TY  - JOUR
AU  - Kop, Tatjana
AU  - Bjelaković, Mira
AU  - Živković, Ljiljana S.
AU  - Žekić, Andrijana
AU  - Milić, Dragana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5234
AB  - Despite many advantages, the practical application of fullerene C60 and curcumin (CUR) has been limited by their hydrophobic nature, deficient solubility in aqueous media and, therefore, poor bioavailability. In this study, aqueous nanoformulations containing C60 and CUR in the absence and presence of three solubility enhancers, β-cyclodextrin (CD), Tween 80 (T80) and polyvinylpyrrolidone (PVP), were prepared and subjected to the antioxidant activity assessment. The content of C60 and CUR, stability, size and morphology of nanoparticles were determined using UV–vis, DLS and SEM techniques. Contrary to better solubility of pure C60 than the corresponding C60-CUR system, the solubilization of CUR in hybrid suspensions was improved compared to corresponding pure CUR suspensions, with the exception of the C60-CUR-PVP formulation. The DLS results revealed nearly monodisperse nature of CUR-T80 nanoformulation, while other ones ranged from widely dispersed to polydispersed. Depending on the type of solubilizer, similarity was observed in the particle size distributions of T80- and PVP-coated nanoformulations as well as water and CD nanoformulations. The presence of T80 differently and significantly reduces the particle size in all three nanoformulations, while PVP slightly reduces CUR-based nanoparticles but increases the size of C60 nanoparticles. Zeta potential values, ranging from − 9 mV to − 34 mV, show variation in the starting stability of nanoparticles, from unstable or relatively stable three PVP formulations and C60-T80 to highly stable CUR-T80 and C60-water. Compared to water nanoformulations as a control, SEM images of dispersant-coated nanoparticles lost the visible morphology of active components, showing variation in their morphology depending on the type of dispersant and active component used. Nanoformulations containing CUR in PVP and T80 expressed a very good antioxidant potential in DPPH radical scavenging assay, much stronger than ascorbic acid. At the same time, a moderate to high antioxidant activity in β-carotene bleaching assay was reached in PVP and T80 nanoformulations containing C60, CUR, and their noncovalent hybrid, as well. Our studies have shown that T80 and PVP colloidal systems containing C60-CUR hybrid, but also their individual components, can be used as stable antioxidant nanoformulations with potential application in the field of food and pharmacology.
PB  - Elsevier
T2  - Colloids and Surfaces A: Physicochemical and Engineering Aspects
T1  - Stable colloidal dispersions of fullerene C60, curcumin and C60-curcumin in water as potential antioxidants
VL  - 648
DO  - 10.1016/j.colsurfa.2022.129379
ER  - 

@article{
author = "Kop, Tatjana and Bjelaković, Mira and Živković, Ljiljana S. and Žekić, Andrijana and Milić, Dragana",
year = "2022",
abstract = "Despite many advantages, the practical application of fullerene C60 and curcumin (CUR) has been limited by their hydrophobic nature, deficient solubility in aqueous media and, therefore, poor bioavailability. In this study, aqueous nanoformulations containing C60 and CUR in the absence and presence of three solubility enhancers, β-cyclodextrin (CD), Tween 80 (T80) and polyvinylpyrrolidone (PVP), were prepared and subjected to the antioxidant activity assessment. The content of C60 and CUR, stability, size and morphology of nanoparticles were determined using UV–vis, DLS and SEM techniques. Contrary to better solubility of pure C60 than the corresponding C60-CUR system, the solubilization of CUR in hybrid suspensions was improved compared to corresponding pure CUR suspensions, with the exception of the C60-CUR-PVP formulation. The DLS results revealed nearly monodisperse nature of CUR-T80 nanoformulation, while other ones ranged from widely dispersed to polydispersed. Depending on the type of solubilizer, similarity was observed in the particle size distributions of T80- and PVP-coated nanoformulations as well as water and CD nanoformulations. The presence of T80 differently and significantly reduces the particle size in all three nanoformulations, while PVP slightly reduces CUR-based nanoparticles but increases the size of C60 nanoparticles. Zeta potential values, ranging from − 9 mV to − 34 mV, show variation in the starting stability of nanoparticles, from unstable or relatively stable three PVP formulations and C60-T80 to highly stable CUR-T80 and C60-water. Compared to water nanoformulations as a control, SEM images of dispersant-coated nanoparticles lost the visible morphology of active components, showing variation in their morphology depending on the type of dispersant and active component used. Nanoformulations containing CUR in PVP and T80 expressed a very good antioxidant potential in DPPH radical scavenging assay, much stronger than ascorbic acid. At the same time, a moderate to high antioxidant activity in β-carotene bleaching assay was reached in PVP and T80 nanoformulations containing C60, CUR, and their noncovalent hybrid, as well. Our studies have shown that T80 and PVP colloidal systems containing C60-CUR hybrid, but also their individual components, can be used as stable antioxidant nanoformulations with potential application in the field of food and pharmacology.",
publisher = "Elsevier",
journal = "Colloids and Surfaces A: Physicochemical and Engineering Aspects",
title = "Stable colloidal dispersions of fullerene C60, curcumin and C60-curcumin in water as potential antioxidants",
volume = "648",
doi = "10.1016/j.colsurfa.2022.129379"
}

