TY  - JOUR
AU  - Jovanović, Dunja
AU  - Filipović, Ana
AU  - Janjić, Goran
AU  - Lazarević-Pašti, Tamara
AU  - Džambaski, Zdravko
AU  - Bondžić, Bojan
AU  - Bondžić, Aleksandra
PY  - 2024
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7423
AB  - We have synthesized 22 C-1 functionalized-N-aryl-1,2,3,4-tetrahydroisoquinoline derivatives showing biological activities towards cholinergic enzymes. Synthesis was performed using visible-light-promoted photo-redox chemistry, starting from a common intermediate, and the application of this synthetic methodology drastically simplified synthetic routes and purification of desired compounds. All synthesized derivates were divided into four groups based on the substituents in the C-1 position, and their inhibition potencies towards two cholinergic enzymes, acetyl- and butyrylcholinesterase were evaluated. Most potent derivatives were selected, and kinetic analysis was further carried out to obtain insights into the mechanisms of inhibition of these two enzymes. Further validation of the mode of inhibition of cholinergic enzymes by the two most potent THIQ compounds, 3c and 3i, was performed using fluorescence-quenching titration studies. Molecular docking studies further confirmed the proposed mechanism of enzymes’ inhibition. In silico predictions of physicochemical properties, pharmacokinetics, drug-likeness, and medicinal chemistry friendliness of the selected most potent derivatives were performed using Swiss ADME tool. This was followed by UPLC-assisted log P determination and in vitro BBB permeability studies performed in order to assess the potential of the synthesized compounds to pass the BBB.
PB  - MDPI
T2  - International Journal of Molecular Sciences
T1  - Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates
VL  - 25
IS  - 2
SP  - 1033
DO  - 10.3390/ijms25021033
ER  - 

@article{
author = "Jovanović, Dunja and Filipović, Ana and Janjić, Goran and Lazarević-Pašti, Tamara and Džambaski, Zdravko and Bondžić, Bojan and Bondžić, Aleksandra",
year = "2024",
abstract = "We have synthesized 22 C-1 functionalized-N-aryl-1,2,3,4-tetrahydroisoquinoline derivatives showing biological activities towards cholinergic enzymes. Synthesis was performed using visible-light-promoted photo-redox chemistry, starting from a common intermediate, and the application of this synthetic methodology drastically simplified synthetic routes and purification of desired compounds. All synthesized derivates were divided into four groups based on the substituents in the C-1 position, and their inhibition potencies towards two cholinergic enzymes, acetyl- and butyrylcholinesterase were evaluated. Most potent derivatives were selected, and kinetic analysis was further carried out to obtain insights into the mechanisms of inhibition of these two enzymes. Further validation of the mode of inhibition of cholinergic enzymes by the two most potent THIQ compounds, 3c and 3i, was performed using fluorescence-quenching titration studies. Molecular docking studies further confirmed the proposed mechanism of enzymes’ inhibition. In silico predictions of physicochemical properties, pharmacokinetics, drug-likeness, and medicinal chemistry friendliness of the selected most potent derivatives were performed using Swiss ADME tool. This was followed by UPLC-assisted log P determination and in vitro BBB permeability studies performed in order to assess the potential of the synthesized compounds to pass the BBB.",
publisher = "MDPI",
journal = "International Journal of Molecular Sciences",
title = "Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates",
volume = "25",
number = "2",
pages = "1033",
doi = "10.3390/ijms25021033"
}

Jovanović, D., Filipović, A., Janjić, G., Lazarević-Pašti, T., Džambaski, Z., Bondžić, B.,& Bondžić, A.. (2024). Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates. in International Journal of Molecular Sciences
MDPI., 25(2), 1033.
https://doi.org/10.3390/ijms25021033

Jovanović D, Filipović A, Janjić G, Lazarević-Pašti T, Džambaski Z, Bondžić B, Bondžić A. Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates. in International Journal of Molecular Sciences. 2024;25(2):1033.
doi:10.3390/ijms25021033 .

Jovanović, Dunja, Filipović, Ana, Janjić, Goran, Lazarević-Pašti, Tamara, Džambaski, Zdravko, Bondžić, Bojan, Bondžić, Aleksandra, "Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates" in International Journal of Molecular Sciences, 25, no. 2 (2024):1033,
https://doi.org/10.3390/ijms25021033 . .

