TY  - JOUR
AU  - Franich, Andjela
AU  - Živković, Marija D.
AU  - Ilić-Tomić, Tatjana
AU  - Đorđević, Ivana
AU  - Nikodinović-Runić, Jasmina
AU  - Pavić, Aleksandar
AU  - Janjić, Goran
AU  - Rajković, Snežana
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3883
AB  - New anticancer platinum(II) compounds simultaneously targeting tumor cells and tumor-derived neoangiogenesis, with new DNA interacting mode and large therapeutic window are appealing alternative to improve efficacy of clinical platinum chemotherapeutics. Herein, we describe three novel dinuclear [{Pt(en)Cl}2(μ-L)]2+ complexes with different pyridine-like bridging ligands (L), 4,4′-bipyridine (Pt1), 1,2-bis(4-pyridyl)ethane (Pt2) and 1,2-bis(4-pyridyl)ethene (Pt3), which highly, positively charged aqua derivatives, [{Pt(en)(H2O)}2(μ-L)]4+, interact with the phosphate backbone forming DNA-Pt adducts with an unique and previously undescribed binding mode, called a minor groove covering. The results of this study suggested that the new binding mode of the aqua-Pt(II) complexes with DNA could be attributed to the higher anticancer activities of their chloride analogues. All three compounds, particularly complex [{Pt(en)Cl}2(μ-4,4′-bipy)]Cl2·2H2O (4,4′-bipy is 4,4′-bipyridine) (Pt1), overcame cisplatin resistance in vivo in the zebrafish–mouse melanoma xenograft model, showed much higher therapeutic potential than antiangiogenic drug sunitinib malate, while effectively blocking tumor neovascularization and melanoma cell metastasis. Overall therapeutic profile showed new dinuclear Pt(II) complexes could be novel, effective and safe anticancer agents. Finally, the correlation with the structural characteristics of these complexes can serve as a useful tool for developing new and more effective anticancer drugs.
PB  - Springer
T2  - Journal of Biological Inorganic Chemistry
T1  - New minor groove covering DNA binding mode of dinuclear Pt(II) complexes with various pyridine-linked bridging ligands and dual anticancer-antiangiogenic activities
VL  - 409
IS  - 25
SP  - 395
EP  - 409
DO  - 10.1007/s00775-020-01770-7
ER  - 

@article{
author = "Franich, Andjela and Živković, Marija D. and Ilić-Tomić, Tatjana and Đorđević, Ivana and Nikodinović-Runić, Jasmina and Pavić, Aleksandar and Janjić, Goran and Rajković, Snežana",
year = "2020",
abstract = "New anticancer platinum(II) compounds simultaneously targeting tumor cells and tumor-derived neoangiogenesis, with new DNA interacting mode and large therapeutic window are appealing alternative to improve efficacy of clinical platinum chemotherapeutics. Herein, we describe three novel dinuclear [{Pt(en)Cl}2(μ-L)]2+ complexes with different pyridine-like bridging ligands (L), 4,4′-bipyridine (Pt1), 1,2-bis(4-pyridyl)ethane (Pt2) and 1,2-bis(4-pyridyl)ethene (Pt3), which highly, positively charged aqua derivatives, [{Pt(en)(H2O)}2(μ-L)]4+, interact with the phosphate backbone forming DNA-Pt adducts with an unique and previously undescribed binding mode, called a minor groove covering. The results of this study suggested that the new binding mode of the aqua-Pt(II) complexes with DNA could be attributed to the higher anticancer activities of their chloride analogues. All three compounds, particularly complex [{Pt(en)Cl}2(μ-4,4′-bipy)]Cl2·2H2O (4,4′-bipy is 4,4′-bipyridine) (Pt1), overcame cisplatin resistance in vivo in the zebrafish–mouse melanoma xenograft model, showed much higher therapeutic potential than antiangiogenic drug sunitinib malate, while effectively blocking tumor neovascularization and melanoma cell metastasis. Overall therapeutic profile showed new dinuclear Pt(II) complexes could be novel, effective and safe anticancer agents. Finally, the correlation with the structural characteristics of these complexes can serve as a useful tool for developing new and more effective anticancer drugs.",
publisher = "Springer",
journal = "Journal of Biological Inorganic Chemistry",
title = "New minor groove covering DNA binding mode of dinuclear Pt(II) complexes with various pyridine-linked bridging ligands and dual anticancer-antiangiogenic activities",
volume = "409",
number = "25",
pages = "395-409",
doi = "10.1007/s00775-020-01770-7"
}

