TY  - JOUR
AU  - Marković, Maja D.
AU  - Panić, Vesna V.
AU  - Savić, Sanja I.
AU  - Ugrinović, Vukašin Đ.
AU  - Pjanović, Rada V.
AU  - Spasojević, Milica M.
AU  - Spasojević, Pavle M.
PY  - 2022
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5092
AB  - Materials sensitive to external stimuli are recognized as safe and effective tool able to respond to specific demands in the therapy of various diseases. Thermo sensitive hydrogels based on poly(N-isopropylacrylamide) (P(NIPAAM)) are widely investigated for targeted drug delivery. Still, the abundance of the stimuli in the human body often requires more than one responsive group able to act simultaneously to achieve optimal therapeutic effects. Due to its pH sensitivity and bio-based production, crotonic acid (CA) was a monomer of choice for preparation of eco-friendly copolymer hydrogels based on NIPAAM and CA (P(NIPAAMcoCA)), which turned to be thermo and pH sensitive at the same time. The potential of the P(NIPAAMcoCA) system for encapsulation and controlled release of drugs with different solubility was investigated engaging water-soluble lidocaine hydrochloride and poorly water-soluble ibuprofen as model drugs. The hydrogels were characterized by various technics: FTIR, DSC, SEM and single compressive tests, while swelling behavior and controlled release of the drugs were analyzed with respect to the CA amount in two environments with different pH values at 25 °C and 37 °C. It was demonstrated that due to their dual responsiveness the P(NIPAAMcoCA) hydrogels have potential for controlled release of drugs with different solubility.
PB  - Elsevier
T2  - Microporous and Mesoporous Materials
T1  - Biobased thermo/pH sensitive poly(N-isopropylacrylamide-co-crotonic acid) hydrogels for targeted drug delivery
SP  - 111817
VL  - 335
DO  - 10.1016/j.micromeso.2022.111817
ER  - 

@article{
author = "Marković, Maja D. and Panić, Vesna V. and Savić, Sanja I. and Ugrinović, Vukašin Đ. and Pjanović, Rada V. and Spasojević, Milica M. and Spasojević, Pavle M.",
year = "2022",
abstract = "Materials sensitive to external stimuli are recognized as safe and effective tool able to respond to specific demands in the therapy of various diseases. Thermo sensitive hydrogels based on poly(N-isopropylacrylamide) (P(NIPAAM)) are widely investigated for targeted drug delivery. Still, the abundance of the stimuli in the human body often requires more than one responsive group able to act simultaneously to achieve optimal therapeutic effects. Due to its pH sensitivity and bio-based production, crotonic acid (CA) was a monomer of choice for preparation of eco-friendly copolymer hydrogels based on NIPAAM and CA (P(NIPAAMcoCA)), which turned to be thermo and pH sensitive at the same time. The potential of the P(NIPAAMcoCA) system for encapsulation and controlled release of drugs with different solubility was investigated engaging water-soluble lidocaine hydrochloride and poorly water-soluble ibuprofen as model drugs. The hydrogels were characterized by various technics: FTIR, DSC, SEM and single compressive tests, while swelling behavior and controlled release of the drugs were analyzed with respect to the CA amount in two environments with different pH values at 25 °C and 37 °C. It was demonstrated that due to their dual responsiveness the P(NIPAAMcoCA) hydrogels have potential for controlled release of drugs with different solubility.",
publisher = "Elsevier",
journal = "Microporous and Mesoporous Materials",
title = "Biobased thermo/pH sensitive poly(N-isopropylacrylamide-co-crotonic acid) hydrogels for targeted drug delivery",
pages = "111817",
volume = "335",
doi = "10.1016/j.micromeso.2022.111817"
}

Marković, M. D., Panić, V. V., Savić, S. I., Ugrinović, V. Đ., Pjanović, R. V., Spasojević, M. M.,& Spasojević, P. M.. (2022). Biobased thermo/pH sensitive poly(N-isopropylacrylamide-co-crotonic acid) hydrogels for targeted drug delivery. in Microporous and Mesoporous Materials
Elsevier., 335, 111817.
https://doi.org/10.1016/j.micromeso.2022.111817

Marković MD, Panić VV, Savić SI, Ugrinović VĐ, Pjanović RV, Spasojević MM, Spasojević PM. Biobased thermo/pH sensitive poly(N-isopropylacrylamide-co-crotonic acid) hydrogels for targeted drug delivery. in Microporous and Mesoporous Materials. 2022;335:111817.
doi:10.1016/j.micromeso.2022.111817 .