TY  - CONF
AU  - Jovanović, Dunja
AU  - Filipović, Ana
AU  - Bondžić, Bojan
AU  - Bondžić, Aleksandra
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7087
AB  - Alzheimer's disease (AD), the most common form of dementia, is a progressive neurological disorder characterized by losing memory and other intellectual abilities that are serious enough to interfere with daily life. The disease is associated with loss of cholinergic neurons in the brain and the decreased level of ACh. In order to raise the ACh level in the brain the acetylcholinesterase (AChE) inhibitors have been applied as relevant drugs in the AD therapy. On the other hand, these inhibitors treat and improve only symptoms indicating necessity for new better therapies. One of them could be based on the inhibition of butyrylcholinesterase (BuChE) because of its increased activity during late stage of AD. Therefore, the BuChE inhibitors should be of great importance in therapy. 1,2,3,4-tetrahydroisoquinolines (THIQ) are a large group of natural and synthetic compounds which exert diverse biological activities against various infectious 
pathogens and neurodegenerative disorders. Due to these reasons, the THIQ have attracted a lot of attention in the scientific community which has resulted in the development of novel THIQ analogues with more potent biological activity. In this study the inhibitory potency of derivates of N-phenyl-1,2,3,4-
tetrahydroisoquinoline, 178, 196 and 202, were investigated toward two cholinergic enzymes, AChE and BuChE. The performed screening tests pointed out the different inhibition potency of the selected compounds toward both enzymes which was related with their structures. The most potent compound has been 178 with IC50 values 1.30 μM and 2.50 μM toward AChE and BuChE, respectively. However, no selectivity was observed. Introducing F-atom in the para position of N-phenyl group of the compound 178, the compound 202 was obtained. In this way, the selectivity was increased towards acetylcholinesterase without significant influence on the IC50 value. However, introducing a methoxy groups in the position C3 and C4 of the tetrahydroisoquinoline’s ring of 202, the compound 196 with decreased inhibitory activity was obtained. IC50 value of 196 was one order of magnitude higher compared with compound 202. Based on the obtained results it is possible to conclude that introducing F atom in the para position of the phenyl ring lead to increased selectivity of the investigated compounds while introducing methoxy group in the position of C3 and C4 of 
tetrahydroisoquinoline ring leads to decrease of their inhibitory potency.
PB  - Niš, Serbia : RAD Centre
C3  - Book of Abstracts - 11th International Conference on Radiation, Natural Science, Medicine, Engineering, Technology and Ecology, June 19-23, Herceg Novi, Montenegro
T1  - Influence of the structures of THIQ derivatives on their inhibitory properties toward acetyl - and butyrylcholinesterase
SP  - 134
EP  - 134
DO  - 10.21175/rad.abstr.book.2023.23.2
ER  - 

