TY  - JOUR
AU  - Nišavić, Marija
AU  - Janjić, Goran V.
AU  - Hozić, Amela
AU  - Petković, Marijana
AU  - Milčić, Miloš K.
AU  - Vujčić, Zoran
AU  - Cindrić, Mario
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10180
AB  - Binding of three ruthenium(ii) compounds of general formula mer-[Ru(L3)(N-N)X][Y] (where L3 = 4-chloro-2,2:6,2-terpyridine (Cl-tpy); N-N = 1,2-diaminoethane (en), 1,2-diaminocyclohexane (dach) or 2,2-bipyridine (bipy); X = Cl; Y = Cl) to human serum albumin (HSA) has been investigated by nano-LC/nano-ESI MS and docking studies. A bottom-up proteomics approach has been applied for the structural characterization of metallated proteins and the data were analyzed in both the positive and negative ion mode. The negative ion mode was achieved after the post-column addition of an isopropanol solution of formaldehyde that enabled sample ionization at micro-flow rates. The negative ion mode MS has been proved to be beneficial for the analysis of binding sites on ruthenated protein in terms of ion charge reduction and consequent simplification of target sequence identification based on isotopic differences between ruthenated and non-ruthenated peptides. Moreover, the negative ion mode ESI MS shows the advantage of singly charged ion formation and, unlike MALDI MS, it does not cause complete ligand fragmentation, merging the benefits of each method into a single experiment. Six target sequences were identified for the binding of en and dach compounds, and four sequences for the binding of bipy. All compounds have been found to bind histidine and one aspartate residue. Docking studies showed that the identified sequences are the constituents of five distinct binding sites for en and dach, or two sites for the bipy complex. The selection of binding sites seems to be dependent on the chelate ligand and the form of the complex prior or after hydrolysis of the leaving chloride ligand.
T2  - Metallomics
T1  - Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins
VL  - 10
IS  - 4
SP  - 587
EP  - 594
DO  - 10.1039/c7mt00330g
ER  - 

@article{
author = "Nišavić, Marija and Janjić, Goran V. and Hozić, Amela and Petković, Marijana and Milčić, Miloš K. and Vujčić, Zoran and Cindrić, Mario",
year = "2018",
abstract = "Binding of three ruthenium(ii) compounds of general formula mer-[Ru(L3)(N-N)X][Y] (where L3 = 4-chloro-2,2:6,2-terpyridine (Cl-tpy); N-N = 1,2-diaminoethane (en), 1,2-diaminocyclohexane (dach) or 2,2-bipyridine (bipy); X = Cl; Y = Cl) to human serum albumin (HSA) has been investigated by nano-LC/nano-ESI MS and docking studies. A bottom-up proteomics approach has been applied for the structural characterization of metallated proteins and the data were analyzed in both the positive and negative ion mode. The negative ion mode was achieved after the post-column addition of an isopropanol solution of formaldehyde that enabled sample ionization at micro-flow rates. The negative ion mode MS has been proved to be beneficial for the analysis of binding sites on ruthenated protein in terms of ion charge reduction and consequent simplification of target sequence identification based on isotopic differences between ruthenated and non-ruthenated peptides. Moreover, the negative ion mode ESI MS shows the advantage of singly charged ion formation and, unlike MALDI MS, it does not cause complete ligand fragmentation, merging the benefits of each method into a single experiment. Six target sequences were identified for the binding of en and dach compounds, and four sequences for the binding of bipy. All compounds have been found to bind histidine and one aspartate residue. Docking studies showed that the identified sequences are the constituents of five distinct binding sites for en and dach, or two sites for the bipy complex. The selection of binding sites seems to be dependent on the chelate ligand and the form of the complex prior or after hydrolysis of the leaving chloride ligand.",
journal = "Metallomics",
title = "Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins",
volume = "10",
number = "4",
pages = "587-594",
doi = "10.1039/c7mt00330g"
}

Nišavić, M., Janjić, G. V., Hozić, A., Petković, M., Milčić, M. K., Vujčić, Z.,& Cindrić, M.. (2018). Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins. in Metallomics, 10(4), 587-594.
https://doi.org/10.1039/c7mt00330g

Nišavić M, Janjić GV, Hozić A, Petković M, Milčić MK, Vujčić Z, Cindrić M. Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins. in Metallomics. 2018;10(4):587-594.
doi:10.1039/c7mt00330g .

Nišavić, Marija, Janjić, Goran V., Hozić, Amela, Petković, Marijana, Milčić, Miloš K., Vujčić, Zoran, Cindrić, Mario, "Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins" in Metallomics, 10, no. 4 (2018):587-594,
https://doi.org/10.1039/c7mt00330g . .