Franich, A., Živković, M. D., Ilić-Tomić, T., Đorđević, I., Nikodinović-Runić, J., Pavić, A., Janjić, G.,& Rajković, S.. (2020). New minor groove covering DNA binding mode of dinuclear Pt(II) complexes with various pyridine-linked bridging ligands and dual anticancer-antiangiogenic activities. in Journal of Biological Inorganic Chemistry
Springer., 409(25), 395-409.
https://doi.org/10.1007/s00775-020-01770-7

Franich A, Živković MD, Ilić-Tomić T, Đorđević I, Nikodinović-Runić J, Pavić A, Janjić G, Rajković S. New minor groove covering DNA binding mode of dinuclear Pt(II) complexes with various pyridine-linked bridging ligands and dual anticancer-antiangiogenic activities. in Journal of Biological Inorganic Chemistry. 2020;409(25):395-409.
doi:10.1007/s00775-020-01770-7 .

Franich, Andjela, Živković, Marija D., Ilić-Tomić, Tatjana, Đorđević, Ivana, Nikodinović-Runić, Jasmina, Pavić, Aleksandar, Janjić, Goran, Rajković, Snežana, "New minor groove covering DNA binding mode of dinuclear Pt(II) complexes with various pyridine-linked bridging ligands and dual anticancer-antiangiogenic activities" in Journal of Biological Inorganic Chemistry, 409, no. 25 (2020):395-409,
https://doi.org/10.1007/s00775-020-01770-7 . .

TY  - JOUR
AU  - Savic, Nada D.
AU  - Vojnovic, Sandra
AU  - Glišić, Biljana
AU  - Crochet, Aurélien
AU  - Pavić, Aleksandar
AU  - Janjić, Goran
AU  - Pekmezovic, Marina
AU  - Opsenica, Igor
AU  - Fromm, Katharina M.
AU  - Nikodinović-Runić, Jasmina
AU  - Đuran, Miloš
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2429
AB  - Mononuclear silver(I) complexes with 1,7-phenanthroline (1,7-phen), [Ag(NO3-O,O') (1,7-phen-N7)(2)] (1) and [Ag(1,7-phen-N7)(2)]X, X = ClO4- (2), CF3SO3- (3), BF4- (4) and SbF6- (5) were synthesized and structurally characterized by NMR (H-1 and C-13), IR and UV-Vis spectroscopy and ESI mass spectrometry. The crystal structures of 1, 3 and 4 were determined by single-crystal X-ray diffraction analysis. In all these complexes, 1,7-phen coordinates to the Ag(I) ion in a monodentate fashion via the less sterically hindered N7 nitrogen atom. The investigation of the solution stability of 1-5 in DMSO revealed that they are sufficiently stable in this solvent at room temperature. Complexes 1-5 showed selectivity towards Candida spp. in comparison to bacteria, effectively inhibiting the growth of four different Candida species with minimal inhibitory concentrations (MIC) between 1.2 and 11.3 mu M. Based on the lowest MIC values and the lowest cytotoxicity against healthy human fibroblasts with selectivity index of more than 30, the antifungal potential was examined in detail for the complex 1. It had the ability to attenuate C. albicans virulence and to reduce epithelial cell damage in the cell infection model. Induction of reactive oxygen species (ROS) response has been detected in C. albicans, with fungal DNA being one of the possible target biomolecules. The toxicity profile of 1 in the zebrafish model (Danio rerio) revealed improved safety and activity in comparison to that of clinically utilized silver(I) sulfadiazine.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth
VL  - 156
SP  - 760
EP  - 773
DO  - 10.1016/j.ejmech.2018.07.049
ER  - 

@article{
author = "Savic, Nada D. and Vojnovic, Sandra and Glišić, Biljana and Crochet, Aurélien and Pavić, Aleksandar and Janjić, Goran and Pekmezovic, Marina and Opsenica, Igor and Fromm, Katharina M. and Nikodinović-Runić, Jasmina and Đuran, Miloš",
year = "2018",
abstract = "Mononuclear silver(I) complexes with 1,7-phenanthroline (1,7-phen), [Ag(NO3-O,O') (1,7-phen-N7)(2)] (1) and [Ag(1,7-phen-N7)(2)]X, X = ClO4- (2), CF3SO3- (3), BF4- (4) and SbF6- (5) were synthesized and structurally characterized by NMR (H-1 and C-13), IR and UV-Vis spectroscopy and ESI mass spectrometry. The crystal structures of 1, 3 and 4 were determined by single-crystal X-ray diffraction analysis. In all these complexes, 1,7-phen coordinates to the Ag(I) ion in a monodentate fashion via the less sterically hindered N7 nitrogen atom. The investigation of the solution stability of 1-5 in DMSO revealed that they are sufficiently stable in this solvent at room temperature. Complexes 1-5 showed selectivity towards Candida spp. in comparison to bacteria, effectively inhibiting the growth of four different Candida species with minimal inhibitory concentrations (MIC) between 1.2 and 11.3 mu M. Based on the lowest MIC values and the lowest cytotoxicity against healthy human fibroblasts with selectivity index of more than 30, the antifungal potential was examined in detail for the complex 1. It had the ability to attenuate C. albicans virulence and to reduce epithelial cell damage in the cell infection model. Induction of reactive oxygen species (ROS) response has been detected in C. albicans, with fungal DNA being one of the possible target biomolecules. The toxicity profile of 1 in the zebrafish model (Danio rerio) revealed improved safety and activity in comparison to that of clinically utilized silver(I) sulfadiazine.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth",
volume = "156",
pages = "760-773",
doi = "10.1016/j.ejmech.2018.07.049"
}