@conference{
author = "Jovanović, Dunja and Filipović, Ana and Bondžić, Bojan and Bondžić, Aleksandra",
year = "2023",
abstract = "Alzheimer's disease (AD), the most common form of dementia, is a progressive neurological disorder characterized by losing memory and other intellectual abilities that are serious enough to interfere with daily life. The disease is associated with loss of cholinergic neurons in the brain and the decreased level of ACh. In order to raise the ACh level in the brain the acetylcholinesterase (AChE) inhibitors have been applied as relevant drugs in the AD therapy. On the other hand, these inhibitors treat and improve only symptoms indicating necessity for new better therapies. One of them could be based on the inhibition of butyrylcholinesterase (BuChE) because of its increased activity during late stage of AD. Therefore, the BuChE inhibitors should be of great importance in therapy. 1,2,3,4-tetrahydroisoquinolines (THIQ) are a large group of natural and synthetic compounds which exert diverse biological activities against various infectious 
pathogens and neurodegenerative disorders. Due to these reasons, the THIQ have attracted a lot of attention in the scientific community which has resulted in the development of novel THIQ analogues with more potent biological activity. In this study the inhibitory potency of derivates of N-phenyl-1,2,3,4-
tetrahydroisoquinoline, 178, 196 and 202, were investigated toward two cholinergic enzymes, AChE and BuChE. The performed screening tests pointed out the different inhibition potency of the selected compounds toward both enzymes which was related with their structures. The most potent compound has been 178 with IC50 values 1.30 μM and 2.50 μM toward AChE and BuChE, respectively. However, no selectivity was observed. Introducing F-atom in the para position of N-phenyl group of the compound 178, the compound 202 was obtained. In this way, the selectivity was increased towards acetylcholinesterase without significant influence on the IC50 value. However, introducing a methoxy groups in the position C3 and C4 of the tetrahydroisoquinoline’s ring of 202, the compound 196 with decreased inhibitory activity was obtained. IC50 value of 196 was one order of magnitude higher compared with compound 202. Based on the obtained results it is possible to conclude that introducing F atom in the para position of the phenyl ring lead to increased selectivity of the investigated compounds while introducing methoxy group in the position of C3 and C4 of 
tetrahydroisoquinoline ring leads to decrease of their inhibitory potency.",
publisher = "Niš, Serbia : RAD Centre",
journal = "Book of Abstracts - 11th International Conference on Radiation, Natural Science, Medicine, Engineering, Technology and Ecology, June 19-23, Herceg Novi, Montenegro",
title = "Influence of the structures of THIQ derivatives on their inhibitory properties toward acetyl - and butyrylcholinesterase",
pages = "134-134",
doi = "10.21175/rad.abstr.book.2023.23.2"
}

Jovanović, D., Filipović, A., Bondžić, B.,& Bondžić, A.. (2023). Influence of the structures of THIQ derivatives on their inhibitory properties toward acetyl - and butyrylcholinesterase. in Book of Abstracts - 11th International Conference on Radiation, Natural Science, Medicine, Engineering, Technology and Ecology, June 19-23, Herceg Novi, Montenegro
Niš, Serbia : RAD Centre., 134-134.
https://doi.org/10.21175/rad.abstr.book.2023.23.2

Jovanović D, Filipović A, Bondžić B, Bondžić A. Influence of the structures of THIQ derivatives on their inhibitory properties toward acetyl - and butyrylcholinesterase. in Book of Abstracts - 11th International Conference on Radiation, Natural Science, Medicine, Engineering, Technology and Ecology, June 19-23, Herceg Novi, Montenegro. 2023;:134-134.
doi:10.21175/rad.abstr.book.2023.23.2 .

Jovanović, Dunja, Filipović, Ana, Bondžić, Bojan, Bondžić, Aleksandra, "Influence of the structures of THIQ derivatives on their inhibitory properties toward acetyl - and butyrylcholinesterase" in Book of Abstracts - 11th International Conference on Radiation, Natural Science, Medicine, Engineering, Technology and Ecology, June 19-23, Herceg Novi, Montenegro (2023):134-134,
https://doi.org/10.21175/rad.abstr.book.2023.23.2 . .

TY  - JOUR
AU  - Filipović, Ana
AU  - Džambaski, Zdravko
AU  - Bondžić, Aleksandra
AU  - Bondžić, Bojan
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7078
AB  - Visible light promoted photoredox catalyzed formation of α-amino radicals from cyclic tertiary amine compounds and their subsequent addition to Michael acceptors performed in flow conditions allowed access to a wide range of functionalized N-aryl-substituted tetrahydroisoquinolines (THIQs) and N-aryl-substituted tetrahydro-β-carbolines (THBCs). Visible light in conjunction with Ru(bpy)3Cl2 photocatalyst allowed the formation and high reactivities of α-amino radicals in flow conditions at room temperature. These reactions gave valuable products with high efficiencies; some previously unavailable reaction 
pathways photo or thermal reaction conditions; i.e. direct synthesis of 1-substituted (THBCs) via α-amino radical path were successfully realized in flow. The use of custom-made FEP tube microreactor proved to be the key to succesfull α-amino-radical formation and overall reaction performance in flow. Three types of light transparent custom-made microfluidic devices were tested, among them glass/silicon and FEP type reactor showed very good results in the conversion of tested compounds. Plausible reaction mechanism is proposed in accordance with known principles of photo activation of tertiary amines.
PB  - Springer
T2  - Photochemical & Photobiological Sciences
T1  - Visible-light promoted photoredox catalysis in Flow: Addition of biologically important α‑Amino radicals to Michael Acceptors
VL  - 22
SP  - 2259
EP  - 2270
DO  - 10.1007/s43630-023-00448-8
ER  - 