TY  - JOUR
AU  - Nišavić, Marija
AU  - Janjić, Goran V.
AU  - Hozić, Amela
AU  - Petković, Marijana
AU  - Milčić, Miloš K.
AU  - Vujčić, Zoran
AU  - Cindrić, Mario
PY  - 2018
UR  - http://xlink.rsc.org/?DOI=C7MT00330G
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7615
AB  - Binding of three ruthenium(ii) compounds of general formula mer-[Ru(L3)(N-N)X][Y] (where L3 = 4-chloro-2,2:6,2-terpyridine (Cl-tpy); N-N = 1,2-diaminoethane (en), 1,2-diaminocyclohexane (dach) or 2,2-bipyridine (bipy); X = Cl; Y = Cl) to human serum albumin (HSA) has been investigated by nano-LC/nano-ESI MS and docking studies. A bottom-up proteomics approach has been applied for the structural characterization of metallated proteins and the data were analyzed in both the positive and negative ion mode. The negative ion mode was achieved after the post-column addition of an isopropanol solution of formaldehyde that enabled sample ionization at micro-flow rates. The negative ion mode MS has been proved to be beneficial for the analysis of binding sites on ruthenated protein in terms of ion charge reduction and consequent simplification of target sequence identification based on isotopic differences between ruthenated and non-ruthenated peptides. Moreover, the negative ion mode ESI MS shows the advantage of singly charged ion formation and, unlike MALDI MS, it does not cause complete ligand fragmentation, merging the benefits of each method into a single experiment. Six target sequences were identified for the binding of en and dach compounds, and four sequences for the binding of bipy. All compounds have been found to bind histidine and one aspartate residue. Docking studies showed that the identified sequences are the constituents of five distinct binding sites for en and dach, or two sites for the bipy complex. The selection of binding sites seems to be dependent on the chelate ligand and the form of the complex prior or after hydrolysis of the leaving chloride ligand.
T2  - Metallomics
T1  - Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins
VL  - 10
IS  - 4
SP  - 587
EP  - 594
DO  - 10.1039/C7MT00330G
ER  - 

@article{
author = "Nišavić, Marija and Janjić, Goran V. and Hozić, Amela and Petković, Marijana and Milčić, Miloš K. and Vujčić, Zoran and Cindrić, Mario",
year = "2018",
abstract = "Binding of three ruthenium(ii) compounds of general formula mer-[Ru(L3)(N-N)X][Y] (where L3 = 4-chloro-2,2:6,2-terpyridine (Cl-tpy); N-N = 1,2-diaminoethane (en), 1,2-diaminocyclohexane (dach) or 2,2-bipyridine (bipy); X = Cl; Y = Cl) to human serum albumin (HSA) has been investigated by nano-LC/nano-ESI MS and docking studies. A bottom-up proteomics approach has been applied for the structural characterization of metallated proteins and the data were analyzed in both the positive and negative ion mode. The negative ion mode was achieved after the post-column addition of an isopropanol solution of formaldehyde that enabled sample ionization at micro-flow rates. The negative ion mode MS has been proved to be beneficial for the analysis of binding sites on ruthenated protein in terms of ion charge reduction and consequent simplification of target sequence identification based on isotopic differences between ruthenated and non-ruthenated peptides. Moreover, the negative ion mode ESI MS shows the advantage of singly charged ion formation and, unlike MALDI MS, it does not cause complete ligand fragmentation, merging the benefits of each method into a single experiment. Six target sequences were identified for the binding of en and dach compounds, and four sequences for the binding of bipy. All compounds have been found to bind histidine and one aspartate residue. Docking studies showed that the identified sequences are the constituents of five distinct binding sites for en and dach, or two sites for the bipy complex. The selection of binding sites seems to be dependent on the chelate ligand and the form of the complex prior or after hydrolysis of the leaving chloride ligand.",
journal = "Metallomics",
title = "Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins",
volume = "10",
number = "4",
pages = "587-594",
doi = "10.1039/C7MT00330G"
}

Nišavić, M., Janjić, G. V., Hozić, A., Petković, M., Milčić, M. K., Vujčić, Z.,& Cindrić, M.. (2018). Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins. in Metallomics, 10(4), 587-594.
https://doi.org/10.1039/C7MT00330G

Nišavić M, Janjić GV, Hozić A, Petković M, Milčić MK, Vujčić Z, Cindrić M. Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins. in Metallomics. 2018;10(4):587-594.
doi:10.1039/C7MT00330G .

Nišavić, Marija, Janjić, Goran V., Hozić, Amela, Petković, Marijana, Milčić, Miloš K., Vujčić, Zoran, Cindrić, Mario, "Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins" in Metallomics, 10, no. 4 (2018):587-594,
https://doi.org/10.1039/C7MT00330G . .