Savic, N. D., Vojnovic, S., Glišić, B., Crochet, A., Pavić, A., Janjić, G., Pekmezovic, M., Opsenica, I., Fromm, K. M., Nikodinović-Runić, J.,& Đuran, M.. (2018). Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 156, 760-773.
https://doi.org/10.1016/j.ejmech.2018.07.049

Savic ND, Vojnovic S, Glišić B, Crochet A, Pavić A, Janjić G, Pekmezovic M, Opsenica I, Fromm KM, Nikodinović-Runić J, Đuran M. Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth. in European Journal of Medicinal Chemistry. 2018;156:760-773.
doi:10.1016/j.ejmech.2018.07.049 .

Savic, Nada D., Vojnovic, Sandra, Glišić, Biljana, Crochet, Aurélien, Pavić, Aleksandar, Janjić, Goran, Pekmezovic, Marina, Opsenica, Igor, Fromm, Katharina M., Nikodinović-Runić, Jasmina, Đuran, Miloš, "Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth" in European Journal of Medicinal Chemistry, 156 (2018):760-773,
https://doi.org/10.1016/j.ejmech.2018.07.049 . .

TY  - JOUR
AU  - Konovalov, Bata
AU  - Zivkovic, Marija D.
AU  - Milovanovic, Jelena Z.
AU  - Đorđević, Dragana B.
AU  - Arsenijevic, Aleksandar N.
AU  - Vasic, Ivana R.
AU  - Janjić, Goran
AU  - Franich, Andjela
AU  - Manojlović, Dragan
AU  - Škrivanj, Sandra
AU  - Milovanovic, Marija Z.
AU  - Đuran, Miloš
AU  - Rajkovic, Snezana
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2353
AB  - The synthesis, spectroscopic characterization, cytotoxic activity and DNA binding evaluation of seven new dinuclear platinum(ii) complexes Pt1-Pt7, with the general formula [{Pt(L)Cl}(2)(-1,5-nphe)](ClO4)(2) (1,5-nphe is 1,5-naphthyridine; while L is two ammines (Pt1) or one bidentate coordinated diamine: ethylenediamine (Pt2), (+/-)-1,2-propylenediamine (Pt3), trans-(+/-)-1,2-diaminocyclohexane (Pt4), 1,3-propylenediamine (Pt5), 2,2-dimethyl-1,3-propylenediamine (Pt6), and 1,3-pentanediamine (Pt7)), were reported. In vitro cytotoxic activity of these complexes was evaluated against three tumor cell lines, murine colon carcinoma (CT26), murine mammary carcinoma (4T1) and murine lung cancer (LLC1) and two normal cell lines, murine mesenchymal stem cells (MSC) and human fibroblast (MRC-5) cells. The results of the MTT assay indicate that all investigated complexes have almost no cytotoxic effects on 4T1 and very low cytotoxicity toward LLC1 cell lines. In contrast to the effects on LLC1 and 4T1 cells, complexes Pt1 and Pt2 had significant cytotoxic activity toward CT26 cells. Complex Pt1 had a much lower IC50 value for activity on CT26 cells compared with cisplatin. In comparison with cisplatin, all dinuclear Pt1-Pt7 complexes showed lower cytotoxicity toward normal MSC and MRC-5 cells. In order to measure the amount of platinum(ii) complexes taken up by the cells, we quantified the cellular platinum content using inductively coupled plasma mass spectrometry (ICP-QMS). Molecular docking studies performed to evaluate the potential binding mode of dinuclear platinum(ii) complexes Pt1-Pt7 and their aqua derivatives W1-W7, respectively, at the double stranded DNA showed that groove spanning and backbone tracking are the most stable binding modes.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure
VL  - 47
IS  - 42
SP  - 15091
EP  - 15102
DO  - 10.1039/c8dt01946k
ER  - 