@article{
author = "Filipović, Ana and Džambaski, Zdravko and Bondžić, Aleksandra and Bondžić, Bojan",
year = "2023",
abstract = "Visible light promoted photoredox catalyzed formation of α-amino radicals from cyclic tertiary amine compounds and their subsequent addition to Michael acceptors performed in flow conditions allowed access to a wide range of functionalized N-aryl-substituted tetrahydroisoquinolines (THIQs) and N-aryl-substituted tetrahydro-β-carbolines (THBCs). Visible light in conjunction with Ru(bpy)3Cl2 photocatalyst allowed the formation and high reactivities of α-amino radicals in flow conditions at room temperature. These reactions gave valuable products with high efficiencies; some previously unavailable reaction 
pathways photo or thermal reaction conditions; i.e. direct synthesis of 1-substituted (THBCs) via α-amino radical path were successfully realized in flow. The use of custom-made FEP tube microreactor proved to be the key to succesfull α-amino-radical formation and overall reaction performance in flow. Three types of light transparent custom-made microfluidic devices were tested, among them glass/silicon and FEP type reactor showed very good results in the conversion of tested compounds. Plausible reaction mechanism is proposed in accordance with known principles of photo activation of tertiary amines.",
publisher = "Springer",
journal = "Photochemical & Photobiological Sciences",
title = "Visible-light promoted photoredox catalysis in Flow: Addition of biologically important α‑Amino radicals to Michael Acceptors",
volume = "22",
pages = "2259-2270",
doi = "10.1007/s43630-023-00448-8"
}

Filipović, A., Džambaski, Z., Bondžić, A.,& Bondžić, B.. (2023). Visible-light promoted photoredox catalysis in Flow: Addition of biologically important α‑Amino radicals to Michael Acceptors. in Photochemical & Photobiological Sciences
Springer., 22, 2259-2270.
https://doi.org/10.1007/s43630-023-00448-8

Filipović A, Džambaski Z, Bondžić A, Bondžić B. Visible-light promoted photoredox catalysis in Flow: Addition of biologically important α‑Amino radicals to Michael Acceptors. in Photochemical & Photobiological Sciences. 2023;22:2259-2270.
doi:10.1007/s43630-023-00448-8 .

Filipović, Ana, Džambaski, Zdravko, Bondžić, Aleksandra, Bondžić, Bojan, "Visible-light promoted photoredox catalysis in Flow: Addition of biologically important α‑Amino radicals to Michael Acceptors" in Photochemical & Photobiological Sciences, 22 (2023):2259-2270,
https://doi.org/10.1007/s43630-023-00448-8 . .

TY  - JOUR
AU  - Bondžić, Aleksandra M.
AU  - Jovanović, Dunja
AU  - Arsenijević, Nevena
AU  - Laban, Bojana
AU  - Lazarević Pašti, Tamara
AU  - Klekotka, Urszula
AU  - Bondžić, Bojan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5374
AB  - The study of the interactions between nanoparticles (NPs) and proteins has had a pivotal role in facilitating the understanding of biological effects and safe application of NPs after exposure to the physiological environment. Herein, for the first time, the interaction between L-methionine capped silver nanoparticles (AgMet), and bovine serum albumin (BSA) is investigated in order to predict the fate of AgMet after its contact with the most abundant blood transport protein. The detailed insights into the mechanism of interaction were achieved using different physicochemical techniques. The UV/Vis, TEM, and DLS were used for the characterization of the newly formed “entity”, while the kinetic and thermodynamic parameters were utilized to describe the adsorption process. Additionally, the fluorescence quenching and synchronous fluorescence studies enabled the prediction of the binding affinity and gave us insight into the influence of the adsorption on the conformation state of the BSA. According to the best of our knowledge, for the first time, we show that BSA can be used as an external stabilizer agent which is able to induce the peptization of previously agglomerated AgMet. We believe that the obtained results could contribute to further improvement of AgNPs’ performances as well as to the understanding of their in vivo behavior, which could contribute to their potential use in preclinical research studies.
PB  - Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)
T2  - International Journal of Molecular Sciences
T1  - "Soft Protein Corona” as the Stabilizer of the Methionine-Coated Silver Nanoparticles in the Physiological Environment: Insights into the Mechanism of the Interaction
VL  - 23
IS  - 16
SP  - 8985
DO  - 10.3390/ijms23168985
ER  - 