TY  - JOUR
AU  - Ajaj, Ismail
AU  - Markovski, Jasmina S.
AU  - Rancic, Milica
AU  - Mijin, Dušan Ž.
AU  - Milčić, Miloš K.
AU  - Jovanović, Maja
AU  - Marinković, Aleksandar D.
PY  - 2015
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/746
AB  - The state of the tautomeric equilibria of 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles, 2-PY/6-PY, was evaluated using experimental and theoretical methodology. The experimental data were interpreted with the aid of time-dependent density functional (TD-DFT) method. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Baders analysis. Linear solvation energy relationships (LSER) rationalized solvent influence on tautomeric equilibrium. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Theoretical calculations and obtained correlations gave insight into the influence of molecular conformation on the transmission of substituent electronic effects, as well as on different solvent solute interactions, and the state of tautomeric equilibrium. (C) 2015 Elsevier B.V. All rights reserved.
T2  - Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy
T1  - Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study
VL  - 150
SP  - 575
EP  - 585
DO  - 10.1016/j.saa.2015.05.055
ER  - 

@article{
author = "Ajaj, Ismail and Markovski, Jasmina S. and Rancic, Milica and Mijin, Dušan Ž. and Milčić, Miloš K. and Jovanović, Maja and Marinković, Aleksandar D.",
year = "2015",
abstract = "The state of the tautomeric equilibria of 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles, 2-PY/6-PY, was evaluated using experimental and theoretical methodology. The experimental data were interpreted with the aid of time-dependent density functional (TD-DFT) method. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Baders analysis. Linear solvation energy relationships (LSER) rationalized solvent influence on tautomeric equilibrium. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Theoretical calculations and obtained correlations gave insight into the influence of molecular conformation on the transmission of substituent electronic effects, as well as on different solvent solute interactions, and the state of tautomeric equilibrium. (C) 2015 Elsevier B.V. All rights reserved.",
journal = "Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy",
title = "Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study",
volume = "150",
pages = "575-585",
doi = "10.1016/j.saa.2015.05.055"
}

Ajaj, I., Markovski, J. S., Rancic, M., Mijin, D. Ž., Milčić, M. K., Jovanović, M.,& Marinković, A. D.. (2015). Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study. in Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 150, 575-585.
https://doi.org/10.1016/j.saa.2015.05.055

Ajaj I, Markovski JS, Rancic M, Mijin DŽ, Milčić MK, Jovanović M, Marinković AD. Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study. in Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy. 2015;150:575-585.
doi:10.1016/j.saa.2015.05.055 .

Ajaj, Ismail, Markovski, Jasmina S., Rancic, Milica, Mijin, Dušan Ž., Milčić, Miloš K., Jovanović, Maja, Marinković, Aleksandar D., "Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study" in Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 150 (2015):575-585,
https://doi.org/10.1016/j.saa.2015.05.055 . .

TY  - JOUR
AU  - Čobeljić, Božidar
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Spasojević, Vojislav
AU  - Milčić, Miloš K.
AU  - Mitić, Dragana
AU  - Sladić, Dušan M.
AU  - Anđelković, Katarina
PY  - 2014
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/5887
AB  - 3-Acetylpyridine thiosemicarbazone hydrochloride was synthesized and structurally characterized. Complexes of Cu(II) with this ligand could not be obtained by direct synthesis. By synthesis in situ mixing Cu(BF4)(2)center dot 6H(2)O, 3-acetylpyridine (3-Acpy) and semicarbazide, a Cu(I) polymer, {[Cu(SCN)(3-Acpy)(2)]}(n) was obtained and structurally characterized. Reaction of Cu(BF4)(2)center dot 6H(2)O, 3-acetylpyridine and ammonium thiocyanate afforded a dinuclear Cu(II) complex with two thiocyanate ions in bridges, which was structurally characterized. Magnetic measurements were performed for the dinuclear complex. OFT calculations provided explanation for inability to obtain a mononuclear complex. (C) 2013 Elsevier Ltd. All rights reserved.
T2  - Polyhedron
T1  - Analysis of the structures of the Cu(I) and Cu(II) complexes with 3-acetylpyridine and thiocyanate
VL  - 69
SP  - 77
EP  - 83
DO  - 10.1016/j.poly.2013.11.027
ER  - 

@article{
author = "Čobeljić, Božidar and Pevec, Andrej and Turel, Iztok and Spasojević, Vojislav and Milčić, Miloš K. and Mitić, Dragana and Sladić, Dušan M. and Anđelković, Katarina",
year = "2014",
abstract = "3-Acetylpyridine thiosemicarbazone hydrochloride was synthesized and structurally characterized. Complexes of Cu(II) with this ligand could not be obtained by direct synthesis. By synthesis in situ mixing Cu(BF4)(2)center dot 6H(2)O, 3-acetylpyridine (3-Acpy) and semicarbazide, a Cu(I) polymer, {[Cu(SCN)(3-Acpy)(2)]}(n) was obtained and structurally characterized. Reaction of Cu(BF4)(2)center dot 6H(2)O, 3-acetylpyridine and ammonium thiocyanate afforded a dinuclear Cu(II) complex with two thiocyanate ions in bridges, which was structurally characterized. Magnetic measurements were performed for the dinuclear complex. OFT calculations provided explanation for inability to obtain a mononuclear complex. (C) 2013 Elsevier Ltd. All rights reserved.",
journal = "Polyhedron",
title = "Analysis of the structures of the Cu(I) and Cu(II) complexes with 3-acetylpyridine and thiocyanate",
volume = "69",
pages = "77-83",
doi = "10.1016/j.poly.2013.11.027"
}

