TY  - JOUR
AU  - Marković, Katarina
AU  - Kesić, Ana
AU  - Novaković, Mirjana M.
AU  - Grujović, Mirjana
AU  - Simijonović, Dušica
AU  - Avdović, Edina H.
AU  - Matić, Sanja
AU  - Paunović, Milica
AU  - Milutinović, Milena
AU  - Nikodijević, Danijela
AU  - Stefanović, Olgica
AU  - Marković, Zoran
PY  - 2024
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/12826
AB  - This research explores the synthesis, characterization, and biological activities of silver nanoparticles (AgNPs) derived from acetone (AgNPs-acetone) and aqueous (AgNPs-H2O) extracts of Agrimonia eupatoria. The nanoparticles exhibit isometric morphology and uniform size distribution, as elucidated through Transmission Electron Microscopy (TEM) and high-resolution TEM (HRTEM) analyses. The utilization of Scanning Transmission Microscopy (STEM) with High-Angle Annular Dark-Field (HAADF) imaging and energy dispersive spectrometry (EDS) confirms the crystalline nature of AgNPs. Fourier Transform Infrared (FTIR) analysis reveals identical functional groups in the plant extracts and their corresponding AgNPs, suggesting the involvement of phytochemicals in the reduction of silver ions. Spectrophotometric monitoring of the synthesis process, influenced by various parameters, provides insights into the kinetics and optimal conditions for AgNP formation. The antioxidant activities of the plant extracts and synthesized AgNPs are evaluated through DPPH and ABTS methods, highlighting AgNPs-acetone as a potent antioxidant. Third-instar larvae exposed to the extracts have differential effects on DNA damage, with the acetone extract demonstrating antigenotoxic properties. Similarly, biosynthesized AgNPs-acetone displays antigenotoxic effects against EMS-induced DNA damage. The genotoxic effect of water extract and AgNPs-acetone was dose-dependent. Hemolytic potential is assessed on rat erythrocytes, revealing that low concentrations of AgNPs-acetone and AgNPs-H2O had a nontoxic effect on erythrocytes. Cytotoxicity assays demonstrate time-dependent and dose-dependent effects, with AgNPs-acetone exhibiting superior cytotoxicity. Proapoptotic activity is confirmed through apoptosis induction, emphasizing the potential therapeutic applications of AgNPs. The antimicrobial activity of AgNPs reveals concentration-dependent effects. AgNPs-H2O display better antibacterial activity, while antifungal activities are comparable between the two nanoparticle types.
T2  - RSC Advances
T1  - Biosynthesis and characterization of silver nanoparticles synthesized using extracts of Agrimonia eupatoria L. and in vitro and in vivo studies of potential medicinal applications
IS  - 7
SP  - 4591
EP  - 4606
DO  - 10.1039/D3RA07819A
ER  - 

@article{
author = "Marković, Katarina and Kesić, Ana and Novaković, Mirjana M. and Grujović, Mirjana and Simijonović, Dušica and Avdović, Edina H. and Matić, Sanja and Paunović, Milica and Milutinović, Milena and Nikodijević, Danijela and Stefanović, Olgica and Marković, Zoran",
year = "2024",
abstract = "This research explores the synthesis, characterization, and biological activities of silver nanoparticles (AgNPs) derived from acetone (AgNPs-acetone) and aqueous (AgNPs-H2O) extracts of Agrimonia eupatoria. The nanoparticles exhibit isometric morphology and uniform size distribution, as elucidated through Transmission Electron Microscopy (TEM) and high-resolution TEM (HRTEM) analyses. The utilization of Scanning Transmission Microscopy (STEM) with High-Angle Annular Dark-Field (HAADF) imaging and energy dispersive spectrometry (EDS) confirms the crystalline nature of AgNPs. Fourier Transform Infrared (FTIR) analysis reveals identical functional groups in the plant extracts and their corresponding AgNPs, suggesting the involvement of phytochemicals in the reduction of silver ions. Spectrophotometric monitoring of the synthesis process, influenced by various parameters, provides insights into the kinetics and optimal conditions for AgNP formation. The antioxidant activities of the plant extracts and synthesized AgNPs are evaluated through DPPH and ABTS methods, highlighting AgNPs-acetone as a potent antioxidant. Third-instar larvae exposed to the extracts have differential effects on DNA damage, with the acetone extract demonstrating antigenotoxic properties. Similarly, biosynthesized AgNPs-acetone displays antigenotoxic effects against EMS-induced DNA damage. The genotoxic effect of water extract and AgNPs-acetone was dose-dependent. Hemolytic potential is assessed on rat erythrocytes, revealing that low concentrations of AgNPs-acetone and AgNPs-H2O had a nontoxic effect on erythrocytes. Cytotoxicity assays demonstrate time-dependent and dose-dependent effects, with AgNPs-acetone exhibiting superior cytotoxicity. Proapoptotic activity is confirmed through apoptosis induction, emphasizing the potential therapeutic applications of AgNPs. The antimicrobial activity of AgNPs reveals concentration-dependent effects. AgNPs-H2O display better antibacterial activity, while antifungal activities are comparable between the two nanoparticle types.",
journal = "RSC Advances",
title = "Biosynthesis and characterization of silver nanoparticles synthesized using extracts of Agrimonia eupatoria L. and in vitro and in vivo studies of potential medicinal applications",
number = "7",
pages = "4591-4606",
doi = "10.1039/D3RA07819A"
}