@article{
author = "Bondžić, Aleksandra M. and Jovanović, Dunja and Arsenijević, Nevena and Laban, Bojana and Lazarević Pašti, Tamara and Klekotka, Urszula and Bondžić, Bojan",
year = "2022",
abstract = "The study of the interactions between nanoparticles (NPs) and proteins has had a pivotal role in facilitating the understanding of biological effects and safe application of NPs after exposure to the physiological environment. Herein, for the first time, the interaction between L-methionine capped silver nanoparticles (AgMet), and bovine serum albumin (BSA) is investigated in order to predict the fate of AgMet after its contact with the most abundant blood transport protein. The detailed insights into the mechanism of interaction were achieved using different physicochemical techniques. The UV/Vis, TEM, and DLS were used for the characterization of the newly formed “entity”, while the kinetic and thermodynamic parameters were utilized to describe the adsorption process. Additionally, the fluorescence quenching and synchronous fluorescence studies enabled the prediction of the binding affinity and gave us insight into the influence of the adsorption on the conformation state of the BSA. According to the best of our knowledge, for the first time, we show that BSA can be used as an external stabilizer agent which is able to induce the peptization of previously agglomerated AgMet. We believe that the obtained results could contribute to further improvement of AgNPs’ performances as well as to the understanding of their in vivo behavior, which could contribute to their potential use in preclinical research studies.",
publisher = "Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)",
journal = "International Journal of Molecular Sciences",
title = ""Soft Protein Corona” as the Stabilizer of the Methionine-Coated Silver Nanoparticles in the Physiological Environment: Insights into the Mechanism of the Interaction",
volume = "23",
number = "16",
pages = "8985",
doi = "10.3390/ijms23168985"
}

Bondžić, A. M., Jovanović, D., Arsenijević, N., Laban, B., Lazarević Pašti, T., Klekotka, U.,& Bondžić, B.. (2022). "Soft Protein Corona” as the Stabilizer of the Methionine-Coated Silver Nanoparticles in the Physiological Environment: Insights into the Mechanism of the Interaction. in International Journal of Molecular Sciences
Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)., 23(16), 8985.
https://doi.org/10.3390/ijms23168985

Bondžić AM, Jovanović D, Arsenijević N, Laban B, Lazarević Pašti T, Klekotka U, Bondžić B. "Soft Protein Corona” as the Stabilizer of the Methionine-Coated Silver Nanoparticles in the Physiological Environment: Insights into the Mechanism of the Interaction. in International Journal of Molecular Sciences. 2022;23(16):8985.
doi:10.3390/ijms23168985 .

Bondžić, Aleksandra M., Jovanović, Dunja, Arsenijević, Nevena, Laban, Bojana, Lazarević Pašti, Tamara, Klekotka, Urszula, Bondžić, Bojan, ""Soft Protein Corona” as the Stabilizer of the Methionine-Coated Silver Nanoparticles in the Physiological Environment: Insights into the Mechanism of the Interaction" in International Journal of Molecular Sciences, 23, no. 16 (2022):8985,
https://doi.org/10.3390/ijms23168985 . .