Kop, T., Bjelaković, M., Živković, L. S., Žekić, A.,& Milić, D.. (2022). Stable colloidal dispersions of fullerene C60, curcumin and C60-curcumin in water as potential antioxidants. in Colloids and Surfaces A: Physicochemical and Engineering Aspects
Elsevier., 648.
https://doi.org/10.1016/j.colsurfa.2022.129379

Kop T, Bjelaković M, Živković LS, Žekić A, Milić D. Stable colloidal dispersions of fullerene C60, curcumin and C60-curcumin in water as potential antioxidants. in Colloids and Surfaces A: Physicochemical and Engineering Aspects. 2022;648.
doi:10.1016/j.colsurfa.2022.129379 .

Kop, Tatjana, Bjelaković, Mira, Živković, Ljiljana S., Žekić, Andrijana, Milić, Dragana, "Stable colloidal dispersions of fullerene C60, curcumin and C60-curcumin in water as potential antioxidants" in Colloids and Surfaces A: Physicochemical and Engineering Aspects, 648 (2022),
https://doi.org/10.1016/j.colsurfa.2022.129379 . .

TY  - JOUR
AU  - Jovanović, Dragana
AU  - Stanojković, Jovana
AU  - Halilović, Dženeta
AU  - Kolašinac, Rejhana
AU  - Kop, Tatjana
AU  - Bjelaković, Mira
AU  - Milić, Dragana
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4921
AB  - A large series of disubstituted fulleropyrrolidines was synthesized and analyzed by cyclic voltammetry. The three main groups of target com­pounds differ by a flexible N-chain, while their further diversity was achieved by the introduction of various rigid, aryl substituents at the pyrrolidine carbon. Some dialkyl analogues were also designed for comparison, A standard [3+2]-cycloaddition of in situ generated azomethine ylides to C60 afforded a variety of disubstituted fulleropyrrolidines. Furthermore, a set of dumbbell-shaped di(fulleropyrrolidine) derivatives containing rigid fumaryl or isophthaloyl diamide platform was prepared with the aim of investigating a long-range effect of the second fulleropyrrolidine moiety on their electrochemical pro­perties. All compounds were fully characterized by comparative analysis of spectral data, while examination of electrochemical properties was performed on representative samples, distinguished by main structural subunits. All com­pounds expressed quite similar electron-accepting ability, lower than C60, but higher in comparison to structurally similar N-methylfulleropyrrolidine.
AB  - Велика серија дисупституисаних фулеропиролидина је синтетисана и анализирана цикличном волтаметријом. Три главне групе циљних једињења разликују се по флекси- билном бочном низу на атому азота, а додатна диверсификација постигнута је увођењем различитих крутих, арил-супституената на пиролидинском атому угљеника. За поре- ђење су синтетисани и одређени диалкил-аналози. Сет дисупституисаних фулеропиро- лидина добијен је стандардном [3+2]-циклоадицијом ин ситу генерисаних азометинских илида на C60. Осим тога, у циљу испитивања даљинског утицаја фулеропиролидинске структуре на електрохемијске особине, синтетисани су и дифулеренски деривати код којих су терминално позициониране фулеренске подјединице премошћене фумарилном или изофталоилном крутом платформом. Сва једињења су у потпуности окарактерисана упоредном анализом спектралних података, док је сет одабраних једињења, са разли- кама у главним структурним подјединицама, искоришћен за испитивање електрохемиј- ских особина. Сва испитивана једињења показала су врло сличну способност прихватања електрона, нижу у односу на C60, а вишу од структурно сличног N-метилфулеропиро- лидина.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Fulleropyrrolidines with orthogonally flexible substituents - synthesis and electrochemical properties
T1  - Фулеропиролидини са ортогонално флексибилним супституентима – синтеза и електрохемијске особине
VL  - 86
IS  - 11
SP  - 1023
EP  - 1037
DO  - 10.2298/JSC210708069J
ER  - 

