TY  - JOUR
AU  - Kop, Tatjana
AU  - Jakovljević, Dragica
AU  - Živković, Ljiljana S.
AU  - Žekić, Andrijana
AU  - Beškoski, Vladimir
AU  - Milić, Dragana
AU  - Gojgić-Cvijović, Gordana
AU  - Bjelaković, Mira
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3332
AB  - An efficient encapsulation of the fullerene into two hydrophobized and one native polysaccharide provided water soluble supramolecular hybrids. After covalent modification of polysaccharides by cholesterol, noncovalent hybrids were prepared by a three-step procedure, including mixing of individual aqueous solutions of hydrophobized, as well as native sugar with solution of the fullerene in pyridine, dialysis and lyophilization. Although the degree of the fullerene incorporation into hydrophobized substrates, cholesterol-levan and cholesterol-pullulan, was lower in comparison to the native polysaccharide levan, hydrophobization provided nanoparticles with improved properties. The particle size distribution, studied by dynamic light scattering and scanning electron microscopy revealed formation of moderately polydisperse aggregates, with the diameter contraction in comparison to the corresponding free polysaccharide, especially in the case of hydrophobized substrates. The morphological examination, done by scanning electron microscopy indicated the self-organization of the fullerene-native polysaccharide to round individual structures, while fullerene-hydrophobized polysaccharide hybrids tend to form networks. The antioxidant activity of the synthesized polysaccharide-C60 noncovalent hybrids versus starting polysaccharides was investigated by the DPPH radical scavenging and the β-carotene-linoleic acid bleaching methods. In all three complexes, the radical scavenging ability of the fullerene remained preserved, and a positive effect of levan hydrophobization was observed.
PB  - Elsevier
T2  - European Polymer Journal
T1  - Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity
VL  - 123
SP  - 109461
DO  - 10.1016/j.eurpolymj.2019.109461
ER  - 

@article{
author = "Kop, Tatjana and Jakovljević, Dragica and Živković, Ljiljana S. and Žekić, Andrijana and Beškoski, Vladimir and Milić, Dragana and Gojgić-Cvijović, Gordana and Bjelaković, Mira",
year = "2020",
abstract = "An efficient encapsulation of the fullerene into two hydrophobized and one native polysaccharide provided water soluble supramolecular hybrids. After covalent modification of polysaccharides by cholesterol, noncovalent hybrids were prepared by a three-step procedure, including mixing of individual aqueous solutions of hydrophobized, as well as native sugar with solution of the fullerene in pyridine, dialysis and lyophilization. Although the degree of the fullerene incorporation into hydrophobized substrates, cholesterol-levan and cholesterol-pullulan, was lower in comparison to the native polysaccharide levan, hydrophobization provided nanoparticles with improved properties. The particle size distribution, studied by dynamic light scattering and scanning electron microscopy revealed formation of moderately polydisperse aggregates, with the diameter contraction in comparison to the corresponding free polysaccharide, especially in the case of hydrophobized substrates. The morphological examination, done by scanning electron microscopy indicated the self-organization of the fullerene-native polysaccharide to round individual structures, while fullerene-hydrophobized polysaccharide hybrids tend to form networks. The antioxidant activity of the synthesized polysaccharide-C60 noncovalent hybrids versus starting polysaccharides was investigated by the DPPH radical scavenging and the β-carotene-linoleic acid bleaching methods. In all three complexes, the radical scavenging ability of the fullerene remained preserved, and a positive effect of levan hydrophobization was observed.",
publisher = "Elsevier",
journal = "European Polymer Journal",
title = "Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity",
volume = "123",
pages = "109461",
doi = "10.1016/j.eurpolymj.2019.109461"
}

Kop, T., Jakovljević, D., Živković, L. S., Žekić, A., Beškoski, V., Milić, D., Gojgić-Cvijović, G.,& Bjelaković, M.. (2020). Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity. in European Polymer Journal
Elsevier., 123, 109461.
https://doi.org/10.1016/j.eurpolymj.2019.109461

Kop T, Jakovljević D, Živković LS, Žekić A, Beškoski V, Milić D, Gojgić-Cvijović G, Bjelaković M. Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity. in European Polymer Journal. 2020;123:109461.
doi:10.1016/j.eurpolymj.2019.109461 .

Kop, Tatjana, Jakovljević, Dragica, Živković, Ljiljana S., Žekić, Andrijana, Beškoski, Vladimir, Milić, Dragana, Gojgić-Cvijović, Gordana, Bjelaković, Mira, "Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity" in European Polymer Journal, 123 (2020):109461,
https://doi.org/10.1016/j.eurpolymj.2019.109461 . .

TY  - JOUR
AU  - Kop, Tatjana
AU  - Jakovljević, Dragica
AU  - Živković, Ljiljana S.
AU  - Žekić, Andrijana
AU  - Beškoski, Vladimir
AU  - Milić, Dragana
AU  - Gojgić-Cvijović, Gordana
AU  - Bjelaković, Mira
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3336
AB  - An efficient encapsulation of the fullerene into two hydrophobized and one native polysaccharide provided water soluble supramolecular hybrids. After covalent modification of polysaccharides by cholesterol, noncovalent hybrids were prepared by a three-step procedure, including mixing of individual aqueous solutions of hydrophobized, as well as native sugar with solution of the fullerene in pyridine, dialysis and lyophilization. Although the degree of the fullerene incorporation into hydrophobized substrates, cholesterol-levan and cholesterol-pullulan, was lower in comparison to the native polysaccharide levan, hydrophobization provided nanoparticles with improved properties. The particle size distribution, studied by dynamic light scattering and scanning electron microscopy revealed formation of moderately polydisperse aggregates, with the diameter contraction in comparison to the corresponding free polysaccharide, especially in the case of hydrophobized substrates. The morphological examination, done by scanning electron microscopy indicated the self-organization of the fullerene-native polysaccharide to round individual structures, while fullerene-hydrophobized polysaccharide hybrids tend to form networks. The antioxidant activity of the synthesized polysaccharide-C60 noncovalent hybrids versus starting polysaccharides was investigated by the DPPH radical scavenging and the β-carotene-linoleic acid bleaching methods. In all three complexes, the radical scavenging ability of the fullerene remained preserved, and a positive effect of levan hydrophobization was observed.
PB  - Elsevier
T2  - European Polymer Journal
T1  - Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity
VL  - 123
SP  - 109461
DO  - 10.1016/j.eurpolymj.2019.109461
ER  - 

@article{
author = "Kop, Tatjana and Jakovljević, Dragica and Živković, Ljiljana S. and Žekić, Andrijana and Beškoski, Vladimir and Milić, Dragana and Gojgić-Cvijović, Gordana and Bjelaković, Mira",
year = "2020",
abstract = "An efficient encapsulation of the fullerene into two hydrophobized and one native polysaccharide provided water soluble supramolecular hybrids. After covalent modification of polysaccharides by cholesterol, noncovalent hybrids were prepared by a three-step procedure, including mixing of individual aqueous solutions of hydrophobized, as well as native sugar with solution of the fullerene in pyridine, dialysis and lyophilization. Although the degree of the fullerene incorporation into hydrophobized substrates, cholesterol-levan and cholesterol-pullulan, was lower in comparison to the native polysaccharide levan, hydrophobization provided nanoparticles with improved properties. The particle size distribution, studied by dynamic light scattering and scanning electron microscopy revealed formation of moderately polydisperse aggregates, with the diameter contraction in comparison to the corresponding free polysaccharide, especially in the case of hydrophobized substrates. The morphological examination, done by scanning electron microscopy indicated the self-organization of the fullerene-native polysaccharide to round individual structures, while fullerene-hydrophobized polysaccharide hybrids tend to form networks. The antioxidant activity of the synthesized polysaccharide-C60 noncovalent hybrids versus starting polysaccharides was investigated by the DPPH radical scavenging and the β-carotene-linoleic acid bleaching methods. In all three complexes, the radical scavenging ability of the fullerene remained preserved, and a positive effect of levan hydrophobization was observed.",
publisher = "Elsevier",
journal = "European Polymer Journal",
title = "Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity",
volume = "123",
pages = "109461",
doi = "10.1016/j.eurpolymj.2019.109461"
}

Kop, T., Jakovljević, D., Živković, L. S., Žekić, A., Beškoski, V., Milić, D., Gojgić-Cvijović, G.,& Bjelaković, M.. (2020). Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity. in European Polymer Journal
Elsevier., 123, 109461.
https://doi.org/10.1016/j.eurpolymj.2019.109461

Kop T, Jakovljević D, Živković LS, Žekić A, Beškoski V, Milić D, Gojgić-Cvijović G, Bjelaković M. Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity. in European Polymer Journal. 2020;123:109461.
doi:10.1016/j.eurpolymj.2019.109461 .