Marković, Maja D., Panić, Vesna V., Savić, Sanja I., Ugrinović, Vukašin Đ., Pjanović, Rada V., Spasojević, Milica M., Spasojević, Pavle M., "Biobased thermo/pH sensitive poly(N-isopropylacrylamide-co-crotonic acid) hydrogels for targeted drug delivery" in Microporous and Mesoporous Materials, 335 (2022):111817,
https://doi.org/10.1016/j.micromeso.2022.111817 . .

TY  - JOUR
AU  - Marković, Maja D.
AU  - Tadić, Julijana D.
AU  - Savić, Sanja I.
AU  - Matić, Ivana Z.
AU  - Stanojković, Tatjana P.
AU  - Mijin, Dušan
AU  - Panić, Vesna V.
PY  - 2022
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5136
AB  - Researchers are faced with everyday demands for safer and more efficient therapy for many diseases, especially serious one such as various types of cancer. Numerous anticancer drugs are poorly-water soluble and therefore their encapsulation and controlled release remain quite challenge. In present study, we deepened our research of hydrophilic carrier based on poly(methacrylic acid) and casein (PMAC) by investigating its potential for encapsulation and controlled release of novel poorly water-soluble dihydropyrimidion-azo-pyridon compound (DHPMP). DHPMP is a dye that has been proven to show cytotoxic activity against chronic myeloid leukemia K562 cells. By encapsulating DHPMP into the carrier and delivering it into the intestines, DHPMP absorption could be the fastest and the number of therapeutic doses and side effects can be reduced. Carriers based on PMAC and DHPMP (PMAC-DHPMP) were synthetized and characterized by FTIR, SEM and single compression tests. The swelling behavior of PMAC-DHPMP carriers and cumulative DHPMP release were investigated depending on the amount of crosslinker and encapsulated DHPMP in two media which were simulating pH environments in human stomach and intestines. The prolonged and controlled release of DHPMP was achieved. In vitro cytotoxic activity of PMAC-DHPMP carriers against K562 cells and the cell cycle analysis showed great potential of the carriers for application in leukemia treatment.
PB  - John Wiley and Sons Inc
T2  - Journal of Biomedical Materials Research - Part A
T1  - Soft 3D hybrid network for delivery and controlled release of poorly soluble dihydropyrimidinone compound: An insight into the novel system for potential application in leukemia treatment
DO  - 10.1002/jbm.a.37396
ER  - 

@article{
author = "Marković, Maja D. and Tadić, Julijana D. and Savić, Sanja I. and Matić, Ivana Z. and Stanojković, Tatjana P. and Mijin, Dušan and Panić, Vesna V.",
year = "2022",
abstract = "Researchers are faced with everyday demands for safer and more efficient therapy for many diseases, especially serious one such as various types of cancer. Numerous anticancer drugs are poorly-water soluble and therefore their encapsulation and controlled release remain quite challenge. In present study, we deepened our research of hydrophilic carrier based on poly(methacrylic acid) and casein (PMAC) by investigating its potential for encapsulation and controlled release of novel poorly water-soluble dihydropyrimidion-azo-pyridon compound (DHPMP). DHPMP is a dye that has been proven to show cytotoxic activity against chronic myeloid leukemia K562 cells. By encapsulating DHPMP into the carrier and delivering it into the intestines, DHPMP absorption could be the fastest and the number of therapeutic doses and side effects can be reduced. Carriers based on PMAC and DHPMP (PMAC-DHPMP) were synthetized and characterized by FTIR, SEM and single compression tests. The swelling behavior of PMAC-DHPMP carriers and cumulative DHPMP release were investigated depending on the amount of crosslinker and encapsulated DHPMP in two media which were simulating pH environments in human stomach and intestines. The prolonged and controlled release of DHPMP was achieved. In vitro cytotoxic activity of PMAC-DHPMP carriers against K562 cells and the cell cycle analysis showed great potential of the carriers for application in leukemia treatment.",
publisher = "John Wiley and Sons Inc",
journal = "Journal of Biomedical Materials Research - Part A",
title = "Soft 3D hybrid network for delivery and controlled release of poorly soluble dihydropyrimidinone compound: An insight into the novel system for potential application in leukemia treatment",
doi = "10.1002/jbm.a.37396"
}