Marković, K., Kesić, A., Novaković, M. M., Grujović, M., Simijonović, D., Avdović, E. H., Matić, S., Paunović, M., Milutinović, M., Nikodijević, D., Stefanović, O.,& Marković, Z.. (2024). Biosynthesis and characterization of silver nanoparticles synthesized using extracts of Agrimonia eupatoria L. and in vitro and in vivo studies of potential medicinal applications. in RSC Advances(7), 4591-4606.
https://doi.org/10.1039/D3RA07819A

Marković K, Kesić A, Novaković MM, Grujović M, Simijonović D, Avdović EH, Matić S, Paunović M, Milutinović M, Nikodijević D, Stefanović O, Marković Z. Biosynthesis and characterization of silver nanoparticles synthesized using extracts of Agrimonia eupatoria L. and in vitro and in vivo studies of potential medicinal applications. in RSC Advances. 2024;(7):4591-4606.
doi:10.1039/D3RA07819A .

Marković, Katarina, Kesić, Ana, Novaković, Mirjana M., Grujović, Mirjana, Simijonović, Dušica, Avdović, Edina H., Matić, Sanja, Paunović, Milica, Milutinović, Milena, Nikodijević, Danijela, Stefanović, Olgica, Marković, Zoran, "Biosynthesis and characterization of silver nanoparticles synthesized using extracts of Agrimonia eupatoria L. and in vitro and in vivo studies of potential medicinal applications" in RSC Advances, no. 7 (2024):4591-4606,
https://doi.org/10.1039/D3RA07819A . .

TY  - JOUR
AU  - Milovanović, Vesna M
AU  - Petrović, Zorica D.
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Petrović, Vladimir P.
AU  - Simijonović, Dušica
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9123
AB  - A series of benzamide-dioxoisoindoline derivatives 3 was obtained, starting from phthalic anhydride and different benzoyl hydrazides 2, by ultrasound irradiation in water as solvent and without any catalyst. Five obtained compounds have been reported in this study for the first time and crystal structure of compound 3h was determined. All compounds were subjected to experimental determination of their antioxidative potential. DPPH test revealed that newly synthesized phenolic compounds 3d, 3e, and 3j are the best antioxidants. Additionally, probable radical scavenging pathway was analysed for reactions of the most active compounds and some radicals that can be found in living cells.
T2  - Tetrahedron
T1  - Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach
VL  - 76
IS  - 38
SP  - 131456
DO  - 10.1016/j.tet.2020.131456
ER  - 

@article{
author = "Milovanović, Vesna M and Petrović, Zorica D. and Novaković, Slađana B. and Bogdanović, Goran A. and Petrović, Vladimir P. and Simijonović, Dušica",
year = "2020",
abstract = "A series of benzamide-dioxoisoindoline derivatives 3 was obtained, starting from phthalic anhydride and different benzoyl hydrazides 2, by ultrasound irradiation in water as solvent and without any catalyst. Five obtained compounds have been reported in this study for the first time and crystal structure of compound 3h was determined. All compounds were subjected to experimental determination of their antioxidative potential. DPPH test revealed that newly synthesized phenolic compounds 3d, 3e, and 3j are the best antioxidants. Additionally, probable radical scavenging pathway was analysed for reactions of the most active compounds and some radicals that can be found in living cells.",
journal = "Tetrahedron",
title = "Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach",
volume = "76",
number = "38",
pages = "131456",
doi = "10.1016/j.tet.2020.131456"
}

Milovanović, V. M., Petrović, Z. D., Novaković, S. B., Bogdanović, G. A., Petrović, V. P.,& Simijonović, D.. (2020). Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach. in Tetrahedron, 76(38), 131456.
https://doi.org/10.1016/j.tet.2020.131456

Milovanović VM, Petrović ZD, Novaković SB, Bogdanović GA, Petrović VP, Simijonović D. Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach. in Tetrahedron. 2020;76(38):131456.
doi:10.1016/j.tet.2020.131456 .