Kop, Tatjana, Jakovljević, Dragica, Živković, Ljiljana S., Žekić, Andrijana, Beškoski, Vladimir, Milić, Dragana, Gojgić-Cvijović, Gordana, Bjelaković, Mira, "Polysaccharide-fullerene supramolecular hybrids: Synthesis, characterization and antioxidant activity" in European Polymer Journal, 123 (2020):109461,
https://doi.org/10.1016/j.eurpolymj.2019.109461 . .

TY  - JOUR
AU  - Đurašević, Siniša
AU  - Nikolić, Gorana
AU  - Todorović, Ana
AU  - Drakulić, Dunja
AU  - Pejić, Snežana
AU  - Martinović, Vesna
AU  - Mitić-Ćulafić, Dragana
AU  - Milić, Dragana
AU  - Kop, Tatjana
AU  - Jasnić, Nebojša
AU  - Đorđević, Jelena
AU  - Todorović, Zoran
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3488
AB  - The effects of twelve weeks of supplementation with fullerene C60 olive/coconut oil solution on a broad spectrum of parameters in rats were examined. The tissue bioaccumulation of C60 was shown to be tissue-specific, with the liver, heart, and adrenal glands being the organs of the greatest, and the kidney, brain, and spleen being the organs of the smallest accumulation. C60 did not change aspartate aminotransferase, alanine aminotransferase, and alkaline phosphatase serum activities level, nor the damage of liver cells DNA. There were no effects of fullerene on prooxidant-antioxidant balance in the liver, kidney, spleen, heart, and brain, nor any visible harmful effects on the liver, heart, aorta, spleen, kidney, and small intestine histology. Fullerene changed the gut microbiota structure towards the bacteria that ameliorate lipid homeostasis, causing a serum triglycerides concentration decrease. However, C60 significantly increased the insulin resistance, serum ascorbate oxidation, and brain malondialdehyde and advanced oxidation protein products level. The deteriorative effects of C60 on the brain and serum could be attributed to the specific physicochemical composition of these tissues, potentiating the C60 aggregation or biotransformation as the key element of its pro-oxidative action.
PB  - Elsevier
T2  - Food and Chemical Toxicology
T1  - Effects of fullerene C60 supplementation on gut microbiota and glucose and lipid homeostasis in rats
VL  - 140
SP  - 111322
DO  - 10.1016/j.fct.2020.111302
ER  - 

@article{
author = "Đurašević, Siniša and Nikolić, Gorana and Todorović, Ana and Drakulić, Dunja and Pejić, Snežana and Martinović, Vesna and Mitić-Ćulafić, Dragana and Milić, Dragana and Kop, Tatjana and Jasnić, Nebojša and Đorđević, Jelena and Todorović, Zoran",
year = "2020",
abstract = "The effects of twelve weeks of supplementation with fullerene C60 olive/coconut oil solution on a broad spectrum of parameters in rats were examined. The tissue bioaccumulation of C60 was shown to be tissue-specific, with the liver, heart, and adrenal glands being the organs of the greatest, and the kidney, brain, and spleen being the organs of the smallest accumulation. C60 did not change aspartate aminotransferase, alanine aminotransferase, and alkaline phosphatase serum activities level, nor the damage of liver cells DNA. There were no effects of fullerene on prooxidant-antioxidant balance in the liver, kidney, spleen, heart, and brain, nor any visible harmful effects on the liver, heart, aorta, spleen, kidney, and small intestine histology. Fullerene changed the gut microbiota structure towards the bacteria that ameliorate lipid homeostasis, causing a serum triglycerides concentration decrease. However, C60 significantly increased the insulin resistance, serum ascorbate oxidation, and brain malondialdehyde and advanced oxidation protein products level. The deteriorative effects of C60 on the brain and serum could be attributed to the specific physicochemical composition of these tissues, potentiating the C60 aggregation or biotransformation as the key element of its pro-oxidative action.",
publisher = "Elsevier",
journal = "Food and Chemical Toxicology",
title = "Effects of fullerene C60 supplementation on gut microbiota and glucose and lipid homeostasis in rats",
volume = "140",
pages = "111322",
doi = "10.1016/j.fct.2020.111302"
}

Đurašević, S., Nikolić, G., Todorović, A., Drakulić, D., Pejić, S., Martinović, V., Mitić-Ćulafić, D., Milić, D., Kop, T., Jasnić, N., Đorđević, J.,& Todorović, Z.. (2020). Effects of fullerene C60 supplementation on gut microbiota and glucose and lipid homeostasis in rats. in Food and Chemical Toxicology
Elsevier., 140, 111322.
https://doi.org/10.1016/j.fct.2020.111302

Đurašević S, Nikolić G, Todorović A, Drakulić D, Pejić S, Martinović V, Mitić-Ćulafić D, Milić D, Kop T, Jasnić N, Đorđević J, Todorović Z. Effects of fullerene C60 supplementation on gut microbiota and glucose and lipid homeostasis in rats. in Food and Chemical Toxicology. 2020;140:111322.
doi:10.1016/j.fct.2020.111302 .

Đurašević, Siniša, Nikolić, Gorana, Todorović, Ana, Drakulić, Dunja, Pejić, Snežana, Martinović, Vesna, Mitić-Ćulafić, Dragana, Milić, Dragana, Kop, Tatjana, Jasnić, Nebojša, Đorđević, Jelena, Todorović, Zoran, "Effects of fullerene C60 supplementation on gut microbiota and glucose and lipid homeostasis in rats" in Food and Chemical Toxicology, 140 (2020):111322,
https://doi.org/10.1016/j.fct.2020.111302 . .

TY  - JOUR
AU  - Pavlovic, Radoslav Z.
AU  - Mitrović, Aleksandra
AU  - Coldren, William H.
AU  - Bjelaković, Mira
AU  - Hadad, Christopher M.
AU  - Maslak, Veselin R.
AU  - Milić, Dragana
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2323
AB  - The reactivity of the C-2v-symmetric pentakisadduct of C-60 with azomethine ylides and conjugated dienes was studied experimentally and computationally. This derivative possesses four [6,6] double bonds, each with unique electrophilicity. The Diels-Alder reaction studied is a regiospecific, kinetically and thermodynamically guided [4 + 2] process producing [5:1]-hexaadducts with an octahedral addition pattern. The kinetically controlled Prato reaction gives a mixture of regioisomeric [5:1]-hexaadducts. The synthesis of geometrically well-defined supramolecular architectures may benefit from these new types of highly functionalized [5:1]-hexaadducts.
PB  - American Chemical Society (ACS)
T2  - Journal of Organic Chemistry
T1  - Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60
VL  - 83
IS  - 4
SP  - 2166
EP  - 2172
DO  - 10.1021/acs.joc.7b03083
ER  - 

@article{
author = "Pavlovic, Radoslav Z. and Mitrović, Aleksandra and Coldren, William H. and Bjelaković, Mira and Hadad, Christopher M. and Maslak, Veselin R. and Milić, Dragana",
year = "2018",
abstract = "The reactivity of the C-2v-symmetric pentakisadduct of C-60 with azomethine ylides and conjugated dienes was studied experimentally and computationally. This derivative possesses four [6,6] double bonds, each with unique electrophilicity. The Diels-Alder reaction studied is a regiospecific, kinetically and thermodynamically guided [4 + 2] process producing [5:1]-hexaadducts with an octahedral addition pattern. The kinetically controlled Prato reaction gives a mixture of regioisomeric [5:1]-hexaadducts. The synthesis of geometrically well-defined supramolecular architectures may benefit from these new types of highly functionalized [5:1]-hexaadducts.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Organic Chemistry",
title = "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60",
volume = "83",
number = "4",
pages = "2166-2172",
doi = "10.1021/acs.joc.7b03083"
}

Pavlovic, R. Z., Mitrović, A., Coldren, W. H., Bjelaković, M., Hadad, C. M., Maslak, V. R.,& Milić, D.. (2018). Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60. in Journal of Organic Chemistry
American Chemical Society (ACS)., 83(4), 2166-2172.
https://doi.org/10.1021/acs.joc.7b03083

Pavlovic RZ, Mitrović A, Coldren WH, Bjelaković M, Hadad CM, Maslak VR, Milić D. Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60. in Journal of Organic Chemistry. 2018;83(4):2166-2172.
doi:10.1021/acs.joc.7b03083 .