@article{
author = "Konovalov, Bata and Zivkovic, Marija D. and Milovanovic, Jelena Z. and Đorđević, Dragana B. and Arsenijevic, Aleksandar N. and Vasic, Ivana R. and Janjić, Goran and Franich, Andjela and Manojlović, Dragan and Škrivanj, Sandra and Milovanovic, Marija Z. and Đuran, Miloš and Rajkovic, Snezana",
year = "2018",
abstract = "The synthesis, spectroscopic characterization, cytotoxic activity and DNA binding evaluation of seven new dinuclear platinum(ii) complexes Pt1-Pt7, with the general formula [{Pt(L)Cl}(2)(-1,5-nphe)](ClO4)(2) (1,5-nphe is 1,5-naphthyridine; while L is two ammines (Pt1) or one bidentate coordinated diamine: ethylenediamine (Pt2), (+/-)-1,2-propylenediamine (Pt3), trans-(+/-)-1,2-diaminocyclohexane (Pt4), 1,3-propylenediamine (Pt5), 2,2-dimethyl-1,3-propylenediamine (Pt6), and 1,3-pentanediamine (Pt7)), were reported. In vitro cytotoxic activity of these complexes was evaluated against three tumor cell lines, murine colon carcinoma (CT26), murine mammary carcinoma (4T1) and murine lung cancer (LLC1) and two normal cell lines, murine mesenchymal stem cells (MSC) and human fibroblast (MRC-5) cells. The results of the MTT assay indicate that all investigated complexes have almost no cytotoxic effects on 4T1 and very low cytotoxicity toward LLC1 cell lines. In contrast to the effects on LLC1 and 4T1 cells, complexes Pt1 and Pt2 had significant cytotoxic activity toward CT26 cells. Complex Pt1 had a much lower IC50 value for activity on CT26 cells compared with cisplatin. In comparison with cisplatin, all dinuclear Pt1-Pt7 complexes showed lower cytotoxicity toward normal MSC and MRC-5 cells. In order to measure the amount of platinum(ii) complexes taken up by the cells, we quantified the cellular platinum content using inductively coupled plasma mass spectrometry (ICP-QMS). Molecular docking studies performed to evaluate the potential binding mode of dinuclear platinum(ii) complexes Pt1-Pt7 and their aqua derivatives W1-W7, respectively, at the double stranded DNA showed that groove spanning and backbone tracking are the most stable binding modes.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure",
volume = "47",
number = "42",
pages = "15091-15102",
doi = "10.1039/c8dt01946k"
}

Konovalov, B., Zivkovic, M. D., Milovanovic, J. Z., Đorđević, D. B., Arsenijevic, A. N., Vasic, I. R., Janjić, G., Franich, A., Manojlović, D., Škrivanj, S., Milovanovic, M. Z., Đuran, M.,& Rajkovic, S.. (2018). Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 47(42), 15091-15102.
https://doi.org/10.1039/c8dt01946k

Konovalov B, Zivkovic MD, Milovanovic JZ, Đorđević DB, Arsenijevic AN, Vasic IR, Janjić G, Franich A, Manojlović D, Škrivanj S, Milovanovic MZ, Đuran M, Rajkovic S. Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure. in Dalton Transactions. 2018;47(42):15091-15102.
doi:10.1039/c8dt01946k .

Konovalov, Bata, Zivkovic, Marija D., Milovanovic, Jelena Z., Đorđević, Dragana B., Arsenijevic, Aleksandar N., Vasic, Ivana R., Janjić, Goran, Franich, Andjela, Manojlović, Dragan, Škrivanj, Sandra, Milovanovic, Marija Z., Đuran, Miloš, Rajkovic, Snezana, "Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure" in Dalton Transactions, 47, no. 42 (2018):15091-15102,
https://doi.org/10.1039/c8dt01946k . .

TY  - JOUR
AU  - Pavić, Aleksandar
AU  - Glišić, Biljana
AU  - Vojnovic, Sandra
AU  - Warzajtis, Beata
AU  - Savic, Nada D.
AU  - Antic, Marija
AU  - Radenković, Slavko
AU  - Janjić, Goran
AU  - Nikodinović-Runić, Jasmina
AU  - Rychlewska, Urszula
AU  - Đuran, Miloš
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2136
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
ER  - 

@article{
author = "Pavić, Aleksandar and Glišić, Biljana and Vojnovic, Sandra and Warzajtis, Beata and Savic, Nada D. and Antic, Marija and Radenković, Slavko and Janjić, Goran and Nikodinović-Runić, Jasmina and Rychlewska, Urszula and Đuran, Miloš",
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"
}

Pavić, A., Glišić, B., Vojnovic, S., Warzajtis, B., Savic, N. D., Antic, M., Radenković, S., Janjić, G., Nikodinović-Runić, J., Rychlewska, U.,& Đuran, M.. (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

Pavić A, Glišić B, Vojnovic S, Warzajtis B, Savic ND, Antic M, Radenković S, Janjić G, Nikodinović-Runić J, Rychlewska U, Đuran M. 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 .