Milovanović, Vesna M, Petrović, Zorica D., Novaković, Slađana B., Bogdanović, Goran A., Petrović, Vladimir P., Simijonović, Dušica, "Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach" in Tetrahedron, 76, no. 38 (2020):131456,
https://doi.org/10.1016/j.tet.2020.131456 . .

TY  - JOUR
AU  - Milovanović, Vesna M.
AU  - Petrović, Zorica D.
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Simijonović, Dušica
AU  - Petrović, Vladimir P.
PY  - 2019
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0022286019306659
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8224
AB  - Simple, one-pot, and low-cost reactions of acetylacetone with a variety of substituted benzoyl hydrazides in lemon juice, as eco-friendly medium, were performed. In reactions of benzoyl hydrazides with electron-donating groups on phenyl ring, the 1-benzoyl-1H-pyrazole derivatives were obtained in short reaction time, and in good to high yields. On the other hand, benzoyl hydrazides with electron-withdrawing groups reacted slower, yielding the mixture of 1-benzoyl-5-hydroxy-4,5-dihydro-1H-pyrazole and benzoyl-1H-pyrazole derivatives. It is worth pointing out that two products, (2-chlorophenyl)(4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)methanone and (4-iodophenyl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone are reported here for the first time. All obtained compounds were characterized using IR, UV–Vis and NMR, experimentally and theoretically, as well as with melting points. Good agreement between experimental and simulated IR, UV–Vis, 1H and 13C NMR spectra was achieved. In addition, crystal structures and Hirshfeld surfaces analysis of (4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)(4-iodophenyl)methanone were reported. © 2019 Elsevier B.V.
T2  - Journal of Molecular Structure
T1  - Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach
VL  - 1195
SP  - 85
EP  - 94
DO  - 10.1016/j.molstruc.2019.05.095
ER  - 

@article{
author = "Milovanović, Vesna M. and Petrović, Zorica D. and Novaković, Slađana B. and Bogdanović, Goran A. and Simijonović, Dušica and Petrović, Vladimir P.",
year = "2019",
abstract = "Simple, one-pot, and low-cost reactions of acetylacetone with a variety of substituted benzoyl hydrazides in lemon juice, as eco-friendly medium, were performed. In reactions of benzoyl hydrazides with electron-donating groups on phenyl ring, the 1-benzoyl-1H-pyrazole derivatives were obtained in short reaction time, and in good to high yields. On the other hand, benzoyl hydrazides with electron-withdrawing groups reacted slower, yielding the mixture of 1-benzoyl-5-hydroxy-4,5-dihydro-1H-pyrazole and benzoyl-1H-pyrazole derivatives. It is worth pointing out that two products, (2-chlorophenyl)(4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)methanone and (4-iodophenyl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone are reported here for the first time. All obtained compounds were characterized using IR, UV–Vis and NMR, experimentally and theoretically, as well as with melting points. Good agreement between experimental and simulated IR, UV–Vis, 1H and 13C NMR spectra was achieved. In addition, crystal structures and Hirshfeld surfaces analysis of (4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)(4-iodophenyl)methanone were reported. © 2019 Elsevier B.V.",
journal = "Journal of Molecular Structure",
title = "Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach",
volume = "1195",
pages = "85-94",
doi = "10.1016/j.molstruc.2019.05.095"
}

Milovanović, V. M., Petrović, Z. D., Novaković, S. B., Bogdanović, G. A., Simijonović, D.,& Petrović, V. P.. (2019). Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach. in Journal of Molecular Structure, 1195, 85-94.
https://doi.org/10.1016/j.molstruc.2019.05.095

Milovanović VM, Petrović ZD, Novaković SB, Bogdanović GA, Simijonović D, Petrović VP. Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach. in Journal of Molecular Structure. 2019;1195:85-94.
doi:10.1016/j.molstruc.2019.05.095 .

Milovanović, Vesna M., Petrović, Zorica D., Novaković, Slađana B., Bogdanović, Goran A., Simijonović, Dušica, Petrović, Vladimir P., "Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach" in Journal of Molecular Structure, 1195 (2019):85-94,
https://doi.org/10.1016/j.molstruc.2019.05.095 . .