Pavlovic, Radoslav Z., Mitrović, Aleksandra, Coldren, William H., Bjelaković, Mira, Hadad, Christopher M., Maslak, Veselin R., Milić, Dragana, "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60" in Journal of Organic Chemistry, 83, no. 4 (2018):2166-2172,
https://doi.org/10.1021/acs.joc.7b03083 . .

TY  - DATA
AU  - Pavlovic, Radoslav Z.
AU  - Mitrović, Aleksandra
AU  - Coldren, William H.
AU  - Bjelaković, Mira
AU  - Hadad, Christopher M.
AU  - Maslak, Veselin R.
AU  - Milić, Dragana
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4504
AB  - General information and optimization of reaction conditions, detailed characterization of products 8–15, including their NMR and mass spectra, and computational results (Figures S1–S20 and Table S1)
PB  - American Chemical Society (ACS)
T2  - Journal of Organic Chemistry
T1  - Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60"
DO  - 10.1021/acs.joc.7b03083.s001
ER  - 

@misc{
author = "Pavlovic, Radoslav Z. and Mitrović, Aleksandra and Coldren, William H. and Bjelaković, Mira and Hadad, Christopher M. and Maslak, Veselin R. and Milić, Dragana",
year = "2018",
abstract = "General information and optimization of reaction conditions, detailed characterization of products 8–15, including their NMR and mass spectra, and computational results (Figures S1–S20 and Table S1)",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Organic Chemistry",
title = "Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60"",
doi = "10.1021/acs.joc.7b03083.s001"
}

Pavlovic, R. Z., Mitrović, A., Coldren, W. H., Bjelaković, M., Hadad, C. M., Maslak, V. R.,& Milić, D.. (2018). Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60". in Journal of Organic Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.joc.7b03083.s001

Pavlovic RZ, Mitrović A, Coldren WH, Bjelaković M, Hadad CM, Maslak VR, Milić D. Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60". in Journal of Organic Chemistry. 2018;.
doi:10.1021/acs.joc.7b03083.s001 .

Pavlovic, Radoslav Z., Mitrović, Aleksandra, Coldren, William H., Bjelaković, Mira, Hadad, Christopher M., Maslak, Veselin R., Milić, Dragana, "Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60"" in Journal of Organic Chemistry (2018),
https://doi.org/10.1021/acs.joc.7b03083.s001 . .

TY  - JOUR
AU  - Kop, Tatjana
AU  - Dordevic, Jelena
AU  - Bjelaković, Mira
AU  - Milić, Dragana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2124
AB  - Four macrocyclic bis(pyrrolidino)fullerene regioisomers with e-edge, e-face, trans-4 and cis-2 addition patterns were synthesized from the corresponding monoadduct by Prato's cycloaddition in a yield of 50%, and fully characterized by spectroscopic techniques. Bisadduct regioisomers were isolated easily in a pure form using dry-flash column chromatography. The relative ratio of the isolated regioisomers e-edge/e-face/trans-41cis-2 was 1.0:1.9:1.5:4.9. Morphology of self-assembled structures of the four bisadduct regioisomers in solution was characterized using scanning electron microscopy.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Fullerene bisadduct regioisomers containing an asymmetric diamide tether
VL  - 73
IS  - 50
SP  - 7073
EP  - 7078
DO  - 10.1016/j.tet.2017.10.069
ER  - 

@article{
author = "Kop, Tatjana and Dordevic, Jelena and Bjelaković, Mira and Milić, Dragana",
year = "2017",
abstract = "Four macrocyclic bis(pyrrolidino)fullerene regioisomers with e-edge, e-face, trans-4 and cis-2 addition patterns were synthesized from the corresponding monoadduct by Prato's cycloaddition in a yield of 50%, and fully characterized by spectroscopic techniques. Bisadduct regioisomers were isolated easily in a pure form using dry-flash column chromatography. The relative ratio of the isolated regioisomers e-edge/e-face/trans-41cis-2 was 1.0:1.9:1.5:4.9. Morphology of self-assembled structures of the four bisadduct regioisomers in solution was characterized using scanning electron microscopy.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Fullerene bisadduct regioisomers containing an asymmetric diamide tether",
volume = "73",
number = "50",
pages = "7073-7078",
doi = "10.1016/j.tet.2017.10.069"
}

Kop, T., Dordevic, J., Bjelaković, M.,& Milić, D.. (2017). Fullerene bisadduct regioisomers containing an asymmetric diamide tether. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 73(50), 7073-7078.
https://doi.org/10.1016/j.tet.2017.10.069

Kop T, Dordevic J, Bjelaković M, Milić D. Fullerene bisadduct regioisomers containing an asymmetric diamide tether. in Tetrahedron. 2017;73(50):7073-7078.
doi:10.1016/j.tet.2017.10.069 .

Kop, Tatjana, Dordevic, Jelena, Bjelaković, Mira, Milić, Dragana, "Fullerene bisadduct regioisomers containing an asymmetric diamide tether" in Tetrahedron, 73, no. 50 (2017):7073-7078,
https://doi.org/10.1016/j.tet.2017.10.069 . .

TY  - JOUR
AU  - Kop, Tatjana
AU  - Dordevic, Jelena
AU  - Bjelaković, Mira
AU  - Milić, Dragana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2124
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3004
AB  - Four macrocyclic bis(pyrrolidino)fullerene regioisomers with e-edge, e-face, trans-4 and cis-2 addition patterns were synthesized from the corresponding monoadduct by Prato's cycloaddition in a yield of 50%, and fully characterized by spectroscopic techniques. Bisadduct regioisomers were isolated easily in a pure form using dry-flash column chromatography. The relative ratio of the isolated regioisomers e-edge/e-face/trans-41cis-2 was 1.0:1.9:1.5:4.9. Morphology of self-assembled structures of the four bisadduct regioisomers in solution was characterized using scanning electron microscopy.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Fullerene bisadduct regioisomers containing an asymmetric diamide tether
VL  - 73
IS  - 50
SP  - 7073
EP  - 7078
DO  - 10.1016/j.tet.2017.10.069
ER  - 

@article{
author = "Kop, Tatjana and Dordevic, Jelena and Bjelaković, Mira and Milić, Dragana",
year = "2017",
abstract = "Four macrocyclic bis(pyrrolidino)fullerene regioisomers with e-edge, e-face, trans-4 and cis-2 addition patterns were synthesized from the corresponding monoadduct by Prato's cycloaddition in a yield of 50%, and fully characterized by spectroscopic techniques. Bisadduct regioisomers were isolated easily in a pure form using dry-flash column chromatography. The relative ratio of the isolated regioisomers e-edge/e-face/trans-41cis-2 was 1.0:1.9:1.5:4.9. Morphology of self-assembled structures of the four bisadduct regioisomers in solution was characterized using scanning electron microscopy.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Fullerene bisadduct regioisomers containing an asymmetric diamide tether",
volume = "73",
number = "50",
pages = "7073-7078",
doi = "10.1016/j.tet.2017.10.069"
}

Kop, T., Dordevic, J., Bjelaković, M.,& Milić, D.. (2017). Fullerene bisadduct regioisomers containing an asymmetric diamide tether. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 73(50), 7073-7078.
https://doi.org/10.1016/j.tet.2017.10.069

Kop T, Dordevic J, Bjelaković M, Milić D. Fullerene bisadduct regioisomers containing an asymmetric diamide tether. in Tetrahedron. 2017;73(50):7073-7078.
doi:10.1016/j.tet.2017.10.069 .

