Studies of enzyme interactions with toxic and pharmacologically active molecules

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Studies of enzyme interactions with toxic and pharmacologically active molecules (en)
Истраживања интеракција ензима са токсичним и фармаколошки активним молекулима (sr)
Istraživanja interakcija enzima sa toksičnim i farmakološki aktivnim molekulima (sr_RS)
Authors

Publications

New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures

Janjic, Goran V.; Jelić, Stefan; Trisović, Nemanja; Popović, Dragan M.; Đorđević, Ivana S.; Milcic, Milos. K.

(Amer Chemical Soc, Washington, 2020)

TY  - JOUR
AU  - Janjic, Goran V.
AU  - Jelić, Stefan
AU  - Trisović, Nemanja
AU  - Popović, Dragan M.
AU  - Đorđević, Ivana S.
AU  - Milcic, Milos. K.
PY  - 2020
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1357
AB  - Fluorination of compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of groups in their vicinity. The formation of F center dot center dot center dot F interactions is followed by the shift of the electron density in the area of F center dot center dot center dot F contact, which creates a new region with a larger surface area, a higher negative potential, and, hence, a more pronounced accepting ability. The new region also has a greater ability to form multiple (simultaneous) interactions with species from the environment, thus compensating for the reduction of the accepting capacity of the groups in the vicinity. This phenomenon explains not only the abundance of F center dot center dot center dot F interactions in crystal structures, but also a large number of structures with F center dot center dot center dot O interactions. Only C-H center dot center dot center dot F interactions are more numerous than F center dot center dot center dot F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.
PB  - Amer Chemical Soc, Washington
T2  - Crystal Growth & Design
T1  - New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures
EP  - 2951
IS  - 5
SP  - 2943
VL  - 20
DO  - 10.1021/acs.cgd.9b01565
ER  - 
@article{
author = "Janjic, Goran V. and Jelić, Stefan and Trisović, Nemanja and Popović, Dragan M. and Đorđević, Ivana S. and Milcic, Milos. K.",
year = "2020",
abstract = "Fluorination of compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of groups in their vicinity. The formation of F center dot center dot center dot F interactions is followed by the shift of the electron density in the area of F center dot center dot center dot F contact, which creates a new region with a larger surface area, a higher negative potential, and, hence, a more pronounced accepting ability. The new region also has a greater ability to form multiple (simultaneous) interactions with species from the environment, thus compensating for the reduction of the accepting capacity of the groups in the vicinity. This phenomenon explains not only the abundance of F center dot center dot center dot F interactions in crystal structures, but also a large number of structures with F center dot center dot center dot O interactions. Only C-H center dot center dot center dot F interactions are more numerous than F center dot center dot center dot F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.",
publisher = "Amer Chemical Soc, Washington",
journal = "Crystal Growth & Design",
title = "New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures",
pages = "2951-2943",
number = "5",
volume = "20",
doi = "10.1021/acs.cgd.9b01565"
}
Janjic, G. V., Jelić, S., Trisović, N., Popović, D. M., Đorđević, I. S.,& Milcic, Milos. K.. (2020). New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures. in Crystal Growth & Design
Amer Chemical Soc, Washington., 20(5), 2943-2951.
https://doi.org/10.1021/acs.cgd.9b01565
Janjic GV, Jelić S, Trisović N, Popović DM, Đorđević IS, Milcic MK. New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures. in Crystal Growth & Design. 2020;20(5):2943-2951.
doi:10.1021/acs.cgd.9b01565 .
Janjic, Goran V., Jelić, Stefan, Trisović, Nemanja, Popović, Dragan M., Đorđević, Ivana S., Milcic, Milos. K., "New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures" in Crystal Growth & Design, 20, no. 5 (2020):2943-2951,
https://doi.org/10.1021/acs.cgd.9b01565 . .
29
9
30

Fabrication and characterization of luminescent Pr3+ doped fluorapatite nanocrystals as bioimaging contrast agents

Milojkov, Dusan V.; Silvestre, Oscar F.; Stanic, Vojislav; Janjic, Goran V.; Mutavdžić, Dragosav; Milanović, Marija; Nieder, Jana B.