@article{
author = "Jovanović, Dragana and Stanojković, Jovana and Halilović, Dženeta and Kolašinac, Rejhana and Kop, Tatjana and Bjelaković, Mira and Milić, Dragana",
year = "2021",
abstract = "A large series of disubstituted fulleropyrrolidines was synthesized and analyzed by cyclic voltammetry. The three main groups of target com­pounds differ by a flexible N-chain, while their further diversity was achieved by the introduction of various rigid, aryl substituents at the pyrrolidine carbon. Some dialkyl analogues were also designed for comparison, A standard [3+2]-cycloaddition of in situ generated azomethine ylides to C60 afforded a variety of disubstituted fulleropyrrolidines. Furthermore, a set of dumbbell-shaped di(fulleropyrrolidine) derivatives containing rigid fumaryl or isophthaloyl diamide platform was prepared with the aim of investigating a long-range effect of the second fulleropyrrolidine moiety on their electrochemical pro­perties. All compounds were fully characterized by comparative analysis of spectral data, while examination of electrochemical properties was performed on representative samples, distinguished by main structural subunits. All com­pounds expressed quite similar electron-accepting ability, lower than C60, but higher in comparison to structurally similar N-methylfulleropyrrolidine., Велика серија дисупституисаних фулеропиролидина је синтетисана и анализирана цикличном волтаметријом. Три главне групе циљних једињења разликују се по флекси- билном бочном низу на атому азота, а додатна диверсификација постигнута је увођењем различитих крутих, арил-супституената на пиролидинском атому угљеника. За поре- ђење су синтетисани и одређени диалкил-аналози. Сет дисупституисаних фулеропиро- лидина добијен је стандардном [3+2]-циклоадицијом ин ситу генерисаних азометинских илида на C60. Осим тога, у циљу испитивања даљинског утицаја фулеропиролидинске структуре на електрохемијске особине, синтетисани су и дифулеренски деривати код којих су терминално позициониране фулеренске подјединице премошћене фумарилном или изофталоилном крутом платформом. Сва једињења су у потпуности окарактерисана упоредном анализом спектралних података, док је сет одабраних једињења, са разли- кама у главним структурним подјединицама, искоришћен за испитивање електрохемиј- ских особина. Сва испитивана једињења показала су врло сличну способност прихватања електрона, нижу у односу на C60, а вишу од структурно сличног N-метилфулеропиро- лидина.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Fulleropyrrolidines with orthogonally flexible substituents - synthesis and electrochemical properties, Фулеропиролидини са ортогонално флексибилним супституентима – синтеза и електрохемијске особине",
volume = "86",
number = "11",
pages = "1023-1037",
doi = "10.2298/JSC210708069J"
}

Jovanović, D., Stanojković, J., Halilović, D., Kolašinac, R., Kop, T., Bjelaković, M.,& Milić, D.. (2021). Fulleropyrrolidines with orthogonally flexible substituents - synthesis and electrochemical properties. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 86(11), 1023-1037.
https://doi.org/10.2298/JSC210708069J

Jovanović D, Stanojković J, Halilović D, Kolašinac R, Kop T, Bjelaković M, Milić D. Fulleropyrrolidines with orthogonally flexible substituents - synthesis and electrochemical properties. in Journal of the Serbian Chemical Society. 2021;86(11):1023-1037.
doi:10.2298/JSC210708069J .

Jovanović, Dragana, Stanojković, Jovana, Halilović, Dženeta, Kolašinac, Rejhana, Kop, Tatjana, Bjelaković, Mira, Milić, Dragana, "Fulleropyrrolidines with orthogonally flexible substituents - synthesis and electrochemical properties" in Journal of the Serbian Chemical Society, 86, no. 11 (2021):1023-1037,
https://doi.org/10.2298/JSC210708069J . .

TY  - JOUR
AU  - Nešić, Maja D.
AU  - Dučić, Tanja
AU  - Liang, Xinyue
AU  - Algarra, Manuel
AU  - Mi, Lan
AU  - Korićanac, Lela
AU  - Žakula, Jelena
AU  - Kop, Tatjana
AU  - Bjelaković, Mira
AU  - Mitrović, Aleksandra
AU  - Gojgić-Cvijović, Gordana
AU  - Stepić, Milutin
AU  - Petković, Marijana
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3891
AB  - Abstract
Objects of the present study are improved fullerene C60 drug carrier properties trough encapsulation by microbial polysaccharides, levan (LEV), pullulan (PUL), and their hydrophobized cholesterol-derivatives (CHL and CHP), that show better interaction with cancer cells. The zeta potential, polydispersity index, and the diameter of particles were determined, and their cytotoxicity against three cancer cell lines were tested. Biochemical changes in HeLa cells are analyzed by synchrotron radiation (SR) FTIR spectro-microscopy combined with the principal component analysis (PCA). The most significant changes occur in HeLa cells treated with LEV-C60 and correspond to the changes in the protein region, i.e. Amide Iband, and the changes in the structure of lipid bodies and membrane fluidity are evident. The highest cytotoxicity was also induced by LEV-C60. In HeLa cells, cytotoxicity could not be strictly associated with biochemical changes in lipids, proteins and nucleic acids, but these findings are significant contribution to the study of the mechanism of interaction of C60-based nanoparticles with cellular biomolecules. In conclusion, LEV, PUL, CHL, and CHP enhanced fullerene C60potential to be used as target drug delivery system with the ability to induce specific intracellular changes in HeLa cancer cells.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives
VL  - 165
IS  - B
SP  - 2541
EP  - 2549
DO  - 10.1016/j.ijbiomac.2020.10.141
ER  - 