Čobeljić, B., Pevec, A., Turel, I., Spasojević, V., Milčić, M. K., Mitić, D., Sladić, D. M.,& Anđelković, K.. (2014). Analysis of the structures of the Cu(I) and Cu(II) complexes with 3-acetylpyridine and thiocyanate. in Polyhedron, 69, 77-83.
https://doi.org/10.1016/j.poly.2013.11.027

Čobeljić B, Pevec A, Turel I, Spasojević V, Milčić MK, Mitić D, Sladić DM, Anđelković K. Analysis of the structures of the Cu(I) and Cu(II) complexes with 3-acetylpyridine and thiocyanate. in Polyhedron. 2014;69:77-83.
doi:10.1016/j.poly.2013.11.027 .

Čobeljić, Božidar, Pevec, Andrej, Turel, Iztok, Spasojević, Vojislav, Milčić, Miloš K., Mitić, Dragana, Sladić, Dušan M., Anđelković, Katarina, "Analysis of the structures of the Cu(I) and Cu(II) complexes with 3-acetylpyridine and thiocyanate" in Polyhedron, 69 (2014):77-83,
https://doi.org/10.1016/j.poly.2013.11.027 . .

TY  - JOUR
AU  - Ajaj, Ismail
AU  - Markovski, Jasmina S.
AU  - Markovic, Jelena
AU  - Jovanović, Maja
AU  - Milčić, Miloš K.
AU  - Assaleh, Fathi
AU  - Marinković, Aleksandar D.
PY  - 2014
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/5453
AB  - The tautomeric equilibria between 2-pyridone and 2-hydroxypyridine forms of methoxy, chloro, and nitro derivatives of 3-cyano-4-(2-, 3-, and 4-substituted phenyl)-6-phenyl-2(1H)-pyridones were evaluated from UV/Vis spectral data. Linear solvation energy relationships of Kamlet-Taft and Catalan-rationalized solvent have influence on tautomeric equilibria. Transmission of substituent effect was analyzed by the Hammett equation. Quantum chemical calculations were performed by density functional theory (B3LYP). The experimental data were interpreted with the aid of time-dependent density functional method. Electron density distribution was analyzed by Baders analysis. It was found that substituents of different electronic properties change the extent of conjugation, and affect intramolecular charge transfer character. Theoretical calculations and experimental results gave insight into the influence of the molecular conformation on the transmission of substituent effects, as well as on contribution of different solvent-solute interactions.
T2  - Structural Chemistry
T1  - Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study
VL  - 25
IS  - 4
SP  - 1257
EP  - 1270
DO  - 10.1007/s11224-014-0401-y
ER  - 

@article{
author = "Ajaj, Ismail and Markovski, Jasmina S. and Markovic, Jelena and Jovanović, Maja and Milčić, Miloš K. and Assaleh, Fathi and Marinković, Aleksandar D.",
year = "2014",
abstract = "The tautomeric equilibria between 2-pyridone and 2-hydroxypyridine forms of methoxy, chloro, and nitro derivatives of 3-cyano-4-(2-, 3-, and 4-substituted phenyl)-6-phenyl-2(1H)-pyridones were evaluated from UV/Vis spectral data. Linear solvation energy relationships of Kamlet-Taft and Catalan-rationalized solvent have influence on tautomeric equilibria. Transmission of substituent effect was analyzed by the Hammett equation. Quantum chemical calculations were performed by density functional theory (B3LYP). The experimental data were interpreted with the aid of time-dependent density functional method. Electron density distribution was analyzed by Baders analysis. It was found that substituents of different electronic properties change the extent of conjugation, and affect intramolecular charge transfer character. Theoretical calculations and experimental results gave insight into the influence of the molecular conformation on the transmission of substituent effects, as well as on contribution of different solvent-solute interactions.",
journal = "Structural Chemistry",
title = "Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study",
volume = "25",
number = "4",
pages = "1257-1270",
doi = "10.1007/s11224-014-0401-y"
}

Ajaj, I., Markovski, J. S., Markovic, J., Jovanović, M., Milčić, M. K., Assaleh, F.,& Marinković, A. D.. (2014). Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study. in Structural Chemistry, 25(4), 1257-1270.
https://doi.org/10.1007/s11224-014-0401-y

Ajaj I, Markovski JS, Markovic J, Jovanović M, Milčić MK, Assaleh F, Marinković AD. Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study. in Structural Chemistry. 2014;25(4):1257-1270.
doi:10.1007/s11224-014-0401-y .

Ajaj, Ismail, Markovski, Jasmina S., Markovic, Jelena, Jovanović, Maja, Milčić, Miloš K., Assaleh, Fathi, Marinković, Aleksandar D., "Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study" in Structural Chemistry, 25, no. 4 (2014):1257-1270,
https://doi.org/10.1007/s11224-014-0401-y . .