TY  - CONF
AU  - Filipović, Ana
AU  - Džambaski, Zdravko
AU  - Bondžić, Bojan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7086
AB  - Application of microfluidic devices in the visible light promoted cross-dehydrogenative coupling reactions (CDC) of N-aryl-tetrahydroisoquinolines (THIQs), priviledged, biologically active structures, using Ru(bpy)3Cl2 complexes as photosenzitizers proved as a very efficient strategy for C-1 functionalization of THIQs including Mannich reaction, Strecker reaction, and alkynylation reaction setups. The use of a gas porous PDMS microreactor proved to be crucial regarding the C–H oxidation step. Based on our results the utilization of microreactors in CDC coupling reactions has great perspective and has high importance in the functionalization of biologically active structures such as THIQs.
AB  - Primena mikrofluidnih uređaja u direktnoj funkcionalizaciji biološki aktivnih N-ariltetrahidroizohinolina, u prisustvu fotokatalizatora Ru(bpy)3Cl2, ukazuje na superiornost ove eksperimentalne tehnike u odnosu na konvencionalne reaktore. Mikrofluidni uređaji su primenjeni za ispitivanje Manihove reakcije, Štrekerove reakcije i reakcije alkinilovanja. Kako je za reoksidaciju fotokatalizatora neophodan kiseonik, mikroreaktor od PDMS-a koji je porozan za gasove omogućio je najefikasniju oksidaciju u poređenju sa drugim ispitivanim mikroreaktorima.
PB  - Belgrade : Serbian Chemical Society
C3  - 58th Meeting of the Serbian Chemical Society - Book of abstracts, Proceedings, June 9-10, 2022 Belgrade / 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Knjiga radova, 9. i 10. jun 2022. godine, Beograd
T1  - Visible Light Promoted Cross Dehydrogenative Coupling Reactions (CDC) of N–Aryl– tetrahydroisoquinolines in Flow
T1  - Fotoredoks funkcionalizacija N-aril-tetrahidroizohinolina u  mikrofluidnim uređajima
SP  - 135
EP  - 135
UR  - https://hdl.handle.net/21.15107/rcub_cer_7086
ER  - 

@conference{
author = "Filipović, Ana and Džambaski, Zdravko and Bondžić, Bojan",
year = "2022",
abstract = "Application of microfluidic devices in the visible light promoted cross-dehydrogenative coupling reactions (CDC) of N-aryl-tetrahydroisoquinolines (THIQs), priviledged, biologically active structures, using Ru(bpy)3Cl2 complexes as photosenzitizers proved as a very efficient strategy for C-1 functionalization of THIQs including Mannich reaction, Strecker reaction, and alkynylation reaction setups. The use of a gas porous PDMS microreactor proved to be crucial regarding the C–H oxidation step. Based on our results the utilization of microreactors in CDC coupling reactions has great perspective and has high importance in the functionalization of biologically active structures such as THIQs., Primena mikrofluidnih uređaja u direktnoj funkcionalizaciji biološki aktivnih N-ariltetrahidroizohinolina, u prisustvu fotokatalizatora Ru(bpy)3Cl2, ukazuje na superiornost ove eksperimentalne tehnike u odnosu na konvencionalne reaktore. Mikrofluidni uređaji su primenjeni za ispitivanje Manihove reakcije, Štrekerove reakcije i reakcije alkinilovanja. Kako je za reoksidaciju fotokatalizatora neophodan kiseonik, mikroreaktor od PDMS-a koji je porozan za gasove omogućio je najefikasniju oksidaciju u poređenju sa drugim ispitivanim mikroreaktorima.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "58th Meeting of the Serbian Chemical Society - Book of abstracts, Proceedings, June 9-10, 2022 Belgrade / 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Knjiga radova, 9. i 10. jun 2022. godine, Beograd",
title = "Visible Light Promoted Cross Dehydrogenative Coupling Reactions (CDC) of N–Aryl– tetrahydroisoquinolines in Flow, Fotoredoks funkcionalizacija N-aril-tetrahidroizohinolina u  mikrofluidnim uređajima",
pages = "135-135",
url = "https://hdl.handle.net/21.15107/rcub_cer_7086"
}

Filipović, A., Džambaski, Z.,& Bondžić, B.. (2022). Visible Light Promoted Cross Dehydrogenative Coupling Reactions (CDC) of N–Aryl– tetrahydroisoquinolines in Flow. in 58th Meeting of the Serbian Chemical Society - Book of abstracts, Proceedings, June 9-10, 2022 Belgrade / 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Knjiga radova, 9. i 10. jun 2022. godine, Beograd
Belgrade : Serbian Chemical Society., 135-135.
https://hdl.handle.net/21.15107/rcub_cer_7086

Filipović A, Džambaski Z, Bondžić B. Visible Light Promoted Cross Dehydrogenative Coupling Reactions (CDC) of N–Aryl– tetrahydroisoquinolines in Flow. in 58th Meeting of the Serbian Chemical Society - Book of abstracts, Proceedings, June 9-10, 2022 Belgrade / 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Knjiga radova, 9. i 10. jun 2022. godine, Beograd. 2022;:135-135.
https://hdl.handle.net/21.15107/rcub_cer_7086 .