Kop, Tatjana, Dordevic, Jelena, Bjelaković, Mira, Milić, Dragana, "Fullerene bisadduct regioisomers containing an asymmetric diamide tether" in Tetrahedron, 73, no. 50 (2017):7073-7078,
https://doi.org/10.1016/j.tet.2017.10.069 . .

TY  - THES
AU  - Kop, Tatjana
PY  - 2016
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=3639
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:12423/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=48013327
UR  - http://nardus.mpn.gov.rs/123456789/6283
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2550
AB  - Derivati fulerena C60, zahvaljujući svojim jedinstvenim fizičkohemijskim ielektronskim svojstvima, koja proističu iz visoko konjugovanog π-sistema, činezanimljive gradivne elemente u sintezama složenijih ciljnih molekula. Različitimderivatizacijama hidrofobne ugljenične sfere dobija se niz proizvoda primenljivih uhemiji materijala, supramolekulskoj i medicinskoj hemiji. Imajući u vidu povećanjerastvorljivosti, kao i promenu stereoelektronskih osobina sa povećenjem broja adenadana fulerenskom jezgru, korisna je svaka metoda višestruke derivatizacije fulerena kojase odigrava pod kontrolisanim uslovima.Prato-va reakcija jedan je od najzastupljenijih vidova kovalentne modifikacijefulerena. U njoj nastaju fuleropirolidini, proizvodi jasno definisane strukture i čestiintermedijeri u složenim hemijskim tranformacijama fulerena. Ozbiljno ograničenje overeakcije predstavlja lako i neselektivno građenje bis- i tris-pirolidinskih adukata, kojiznačajno umanjuju prinose i čistoću monoadukata. S druge strane, bisadukti su sepokazali korisnima u nekim sferama medicinske hemije i elektrohemije.Regioselektivno dobijanje bisadukata fulerena upotrebom posebno dizajniranihpremošćenih supstrata bio je predmet interesovanja nekolicine istraživačkih grupa uproteklom periodu.U toku ovog rada sintetisan je niz alkil-premošćenih diglicina, u cilju dobijanjapremošćenih bis-pirolidinskih adukata fulerena u reakciji dvostruke Prato-vecikloadicije. U prvom delu rada, na supstratu premošćenom oktametilenskim nizom,optimizovani su reakcioni uslovi za dobijanje bisadukata. Optimalnim reakcionimuslovima podvrgnuti su i ostali supstrati, premošćeni alkil-nizovima dužine od 6 do 12C-atoma i utvrđena je zavisnost regioselektivnosti od dužine niza. Istim reakcionimuslovima podvrgnuta su i dva supstrata koji sadrže dve, odnosno tri etarske podstruktureu mostu i ispitan je uticaj kiseonikovih atoma u linkeru na selektivnost reakcije...
AB  - Due to their unique physicochemical and electronic properties, emerging fromhighly conjugated π-system, derivatives of the fullerene C60 are interesting buildingblocks in the synthesis of the more complex target molecules. Diverse derivatizationsof hydrophobic carbone sphere provide a wide range of products for the use inmatherial, supramolecular and medicinal chemistry. Since the increase of the numberof addends on the carbon core improves the solubility and varies the stereoelectronicproperties, each method of the controlable multiple derivatization of fullerenes ishighly useful.Prato's reaction is one of the most common methodes for the covalentmodification of fullerenes. The fulleropyrrolidines, products with well definedstructures, are frequently used as intermediers in further chemical transformations offullerenes. This reaction is limited with the easy and unselective formation of bis- andtris(pyrrolidino) adducts and, hence, decrease of the yields and the purity ofmonoadducts. On the other hand, bisadducts are very useful in some aspects of themedicinal and electrochemistry. During the recent period, the regioselective synthesisof the fullerene bisadducts via templated supstrates has been the topic of interest ofseveral researcher groups.In this work, a series of alkyl-tethered diglycines were synthesized andunderwent the Prato's biscycloaddition conditions in aim to obtain templatedbis(pyrrolidino)fullerenes. The first part of the work refers to the optimization of thebiscycloaddition conditions on the octamethylene-tethered substrate. Other diglycines,wearing from C6 to C12 alkyl-linkers, were subjected to this optimal reactionconditions and the correlation between the distribution of the regioisomers and thelenght of the linker is determined. Another two diglycines, wearing two and threeoxygen atoms in the tether, underwent the same reaction conditions in aim toinvestigate the influence of the etheric subunits on the selectivity of the reaction...
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Sinteza i ispitivanje morfološkihelektrohemijskih i antioksidativnih osobina premošćenih bis-pirolidinskih derivatafulerena C60
T1  - Synthesis and investigation of morphological,electrochemical, and antioxidative properties of tethered bis-pyrrolidinoderivatives of fullerene c60
UR  - https://hdl.handle.net/21.15107/rcub_nardus_6283
ER  - 

@phdthesis{
author = "Kop, Tatjana",
year = "2016",
abstract = "Derivati fulerena C60, zahvaljujući svojim jedinstvenim fizičkohemijskim ielektronskim svojstvima, koja proističu iz visoko konjugovanog π-sistema, činezanimljive gradivne elemente u sintezama složenijih ciljnih molekula. Različitimderivatizacijama hidrofobne ugljenične sfere dobija se niz proizvoda primenljivih uhemiji materijala, supramolekulskoj i medicinskoj hemiji. Imajući u vidu povećanjerastvorljivosti, kao i promenu stereoelektronskih osobina sa povećenjem broja adenadana fulerenskom jezgru, korisna je svaka metoda višestruke derivatizacije fulerena kojase odigrava pod kontrolisanim uslovima.Prato-va reakcija jedan je od najzastupljenijih vidova kovalentne modifikacijefulerena. U njoj nastaju fuleropirolidini, proizvodi jasno definisane strukture i čestiintermedijeri u složenim hemijskim tranformacijama fulerena. Ozbiljno ograničenje overeakcije predstavlja lako i neselektivno građenje bis- i tris-pirolidinskih adukata, kojiznačajno umanjuju prinose i čistoću monoadukata. S druge strane, bisadukti su sepokazali korisnima u nekim sferama medicinske hemije i elektrohemije.Regioselektivno dobijanje bisadukata fulerena upotrebom posebno dizajniranihpremošćenih supstrata bio je predmet interesovanja nekolicine istraživačkih grupa uproteklom periodu.U toku ovog rada sintetisan je niz alkil-premošćenih diglicina, u cilju dobijanjapremošćenih bis-pirolidinskih adukata fulerena u reakciji dvostruke Prato-vecikloadicije. U prvom delu rada, na supstratu premošćenom oktametilenskim nizom,optimizovani su reakcioni uslovi za dobijanje bisadukata. Optimalnim reakcionimuslovima podvrgnuti su i ostali supstrati, premošćeni alkil-nizovima dužine od 6 do 12C-atoma i utvrđena je zavisnost regioselektivnosti od dužine niza. Istim reakcionimuslovima podvrgnuta su i dva supstrata koji sadrže dve, odnosno tri etarske podstruktureu mostu i ispitan je uticaj kiseonikovih atoma u linkeru na selektivnost reakcije..., Due to their unique physicochemical and electronic properties, emerging fromhighly conjugated π-system, derivatives of the fullerene C60 are interesting buildingblocks in the synthesis of the more complex target molecules. Diverse derivatizationsof hydrophobic carbone sphere provide a wide range of products for the use inmatherial, supramolecular and medicinal chemistry. Since the increase of the numberof addends on the carbon core improves the solubility and varies the stereoelectronicproperties, each method of the controlable multiple derivatization of fullerenes ishighly useful.Prato's reaction is one of the most common methodes for the covalentmodification of fullerenes. The fulleropyrrolidines, products with well definedstructures, are frequently used as intermediers in further chemical transformations offullerenes. This reaction is limited with the easy and unselective formation of bis- andtris(pyrrolidino) adducts and, hence, decrease of the yields and the purity ofmonoadducts. On the other hand, bisadducts are very useful in some aspects of themedicinal and electrochemistry. During the recent period, the regioselective synthesisof the fullerene bisadducts via templated supstrates has been the topic of interest ofseveral researcher groups.In this work, a series of alkyl-tethered diglycines were synthesized andunderwent the Prato's biscycloaddition conditions in aim to obtain templatedbis(pyrrolidino)fullerenes. The first part of the work refers to the optimization of thebiscycloaddition conditions on the octamethylene-tethered substrate. Other diglycines,wearing from C6 to C12 alkyl-linkers, were subjected to this optimal reactionconditions and the correlation between the distribution of the regioisomers and thelenght of the linker is determined. Another two diglycines, wearing two and threeoxygen atoms in the tether, underwent the same reaction conditions in aim toinvestigate the influence of the etheric subunits on the selectivity of the reaction...",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Sinteza i ispitivanje morfološkihelektrohemijskih i antioksidativnih osobina premošćenih bis-pirolidinskih derivatafulerena C60, Synthesis and investigation of morphological,electrochemical, and antioxidative properties of tethered bis-pyrrolidinoderivatives of fullerene c60",
url = "https://hdl.handle.net/21.15107/rcub_nardus_6283"
}