TY  - JOUR
AU  - Medaković, Vesna B.
AU  - Bogdanović, Goran A.
AU  - Milčić, Miloš K.
AU  - Janjić, Goran V.
AU  - Zarić, Snežana D.
PY  - 2012
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/5184
AB  - CH/pi interactions in metal porphyrinato complexes were studied by analyzing data in crystal structures from the Cambridge Structural Database (CSD) and by quantum chemical calculations. The analysis of the data in the CSD shows that both five-membered pyrrole and six-membered chelate rings form CH/pi interactions. The interactions occur more frequently with five-membered rings. The analysis of distances in crystal structures and calculated energies show stronger interactions with six-membered chelate rings, indicating that a larger number of interactions with five-membered rings are not the consequence of stronger interactions, but better accessibility of five-membered pyrrole rings. The calculated energies of the interactions with positions in six-membered rings are -2.09 to -2.83 kcal/mol, while the energies with five-membered rings are -2.05 to -2.26 kcal/mol. The results reveal that stronger interactions of six-membered rings are the consequence of stronger electrostatic interactions. Substituents on the porphyrin ring significantly strengthen the interactions. Substituents on the six-membered ring strengthen the interaction energy by about 20%. The results show that CH/pi interactions play an important role in molecular recognition of metalloporphyrins. The significant influence of the substituents on interaction energies can be very important for the design of model systems in bioinorganic chemistry. (C) 2012 Elsevier Inc. All rights reserved.
T2  - Journal of Inorganic Biochemistry
T1  - CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors
VL  - 117
SP  - 157
EP  - 163
DO  - 10.1016/j.jinorgbio.2012.09.002
ER  - 

@article{
author = "Medaković, Vesna B. and Bogdanović, Goran A. and Milčić, Miloš K. and Janjić, Goran V. and Zarić, Snežana D.",
year = "2012",
abstract = "CH/pi interactions in metal porphyrinato complexes were studied by analyzing data in crystal structures from the Cambridge Structural Database (CSD) and by quantum chemical calculations. The analysis of the data in the CSD shows that both five-membered pyrrole and six-membered chelate rings form CH/pi interactions. The interactions occur more frequently with five-membered rings. The analysis of distances in crystal structures and calculated energies show stronger interactions with six-membered chelate rings, indicating that a larger number of interactions with five-membered rings are not the consequence of stronger interactions, but better accessibility of five-membered pyrrole rings. The calculated energies of the interactions with positions in six-membered rings are -2.09 to -2.83 kcal/mol, while the energies with five-membered rings are -2.05 to -2.26 kcal/mol. The results reveal that stronger interactions of six-membered rings are the consequence of stronger electrostatic interactions. Substituents on the porphyrin ring significantly strengthen the interactions. Substituents on the six-membered ring strengthen the interaction energy by about 20%. The results show that CH/pi interactions play an important role in molecular recognition of metalloporphyrins. The significant influence of the substituents on interaction energies can be very important for the design of model systems in bioinorganic chemistry. (C) 2012 Elsevier Inc. All rights reserved.",
journal = "Journal of Inorganic Biochemistry",
title = "CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors",
volume = "117",
pages = "157-163",
doi = "10.1016/j.jinorgbio.2012.09.002"
}

Medaković, V. B., Bogdanović, G. A., Milčić, M. K., Janjić, G. V.,& Zarić, S. D.. (2012). CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors. in Journal of Inorganic Biochemistry, 117, 157-163.
https://doi.org/10.1016/j.jinorgbio.2012.09.002

Medaković VB, Bogdanović GA, Milčić MK, Janjić GV, Zarić SD. CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors. in Journal of Inorganic Biochemistry. 2012;117:157-163.
doi:10.1016/j.jinorgbio.2012.09.002 .

Medaković, Vesna B., Bogdanović, Goran A., Milčić, Miloš K., Janjić, Goran V., Zarić, Snežana D., "CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors" in Journal of Inorganic Biochemistry, 117 (2012):157-163,
https://doi.org/10.1016/j.jinorgbio.2012.09.002 . .

TY  - CONF
AU  - Medaković, Vesna B.
AU  - Milčić, Miloš K.
AU  - Bogdanović, Goran A.
PY  - 2006
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9473
AB  - The Cambridge Structural Database (CSD) was screened in order to find and investigate specific C−H⋅⋅⋅π interactions between C−H groups and two types of rings with delocalized π-bonds that exist in porphyrin: pyrrole and six-membered chelate. Statistical analysis of geometrical parameters for interactions in both types of rings was done. In order to determine preferred positions in porphyrinato ring for C−H⋅⋅⋅π interactions fifteen different points distributed over porphyrin ring have been chosen and each of them have been analyzed. Calculations of these interactions by density functional theory (DFT) have been done on three different model systems.
PB  - Society of Physical Chemists of Serbia
C3  - Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry
T1  - Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes
SP  - 701
EP  - 703
UR  - https://hdl.handle.net/21.15107/rcub_vinar_9473
ER  - 