@article{
author = "Nešić, Maja D. and Dučić, Tanja and Liang, Xinyue and Algarra, Manuel and Mi, Lan and Korićanac, Lela and Žakula, Jelena and Kop, Tatjana and Bjelaković, Mira and Mitrović, Aleksandra and Gojgić-Cvijović, Gordana and Stepić, Milutin and Petković, Marijana",
year = "2020",
abstract = "Abstract
Objects of the present study are improved fullerene C60 drug carrier properties trough encapsulation by microbial polysaccharides, levan (LEV), pullulan (PUL), and their hydrophobized cholesterol-derivatives (CHL and CHP), that show better interaction with cancer cells. The zeta potential, polydispersity index, and the diameter of particles were determined, and their cytotoxicity against three cancer cell lines were tested. Biochemical changes in HeLa cells are analyzed by synchrotron radiation (SR) FTIR spectro-microscopy combined with the principal component analysis (PCA). The most significant changes occur in HeLa cells treated with LEV-C60 and correspond to the changes in the protein region, i.e. Amide Iband, and the changes in the structure of lipid bodies and membrane fluidity are evident. The highest cytotoxicity was also induced by LEV-C60. In HeLa cells, cytotoxicity could not be strictly associated with biochemical changes in lipids, proteins and nucleic acids, but these findings are significant contribution to the study of the mechanism of interaction of C60-based nanoparticles with cellular biomolecules. In conclusion, LEV, PUL, CHL, and CHP enhanced fullerene C60potential to be used as target drug delivery system with the ability to induce specific intracellular changes in HeLa cancer cells.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives",
volume = "165",
number = "B",
pages = "2541-2549",
doi = "10.1016/j.ijbiomac.2020.10.141"
}

Nešić, M. D., Dučić, T., Liang, X., Algarra, M., Mi, L., Korićanac, L., Žakula, J., Kop, T., Bjelaković, M., Mitrović, A., Gojgić-Cvijović, G., Stepić, M.,& Petković, M.. (2020). SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives. in International Journal of Biological Macromolecules
Elsevier., 165(B), 2541-2549.
https://doi.org/10.1016/j.ijbiomac.2020.10.141

Nešić MD, Dučić T, Liang X, Algarra M, Mi L, Korićanac L, Žakula J, Kop T, Bjelaković M, Mitrović A, Gojgić-Cvijović G, Stepić M, Petković M. SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives. in International Journal of Biological Macromolecules. 2020;165(B):2541-2549.
doi:10.1016/j.ijbiomac.2020.10.141 .

Nešić, Maja D., Dučić, Tanja, Liang, Xinyue, Algarra, Manuel, Mi, Lan, Korićanac, Lela, Žakula, Jelena, Kop, Tatjana, Bjelaković, Mira, Mitrović, Aleksandra, Gojgić-Cvijović, Gordana, Stepić, Milutin, Petković, Marijana, "SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives" in International Journal of Biological Macromolecules, 165, no. B (2020):2541-2549,
https://doi.org/10.1016/j.ijbiomac.2020.10.141 . .

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  - 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  - 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  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Pavlović, Vladimir D.
AU  - Robeyns, Koen
AU  - Juranić, Zorica
AU  - Matić, Ivana Z.
AU  - Novaković, Irena
AU  - Sladić, Dušan
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/945
AB  - The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity.
PB  - Elsevier Science Inc, New York
T2  - Steroids
T1  - New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities
VL  - 77
IS  - 5
SP  - 558
EP  - 565
DO  - 10.1016/j.steroids.2012.01.021
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Pavlović, Vladimir D. and Robeyns, Koen and Juranić, Zorica and Matić, Ivana Z. and Novaković, Irena and Sladić, Dušan",
year = "2012",
abstract = "The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities",
volume = "77",
number = "5",
pages = "558-565",
doi = "10.1016/j.steroids.2012.01.021"
}

Krstić, N., Bjelaković, M., Pavlović, V. D., Robeyns, K., Juranić, Z., Matić, I. Z., Novaković, I.,& Sladić, D.. (2012). New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities. in Steroids
Elsevier Science Inc, New York., 77(5), 558-565.
https://doi.org/10.1016/j.steroids.2012.01.021

Krstić N, Bjelaković M, Pavlović VD, Robeyns K, Juranić Z, Matić IZ, Novaković I, Sladić D. New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities. in Steroids. 2012;77(5):558-565.
doi:10.1016/j.steroids.2012.01.021 .