Kop, T.. (2016). Sinteza i ispitivanje morfološkihelektrohemijskih i antioksidativnih osobina premošćenih bis-pirolidinskih derivatafulerena C60. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_6283

Kop T. Sinteza i ispitivanje morfološkihelektrohemijskih i antioksidativnih osobina premošćenih bis-pirolidinskih derivatafulerena C60. in Универзитет у Београду. 2016;.
https://hdl.handle.net/21.15107/rcub_nardus_6283 .

Kop, Tatjana, "Sinteza i ispitivanje morfološkihelektrohemijskih i antioksidativnih osobina premošćenih bis-pirolidinskih derivatafulerena C60" in Универзитет у Београду (2016),
https://hdl.handle.net/21.15107/rcub_nardus_6283 .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Kop, Tatjana
AU  - Maslak, Veselin
AU  - Milić, Dragana
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1983
AB  - A series of N-substituted fulleropyrrolidines containing peptide side chain was synthesized by the quantitative, TFA-mediated deprotection of the corresponding tert-butyl esters. The structures of all compounds were determined by comparative analysis of spectroscopic and spectrometric data. The electrochemical characterization, conducted by cyclic voltammetry at room temperature confirmed slightly attenuated reducibility in comparison to pristine C-60 and a weak long-range electron-accepting effect of the Gly(3)-fragment. The introduction of the peptide subunit led to improved solubility and enabled examination of the antioxidant properties in water environment. A notable radical scavenging activity of the fullerene subunit remained almost unchanged in all compounds. The investigation of the supramolecular self-assembling, performed by the scanning electron microscopy revealed an influence of the side chain, particularly the fraction of the hydrophobic residue, as well as the substrate structure on the final morphology. Most of the compounds underwent highly ordered multi-stage hierarchical assembling to the attractive, flower-shaped supramolecular aggregates during both the precipitation and slow evaporation of the solvent.
PB  - Springer, New York
T2  - Journal of Materials Science
T1  - Synthesis and characterization of highly ordered self-assembled bioactive fulleropeptides
VL  - 51
IS  - 2
SP  - 739
EP  - 747
DO  - 10.1007/s10853-015-9396-z
ER  - 

@article{
author = "Bjelaković, Mira and Kop, Tatjana and Maslak, Veselin and Milić, Dragana",
year = "2016",
abstract = "A series of N-substituted fulleropyrrolidines containing peptide side chain was synthesized by the quantitative, TFA-mediated deprotection of the corresponding tert-butyl esters. The structures of all compounds were determined by comparative analysis of spectroscopic and spectrometric data. The electrochemical characterization, conducted by cyclic voltammetry at room temperature confirmed slightly attenuated reducibility in comparison to pristine C-60 and a weak long-range electron-accepting effect of the Gly(3)-fragment. The introduction of the peptide subunit led to improved solubility and enabled examination of the antioxidant properties in water environment. A notable radical scavenging activity of the fullerene subunit remained almost unchanged in all compounds. The investigation of the supramolecular self-assembling, performed by the scanning electron microscopy revealed an influence of the side chain, particularly the fraction of the hydrophobic residue, as well as the substrate structure on the final morphology. Most of the compounds underwent highly ordered multi-stage hierarchical assembling to the attractive, flower-shaped supramolecular aggregates during both the precipitation and slow evaporation of the solvent.",
publisher = "Springer, New York",
journal = "Journal of Materials Science",
title = "Synthesis and characterization of highly ordered self-assembled bioactive fulleropeptides",
volume = "51",
number = "2",
pages = "739-747",
doi = "10.1007/s10853-015-9396-z"
}

Bjelaković, M., Kop, T., Maslak, V.,& Milić, D.. (2016). Synthesis and characterization of highly ordered self-assembled bioactive fulleropeptides. in Journal of Materials Science
Springer, New York., 51(2), 739-747.
https://doi.org/10.1007/s10853-015-9396-z

Bjelaković M, Kop T, Maslak V, Milić D. Synthesis and characterization of highly ordered self-assembled bioactive fulleropeptides. in Journal of Materials Science. 2016;51(2):739-747.
doi:10.1007/s10853-015-9396-z .

Bjelaković, Mira, Kop, Tatjana, Maslak, Veselin, Milić, Dragana, "Synthesis and characterization of highly ordered self-assembled bioactive fulleropeptides" in Journal of Materials Science, 51, no. 2 (2016):739-747,
https://doi.org/10.1007/s10853-015-9396-z . .

TY  - JOUR
AU  - Pavlovic, Radoslav Z
AU  - Bjelaković, Mira
AU  - Milić, Dragana
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2029
AB  - The synthesis, characterization and behaviour of two novel Leigh-type amide [2]rotaxanes are reported. NMR study shows that fullerosteroidal and disteroidal rotaxanes occur in a peptide co-conformation in CDCl3. [D-6]DMSO induces fast unthreading of disteroidal rotaxane, which includes steroid co-conformers as intermediates. On the other hand, fullerosteroidal rotaxane undergoes predominantly a shuttling process occupying the stacked co-conformation, whereas unthreading is very slow in comparison with its disteroidal analogue (25% after 7 days). Moreover, organogelation and self-organization properties were studied. It was found that disteroidal rotaxane is an organogelator and its SEM image shows that it forms a branched film-like network in a PhMe/EtOAc 1 : 1 mixture.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading
VL  - 6
IS  - 43
SP  - 37246
EP  - 37253
DO  - 10.1039/c6ra03872g
ER  - 

@article{
author = "Pavlovic, Radoslav Z and Bjelaković, Mira and Milić, Dragana",
year = "2016",
abstract = "The synthesis, characterization and behaviour of two novel Leigh-type amide [2]rotaxanes are reported. NMR study shows that fullerosteroidal and disteroidal rotaxanes occur in a peptide co-conformation in CDCl3. [D-6]DMSO induces fast unthreading of disteroidal rotaxane, which includes steroid co-conformers as intermediates. On the other hand, fullerosteroidal rotaxane undergoes predominantly a shuttling process occupying the stacked co-conformation, whereas unthreading is very slow in comparison with its disteroidal analogue (25% after 7 days). Moreover, organogelation and self-organization properties were studied. It was found that disteroidal rotaxane is an organogelator and its SEM image shows that it forms a branched film-like network in a PhMe/EtOAc 1 : 1 mixture.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading",
volume = "6",
number = "43",
pages = "37246-37253",
doi = "10.1039/c6ra03872g"
}

Pavlovic, R. Z., Bjelaković, M.,& Milić, D.. (2016). Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(43), 37246-37253.
https://doi.org/10.1039/c6ra03872g

Pavlovic RZ, Bjelaković M, Milić D. Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading. in RSC Advances. 2016;6(43):37246-37253.
doi:10.1039/c6ra03872g .