@conference{
author = "Medaković, Vesna B. and Milčić, Miloš K. and Bogdanović, Goran A.",
year = "2006",
abstract = "The Cambridge Structural Database (CSD) was screened in order to find and investigate specific C−H⋅⋅⋅π interactions between C−H groups and two types of rings with delocalized π-bonds that exist in porphyrin: pyrrole and six-membered chelate. Statistical analysis of geometrical parameters for interactions in both types of rings was done. In order to determine preferred positions in porphyrinato ring for C−H⋅⋅⋅π interactions fifteen different points distributed over porphyrin ring have been chosen and each of them have been analyzed. Calculations of these interactions by density functional theory (DFT) have been done on three different model systems.",
publisher = "Society of Physical Chemists of Serbia",
journal = "Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry",
title = "Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes",
pages = "701-703",
url = "https://hdl.handle.net/21.15107/rcub_vinar_9473"
}

Medaković, V. B., Milčić, M. K.,& Bogdanović, G. A.. (2006). Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes. in Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry
Society of Physical Chemists of Serbia., 701-703.
https://hdl.handle.net/21.15107/rcub_vinar_9473

Medaković VB, Milčić MK, Bogdanović GA. Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes. in Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry. 2006;:701-703.
https://hdl.handle.net/21.15107/rcub_vinar_9473 .

Medaković, Vesna B., Milčić, Miloš K., Bogdanović, Goran A., "Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes" in Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry (2006):701-703,
https://hdl.handle.net/21.15107/rcub_vinar_9473 .

TY  - JOUR
AU  - Milčić, Miloš K.
AU  - Tomić, Zoran D.
AU  - Zarić, Snežana D.
PY  - 2004
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/2831
AB  - Strong intermolecular interactions between ligands in cationic metal complexes and aromatic rings of tetraphenylborate anion, so-called metal ligand aromatic cation-pi (MLACpi) interactions, were found by screening Cambridge Structural Database. Distances between phenyl ring and ligand are shorter in these structures than in previously reported MLACpi interactions by 0.2 Angstrom. (C) 2004 Elsevier B.V. All rights reserved.
T2  - Inorganica Chimica Acta
T1  - Very strong metal ligand aromatic cation-pi interactions in transition metal complexes: intermolecular interaction in tetraphenylborate salts
VL  - 357
IS  - 14
SP  - 4327
EP  - 4329
DO  - 10.1016/j.ica.2004.06.019
ER  - 

@article{
author = "Milčić, Miloš K. and Tomić, Zoran D. and Zarić, Snežana D.",
year = "2004",
abstract = "Strong intermolecular interactions between ligands in cationic metal complexes and aromatic rings of tetraphenylborate anion, so-called metal ligand aromatic cation-pi (MLACpi) interactions, were found by screening Cambridge Structural Database. Distances between phenyl ring and ligand are shorter in these structures than in previously reported MLACpi interactions by 0.2 Angstrom. (C) 2004 Elsevier B.V. All rights reserved.",
journal = "Inorganica Chimica Acta",
title = "Very strong metal ligand aromatic cation-pi interactions in transition metal complexes: intermolecular interaction in tetraphenylborate salts",
volume = "357",
number = "14",
pages = "4327-4329",
doi = "10.1016/j.ica.2004.06.019"
}

Milčić, M. K., Tomić, Z. D.,& Zarić, S. D.. (2004). Very strong metal ligand aromatic cation-pi interactions in transition metal complexes: intermolecular interaction in tetraphenylborate salts. in Inorganica Chimica Acta, 357(14), 4327-4329.
https://doi.org/10.1016/j.ica.2004.06.019

Milčić MK, Tomić ZD, Zarić SD. Very strong metal ligand aromatic cation-pi interactions in transition metal complexes: intermolecular interaction in tetraphenylborate salts. in Inorganica Chimica Acta. 2004;357(14):4327-4329.
doi:10.1016/j.ica.2004.06.019 .

Milčić, Miloš K., Tomić, Zoran D., Zarić, Snežana D., "Very strong metal ligand aromatic cation-pi interactions in transition metal complexes: intermolecular interaction in tetraphenylborate salts" in Inorganica Chimica Acta, 357, no. 14 (2004):4327-4329,
https://doi.org/10.1016/j.ica.2004.06.019 . .

TY  - JOUR
AU  - Bogdanović, Goran A.
AU  - Medakovkic, V
AU  - Milčić, Miloš K.
AU  - Zarić, Snežana D.
PY  - 2004
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/6448
AB  - Cambridge Structural Database (CSD) was screened in order to find intramolecular C-H...pi interactions with a chelate ring of coordinated porphyrin. It was found 154 crystal structures with 244 intramolecular C-H...pi interactions in transition metal complexes with derivatives of porphyrin. Comparison of interacting distances indicates that interactions of hydrogen atoms in positions 2 and 6 of axially coordinated pyridine are more favorable with ruffled than with planar porphyrin.
T2  - International Journal of Molecular Sciences
T1  - Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes
VL  - 5
IS  - 4-7
SP  - 174
EP  - 185
DO  - 10.3390/i5040174
ER  - 