Krstić, Natalija, Bjelaković, Mira, Pavlović, Vladimir D., Robeyns, Koen, Juranić, Zorica, Matić, Ivana Z., Novaković, Irena, Sladić, Dušan, "New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities" in Steroids, 77, no. 5 (2012):558-565,
https://doi.org/10.1016/j.steroids.2012.01.021 . .

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 . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Dabović, Milan
AU  - Pavlović, Vladimir D.
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/629
AB  - The reactions of selected alpha,beta-unsaturated steroidal ketones with Lawesson's reagent (LR) in CH(2)Cl(2) and toluene under the standard reaction conditions and with a combination of phosphorus pentasulfide with hexamethyldisiloxane (P(4)S(10)/HMDO) in 1,2-dichlorobenzene (ODCB) under microwave irradiation were investigated and for this purpose several cholestane, androstane and pregnane carbonyl derivatives were chosen. Depending on the reagent and the solvent, 19 new sulfur containing compounds, including dithiones 4c and 4d, alpha,beta-unsaturated 3-thiones 3a-e, dimer-sulfides 2a-e, 1,2,4-trithiolanes 5a-e and phosphonotrithioates 6b-e were synthesized. All newly prepared compounds were characterized by IR, (1)H- and (13)C-NMR spectroscopy and elemental analysis.
PB  - MDPI
T2  - Molecules
T1  - Thionation of Some alpha,beta-Unsaturated Steroidal Ketones
VL  - 15
IS  - 5
SP  - 3462
EP  - 3477
DO  - 10.3390/molecules15053462
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Dabović, Milan and Pavlović, Vladimir D.",
year = "2010",
abstract = "The reactions of selected alpha,beta-unsaturated steroidal ketones with Lawesson's reagent (LR) in CH(2)Cl(2) and toluene under the standard reaction conditions and with a combination of phosphorus pentasulfide with hexamethyldisiloxane (P(4)S(10)/HMDO) in 1,2-dichlorobenzene (ODCB) under microwave irradiation were investigated and for this purpose several cholestane, androstane and pregnane carbonyl derivatives were chosen. Depending on the reagent and the solvent, 19 new sulfur containing compounds, including dithiones 4c and 4d, alpha,beta-unsaturated 3-thiones 3a-e, dimer-sulfides 2a-e, 1,2,4-trithiolanes 5a-e and phosphonotrithioates 6b-e were synthesized. All newly prepared compounds were characterized by IR, (1)H- and (13)C-NMR spectroscopy and elemental analysis.",
publisher = "MDPI",
journal = "Molecules",
title = "Thionation of Some alpha,beta-Unsaturated Steroidal Ketones",
volume = "15",
number = "5",
pages = "3462-3477",
doi = "10.3390/molecules15053462"
}

Krstić, N., Bjelaković, M., Dabović, M.,& Pavlović, V. D.. (2010). Thionation of Some alpha,beta-Unsaturated Steroidal Ketones. in Molecules
MDPI., 15(5), 3462-3477.
https://doi.org/10.3390/molecules15053462

Krstić N, Bjelaković M, Dabović M, Pavlović VD. Thionation of Some alpha,beta-Unsaturated Steroidal Ketones. in Molecules. 2010;15(5):3462-3477.
doi:10.3390/molecules15053462 .