(Amsterdam : Elsevier, 2020)

TY  - JOUR
AU  - Milojkov, Dusan V.
AU  - Silvestre, Oscar F.
AU  - Stanic, Vojislav
AU  - Janjic, Goran V.
AU  - Mutavdžić, Dragosav
AU  - Milanović, Marija
AU  - Nieder, Jana B.
PY  - 2020
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1387
AB  - Fluorapatite doped with rare-earth elements has a wide-range of biomedical applications. Here, a new type of fluorapatite nanocrystals doped with praseodymium (FAP-Pr) with excitation-emission profiles in visible part of the spectrum is fabricated. Energy levels of Pr3+ activator ion contain metastable multiples states that offer the possibility of efficient multicolor emission lines in FAP nanocrystals. Three types of FAP-Pr nanocrystals with 0.1%, 0.5% and 1% atomic percent of Pr3+ (along with the undoped FAP control sample) are studied. Their novel chemical production method is described, the FAP-Pr nanocrystals structure, biocompatibility and the suitability for cell imaging are analyzed. Physicochemical characterization confirms crystals down to nanometer size. In addition, quantum-chemical calculation predicts that Pr3+ ions are incorporated into the FAP crystal lattice at Ca2 (6 h) sites. In vitro viability results shows that FAP-Pr nanocrystals are nontoxic to live cells. Additionally, the cell uptake of the FAP-Pr nanocrystals is studied using fluorescence-based widefield and confocal microscopy. The nanocrystals show characteristic green emission at 545 nm (P-3(0)-> H-3(5) transition of Pr3+ ion) and orange emission at 600 nm (D-1(2)-> H-3(4)), which we use to discriminate from cell autofluorescence background. Orthogonal projections across 3D confocal stacks show that the nanocrystals are able to enter the cells positioning themselves within the cytoplasm. Overall, the new FAP-Pr nanocrystals are biocompatible and of the tested types, the 0.5% Pr3+ doped nanocrystals show the highest promise as a tracking nanoparticle probe for bioimaging applications.
PB  - Amsterdam : Elsevier
T2  - Journal of Luminescence
T1  - Fabrication and characterization of luminescent Pr3+ doped fluorapatite nanocrystals as bioimaging contrast agents
VL  - 217
DO  - 10.1016/j.jlumin.2019.116757
ER  - 
@article{
author = "Milojkov, Dusan V. and Silvestre, Oscar F. and Stanic, Vojislav and Janjic, Goran V. and Mutavdžić, Dragosav and Milanović, Marija and Nieder, Jana B.",
year = "2020",
abstract = "Fluorapatite doped with rare-earth elements has a wide-range of biomedical applications. Here, a new type of fluorapatite nanocrystals doped with praseodymium (FAP-Pr) with excitation-emission profiles in visible part of the spectrum is fabricated. Energy levels of Pr3+ activator ion contain metastable multiples states that offer the possibility of efficient multicolor emission lines in FAP nanocrystals. Three types of FAP-Pr nanocrystals with 0.1%, 0.5% and 1% atomic percent of Pr3+ (along with the undoped FAP control sample) are studied. Their novel chemical production method is described, the FAP-Pr nanocrystals structure, biocompatibility and the suitability for cell imaging are analyzed. Physicochemical characterization confirms crystals down to nanometer size. In addition, quantum-chemical calculation predicts that Pr3+ ions are incorporated into the FAP crystal lattice at Ca2 (6 h) sites. In vitro viability results shows that FAP-Pr nanocrystals are nontoxic to live cells. Additionally, the cell uptake of the FAP-Pr nanocrystals is studied using fluorescence-based widefield and confocal microscopy. The nanocrystals show characteristic green emission at 545 nm (P-3(0)-> H-3(5) transition of Pr3+ ion) and orange emission at 600 nm (D-1(2)-> H-3(4)), which we use to discriminate from cell autofluorescence background. Orthogonal projections across 3D confocal stacks show that the nanocrystals are able to enter the cells positioning themselves within the cytoplasm. Overall, the new FAP-Pr nanocrystals are biocompatible and of the tested types, the 0.5% Pr3+ doped nanocrystals show the highest promise as a tracking nanoparticle probe for bioimaging applications.",
publisher = "Amsterdam : Elsevier",
journal = "Journal of Luminescence",
title = "Fabrication and characterization of luminescent Pr3+ doped fluorapatite nanocrystals as bioimaging contrast agents",
volume = "217",
doi = "10.1016/j.jlumin.2019.116757"
}
Milojkov, D. V., Silvestre, O. F., Stanic, V., Janjic, G. V., Mutavdžić, D., Milanović, M.,& Nieder, J. B.. (2020). Fabrication and characterization of luminescent Pr3+ doped fluorapatite nanocrystals as bioimaging contrast agents. in Journal of Luminescence
Amsterdam : Elsevier., 217.
https://doi.org/10.1016/j.jlumin.2019.116757
Milojkov DV, Silvestre OF, Stanic V, Janjic GV, Mutavdžić D, Milanović M, Nieder JB. Fabrication and characterization of luminescent Pr3+ doped fluorapatite nanocrystals as bioimaging contrast agents. in Journal of Luminescence. 2020;217.
doi:10.1016/j.jlumin.2019.116757 .
Milojkov, Dusan V., Silvestre, Oscar F., Stanic, Vojislav, Janjic, Goran V., Mutavdžić, Dragosav, Milanović, Marija, Nieder, Jana B., "Fabrication and characterization of luminescent Pr3+ doped fluorapatite nanocrystals as bioimaging contrast agents" in Journal of Luminescence, 217 (2020),
https://doi.org/10.1016/j.jlumin.2019.116757 . .
23
8
21

Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study

Trisović, Nemanja; Radovanović, Lidija; Janjic, Goran V.; Jelić, Stefan; Rogan, Jelena

(Amer Chemical Soc, Washington, 2019)

TY  - JOUR
AU  - Trisović, Nemanja
AU  - Radovanović, Lidija
AU  - Janjic, Goran V.
AU  - Jelić, Stefan
AU  - Rogan, Jelena
PY  - 2019
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1205
AB  - A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N-H center dot center dot center dot O hydrogen bonds, which further self-organize through pairs of C-H center dot center dot center dot O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.
PB  - Amer Chemical Soc, Washington
T2  - Crystal Growth & Design
T1  - Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study
EP  - 2174
IS  - 4
SP  - 2163
VL  - 19
DO  - 10.1021/acs.cgd.8b01776
ER  - 
@article{
author = "Trisović, Nemanja and Radovanović, Lidija and Janjic, Goran V. and Jelić, Stefan and Rogan, Jelena",
year = "2019",
abstract = "A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N-H center dot center dot center dot O hydrogen bonds, which further self-organize through pairs of C-H center dot center dot center dot O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.",
publisher = "Amer Chemical Soc, Washington",
journal = "Crystal Growth & Design",
title = "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study",
pages = "2174-2163",
number = "4",
volume = "19",
doi = "10.1021/acs.cgd.8b01776"
}
Trisović, N., Radovanović, L., Janjic, G. V., Jelić, S.,& Rogan, J.. (2019). Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design
Amer Chemical Soc, Washington., 19(4), 2163-2174.
https://doi.org/10.1021/acs.cgd.8b01776
Trisović N, Radovanović L, Janjic GV, Jelić S, Rogan J. Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design. 2019;19(4):2163-2174.
doi:10.1021/acs.cgd.8b01776 .
Trisović, Nemanja, Radovanović, Lidija, Janjic, Goran V., Jelić, Stefan, Rogan, Jelena, "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study" in Crystal Growth & Design, 19, no. 4 (2019):2163-2174,
https://doi.org/10.1021/acs.cgd.8b01776 . .
3
3

ANALYSIS OF 4,4′-BIS(2,2′DIPHENYL VINYL)-1,1′- BIPHENYL USING THE ATMOSPHERIC-PRESSURE SOLIDS ANALYSIS PROBE FOR IONIZATION

Nastasijević, Branislav; Tomović, Aleksandar; Jovanović, Vladimir P.; Žikić, Radomir; Veličković, Suzana

(Society of Physical Chemists of Serbia, 2014)