@article{
author = "Bogdanović, Goran A. and Medakovkic, V and Milčić, Miloš K. and Zarić, Snežana D.",
year = "2004",
abstract = "Cambridge Structural Database (CSD) was screened in order to find intramolecular C-H...pi interactions with a chelate ring of coordinated porphyrin. It was found 154 crystal structures with 244 intramolecular C-H...pi interactions in transition metal complexes with derivatives of porphyrin. Comparison of interacting distances indicates that interactions of hydrogen atoms in positions 2 and 6 of axially coordinated pyridine are more favorable with ruffled than with planar porphyrin.",
journal = "International Journal of Molecular Sciences",
title = "Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes",
volume = "5",
number = "4-7",
pages = "174-185",
doi = "10.3390/i5040174"
}

Bogdanović, G. A., Medakovkic, V., Milčić, M. K.,& Zarić, S. D.. (2004). Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes. in International Journal of Molecular Sciences, 5(4-7), 174-185.
https://doi.org/10.3390/i5040174

Bogdanović GA, Medakovkic V, Milčić MK, Zarić SD. Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes. in International Journal of Molecular Sciences. 2004;5(4-7):174-185.
doi:10.3390/i5040174 .

Bogdanović, Goran A., Medakovkic, V, Milčić, Miloš K., Zarić, Snežana D., "Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes" in International Journal of Molecular Sciences, 5, no. 4-7 (2004):174-185,
https://doi.org/10.3390/i5040174 . .

TY  - JOUR
AU  - Bogdanović, Goran A.
AU  - Medaković, Vesna B.
AU  - Milčić, Miloš K.
AU  - Zarić, Snežana D.
PY  - 2004
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/6486
AB  - Cambridge Structural Database (CSD) was screened in order to find intramolecular C-H...pi interactions with a chelate ring of coordinated porphyrin. It was found 154 crystal structures with 244 intramolecular C-H...pi interactions in transition metal complexes with derivatives of porphyrin. Comparison of interacting distances indicates that interactions of hydrogen atoms in positions 2 and 6 of axially coordinated pyridine are more favorable with ruffled than with planar porphyrin.
T2  - International Journal of Molecular Sciences
T1  - Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes
VL  - 5
SP  - 174
EP  - 185
DO  - 10.3390/i5040174
ER  - 

@article{
author = "Bogdanović, Goran A. and Medaković, Vesna B. and Milčić, Miloš K. and Zarić, Snežana D.",
year = "2004",
abstract = "Cambridge Structural Database (CSD) was screened in order to find intramolecular C-H...pi interactions with a chelate ring of coordinated porphyrin. It was found 154 crystal structures with 244 intramolecular C-H...pi interactions in transition metal complexes with derivatives of porphyrin. Comparison of interacting distances indicates that interactions of hydrogen atoms in positions 2 and 6 of axially coordinated pyridine are more favorable with ruffled than with planar porphyrin.",
journal = "International Journal of Molecular Sciences",
title = "Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes",
volume = "5",
pages = "174-185",
doi = "10.3390/i5040174"
}

Bogdanović, G. A., Medaković, V. B., Milčić, M. K.,& Zarić, S. D.. (2004). Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes. in International Journal of Molecular Sciences, 5, 174-185.
https://doi.org/10.3390/i5040174

Bogdanović GA, Medaković VB, Milčić MK, Zarić SD. Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes. in International Journal of Molecular Sciences. 2004;5:174-185.
doi:10.3390/i5040174 .

Bogdanović, Goran A., Medaković, Vesna B., Milčić, Miloš K., Zarić, Snežana D., "Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes" in International Journal of Molecular Sciences, 5 (2004):174-185,
https://doi.org/10.3390/i5040174 . .

TY  - CONF
AU  - Medaković, Vesna B.
AU  - Milčić, Miloš K.
AU  - Zarić, Snežana D.
PY  - 2004
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9597
AB  - Specific C − H···π interactions with the π-system of porphyrinato chelate ring were found in crystal structures of transition metal complexes from the CSD and statistical analysis of geometrical parameters for intramolecular and intermolecular interactions was done. DFT calculations on a model system show that energy of the interaction is 1.58 kcal/mol and that the strongest interaction occurs when the distance between hydrogen atom and the center of the chelate ring is 2.6 Å. This prediction is in good agreement with the distances for intermolecular interactions found in the crystal structures. In many cases the intramolecular interaction distances are much shorter than 2.6 Å, and these short distances appear to be caused by geometrical constrains. The C − H···π interactions with chelate ring of porphyrinato ligand can be important in biomolecules with porphyrin as they can influence the structure, contribute to the stability and play some role in function of biomolecules.
PB  - Society of Physical Chemists of Serbia
C3  - Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry
T1  - C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor
VL  - 2
SP  - 763
EP  - 765
UR  - https://hdl.handle.net/21.15107/rcub_vinar_9597
ER  - 