Pavlovic, Radoslav Z, Bjelaković, Mira, Milić, Dragana, "Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading" in RSC Advances, 6, no. 43 (2016):37246-37253,
https://doi.org/10.1039/c6ra03872g . .

TY  - JOUR
AU  - Kop, Tatjana
AU  - Bjelaković, Mira
AU  - Milić, Dragana
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1631
AB  - The one-pot bistycloaddition of alkyl-tethered diglycines to C-60 provided five series of bridged bis(pyrrolidino)fullerenes with good regioselectivity, giving mainly cis-2 and cis-3 products. An influence of the bridge length and addition pattern on spectroscopic properties, as well as on the shape of hierarchically organized supramolecular structures was observed. Additional investigation of all synthesized compounds confirmed their strong in vitro antioxidant activity 4-10-fold better than the standard antioxidant vitamin C.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Synthesis and properties of bis(pyrrolidino)fullerenes bridged by a flexible alkyl-tether
VL  - 71
IS  - 29
SP  - 4801
EP  - 4809
DO  - 10.1016/j.tet.2015.05.038
ER  - 

@article{
author = "Kop, Tatjana and Bjelaković, Mira and Milić, Dragana",
year = "2015",
abstract = "The one-pot bistycloaddition of alkyl-tethered diglycines to C-60 provided five series of bridged bis(pyrrolidino)fullerenes with good regioselectivity, giving mainly cis-2 and cis-3 products. An influence of the bridge length and addition pattern on spectroscopic properties, as well as on the shape of hierarchically organized supramolecular structures was observed. Additional investigation of all synthesized compounds confirmed their strong in vitro antioxidant activity 4-10-fold better than the standard antioxidant vitamin C.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Synthesis and properties of bis(pyrrolidino)fullerenes bridged by a flexible alkyl-tether",
volume = "71",
number = "29",
pages = "4801-4809",
doi = "10.1016/j.tet.2015.05.038"
}

Kop, T., Bjelaković, M.,& Milić, D.. (2015). Synthesis and properties of bis(pyrrolidino)fullerenes bridged by a flexible alkyl-tether. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 71(29), 4801-4809.
https://doi.org/10.1016/j.tet.2015.05.038

Kop T, Bjelaković M, Milić D. Synthesis and properties of bis(pyrrolidino)fullerenes bridged by a flexible alkyl-tether. in Tetrahedron. 2015;71(29):4801-4809.
doi:10.1016/j.tet.2015.05.038 .

Kop, Tatjana, Bjelaković, Mira, Milić, Dragana, "Synthesis and properties of bis(pyrrolidino)fullerenes bridged by a flexible alkyl-tether" in Tetrahedron, 71, no. 29 (2015):4801-4809,
https://doi.org/10.1016/j.tet.2015.05.038 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Kop, Tatjana
AU  - Dordevic, Jelena
AU  - Milić, Dragana
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1750
AB  - The potential use of amphiphilic fullerene derivatives as a bionanomaterial was investigated by cyclic voltammetry (CV), scanning electron microscopy (SEM), and the ferrous ion oxidation-xylenol orange (FOX) method. Despite the disrupted delocalization of the pi-electronic system over the C-60 sphere, its antioxidant capacity remained high for all twelve derivatives. The compounds expressed up to two-fold and 5-12-fold better peroxide quenching capacity as compared to pristine C-60 and standard antioxidant vitamin C, respectively. During precipitation and slow evaporation of the solvent, all compounds underwent spontaneous self-assembly giving ordered structures. The size and morphology of the resulting particles depend primarily on the sample concentration, and somewhat on the side chain structure.
PB  - Beilstein-Institut, Frankfurt Am Main
T2  - Beilstein Journal of Nanotechnology
T1  - Fulleropeptide esters as potential self-assembled antioxidants
VL  - 6
SP  - 1065
EP  - 1071
DO  - 10.3762/bjnano.6.107
ER  - 

@article{
author = "Bjelaković, Mira and Kop, Tatjana and Dordevic, Jelena and Milić, Dragana",
year = "2015",
abstract = "The potential use of amphiphilic fullerene derivatives as a bionanomaterial was investigated by cyclic voltammetry (CV), scanning electron microscopy (SEM), and the ferrous ion oxidation-xylenol orange (FOX) method. Despite the disrupted delocalization of the pi-electronic system over the C-60 sphere, its antioxidant capacity remained high for all twelve derivatives. The compounds expressed up to two-fold and 5-12-fold better peroxide quenching capacity as compared to pristine C-60 and standard antioxidant vitamin C, respectively. During precipitation and slow evaporation of the solvent, all compounds underwent spontaneous self-assembly giving ordered structures. The size and morphology of the resulting particles depend primarily on the sample concentration, and somewhat on the side chain structure.",
publisher = "Beilstein-Institut, Frankfurt Am Main",
journal = "Beilstein Journal of Nanotechnology",
title = "Fulleropeptide esters as potential self-assembled antioxidants",
volume = "6",
pages = "1065-1071",
doi = "10.3762/bjnano.6.107"
}

Bjelaković, M., Kop, T., Dordevic, J.,& Milić, D.. (2015). Fulleropeptide esters as potential self-assembled antioxidants. in Beilstein Journal of Nanotechnology
Beilstein-Institut, Frankfurt Am Main., 6, 1065-1071.
https://doi.org/10.3762/bjnano.6.107

Bjelaković M, Kop T, Dordevic J, Milić D. Fulleropeptide esters as potential self-assembled antioxidants. in Beilstein Journal of Nanotechnology. 2015;6:1065-1071.
doi:10.3762/bjnano.6.107 .

Bjelaković, Mira, Kop, Tatjana, Dordevic, Jelena, Milić, Dragana, "Fulleropeptide esters as potential self-assembled antioxidants" in Beilstein Journal of Nanotechnology, 6 (2015):1065-1071,
https://doi.org/10.3762/bjnano.6.107 . .

TY  - JOUR
AU  - Kop, Tatjana
AU  - Bjelaković, Mira
AU  - Dordevic, Jelena
AU  - Zekic, Andrijana
AU  - Milić, Dragana
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1829
AB  - Two different alpha,omega-diglicynes linked by linear polyoxaalkyl chains in the presence of formaldehyde underwent Prato reaction to the fullerene C-60. The shorter linker templated formation of only cis-bisadducts, while the longer one afforded a mixture of four bisadducts (all cis and the equatorial) and difullerene dumbbell compound. Their structures were confirmed by the extensive analysis of the spectral data and molecular symmetry, as well. All compounds expressed an ability to arrange into hierarchically ordered supramolecular aggregates, the form of which depended both on the addition pattern and the spacer structure. The attenuated electron-accepting affinity, examined by cyclic voltammetry was in agreement with diminished delocalization of the pi-electronic system. In addition, all compounds exerted a notable radical scavenging activity.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Fulleropyrrolidines derived from dioxa- and trioxaalkyl-tethered diglycines
VL  - 5
IS  - 115
SP  - 94599
EP  - 94606
DO  - 10.1039/c5ra17392b
ER  - 

@article{
author = "Kop, Tatjana and Bjelaković, Mira and Dordevic, Jelena and Zekic, Andrijana and Milić, Dragana",
year = "2015",
abstract = "Two different alpha,omega-diglicynes linked by linear polyoxaalkyl chains in the presence of formaldehyde underwent Prato reaction to the fullerene C-60. The shorter linker templated formation of only cis-bisadducts, while the longer one afforded a mixture of four bisadducts (all cis and the equatorial) and difullerene dumbbell compound. Their structures were confirmed by the extensive analysis of the spectral data and molecular symmetry, as well. All compounds expressed an ability to arrange into hierarchically ordered supramolecular aggregates, the form of which depended both on the addition pattern and the spacer structure. The attenuated electron-accepting affinity, examined by cyclic voltammetry was in agreement with diminished delocalization of the pi-electronic system. In addition, all compounds exerted a notable radical scavenging activity.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Fulleropyrrolidines derived from dioxa- and trioxaalkyl-tethered diglycines",
volume = "5",
number = "115",
pages = "94599-94606",
doi = "10.1039/c5ra17392b"
}

Kop, T., Bjelaković, M., Dordevic, J., Zekic, A.,& Milić, D.. (2015). Fulleropyrrolidines derived from dioxa- and trioxaalkyl-tethered diglycines. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(115), 94599-94606.
https://doi.org/10.1039/c5ra17392b

Kop T, Bjelaković M, Dordevic J, Zekic A, Milić D. Fulleropyrrolidines derived from dioxa- and trioxaalkyl-tethered diglycines. in RSC Advances. 2015;5(115):94599-94606.
doi:10.1039/c5ra17392b .

