 1,7- and 4,7-phenanthroline ligands, [AuCl3(1,7-phen-kappa N7)] (1) and [AuCl3(4,7-phen-kappa N4)] (2) were synthesized and structurally characterized by spectroscopic (NMR, IR and UV-vis) and single crystal X-ray diffraction techniques. In these complexes, 1,7- and 4,7-phenanthrolines are monodentatedly coordinated to the Au(III) ion through the N7 and N4 nitrogen atoms, respectively. In comparison to the clinically relevant anti-angiogenic compounds auranofin and sunitinib, gold(III)-phenanthroline complexes showed from 1.5- to 20-fold higher anti-angiogenic potential, and 13- and 118-fold lower toxicity. Among the tested compounds, complex 1 was the most potent and may be an excellent anti-angiogenic drug candidate, since it showed strong anti-angiogenic activity in zebrafish embryos achieving IC50 value (concentration resulting in an anti-angiogenic phenotype at 50% of embryos) of 2.89 mu M, while had low toxicity with LC50 value (the concentration inducing the lethal effect of 50% embryos) of 128 mu M. Molecular docking study revealed that both complexes and ligands could suppress angiogenesis targeting the multiple major regulators of angiogenesis, such as the vascular endothelial growth factor receptor (VEGFR-2), the matrix metalloproteases (MMP-2 and MMP-9), and thioredoxin reductase (TrxR1), where the complexes showed higher binding affinity in comparison to ligands, and particularly to auranofin, but comparable to sunitinib, an anti-angiogenic drug of clinical relevance.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib
VL  - 174
SP  - 156
EP  - 168
DO  - 10.1016/j.jinorgbio.2017.06.009
UR  - Kon_3312
ER  - 
@article{
author = "Pavić, Aleksandar and Glišić, Biljana Đ. and Vojnović, Sandra and Warżajtis, Beata and Savić, Nada D. and Antić, Marija and Radenković, Slavko and Janjić, Goran V. and Nikodinović-Runić, Jasmina and Rychlewska, Urszula and Đuran, Miloš I.",
year = "2017",
abstract = "Gold(III) complexes with 1,7- and 4,7-phenanthroline ligands, [AuCl3(1,7-phen-kappa N7)] (1) and [AuCl3(4,7-phen-kappa N4)] (2) were synthesized and structurally characterized by spectroscopic (NMR, IR and UV-vis) and single crystal X-ray diffraction techniques. In these complexes, 1,7- and 4,7-phenanthrolines are monodentatedly coordinated to the Au(III) ion through the N7 and N4 nitrogen atoms, respectively. In comparison to the clinically relevant anti-angiogenic compounds auranofin and sunitinib, gold(III)-phenanthroline complexes showed from 1.5- to 20-fold higher anti-angiogenic potential, and 13- and 118-fold lower toxicity. Among the tested compounds, complex 1 was the most potent and may be an excellent anti-angiogenic drug candidate, since it showed strong anti-angiogenic activity in zebrafish embryos achieving IC50 value (concentration resulting in an anti-angiogenic phenotype at 50% of embryos) of 2.89 mu M, while had low toxicity with LC50 value (the concentration inducing the lethal effect of 50% embryos) of 128 mu M. Molecular docking study revealed that both complexes and ligands could suppress angiogenesis targeting the multiple major regulators of angiogenesis, such as the vascular endothelial growth factor receptor (VEGFR-2), the matrix metalloproteases (MMP-2 and MMP-9), and thioredoxin reductase (TrxR1), where the complexes showed higher binding affinity in comparison to ligands, and particularly to auranofin, but comparable to sunitinib, an anti-angiogenic drug of clinical relevance.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib",
volume = "174",
pages = "156-168",
doi = "10.1016/j.jinorgbio.2017.06.009",
url = "Kon_3312"
}
Pavić, A., Glišić, B. Đ., Vojnović, S., Warżajtis, B., Savić, N. D., Antić, M., Radenković, S., Janjić, G. V., Nikodinović-Runić, J., Rychlewska, U.,& Đuran, M. I.. (2017). Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 174, 156-168.
https://doi.org/10.1016/j.jinorgbio.2017.06.009
Kon_3312
Pavić A, Glišić BĐ, Vojnović S, Warżajtis B, Savić ND, Antić M, Radenković S, Janjić GV, Nikodinović-Runić J, Rychlewska U, Đuran MI. Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib. in Journal of Inorganic Biochemistry. 2017;174:156-168.
doi:10.1016/j.jinorgbio.2017.06.009
Kon_3312 .
Pavić, Aleksandar, Glišić, Biljana Đ., Vojnović, Sandra, Warżajtis, Beata, Savić, Nada D., Antić, Marija, Radenković, Slavko, Janjić, Goran V., Nikodinović-Runić, Jasmina, Rychlewska, Urszula, Đuran, Miloš I., "Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib" in Journal of Inorganic Biochemistry, 174 (2017):156-168,
https://doi.org/10.1016/j.jinorgbio.2017.06.009 .,
Kon_3312 .

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