Krstić, Natalija, Bjelaković, Mira, Dabović, Milan, Pavlović, Vladimir D., "Thionation of Some alpha,beta-Unsaturated Steroidal Ketones" in Molecules, 15, no. 5 (2010):3462-3477,
https://doi.org/10.3390/molecules15053462 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Todorović, Nina
AU  - Krunić, Aleksej
AU  - Tinant, Bernard
AU  - Dabović, Milan
AU  - Pavlović, Vladimir D.
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/620
AB  - In this paper a synthetic pathway to the modified 5,10:13,14-bisfragmentation cholestane derivatives 8-14 is described. The synthesis involves introduction of the 5α- and 14α-hydroxyl groups in the cholestane molecule and subsequent cleavage of the C(5)-C(10) bond in 5α,14α-dihydroxycholestan-3β-yl acetate (4) with the HgO/I2 reagent and the C(13)-C(14) bond in the stereoisomeric 14α-hydroxy-5,10-secosteroids 5 and 6 with the Pb(OAc)4/I2 reagent. Complete and unambiguous 1H and 13C NMR resonance assignments of the obtained secosteroids, as well as the solution conformations of their 10- and 9-membered rings were determined by extensive analysis of 1D and 2D NMR spectral data. The structures and the solid-state conformations of 5,10-secosteroids 5-7 were confirmed by X-ray analysis. All diseco-compounds have a novel 5,10:13,14-disecocholestane skeleton.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings
VL  - 65
IS  - 46
SP  - 9557
EP  - 9568
DO  - 10.1016/j.tet.2009.09.066
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Todorović, Nina and Krunić, Aleksej and Tinant, Bernard and Dabović, Milan and Pavlović, Vladimir D.",
year = "2009",
abstract = "In this paper a synthetic pathway to the modified 5,10:13,14-bisfragmentation cholestane derivatives 8-14 is described. The synthesis involves introduction of the 5α- and 14α-hydroxyl groups in the cholestane molecule and subsequent cleavage of the C(5)-C(10) bond in 5α,14α-dihydroxycholestan-3β-yl acetate (4) with the HgO/I2 reagent and the C(13)-C(14) bond in the stereoisomeric 14α-hydroxy-5,10-secosteroids 5 and 6 with the Pb(OAc)4/I2 reagent. Complete and unambiguous 1H and 13C NMR resonance assignments of the obtained secosteroids, as well as the solution conformations of their 10- and 9-membered rings were determined by extensive analysis of 1D and 2D NMR spectral data. The structures and the solid-state conformations of 5,10-secosteroids 5-7 were confirmed by X-ray analysis. All diseco-compounds have a novel 5,10:13,14-disecocholestane skeleton.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings",
volume = "65",
number = "46",
pages = "9557-9568",
doi = "10.1016/j.tet.2009.09.066"
}

Bjelaković, M., Krstić, N., Todorović, N., Krunić, A., Tinant, B., Dabović, M.,& Pavlović, V. D.. (2009). 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 65(46), 9557-9568.
https://doi.org/10.1016/j.tet.2009.09.066

Bjelaković M, Krstić N, Todorović N, Krunić A, Tinant B, Dabović M, Pavlović VD. 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings. in Tetrahedron. 2009;65(46):9557-9568.
doi:10.1016/j.tet.2009.09.066 .

Bjelaković, Mira, Krstić, Natalija, Todorović, Nina, Krunić, Aleksej, Tinant, Bernard, Dabović, Milan, Pavlović, Vladimir D., "5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings" in Tetrahedron, 65, no. 46 (2009):9557-9568,
https://doi.org/10.1016/j.tet.2009.09.066 . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Žižak, Željko
AU  - Pavlović, Mirjana
AU  - Juranić, Zorica
AU  - Pavlović, Vladimir D.
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/363
AB  - The antiproliferative activity of previously synthesized (Z)-cholest-4-en-6-one oxime (1), (E)-cholest-4-en-6-one oxime (2), 7-aza-B-homocholest-4-en-6-one (3) and 6-aza-B-homocholest-4-en-7-one (4) and newly synthesized 6-thioxo-7-aza-B-homocholest-4-ene (5) and 6-aza-7-thioxo-B-homocholest-4-ene (6) was tested for their possible effects against two human tumor cell lines, cervical carcinoma (HeLa) and chronic myelogenous leukemia (K-562). Compounds 1-6, exerted a dose-dependent antiproliferative effect toward cell lines used in experimental design, showing high selectivity in their action for tumor cells in comparison to normal immunocompetent cells (non-stimulated PBMC and PHA-stimulated PBMC). Compounds 2, 3 and 4 exhibited a very high but selective antitumor activity, by inducing apoptosis in sensitive, for that purpose targeted tumor cell line (HeLa cells). Low toxic effect upon both non-stimulated, and PHA stimulated PBMCs from control, healthy volunteers, has been detected for compounds 1, 2, 3 and 4. The possible reasons for profound differences in the effects of this spectrum of steroidal compounds between tumor cell lines and normal stimulated and non-stimulated PBMCs are discussed. The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined.
PB  - Elsevier
T2  - Steroids
T1  - Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities
VL  - 72
IS  - 5
SP  - 406
EP  - 414
DO  - 10.1016/j.steroids.2007.02.005
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Žižak, Željko and Pavlović, Mirjana and Juranić, Zorica and Pavlović, Vladimir D.",
year = "2007",
abstract = "The antiproliferative activity of previously synthesized (Z)-cholest-4-en-6-one oxime (1), (E)-cholest-4-en-6-one oxime (2), 7-aza-B-homocholest-4-en-6-one (3) and 6-aza-B-homocholest-4-en-7-one (4) and newly synthesized 6-thioxo-7-aza-B-homocholest-4-ene (5) and 6-aza-7-thioxo-B-homocholest-4-ene (6) was tested for their possible effects against two human tumor cell lines, cervical carcinoma (HeLa) and chronic myelogenous leukemia (K-562). Compounds 1-6, exerted a dose-dependent antiproliferative effect toward cell lines used in experimental design, showing high selectivity in their action for tumor cells in comparison to normal immunocompetent cells (non-stimulated PBMC and PHA-stimulated PBMC). Compounds 2, 3 and 4 exhibited a very high but selective antitumor activity, by inducing apoptosis in sensitive, for that purpose targeted tumor cell line (HeLa cells). Low toxic effect upon both non-stimulated, and PHA stimulated PBMCs from control, healthy volunteers, has been detected for compounds 1, 2, 3 and 4. The possible reasons for profound differences in the effects of this spectrum of steroidal compounds between tumor cell lines and normal stimulated and non-stimulated PBMCs are discussed. The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined.",
publisher = "Elsevier",
journal = "Steroids",
title = "Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities",
volume = "72",
number = "5",
pages = "406-414",
doi = "10.1016/j.steroids.2007.02.005"
}