Pavić, Aleksandar, Glišić, Biljana, Vojnovic, Sandra, Warzajtis, Beata, Savic, Nada D., Antic, Marija, Radenković, Slavko, Janjić, Goran, Nikodinović-Runić, Jasmina, Rychlewska, Urszula, Đuran, Miloš, "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 . .

TY  - JOUR
AU  - Pavić, Aleksandar
AU  - Glišić, Biljana
AU  - Vojnovic, Sandra
AU  - Warzajtis, Beata
AU  - Savic, Nada D.
AU  - Antic, Marija
AU  - Radenković, Slavko
AU  - Janjić, Goran
AU  - Nikodinović-Runić, Jasmina
AU  - Rychlewska, Urszula
AU  - Đuran, Miloš
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2939
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
ER  - 

@article{
author = "Pavić, Aleksandar and Glišić, Biljana and Vojnovic, Sandra and Warzajtis, Beata and Savic, Nada D. and Antic, Marija and Radenković, Slavko and Janjić, Goran and Nikodinović-Runić, Jasmina and Rychlewska, Urszula and Đuran, Miloš",
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"
}

Pavić, A., Glišić, B., Vojnovic, S., Warzajtis, B., Savic, N. D., Antic, M., Radenković, S., Janjić, G., Nikodinović-Runić, J., Rychlewska, U.,& Đuran, M.. (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

Pavić A, Glišić B, Vojnovic S, Warzajtis B, Savic ND, Antic M, Radenković S, Janjić G, Nikodinović-Runić J, Rychlewska U, Đuran M. 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 .

Pavić, Aleksandar, Glišić, Biljana, Vojnovic, Sandra, Warzajtis, Beata, Savic, Nada D., Antic, Marija, Radenković, Slavko, Janjić, Goran, Nikodinović-Runić, Jasmina, Rychlewska, Urszula, Đuran, Miloš, "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 . .

TY  - JOUR
AU  - Warzajtis, Beata
AU  - Rychlewska, Urszula
AU  - Radanović, Dušanka
AU  - Stanojević, Ivana M.
AU  - Draskovic, Nenad S.
AU  - Radulovic, Niko S.
AU  - Đuran, Miloš
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1525
AB  - A series of Na+, K+ and Ca2+ salts of chromium(III) complexes with the hexadentate (+/-)-1,3-pentanediamine-N,N,N',N'-tetraacetate (1,3-pndta) ligand was evaluated. The extent of distortion exhibited in the geometry of these octahedral complexes was computed and related to the configuration at the metal center and the ligand stereogenic center. The materials have been used to investigate the effect of the counter ion and the diamine ring substitution on the self organization and degree of hydration of these molecules in crystals. Various modes of carboxylate binding to metal atoms have been related to the formation of 3D, 2D and 1D polymeric structures. The electronic absorption and H-1 NMR spectra of 1,3-pndta-Cr(III) complexes are discussed in relation to those of 1,3-pdta-Cr(III) complex (1,3-propanediamine-N,N,N',N'-tetraacetate ion) of known structure.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Polyhedron
T1  - Carboxylato-bridged polymeric complexes of chromium(III) with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand carrying different counter ions. Stereospecific formation and crystal structures of Na[Cr(1,3-pndta)]center dot H2O, K[C
VL  - 67
SP  - 270
EP  - 278
DO  - 10.1016/j.poly.2013.09.009
ER  - 

@article{
author = "Warzajtis, Beata and Rychlewska, Urszula and Radanović, Dušanka and Stanojević, Ivana M. and Draskovic, Nenad S. and Radulovic, Niko S. and Đuran, Miloš",
year = "2014",
abstract = "A series of Na+, K+ and Ca2+ salts of chromium(III) complexes with the hexadentate (+/-)-1,3-pentanediamine-N,N,N',N'-tetraacetate (1,3-pndta) ligand was evaluated. The extent of distortion exhibited in the geometry of these octahedral complexes was computed and related to the configuration at the metal center and the ligand stereogenic center. The materials have been used to investigate the effect of the counter ion and the diamine ring substitution on the self organization and degree of hydration of these molecules in crystals. Various modes of carboxylate binding to metal atoms have been related to the formation of 3D, 2D and 1D polymeric structures. The electronic absorption and H-1 NMR spectra of 1,3-pndta-Cr(III) complexes are discussed in relation to those of 1,3-pdta-Cr(III) complex (1,3-propanediamine-N,N,N',N'-tetraacetate ion) of known structure.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Polyhedron",
title = "Carboxylato-bridged polymeric complexes of chromium(III) with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand carrying different counter ions. Stereospecific formation and crystal structures of Na[Cr(1,3-pndta)]center dot H2O, K[C",
volume = "67",
pages = "270-278",
doi = "10.1016/j.poly.2013.09.009"
}