Marković, M. D., Tadić, J. D., Savić, S. I., Matić, I. Z., Stanojković, T. P., Mijin, D.,& Panić, V. V.. (2022). Soft 3D hybrid network for delivery and controlled release of poorly soluble dihydropyrimidinone compound: An insight into the novel system for potential application in leukemia treatment. in Journal of Biomedical Materials Research - Part A
John Wiley and Sons Inc..
https://doi.org/10.1002/jbm.a.37396

Marković MD, Tadić JD, Savić SI, Matić IZ, Stanojković TP, Mijin D, Panić VV. Soft 3D hybrid network for delivery and controlled release of poorly soluble dihydropyrimidinone compound: An insight into the novel system for potential application in leukemia treatment. in Journal of Biomedical Materials Research - Part A. 2022;.
doi:10.1002/jbm.a.37396 .

Marković, Maja D., Tadić, Julijana D., Savić, Sanja I., Matić, Ivana Z., Stanojković, Tatjana P., Mijin, Dušan, Panić, Vesna V., "Soft 3D hybrid network for delivery and controlled release of poorly soluble dihydropyrimidinone compound: An insight into the novel system for potential application in leukemia treatment" in Journal of Biomedical Materials Research - Part A (2022),
https://doi.org/10.1002/jbm.a.37396 . .

TY  - JOUR
AU  - Assaleh, Mohamed H.
AU  - Bjelogrlic, Snezana K.
AU  - Prlainović, Nevena
AU  - Cvijetić, Ilija
AU  - Bozic, Aleksandra
AU  - Aranđelović, Irena
AU  - Vukovic, Dragana
AU  - Marinković, Aleksandar
PY  - 2022
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4986
AB  - A series of twelve novel hybrids of cinnamic acid and thiocarbohydrazones were designed, synthesized in high yield using a simple coupling strategy via acid chlorides, and evaluated for their impact against Mycobacterium tuberculosis (Mtb) and cancer cells survival. Among them, compound 3 demonstrated strong anti-Mtb activity by reducing bacilli survival for>90 % in all three treated Mtb isolates, whereas isoniazid and rifampicin did not. Moreover, compound 3 didn't affect vitality of HepG-2 cells, implying on advantageous hepatotoxicity profile compared to current therapeutic options for tuberculosis. Compounds 2a and 3b displayed as strong inducers of apoptosis in A549 cells, both activating intrinsic caspase pathway and cell cycle arrest at the G0/ G1 phase. Subsequent analyses disclosed differences in their activities, where 3b has ability to induce production of mitochondrial superoxide anions, while 2a significantly inhibited cellular mobility. More importantly, 3b considerably affected viability of HepG-2 and HaCaT cells, whereas 2a had moderate impact only on the later. Molecular modeling studies indicated high permeability and good absorption through the human intestine, and moderate aqueous solubility with poor blood-brain barrier permeability. In summary, our results reveal that novel compounds 3 and 2a represent promising agents for tuberculosis and cancer treatment, respectively, indicating that fur-ther investigation needs to be performed to clarify the mechanisms of their anti-Mtb and anticancer activity. (c) 2021 The Authors. Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
T2  - Arabian Journal of Chemistry
T1  - Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid
IS  - 1
SP  - 103532
VL  - 15
DO  - 10.1016/j.arabjc.2021.103532
ER  - 