TY  - JOUR
AU  - Simijonović, Dušica
AU  - Petrović, Zorica D.
AU  - Milovanović, Vesna M.
AU  - Petrović, Vladimir P.
AU  - Bogdanović, Goran A.
PY  - 2018
UR  - http://xlink.rsc.org/?DOI=C8RA02702A
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7682
AB  - Pyrazolyl-phthalazine-dione derivatives (PPDs) were synthetized in the ionic liquid catalyzed one-pot multicomponent reaction of acetylacetone, 2,3-dihydrophthalazine-1,4-dione, and different aldehydes in moderate to good yields. Six new PPDs were obtained, and the crystal structure of 2-acetyl-1-(4-fluorophenyl)- 3-methyl-1H-pyrazolo[1,2-b] phthalazine-5,10-dione (PPD-4) was determined. The most interesting structural features of the novel PPD-4 is the formation of a rather short intermolecular distance between the F atom of one molecule and the midpoint of the neighbouring six-membered heterocyclic ring. This interaction arranges all molecules into parallel supramolecular chains. UV-Vis spectra of all PPDs were acquired and compared to the simulated ones obtained with TD-DFT. All synthetized compounds were subjected to evaluation of their in vitro antioxidative activity using a stable DPPH radical. It was shown that PPD-7, with a catechol motive, is the most active antioxidant, while PPD-9, with two neighbouring methoxy groups to the phenolic OH, exerted a somewhat lower, but significant antioxidative potential. The results of DFT thermodynamical study are in agreement with experimental findings that PPD-7 and PPD-9 should be considered as powerful radical scavengers. In addition, the obtained theoretical results (bond dissociation and proton abstraction energies) specify SPLET as a prevailing radical scavenging mechanism in polar solvents, and HAT in solvents with lower polarity. On the other hand, the obtained reaction enthalpies for inactivation of free radicals suggest competition between HAT and SPLET mechanisms, except in the case of the (OH)-O-center dot radical in polar solvents, where HAT is labeled as prefered.
T2  - RSC Advances
T1  - A new efficient domino approach for the synthesis of pyrazolyl-phthalazine-diones. Antiradical activity of novel phenolic products
VL  - 8
IS  - 30
SP  - 16663
EP  - 16673
DO  - 10.1039/C8RA02702A
ER  - 

@article{
author = "Simijonović, Dušica and Petrović, Zorica D. and Milovanović, Vesna M. and Petrović, Vladimir P. and Bogdanović, Goran A.",
year = "2018",
abstract = "Pyrazolyl-phthalazine-dione derivatives (PPDs) were synthetized in the ionic liquid catalyzed one-pot multicomponent reaction of acetylacetone, 2,3-dihydrophthalazine-1,4-dione, and different aldehydes in moderate to good yields. Six new PPDs were obtained, and the crystal structure of 2-acetyl-1-(4-fluorophenyl)- 3-methyl-1H-pyrazolo[1,2-b] phthalazine-5,10-dione (PPD-4) was determined. The most interesting structural features of the novel PPD-4 is the formation of a rather short intermolecular distance between the F atom of one molecule and the midpoint of the neighbouring six-membered heterocyclic ring. This interaction arranges all molecules into parallel supramolecular chains. UV-Vis spectra of all PPDs were acquired and compared to the simulated ones obtained with TD-DFT. All synthetized compounds were subjected to evaluation of their in vitro antioxidative activity using a stable DPPH radical. It was shown that PPD-7, with a catechol motive, is the most active antioxidant, while PPD-9, with two neighbouring methoxy groups to the phenolic OH, exerted a somewhat lower, but significant antioxidative potential. The results of DFT thermodynamical study are in agreement with experimental findings that PPD-7 and PPD-9 should be considered as powerful radical scavengers. In addition, the obtained theoretical results (bond dissociation and proton abstraction energies) specify SPLET as a prevailing radical scavenging mechanism in polar solvents, and HAT in solvents with lower polarity. On the other hand, the obtained reaction enthalpies for inactivation of free radicals suggest competition between HAT and SPLET mechanisms, except in the case of the (OH)-O-center dot radical in polar solvents, where HAT is labeled as prefered.",
journal = "RSC Advances",
title = "A new efficient domino approach for the synthesis of pyrazolyl-phthalazine-diones. Antiradical activity of novel phenolic products",
volume = "8",
number = "30",
pages = "16663-16673",
doi = "10.1039/C8RA02702A"
}

Simijonović, D., Petrović, Z. D., Milovanović, V. M., Petrović, V. P.,& Bogdanović, G. A.. (2018). A new efficient domino approach for the synthesis of pyrazolyl-phthalazine-diones. Antiradical activity of novel phenolic products. in RSC Advances, 8(30), 16663-16673.
https://doi.org/10.1039/C8RA02702A

Simijonović D, Petrović ZD, Milovanović VM, Petrović VP, Bogdanović GA. A new efficient domino approach for the synthesis of pyrazolyl-phthalazine-diones. Antiradical activity of novel phenolic products. in RSC Advances. 2018;8(30):16663-16673.
doi:10.1039/C8RA02702A .