Warzajtis, B., Rychlewska, U., Radanović, D., Stanojević, I. M., Draskovic, N. S., Radulovic, N. S.,& Đuran, M.. (2014). Carboxylato-bridged polymeric complexes of chromium(III) with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand carrying different counter ions. Stereospecific formation and crystal structures of Na[Cr(1,3-pndta)]center dot H2O, K[C. in Polyhedron
Oxford : Pergamon-Elsevier Science Ltd., 67, 270-278.
https://doi.org/10.1016/j.poly.2013.09.009

Warzajtis B, Rychlewska U, Radanović D, Stanojević IM, Draskovic NS, Radulovic NS, Đuran M. Carboxylato-bridged polymeric complexes of chromium(III) with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand carrying different counter ions. Stereospecific formation and crystal structures of Na[Cr(1,3-pndta)]center dot H2O, K[C. in Polyhedron. 2014;67:270-278.
doi:10.1016/j.poly.2013.09.009 .

Warzajtis, Beata, Rychlewska, Urszula, Radanović, Dušanka, Stanojević, Ivana M., Draskovic, Nenad S., Radulovic, Niko S., Đuran, Miloš, "Carboxylato-bridged polymeric complexes of chromium(III) with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand carrying different counter ions. Stereospecific formation and crystal structures of Na[Cr(1,3-pndta)]center dot H2O, K[C" in Polyhedron, 67 (2014):270-278,
https://doi.org/10.1016/j.poly.2013.09.009 . .

TY  - JOUR
AU  - Draskovic, Nenad S.
AU  - Radanović, Dušanka
AU  - Rychlewska, Urszula
AU  - Warzajtis, Beata
AU  - Stanojević, Ivana M.
AU  - Đuran, Miloš
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1107
AB  - Structural variations modulated by ethyl side group have been analyzed for nickel(II) and copper(II) complexes with (+/-)-1,3-pentanediamine-N,N,N',N'-tetraacetate ligand (1,3-pndta) and its pentadentate derivative (+/-)-1,3-pentanediamine-N,N,N'-triacetate (1,3-pnd3a). X-ray results obtained for the octahedral 1,3-pndta-Ni(II) complex indicate the distinct correlation of the central chirality of the metal with the chirality at the diamine alpha-carbon, which leads to the formation of a racemic mixture of Delta Lambda Delta(R) and Lambda Delta Lambda(S) enantiomeric anionic complexes, where the R and S labels designate the absolute configuration at the ligand (ethyl-substituted) stereogenic center. These stereoisomers are those required to maintain an equatorial ethyl group on the central six-membered chelate ring, whose conformation is lambda twist-boat for the Delta Lambda Delta isomer and 8 twist-boat for the Lambda Delta Lambda isomer. Ethyl group discernibly affects the variation of the Ni-N and Ni-O bond lengths compared to the analogous complex lacking the substitution of one of the diastereotopic diamine CH2 hydrogens and functions as steric bulkiness which hampers an efficient and of high symmetry packing, observed in the crystals of the parent complex. The infrared and electronic absorption spectra of hexadentate Mg[Ni(1,3-pndta)]center dot 10H(2)O (1) and Mg[Cu(1,3-pndta)]center dot 7H(2)O (3), and pentadentate Mg[Ni-2(1,3-pnd3a)(2)]center dot 8H(2)O (2) and MgiCu2(1,3-pnd3a)(2)]center dot 7H(2)O (4) complexes are presented and discussed in comparison with those of the analogous Mg[Ni(1,3-pdta)center dot 8H(2)O (5), Ma[Cu(1,3-pdta)]center dot 8H(2)O (6) and Mg[Cu-2(1,3-pd3a)(2)]center dot 7H(2)O (7) complexes of known crystal structures.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Polyhedron
T1  - Synthesis and spectral characterization of nickel(II) and copper(II) complexes with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand and its pentadentate derivative: Stereospecific formation and crystal structure of [Mg(H2O)(6)][Ni
VL  - 43
IS  - 1
SP  - 185
EP  - 193
DO  - 10.1016/j.poly.2012.06.013
ER  - 