Kop, Tatjana, Bjelaković, Mira, Dordevic, Jelena, Zekic, Andrijana, Milić, Dragana, "Fulleropyrrolidines derived from dioxa- and trioxaalkyl-tethered diglycines" in RSC Advances, 5, no. 115 (2015):94599-94606,
https://doi.org/10.1039/c5ra17392b . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Kop, Tatjana
AU  - Vajić, Marina
AU  - Đordevic, Jelena
AU  - Milić, Dragana
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1471
AB  - The present study reports the synthesis, spectral characterization, self-assembly properties, and preliminary in vitro study of antioxidant capacity of two triple covalent hybrids consisting of fullerene C-60, peptide, and steroidal moiety. Previously synthesized fulleropyrrolidinic acid and pregnenolone were connected by peptide linker using a multistep DCC/DMAP and/or EDC/HOBT esterification/amidation procedure. The hybrids were characterized by comparative analysis of spectroscopic data obtained from FUR, UV-vis, HRMS, and extensive NMR experiments (H-1, C-13, COSY, HSQC, and HMBC). The self-assembling properties and morphology of triads samples prepared by drop-drying method were examined by scanning electron microscopy (SEM). Preliminary in vitro antioxidant activity was studied by Ferrous ion Oxidation-Xylenol orange (FOX) method.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Design, synthesis, and characterization of fullerene-peptide-steroid covalent hybrids
VL  - 70
IS  - 45
SP  - 8564
EP  - 8570
DO  - 10.1016/j.tet.2014.09.070
ER  - 

@article{
author = "Bjelaković, Mira and Kop, Tatjana and Vajić, Marina and Đordevic, Jelena and Milić, Dragana",
year = "2014",
abstract = "The present study reports the synthesis, spectral characterization, self-assembly properties, and preliminary in vitro study of antioxidant capacity of two triple covalent hybrids consisting of fullerene C-60, peptide, and steroidal moiety. Previously synthesized fulleropyrrolidinic acid and pregnenolone were connected by peptide linker using a multistep DCC/DMAP and/or EDC/HOBT esterification/amidation procedure. The hybrids were characterized by comparative analysis of spectroscopic data obtained from FUR, UV-vis, HRMS, and extensive NMR experiments (H-1, C-13, COSY, HSQC, and HMBC). The self-assembling properties and morphology of triads samples prepared by drop-drying method were examined by scanning electron microscopy (SEM). Preliminary in vitro antioxidant activity was studied by Ferrous ion Oxidation-Xylenol orange (FOX) method.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Design, synthesis, and characterization of fullerene-peptide-steroid covalent hybrids",
volume = "70",
number = "45",
pages = "8564-8570",
doi = "10.1016/j.tet.2014.09.070"
}

Bjelaković, M., Kop, T., Vajić, M., Đordevic, J.,& Milić, D.. (2014). Design, synthesis, and characterization of fullerene-peptide-steroid covalent hybrids. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 70(45), 8564-8570.
https://doi.org/10.1016/j.tet.2014.09.070

Bjelaković M, Kop T, Vajić M, Đordevic J, Milić D. Design, synthesis, and characterization of fullerene-peptide-steroid covalent hybrids. in Tetrahedron. 2014;70(45):8564-8570.
doi:10.1016/j.tet.2014.09.070 .

Bjelaković, Mira, Kop, Tatjana, Vajić, Marina, Đordevic, Jelena, Milić, Dragana, "Design, synthesis, and characterization of fullerene-peptide-steroid covalent hybrids" in Tetrahedron, 70, no. 45 (2014):8564-8570,
https://doi.org/10.1016/j.tet.2014.09.070 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Kop, Tatjana
AU  - Baošić, Rada
AU  - Zlatović, Mario
AU  - Zekic, Andrijana
AU  - Maslak, Veselin
AU  - Milić, Dragana
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1394
AB  - Four fullerosteroidal conjugates, previously confirmed to express two- to threefold better antioxidant activity in vitro than C-60, were subjected to additional studies, including electrochemical, theoretical, and morphological examination. All tested compounds underwent reversible, diffusion-controlled reductions. A notable influence of the solvent properties on the reduction potential, the level of aggregation, and the lowest unoccupied molecular orbital (LUMO) energy was observed. Theoretical calculations indicated that the energy gain obtained by an intermediate formation, together with compounds' polarizability, polarity, and lipophilicity contributed to the radical quenching capacity. Very large supramolecular aggregates of all fullerosteroidal esters with no hierarchical arrangement were observed in precipitated samples, while solvent induced self-assembling led to round nanoplates, which further arranged to flower-shaped hierarchically ordered architectures or uniformly distributed discoid particles. As in electrochemical studies, fine tuning of the aggregation level was achieved by the solvent.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - Electrochemical, theoretical, and morphological studies of antioxidant fullerosteroids
VL  - 145
IS  - 11
SP  - 1715
EP  - 1725
DO  - 10.1007/s00706-014-1287-5
ER  - 

@article{
author = "Bjelaković, Mira and Kop, Tatjana and Baošić, Rada and Zlatović, Mario and Zekic, Andrijana and Maslak, Veselin and Milić, Dragana",
year = "2014",
abstract = "Four fullerosteroidal conjugates, previously confirmed to express two- to threefold better antioxidant activity in vitro than C-60, were subjected to additional studies, including electrochemical, theoretical, and morphological examination. All tested compounds underwent reversible, diffusion-controlled reductions. A notable influence of the solvent properties on the reduction potential, the level of aggregation, and the lowest unoccupied molecular orbital (LUMO) energy was observed. Theoretical calculations indicated that the energy gain obtained by an intermediate formation, together with compounds' polarizability, polarity, and lipophilicity contributed to the radical quenching capacity. Very large supramolecular aggregates of all fullerosteroidal esters with no hierarchical arrangement were observed in precipitated samples, while solvent induced self-assembling led to round nanoplates, which further arranged to flower-shaped hierarchically ordered architectures or uniformly distributed discoid particles. As in electrochemical studies, fine tuning of the aggregation level was achieved by the solvent.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Electrochemical, theoretical, and morphological studies of antioxidant fullerosteroids",
volume = "145",
number = "11",
pages = "1715-1725",
doi = "10.1007/s00706-014-1287-5"
}

Bjelaković, M., Kop, T., Baošić, R., Zlatović, M., Zekic, A., Maslak, V.,& Milić, D.. (2014). Electrochemical, theoretical, and morphological studies of antioxidant fullerosteroids. in Monatshefte Fur Chemie
Springer Wien, Wien., 145(11), 1715-1725.
https://doi.org/10.1007/s00706-014-1287-5

Bjelaković M, Kop T, Baošić R, Zlatović M, Zekic A, Maslak V, Milić D. Electrochemical, theoretical, and morphological studies of antioxidant fullerosteroids. in Monatshefte Fur Chemie. 2014;145(11):1715-1725.
doi:10.1007/s00706-014-1287-5 .

Bjelaković, Mira, Kop, Tatjana, Baošić, Rada, Zlatović, Mario, Zekic, Andrijana, Maslak, Veselin, Milić, Dragana, "Electrochemical, theoretical, and morphological studies of antioxidant fullerosteroids" in Monatshefte Fur Chemie, 145, no. 11 (2014):1715-1725,
https://doi.org/10.1007/s00706-014-1287-5 . .