Krstić, N., Bjelaković, M., Žižak, Ž., Pavlović, M., Juranić, Z.,& Pavlović, V. D.. (2007). Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities. in Steroids
Elsevier., 72(5), 406-414.
https://doi.org/10.1016/j.steroids.2007.02.005

Krstić N, Bjelaković M, Žižak Ž, Pavlović M, Juranić Z, Pavlović VD. Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities. in Steroids. 2007;72(5):406-414.
doi:10.1016/j.steroids.2007.02.005 .

Krstić, Natalija, Bjelaković, Mira, Žižak, Željko, Pavlović, Mirjana, Juranić, Zorica, Pavlović, Vladimir D., "Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities" in Steroids, 72, no. 5 (2007):406-414,
https://doi.org/10.1016/j.steroids.2007.02.005 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Gođevac, Dejan
AU  - Milić, Dragana
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4183
AB  - Four new fullero-steroids were synthesized starting from gamma-aminobutyric acid (GABA)-incorporated fulleropyrrolidine and corresponding sterols. The synthesis, characterization, preliminary study on in vitro antioxidant activity as well as the steady state photophysical properties are presented. All synthesized compounds showed antioxidant activity 2-3-fold higher than the parent fullerene. The most active compound appeared to be as potent as standard antioxidant BHT (2,6-di-tert-butyl-4-methylphenol). Also, all of them fluoresce 6-8-fold stronger than C-60, thus representing potential irradiation assisted pro-oxidants. With significantly increased lipophilicity, it could be expected that attached steroidal subunit enables better penetration Of C60 to living cell membranes, thus facilitating its antioxidant activity. Based on all obtained results, newly synthesized covalent fullero-steroidal conjugates represent good candidates for potential antioxidants as well as pro-oxidants. (c) 2007 Elsevier Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Carbon
T1  - Synthesis and antioxidant properties of fullero-steroidal covalent conjugates
VL  - 45
IS  - 11
SP  - 2260
EP  - 2265
DO  - 10.1016/j.carbon.2007.06.027
ER  - 

@article{
author = "Bjelaković, Mira and Gođevac, Dejan and Milić, Dragana",
year = "2007",
abstract = "Four new fullero-steroids were synthesized starting from gamma-aminobutyric acid (GABA)-incorporated fulleropyrrolidine and corresponding sterols. The synthesis, characterization, preliminary study on in vitro antioxidant activity as well as the steady state photophysical properties are presented. All synthesized compounds showed antioxidant activity 2-3-fold higher than the parent fullerene. The most active compound appeared to be as potent as standard antioxidant BHT (2,6-di-tert-butyl-4-methylphenol). Also, all of them fluoresce 6-8-fold stronger than C-60, thus representing potential irradiation assisted pro-oxidants. With significantly increased lipophilicity, it could be expected that attached steroidal subunit enables better penetration Of C60 to living cell membranes, thus facilitating its antioxidant activity. Based on all obtained results, newly synthesized covalent fullero-steroidal conjugates represent good candidates for potential antioxidants as well as pro-oxidants. (c) 2007 Elsevier Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Carbon",
title = "Synthesis and antioxidant properties of fullero-steroidal covalent conjugates",
volume = "45",
number = "11",
pages = "2260-2265",
doi = "10.1016/j.carbon.2007.06.027"
}

Bjelaković, M., Gođevac, D.,& Milić, D.. (2007). Synthesis and antioxidant properties of fullero-steroidal covalent conjugates. in Carbon
Oxford : Pergamon-Elsevier Science Ltd., 45(11), 2260-2265.
https://doi.org/10.1016/j.carbon.2007.06.027

Bjelaković M, Gođevac D, Milić D. Synthesis and antioxidant properties of fullero-steroidal covalent conjugates. in Carbon. 2007;45(11):2260-2265.
doi:10.1016/j.carbon.2007.06.027 .