TY  - CONF
AU  - Nastasijević, Branislav
AU  - Tomović, Aleksandar
AU  - Jovanović, Vladimir P.
AU  - Žikić, Radomir
AU  - Veličković, Suzana
PY  - 2014
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1897
AB  - An Atmospheric pressure Solids Analysis Probe (ASAP) mass spectrometer are used for investigation the ionization mechanism and fragmentation pathways of 4,4′-bis(2,2′diphenyl vinyl)-1,1′-biphenyl (DPVBi). DPVBi is material used in OLEDs (organic light-emitting diode). Results obtained indicate that by controlling ion source conditions it is possible to optimize forming of desired precursor ion, primarily radical cation and in less content protonated ion of DPVBi. The results presented illustrate the usefulness of ASAP MS in the characterization of DPVBi compounds.
PB  - Society of Physical Chemists of Serbia
C3  - PHYSICAL CHEMISTRY 2014 (Proceedings, Volume III)
T1  - ANALYSIS OF 4,4′-BIS(2,2′DIPHENYL VINYL)-1,1′- BIPHENYL USING THE ATMOSPHERIC-PRESSURE SOLIDS ANALYSIS PROBE FOR IONIZATION
EP  - 1066
SP  - 1063
UR  - https://hdl.handle.net/21.15107/rcub_rimsi_1897
ER  - 
@conference{
author = "Nastasijević, Branislav and Tomović, Aleksandar and Jovanović, Vladimir P. and Žikić, Radomir and Veličković, Suzana",
year = "2014",
abstract = "An Atmospheric pressure Solids Analysis Probe (ASAP) mass spectrometer are used for investigation the ionization mechanism and fragmentation pathways of 4,4′-bis(2,2′diphenyl vinyl)-1,1′-biphenyl (DPVBi). DPVBi is material used in OLEDs (organic light-emitting diode). Results obtained indicate that by controlling ion source conditions it is possible to optimize forming of desired precursor ion, primarily radical cation and in less content protonated ion of DPVBi. The results presented illustrate the usefulness of ASAP MS in the characterization of DPVBi compounds.",
publisher = "Society of Physical Chemists of Serbia",
journal = "PHYSICAL CHEMISTRY 2014 (Proceedings, Volume III)",
title = "ANALYSIS OF 4,4′-BIS(2,2′DIPHENYL VINYL)-1,1′- BIPHENYL USING THE ATMOSPHERIC-PRESSURE SOLIDS ANALYSIS PROBE FOR IONIZATION",
pages = "1066-1063",
url = "https://hdl.handle.net/21.15107/rcub_rimsi_1897"
}
Nastasijević, B., Tomović, A., Jovanović, V. P., Žikić, R.,& Veličković, S.. (2014). ANALYSIS OF 4,4′-BIS(2,2′DIPHENYL VINYL)-1,1′- BIPHENYL USING THE ATMOSPHERIC-PRESSURE SOLIDS ANALYSIS PROBE FOR IONIZATION. in PHYSICAL CHEMISTRY 2014 (Proceedings, Volume III)
Society of Physical Chemists of Serbia., 1063-1066.
https://hdl.handle.net/21.15107/rcub_rimsi_1897
Nastasijević B, Tomović A, Jovanović VP, Žikić R, Veličković S. ANALYSIS OF 4,4′-BIS(2,2′DIPHENYL VINYL)-1,1′- BIPHENYL USING THE ATMOSPHERIC-PRESSURE SOLIDS ANALYSIS PROBE FOR IONIZATION. in PHYSICAL CHEMISTRY 2014 (Proceedings, Volume III). 2014;:1063-1066.
https://hdl.handle.net/21.15107/rcub_rimsi_1897 .
Nastasijević, Branislav, Tomović, Aleksandar, Jovanović, Vladimir P., Žikić, Radomir, Veličković, Suzana, "ANALYSIS OF 4,4′-BIS(2,2′DIPHENYL VINYL)-1,1′- BIPHENYL USING THE ATMOSPHERIC-PRESSURE SOLIDS ANALYSIS PROBE FOR IONIZATION" in PHYSICAL CHEMISTRY 2014 (Proceedings, Volume III) (2014):1063-1066,
https://hdl.handle.net/21.15107/rcub_rimsi_1897 .