@article{
author = "Draskovic, Nenad S. and Radanović, Dušanka and Rychlewska, Urszula and Warzajtis, Beata and Stanojević, Ivana M. and Đuran, Miloš",
year = "2012",
abstract = "Structural variations modulated by ethyl side group have been analyzed for nickel(II) and copper(II) complexes with (+/-)-1,3-pentanediamine-N,N,N',N'-tetraacetate ligand (1,3-pndta) and its pentadentate derivative (+/-)-1,3-pentanediamine-N,N,N'-triacetate (1,3-pnd3a). X-ray results obtained for the octahedral 1,3-pndta-Ni(II) complex indicate the distinct correlation of the central chirality of the metal with the chirality at the diamine alpha-carbon, which leads to the formation of a racemic mixture of Delta Lambda Delta(R) and Lambda Delta Lambda(S) enantiomeric anionic complexes, where the R and S labels designate the absolute configuration at the ligand (ethyl-substituted) stereogenic center. These stereoisomers are those required to maintain an equatorial ethyl group on the central six-membered chelate ring, whose conformation is lambda twist-boat for the Delta Lambda Delta isomer and 8 twist-boat for the Lambda Delta Lambda isomer. Ethyl group discernibly affects the variation of the Ni-N and Ni-O bond lengths compared to the analogous complex lacking the substitution of one of the diastereotopic diamine CH2 hydrogens and functions as steric bulkiness which hampers an efficient and of high symmetry packing, observed in the crystals of the parent complex. The infrared and electronic absorption spectra of hexadentate Mg[Ni(1,3-pndta)]center dot 10H(2)O (1) and Mg[Cu(1,3-pndta)]center dot 7H(2)O (3), and pentadentate Mg[Ni-2(1,3-pnd3a)(2)]center dot 8H(2)O (2) and MgiCu2(1,3-pnd3a)(2)]center dot 7H(2)O (4) complexes are presented and discussed in comparison with those of the analogous Mg[Ni(1,3-pdta)center dot 8H(2)O (5), Ma[Cu(1,3-pdta)]center dot 8H(2)O (6) and Mg[Cu-2(1,3-pd3a)(2)]center dot 7H(2)O (7) complexes of known crystal structures.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Polyhedron",
title = "Synthesis and spectral characterization of nickel(II) and copper(II) complexes with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand and its pentadentate derivative: Stereospecific formation and crystal structure of [Mg(H2O)(6)][Ni",
volume = "43",
number = "1",
pages = "185-193",
doi = "10.1016/j.poly.2012.06.013"
}

Draskovic, N. S., Radanović, D., Rychlewska, U., Warzajtis, B., Stanojević, I. M.,& Đuran, M.. (2012). Synthesis and spectral characterization of nickel(II) and copper(II) complexes with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand and its pentadentate derivative: Stereospecific formation and crystal structure of [Mg(H2O)(6)][Ni. in Polyhedron
Oxford : Pergamon-Elsevier Science Ltd., 43(1), 185-193.
https://doi.org/10.1016/j.poly.2012.06.013

Draskovic NS, Radanović D, Rychlewska U, Warzajtis B, Stanojević IM, Đuran M. Synthesis and spectral characterization of nickel(II) and copper(II) complexes with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand and its pentadentate derivative: Stereospecific formation and crystal structure of [Mg(H2O)(6)][Ni. in Polyhedron. 2012;43(1):185-193.
doi:10.1016/j.poly.2012.06.013 .

Draskovic, Nenad S., Radanović, Dušanka, Rychlewska, Urszula, Warzajtis, Beata, Stanojević, Ivana M., Đuran, Miloš, "Synthesis and spectral characterization of nickel(II) and copper(II) complexes with the hexadentate (+/-)-1,3-pentanediamine-N,N,N ',N '-tetraacetate ligand and its pentadentate derivative: Stereospecific formation and crystal structure of [Mg(H2O)(6)][Ni" in Polyhedron, 43, no. 1 (2012):185-193,
https://doi.org/10.1016/j.poly.2012.06.013 . .