TY  - JOUR
AU  - Mitrović, Aleksandra
AU  - Todorović, Nina
AU  - Zekic, Andrijana
AU  - Stanković, Dalibor
AU  - Milić, Dragana
AU  - Maslak, Veselin
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1345
AB  - A series of novel fulleropyrrolidine-phthalimide dyads was synthesized and their electrochemical and self-assembly properties were investigated. Efficient synthesis of acceptor-acceptor dyads was performed under microwave irradiation. Fine-tuning of the second redox potentials in the dyads was achieved by varying the length of the aliphatic spacer (C-2 to C-12) between the fulleropyrrolidine and phthalimide moieties. Shape-shifting and supramolecular polymorphism were observed for these compounds during self-assembly.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads
IS  - 11
SP  - 2188
EP  - 2193
DO  - 10.1002/ejoc.201201631
ER  - 

@article{
author = "Mitrović, Aleksandra and Todorović, Nina and Zekic, Andrijana and Stanković, Dalibor and Milić, Dragana and Maslak, Veselin",
year = "2013",
abstract = "A series of novel fulleropyrrolidine-phthalimide dyads was synthesized and their electrochemical and self-assembly properties were investigated. Efficient synthesis of acceptor-acceptor dyads was performed under microwave irradiation. Fine-tuning of the second redox potentials in the dyads was achieved by varying the length of the aliphatic spacer (C-2 to C-12) between the fulleropyrrolidine and phthalimide moieties. Shape-shifting and supramolecular polymorphism were observed for these compounds during self-assembly.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads",
number = "11",
pages = "2188-2193",
doi = "10.1002/ejoc.201201631"
}

Mitrović, A., Todorović, N., Zekic, A., Stanković, D., Milić, D.,& Maslak, V.. (2013). Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(11), 2188-2193.
https://doi.org/10.1002/ejoc.201201631

Mitrović A, Todorović N, Zekic A, Stanković D, Milić D, Maslak V. Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads. in European Journal of Organic Chemistry. 2013;(11):2188-2193.
doi:10.1002/ejoc.201201631 .

Mitrović, Aleksandra, Todorović, Nina, Zekic, Andrijana, Stanković, Dalibor, Milić, Dragana, Maslak, Veselin, "Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads" in European Journal of Organic Chemistry, no. 11 (2013):2188-2193,
https://doi.org/10.1002/ejoc.201201631 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Todorović, Nina
AU  - Milić, Dragana
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1106
AB  - Two sets of new peptides incorporating fulleropyrrolidine units Fp-GABAn-Glym-OtBu have been designed, synthesized and completely characterized. In the first series the chain contained only GABA (?-aminobutyric) residues, whereas in the second one glycine moieties were also inserted as well as GABA. Most of the target compounds were prepared by DCC/DMAP-assisted coupling of previously synthesized GABA-containing fulleropyrrolidinic acid and corresponding C-protected small peptides, although for two fulleropeptides [3+2] cycloadditions of azomethine ylides to C60 were employed. All new compounds were characterized by standard spectroscopic methods. Complete assignments of peptide spin systems were achieved by extensive NMR analysis (1H, 13C, H,H-COSY, HSQC, HMBC and TOCSY).
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - An Approach to Nanobioparticles - Synthesis and Characterization of Fulleropeptides
IS  - 27
SP  - 5291
EP  - 5300
DO  - 10.1002/ejoc.201200274
ER  - 

@article{
author = "Bjelaković, Mira and Todorović, Nina and Milić, Dragana",
year = "2012",
abstract = "Two sets of new peptides incorporating fulleropyrrolidine units Fp-GABAn-Glym-OtBu have been designed, synthesized and completely characterized. In the first series the chain contained only GABA (?-aminobutyric) residues, whereas in the second one glycine moieties were also inserted as well as GABA. Most of the target compounds were prepared by DCC/DMAP-assisted coupling of previously synthesized GABA-containing fulleropyrrolidinic acid and corresponding C-protected small peptides, although for two fulleropeptides [3+2] cycloadditions of azomethine ylides to C60 were employed. All new compounds were characterized by standard spectroscopic methods. Complete assignments of peptide spin systems were achieved by extensive NMR analysis (1H, 13C, H,H-COSY, HSQC, HMBC and TOCSY).",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "An Approach to Nanobioparticles - Synthesis and Characterization of Fulleropeptides",
number = "27",
pages = "5291-5300",
doi = "10.1002/ejoc.201200274"
}

Bjelaković, M., Todorović, N.,& Milić, D.. (2012). An Approach to Nanobioparticles - Synthesis and Characterization of Fulleropeptides. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(27), 5291-5300.
https://doi.org/10.1002/ejoc.201200274

Bjelaković M, Todorović N, Milić D. An Approach to Nanobioparticles - Synthesis and Characterization of Fulleropeptides. in European Journal of Organic Chemistry. 2012;(27):5291-5300.
doi:10.1002/ejoc.201200274 .

Bjelaković, Mira, Todorović, Nina, Milić, Dragana, "An Approach to Nanobioparticles - Synthesis and Characterization of Fulleropeptides" in European Journal of Organic Chemistry, no. 27 (2012):5291-5300,
https://doi.org/10.1002/ejoc.201200274 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Milić, Dragana
AU  - Kop, Tatjana
AU  - Robeyns, Koen
AU  - Pavlović, Vladimir D.
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1114
AB  - The present study is concerned with the oxidative behaviour of unsaturated and epoxy 5-oxo-5,10-secosteroids in the presence of m-CPBA or TFAA-UHP as oxidants in order to investigate potential parameters controlling the chemoselectivity and regioselectivity. In the study we discovered a striking difference in the chemical behaviour of stereoisomeric compounds, (Z)- and (E)-3 beta-acetoxy-5,10-secocholest-1(10)-en-5-ones, as well as 1S,10R- and 1R,10R-epoxides. The secoketones were oxidized with exclusively C-6 migration and Baeyer-Villiger rearrangement product formation, whereas their stereoisomers provided the ring-contracted products, without lactone formation. The preferred conformation of expanded and contracted rings was established by NOESY correlations. The structures of two obtained lactones were also confirmed by X-ray analysis. The mechanistic and stereochemical aspects of these transformations are discussed.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids
VL  - 68
IS  - 36
SP  - 7479
EP  - 7488
DO  - 10.1016/j.tet.2012.06.024
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Milić, Dragana and Kop, Tatjana and Robeyns, Koen and Pavlović, Vladimir D.",
year = "2012",
abstract = "The present study is concerned with the oxidative behaviour of unsaturated and epoxy 5-oxo-5,10-secosteroids in the presence of m-CPBA or TFAA-UHP as oxidants in order to investigate potential parameters controlling the chemoselectivity and regioselectivity. In the study we discovered a striking difference in the chemical behaviour of stereoisomeric compounds, (Z)- and (E)-3 beta-acetoxy-5,10-secocholest-1(10)-en-5-ones, as well as 1S,10R- and 1R,10R-epoxides. The secoketones were oxidized with exclusively C-6 migration and Baeyer-Villiger rearrangement product formation, whereas their stereoisomers provided the ring-contracted products, without lactone formation. The preferred conformation of expanded and contracted rings was established by NOESY correlations. The structures of two obtained lactones were also confirmed by X-ray analysis. The mechanistic and stereochemical aspects of these transformations are discussed.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids",
volume = "68",
number = "36",
pages = "7479-7488",
doi = "10.1016/j.tet.2012.06.024"
}

Bjelaković, M., Krstić, N., Milić, D., Kop, T., Robeyns, K.,& Pavlović, V. D.. (2012). Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 68(36), 7479-7488.
https://doi.org/10.1016/j.tet.2012.06.024

Bjelaković M, Krstić N, Milić D, Kop T, Robeyns K, Pavlović VD. Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids. in Tetrahedron. 2012;68(36):7479-7488.
doi:10.1016/j.tet.2012.06.024 .

Bjelaković, Mira, Krstić, Natalija, Milić, Dragana, Kop, Tatjana, Robeyns, Koen, Pavlović, Vladimir D., "Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids" in Tetrahedron, 68, no. 36 (2012):7479-7488,
https://doi.org/10.1016/j.tet.2012.06.024 . .