@article{
author = "Assaleh, Mohamed H. and Bjelogrlic, Snezana K. and Prlainović, Nevena and Cvijetić, Ilija and Bozic, Aleksandra and Aranđelović, Irena and Vukovic, Dragana and Marinković, Aleksandar",
year = "2022",
abstract = "A series of twelve novel hybrids of cinnamic acid and thiocarbohydrazones were designed, synthesized in high yield using a simple coupling strategy via acid chlorides, and evaluated for their impact against Mycobacterium tuberculosis (Mtb) and cancer cells survival. Among them, compound 3 demonstrated strong anti-Mtb activity by reducing bacilli survival for>90 % in all three treated Mtb isolates, whereas isoniazid and rifampicin did not. Moreover, compound 3 didn't affect vitality of HepG-2 cells, implying on advantageous hepatotoxicity profile compared to current therapeutic options for tuberculosis. Compounds 2a and 3b displayed as strong inducers of apoptosis in A549 cells, both activating intrinsic caspase pathway and cell cycle arrest at the G0/ G1 phase. Subsequent analyses disclosed differences in their activities, where 3b has ability to induce production of mitochondrial superoxide anions, while 2a significantly inhibited cellular mobility. More importantly, 3b considerably affected viability of HepG-2 and HaCaT cells, whereas 2a had moderate impact only on the later. Molecular modeling studies indicated high permeability and good absorption through the human intestine, and moderate aqueous solubility with poor blood-brain barrier permeability. In summary, our results reveal that novel compounds 3 and 2a represent promising agents for tuberculosis and cancer treatment, respectively, indicating that fur-ther investigation needs to be performed to clarify the mechanisms of their anti-Mtb and anticancer activity. (c) 2021 The Authors. Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).",
journal = "Arabian Journal of Chemistry",
title = "Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid",
number = "1",
pages = "103532",
volume = "15",
doi = "10.1016/j.arabjc.2021.103532"
}

Assaleh, M. H., Bjelogrlic, S. K., Prlainović, N., Cvijetić, I., Bozic, A., Aranđelović, I., Vukovic, D.,& Marinković, A.. (2022). Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid. in Arabian Journal of Chemistry, 15(1), 103532.
https://doi.org/10.1016/j.arabjc.2021.103532

Assaleh MH, Bjelogrlic SK, Prlainović N, Cvijetić I, Bozic A, Aranđelović I, Vukovic D, Marinković A. Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid. in Arabian Journal of Chemistry. 2022;15(1):103532.
doi:10.1016/j.arabjc.2021.103532 .

Assaleh, Mohamed H., Bjelogrlic, Snezana K., Prlainović, Nevena, Cvijetić, Ilija, Bozic, Aleksandra, Aranđelović, Irena, Vukovic, Dragana, Marinković, Aleksandar, "Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid" in Arabian Journal of Chemistry, 15, no. 1 (2022):103532,
https://doi.org/10.1016/j.arabjc.2021.103532 . .