TY  - JOUR
AU  - Rychlewska, Urszula
AU  - Warzajtis, Beata
AU  - Radanović, Dušanka
AU  - Draskovic, Nenad S.
AU  - Stanojević, Ivana M.
AU  - Đuran, Miloš
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/915
AB  - This paper reports the synthesis and X-ray characteristics of the missing homonuclear s-block metal complex {[Sr-2(1,3-pdta)(H2O)(6)]center dot H2O}(n). In the title compound, the hexadentate 1,3-propanediaminetetraacetate (1,3-pdta) ligand joins to two Sr(II) centers via the diamine chain. Moreover, each Sr(II) is bridged through two carboxylate O atoms and a water molecule to two neighboring Sr(II) ions. The coordination sphere around each Sr(II) ion consists of one diamine nitrogen, four carboxylate oxygens and four water molecules. Comparison with the previously reported M(II)-1,3-pdta complexes reveals that increasing of the ion size results in the incorporation of water molecules into its first coordination sphere and consequent increase of the coordination number (C.N.) from six to seven or eight, while keeping the hexadentate coordination mode of the ligand. Further increase of the metal ion size leads to the loss of the chelating properties of the diamine and formation of a bis-tridentate complex. Associated with it is the change in the binding mode of the carboxylate groups. This forms the basis for classification of divalent metal 1,3-pdta complexes into five distinct structural classes. Additionally, in the present study X-ray powder diffraction and IR spectroscopy were used to distinguish the different structural types of M(II)-1,3-pdta complexes, including Ba[Ba(1,3-pdta)]center dot 2H(2)O which has been used for their preparation.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Polyhedron
T1  - Structural diversification of the coordination mode of divalent metals with 1,3-propanediaminetetraacetate (1,3-pdta): The missing crystal structure of the s-block metal complex [Sr-2(1,3-pdta)(H2O)(6)]center dot H2O
VL  - 30
IS  - 6
SP  - 983
EP  - 989
DO  - 10.1016/j.poly.2010.12.045
ER  - 

@article{
author = "Rychlewska, Urszula and Warzajtis, Beata and Radanović, Dušanka and Draskovic, Nenad S. and Stanojević, Ivana M. and Đuran, Miloš",
year = "2011",
abstract = "This paper reports the synthesis and X-ray characteristics of the missing homonuclear s-block metal complex {[Sr-2(1,3-pdta)(H2O)(6)]center dot H2O}(n). In the title compound, the hexadentate 1,3-propanediaminetetraacetate (1,3-pdta) ligand joins to two Sr(II) centers via the diamine chain. Moreover, each Sr(II) is bridged through two carboxylate O atoms and a water molecule to two neighboring Sr(II) ions. The coordination sphere around each Sr(II) ion consists of one diamine nitrogen, four carboxylate oxygens and four water molecules. Comparison with the previously reported M(II)-1,3-pdta complexes reveals that increasing of the ion size results in the incorporation of water molecules into its first coordination sphere and consequent increase of the coordination number (C.N.) from six to seven or eight, while keeping the hexadentate coordination mode of the ligand. Further increase of the metal ion size leads to the loss of the chelating properties of the diamine and formation of a bis-tridentate complex. Associated with it is the change in the binding mode of the carboxylate groups. This forms the basis for classification of divalent metal 1,3-pdta complexes into five distinct structural classes. Additionally, in the present study X-ray powder diffraction and IR spectroscopy were used to distinguish the different structural types of M(II)-1,3-pdta complexes, including Ba[Ba(1,3-pdta)]center dot 2H(2)O which has been used for their preparation.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Polyhedron",
title = "Structural diversification of the coordination mode of divalent metals with 1,3-propanediaminetetraacetate (1,3-pdta): The missing crystal structure of the s-block metal complex [Sr-2(1,3-pdta)(H2O)(6)]center dot H2O",
volume = "30",
number = "6",
pages = "983-989",
doi = "10.1016/j.poly.2010.12.045"
}

Rychlewska, U., Warzajtis, B., Radanović, D., Draskovic, N. S., Stanojević, I. M.,& Đuran, M.. (2011). Structural diversification of the coordination mode of divalent metals with 1,3-propanediaminetetraacetate (1,3-pdta): The missing crystal structure of the s-block metal complex [Sr-2(1,3-pdta)(H2O)(6)]center dot H2O. in Polyhedron
Oxford : Pergamon-Elsevier Science Ltd., 30(6), 983-989.
https://doi.org/10.1016/j.poly.2010.12.045

Rychlewska U, Warzajtis B, Radanović D, Draskovic NS, Stanojević IM, Đuran M. Structural diversification of the coordination mode of divalent metals with 1,3-propanediaminetetraacetate (1,3-pdta): The missing crystal structure of the s-block metal complex [Sr-2(1,3-pdta)(H2O)(6)]center dot H2O. in Polyhedron. 2011;30(6):983-989.
doi:10.1016/j.poly.2010.12.045 .

Rychlewska, Urszula, Warzajtis, Beata, Radanović, Dušanka, Draskovic, Nenad S., Stanojević, Ivana M., Đuran, Miloš, "Structural diversification of the coordination mode of divalent metals with 1,3-propanediaminetetraacetate (1,3-pdta): The missing crystal structure of the s-block metal complex [Sr-2(1,3-pdta)(H2O)(6)]center dot H2O" in Polyhedron, 30, no. 6 (2011):983-989,
https://doi.org/10.1016/j.poly.2010.12.045 . .