Simijonović, Dušica, Petrović, Zorica D., Milovanović, Vesna M., Petrović, Vladimir P., Bogdanović, Goran A., "A new efficient domino approach for the synthesis of pyrazolyl-phthalazine-diones. Antiradical activity of novel phenolic products" in RSC Advances, 8, no. 30 (2018):16663-16673,
https://doi.org/10.1039/C8RA02702A . .

TY  - JOUR
AU  - Petrović, Vladimir P.
AU  - Simijonović, Dušica
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Marković, Svetlana
AU  - Petrović, Zorica D.
PY  - 2015
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/724
AB  - In this paper, synthesis and structural determination of 2-[1-(N-4-fluorophenylamino)-1-(4-hydroxy-3methoxyphenyl)]methylcyclohexanone (MB-F) is presented. To determine the structure of this new compound, IR and NMR spectral characterisation was performed experimentally and theoretically. Simulation of spectral data was carried out using three functionals: B3LYP, B3LYP-D2, and M06-2X. The results obtained for MB-F were compared to those attained for similar, known compound 2-[1-(N-phenylamino)-1-(4-hydroxy-3-methoxyphenyl)]methylcyclohexanone (MB-H), whose crystal structure is presented here. Taking into account all experimental and theoretical findings, the structure of MB-F was proposed. (C) 2015 Elsevier B.V. All rights reserved.
T2  - Journal of Molecular Structure
T1  - Structural characterisation of some vanillic Mannich bases: Experimental and theoretical study
VL  - 1098
SP  - 34
EP  - 40
DO  - 10.1016/j.molstruc.2015.05.040
ER  - 

@article{
author = "Petrović, Vladimir P. and Simijonović, Dušica and Novaković, Slađana B. and Bogdanović, Goran A. and Marković, Svetlana and Petrović, Zorica D.",
year = "2015",
abstract = "In this paper, synthesis and structural determination of 2-[1-(N-4-fluorophenylamino)-1-(4-hydroxy-3methoxyphenyl)]methylcyclohexanone (MB-F) is presented. To determine the structure of this new compound, IR and NMR spectral characterisation was performed experimentally and theoretically. Simulation of spectral data was carried out using three functionals: B3LYP, B3LYP-D2, and M06-2X. The results obtained for MB-F were compared to those attained for similar, known compound 2-[1-(N-phenylamino)-1-(4-hydroxy-3-methoxyphenyl)]methylcyclohexanone (MB-H), whose crystal structure is presented here. Taking into account all experimental and theoretical findings, the structure of MB-F was proposed. (C) 2015 Elsevier B.V. All rights reserved.",
journal = "Journal of Molecular Structure",
title = "Structural characterisation of some vanillic Mannich bases: Experimental and theoretical study",
volume = "1098",
pages = "34-40",
doi = "10.1016/j.molstruc.2015.05.040"
}

Petrović, V. P., Simijonović, D., Novaković, S. B., Bogdanović, G. A., Marković, S.,& Petrović, Z. D.. (2015). Structural characterisation of some vanillic Mannich bases: Experimental and theoretical study. in Journal of Molecular Structure, 1098, 34-40.
https://doi.org/10.1016/j.molstruc.2015.05.040

Petrović VP, Simijonović D, Novaković SB, Bogdanović GA, Marković S, Petrović ZD. Structural characterisation of some vanillic Mannich bases: Experimental and theoretical study. in Journal of Molecular Structure. 2015;1098:34-40.
doi:10.1016/j.molstruc.2015.05.040 .

Petrović, Vladimir P., Simijonović, Dušica, Novaković, Slađana B., Bogdanović, Goran A., Marković, Svetlana, Petrović, Zorica D., "Structural characterisation of some vanillic Mannich bases: Experimental and theoretical study" in Journal of Molecular Structure, 1098 (2015):34-40,
https://doi.org/10.1016/j.molstruc.2015.05.040 . .