TY  - JOUR
AU  - Tadić, Julijana
AU  - Lađarević, Jelena
AU  - Vitnik, Zeljko J.
AU  - Vitnik, Vesna D.
AU  - Stanojkovic, Tatjana P.
AU  - Matic, Ivana Z.
AU  - Mijin, Dušan
PY  - 2021
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4895
AB  - Seven novel azo dyes with 2-pyridone and dihydropyrimidinone moieties have been synthesized and thoroughly characterized. The azo-hydrazone tautomerism has been investigated by experimental and theoretical approaches. The optimizations of geometries have been performed with density functional theory (DFT). The vibrational and NMR spectra were calculated and correlated with experimental ones. Furthermore, quantum chemical descriptors were calculated and MEP maps were plotted to determine biological reactivity of dyes. The antioxidant assay evinced that 5, 6 and 7 are promising antioxidant candidates. In vitro cytotoxic activity was studied against three malignant cell lines: prostate adenocarcinoma (PC-3), lung carcinoma (A549) and chronic myelogenous leukemia (K562), as well as against human normal lung fibroblasts (MRC-5), using MTT assay. Examination of cytotoxic effects on human cancer cell lines showed the concentration dependent cytotoxicity of all investigated compounds. The K562 cells were the most sensitive to the cytotoxicity of the compounds 3, 5 and 6, wherein compound 5 was particularly prominent and selective in cytotoxic action between K562 (24.97 mu M) and PC-3 (48.98 mu M) cancer cells, and normal MRC-5 (91.11 mu M) cells. Moreover, the cell cycle analysis of compound 5 was examined in K562 cells, by flow cytometry, to study its mechanism of anticancer action. Finally, in silico evaluation of physicochemical parameters, druglikeness and ADME properties showed that investigated compounds are orally bioavailable with no permeation to the blood brain barrier.
T2  - Dyes and Pigments
T1  - Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity
VL  - 187
DO  - 10.1016/j.dyepig.2020.109123
ER  - 

@article{
author = "Tadić, Julijana and Lađarević, Jelena and Vitnik, Zeljko J. and Vitnik, Vesna D. and Stanojkovic, Tatjana P. and Matic, Ivana Z. and Mijin, Dušan",
year = "2021",
abstract = "Seven novel azo dyes with 2-pyridone and dihydropyrimidinone moieties have been synthesized and thoroughly characterized. The azo-hydrazone tautomerism has been investigated by experimental and theoretical approaches. The optimizations of geometries have been performed with density functional theory (DFT). The vibrational and NMR spectra were calculated and correlated with experimental ones. Furthermore, quantum chemical descriptors were calculated and MEP maps were plotted to determine biological reactivity of dyes. The antioxidant assay evinced that 5, 6 and 7 are promising antioxidant candidates. In vitro cytotoxic activity was studied against three malignant cell lines: prostate adenocarcinoma (PC-3), lung carcinoma (A549) and chronic myelogenous leukemia (K562), as well as against human normal lung fibroblasts (MRC-5), using MTT assay. Examination of cytotoxic effects on human cancer cell lines showed the concentration dependent cytotoxicity of all investigated compounds. The K562 cells were the most sensitive to the cytotoxicity of the compounds 3, 5 and 6, wherein compound 5 was particularly prominent and selective in cytotoxic action between K562 (24.97 mu M) and PC-3 (48.98 mu M) cancer cells, and normal MRC-5 (91.11 mu M) cells. Moreover, the cell cycle analysis of compound 5 was examined in K562 cells, by flow cytometry, to study its mechanism of anticancer action. Finally, in silico evaluation of physicochemical parameters, druglikeness and ADME properties showed that investigated compounds are orally bioavailable with no permeation to the blood brain barrier.",
journal = "Dyes and Pigments",
title = "Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity",
volume = "187",
doi = "10.1016/j.dyepig.2020.109123"
}

Tadić, J., Lađarević, J., Vitnik, Z. J., Vitnik, V. D., Stanojkovic, T. P., Matic, I. Z.,& Mijin, D.. (2021). Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity. in Dyes and Pigments, 187.
https://doi.org/10.1016/j.dyepig.2020.109123

Tadić J, Lađarević J, Vitnik ZJ, Vitnik VD, Stanojkovic TP, Matic IZ, Mijin D. Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity. in Dyes and Pigments. 2021;187.
doi:10.1016/j.dyepig.2020.109123 .

Tadić, Julijana, Lađarević, Jelena, Vitnik, Zeljko J., Vitnik, Vesna D., Stanojkovic, Tatjana P., Matic, Ivana Z., Mijin, Dušan, "Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity" in Dyes and Pigments, 187 (2021),
https://doi.org/10.1016/j.dyepig.2020.109123 . .