@conference{
author = "Medaković, Vesna B. and Milčić, Miloš K. and Zarić, Snežana D.",
year = "2004",
abstract = "Specific C − H···π interactions with the π-system of porphyrinato chelate ring were found in crystal structures of transition metal complexes from the CSD and statistical analysis of geometrical parameters for intramolecular and intermolecular interactions was done. DFT calculations on a model system show that energy of the interaction is 1.58 kcal/mol and that the strongest interaction occurs when the distance between hydrogen atom and the center of the chelate ring is 2.6 Å. This prediction is in good agreement with the distances for intermolecular interactions found in the crystal structures. In many cases the intramolecular interaction distances are much shorter than 2.6 Å, and these short distances appear to be caused by geometrical constrains. The C − H···π interactions with chelate ring of porphyrinato ligand can be important in biomolecules with porphyrin as they can influence the structure, contribute to the stability and play some role in function of biomolecules.",
publisher = "Society of Physical Chemists of Serbia",
journal = "Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry",
title = "C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor",
volume = "2",
pages = "763-765",
url = "https://hdl.handle.net/21.15107/rcub_vinar_9597"
}

Medaković, V. B., Milčić, M. K.,& Zarić, S. D.. (2004). C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor. in Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry
Society of Physical Chemists of Serbia., 2, 763-765.
https://hdl.handle.net/21.15107/rcub_vinar_9597

Medaković VB, Milčić MK, Zarić SD. C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor. in Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry. 2004;2:763-765.
https://hdl.handle.net/21.15107/rcub_vinar_9597 .

Medaković, Vesna B., Milčić, Miloš K., Zarić, Snežana D., "C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor" in Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry, 2 (2004):763-765,
https://hdl.handle.net/21.15107/rcub_vinar_9597 .

TY  - JOUR
AU  - Medaković, Vesna B.
AU  - Milčić, Miloš K.
AU  - Bogdanović, Goran A.
AU  - Zarić, Snežana D.
PY  - 2004
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/2818
AB  - Specific C-H(...)pi interactions with the pi-system of porphyrinato chelate ring were found in crystal structures of transition metal complexes from the Cambridge Structural Database and statistical analysis of geometrical parameters for intramolecular and intermolecular interactions was done. By density functional theory calculations on a model system it was evaluated that an interaction energy is above 1.5 kcal/mol and that the strongest interaction occurs when the distance between hydrogen atom and the center of the chelate ring is 2.6 Angstrom. This prediction is in good agreement with the distances for intermolecular interactions found in the crystal structures. In many cases the intramolecular interaction distances are much shorter than 2.6 Angstrom, and these short distances are caused by geometrical constrains. The C-H(...)pi interactions with chelate ring of porphyrinato ligand can influence the structure, contribute to its stability, and play some role in the function of biomolecules with metalo porphyrins. (C) 2004 Elsevier Inc. All rights reserved.
T2  - Journal of Inorganic Biochemistry
T1  - C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor
VL  - 98
IS  - 11
SP  - 1867
EP  - 1873
DO  - 10.1016/j.jinorgbio.2004.08.012
ER  - 

@article{
author = "Medaković, Vesna B. and Milčić, Miloš K. and Bogdanović, Goran A. and Zarić, Snežana D.",
year = "2004",
abstract = "Specific C-H(...)pi interactions with the pi-system of porphyrinato chelate ring were found in crystal structures of transition metal complexes from the Cambridge Structural Database and statistical analysis of geometrical parameters for intramolecular and intermolecular interactions was done. By density functional theory calculations on a model system it was evaluated that an interaction energy is above 1.5 kcal/mol and that the strongest interaction occurs when the distance between hydrogen atom and the center of the chelate ring is 2.6 Angstrom. This prediction is in good agreement with the distances for intermolecular interactions found in the crystal structures. In many cases the intramolecular interaction distances are much shorter than 2.6 Angstrom, and these short distances are caused by geometrical constrains. The C-H(...)pi interactions with chelate ring of porphyrinato ligand can influence the structure, contribute to its stability, and play some role in the function of biomolecules with metalo porphyrins. (C) 2004 Elsevier Inc. All rights reserved.",
journal = "Journal of Inorganic Biochemistry",
title = "C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor",
volume = "98",
number = "11",
pages = "1867-1873",
doi = "10.1016/j.jinorgbio.2004.08.012"
}

Medaković, V. B., Milčić, M. K., Bogdanović, G. A.,& Zarić, S. D.. (2004). C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor. in Journal of Inorganic Biochemistry, 98(11), 1867-1873.
https://doi.org/10.1016/j.jinorgbio.2004.08.012

Medaković VB, Milčić MK, Bogdanović GA, Zarić SD. C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor. in Journal of Inorganic Biochemistry. 2004;98(11):1867-1873.
doi:10.1016/j.jinorgbio.2004.08.012 .

Medaković, Vesna B., Milčić, Miloš K., Bogdanović, Goran A., Zarić, Snežana D., "C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor" in Journal of Inorganic Biochemistry, 98, no. 11 (2004):1867-1873,
https://doi.org/10.1016/j.jinorgbio.2004.08.012 . .