Bjelaković, Mira, Gođevac, Dejan, Milić, Dragana, "Synthesis and antioxidant properties of fullero-steroidal covalent conjugates" in Carbon, 45, no. 11 (2007):2260-2265,
https://doi.org/10.1016/j.carbon.2007.06.027 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Juranić, Nenad
AU  - Dabović, Milan
AU  - Gojković, S.V.
AU  - Kessler, M.
AU  - Kalvoda, J.
AU  - Pavlović, Vladimir D.
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/358
AB  - We report herein the synthesis of a novel modified steroid with two rigidly positioned amino acids in C- and N-protected forms (Gly-OtBu and N-Fmoc-l-Phe) at the angular positions (C-18 methylamino group and C-19 carboxylic function) of the steroid nucleus via amide bonds, starting from 18-cyanopregnenolone acetate over 10 steps. In an attempt to gain more insight into the structural and conformational features of this novel 18-Phe,19-Gly-containing steroidal compound, we describe the detailed 2D NMR spectral analysis. Despite the large size and the conformational flexibility of the amino acid units in this molecule, conformational analysis by NOESY connectivities showed the existence of mainly one conformation (∼95%) in CDCl3 solution with approximately parallel orientation of the phenylalanine and glycine moieties.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound
VL  - 63
IS  - 40
SP  - 9960
EP  - 9969
DO  - 10.1016/j.tet.2007.07.056
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Juranić, Nenad and Dabović, Milan and Gojković, S.V. and Kessler, M. and Kalvoda, J. and Pavlović, Vladimir D.",
year = "2007",
abstract = "We report herein the synthesis of a novel modified steroid with two rigidly positioned amino acids in C- and N-protected forms (Gly-OtBu and N-Fmoc-l-Phe) at the angular positions (C-18 methylamino group and C-19 carboxylic function) of the steroid nucleus via amide bonds, starting from 18-cyanopregnenolone acetate over 10 steps. In an attempt to gain more insight into the structural and conformational features of this novel 18-Phe,19-Gly-containing steroidal compound, we describe the detailed 2D NMR spectral analysis. Despite the large size and the conformational flexibility of the amino acid units in this molecule, conformational analysis by NOESY connectivities showed the existence of mainly one conformation (∼95%) in CDCl3 solution with approximately parallel orientation of the phenylalanine and glycine moieties.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound",
volume = "63",
number = "40",
pages = "9960-9969",
doi = "10.1016/j.tet.2007.07.056"
}

Bjelaković, M., Krstić, N., Juranić, N., Dabović, M., Gojković, S.V., Kessler, M., Kalvoda, J.,& Pavlović, V. D.. (2007). Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 63(40), 9960-9969.
https://doi.org/10.1016/j.tet.2007.07.056

Bjelaković M, Krstić N, Juranić N, Dabović M, Gojković S, Kessler M, Kalvoda J, Pavlović VD. Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound. in Tetrahedron. 2007;63(40):9960-9969.
doi:10.1016/j.tet.2007.07.056 .

Bjelaković, Mira, Krstić, Natalija, Juranić, Nenad, Dabović, Milan, Gojković, S.V., Kessler, M., Kalvoda, J., Pavlović, Vladimir D., "Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound" in Tetrahedron, 63, no. 40 (2007):9960-9969,
https://doi.org/10.1016/j.tet.2007.07.056 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Tinant, Bernard
AU  - Kalvoda, Jaroslav
AU  - Csanadi, Janos
AU  - Pavlović, Vladimir D.
PY  - 2005
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4186
AB  - The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation of type C1 in CDCl3 solution.
PB  - Wiley
T2  - Helvetica Chimica Acta
T1  - Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis
VL  - 88
IS  - 10
SP  - 2812
EP  - 2821
DO  - 10.1002/hlca.200590221
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Tinant, Bernard and Kalvoda, Jaroslav and Csanadi, Janos and Pavlović, Vladimir D.",
year = "2005",
abstract = "The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation of type C1 in CDCl3 solution.",
publisher = "Wiley",
journal = "Helvetica Chimica Acta",
title = "Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis",
volume = "88",
number = "10",
pages = "2812-2821",
doi = "10.1002/hlca.200590221"
}

Bjelaković, M., Krstić, N., Tinant, B., Kalvoda, J., Csanadi, J.,& Pavlović, Vladimir D.. (2005). Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis. in Helvetica Chimica Acta
Wiley., 88(10), 2812-2821.
https://doi.org/10.1002/hlca.200590221

Bjelaković M, Krstić N, Tinant B, Kalvoda J, Csanadi J, Pavlović V. Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis. in Helvetica Chimica Acta. 2005;88(10):2812-2821.
doi:10.1002/hlca.200590221 .

Bjelaković, Mira, Krstić, Natalija, Tinant, Bernard, Kalvoda, Jaroslav, Csanadi, Janos, Pavlović, Vladimir D., "Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis" in Helvetica Chimica Acta, 88, no. 10 (2005):2812-2821,
https://doi.org/10.1002/hlca.200590221 . .