Filipović, Ana, Džambaski, Zdravko, Bondžić, Bojan, "Visible Light Promoted Cross Dehydrogenative Coupling Reactions (CDC) of N–Aryl– tetrahydroisoquinolines in Flow" in 58th Meeting of the Serbian Chemical Society - Book of abstracts, Proceedings, June 9-10, 2022 Belgrade / 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Knjiga radova, 9. i 10. jun 2022. godine, Beograd (2022):135-135,
https://hdl.handle.net/21.15107/rcub_cer_7086 .

TY  - CONF
AU  - Filipović, Ana
AU  - Džambaski, Zdravko
AU  - Bondžić, Bojan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7082
AB  - In recent years, the application of microfluidic devices demonstrated significant promise as a novel method in organic chemistry. One of the research fields in which microfluidics have shown a great potential is visible light photoredox catalysis. The implementation of microreactors offers considerable advantages over the batch reactor as follows: a more predictable reaction scale-up, ecreased safety hazards, preserves atom economy, improved reproducibility and yields, and decreased energy consumption. The high surface-area-to-volume ratios provide more efficient irradiation of a reaction mixture, reduction of irradiation times, and hence prevention of undesired side reactions. As a result, enhanced selectivity, product purity, and lower catalyst loading are achieved, which leads to overall more sustainable and greener processes. Even though significant rogress has been achieved, greener alternatives to many common industrial processes still remain elusive, especially in the fine chemicals industry. To perform rocesses greener and cheaper, catalysis is a key tool to reduce energy consumption and develop more atom-economical transformations. To show the potential use of 
microdevices in organic synthesis, we have applied microfluidic chemistry in mutual photoredox and organocatalytic synthesis of the functionalized tetrahydroisoquinoline, a biologically active compound with interesting pharmaceutical properties. The results obtained in microreactor devices were compared with those obtained in batch reactions and it was demonstrated that microreactors can achieve superb yields and decreased waste generation. Thus, microflow photochemistry unambiguously has demonstrated its superiority over conventional reactor systems and its potential as green technology in synthesis processes.
PB  - Zagreb, Croatia : Faculty of Food Technology and Biotechnology,  University of Zagreb
C3  - Book of abstracts - Natural resources, green technology and sustainable development - 4-GREEN2022, 14-16 September 2022, Zagreb, Croatia
T1  - Microreactor technology for green and sustainable photo– and organo– catalytic synthesis
SP  - 129
EP  - 129
UR  - https://hdl.handle.net/21.15107/rcub_cer_7082
ER  - 

@conference{
author = "Filipović, Ana and Džambaski, Zdravko and Bondžić, Bojan",
year = "2022",
abstract = "In recent years, the application of microfluidic devices demonstrated significant promise as a novel method in organic chemistry. One of the research fields in which microfluidics have shown a great potential is visible light photoredox catalysis. The implementation of microreactors offers considerable advantages over the batch reactor as follows: a more predictable reaction scale-up, ecreased safety hazards, preserves atom economy, improved reproducibility and yields, and decreased energy consumption. The high surface-area-to-volume ratios provide more efficient irradiation of a reaction mixture, reduction of irradiation times, and hence prevention of undesired side reactions. As a result, enhanced selectivity, product purity, and lower catalyst loading are achieved, which leads to overall more sustainable and greener processes. Even though significant rogress has been achieved, greener alternatives to many common industrial processes still remain elusive, especially in the fine chemicals industry. To perform rocesses greener and cheaper, catalysis is a key tool to reduce energy consumption and develop more atom-economical transformations. To show the potential use of 
microdevices in organic synthesis, we have applied microfluidic chemistry in mutual photoredox and organocatalytic synthesis of the functionalized tetrahydroisoquinoline, a biologically active compound with interesting pharmaceutical properties. The results obtained in microreactor devices were compared with those obtained in batch reactions and it was demonstrated that microreactors can achieve superb yields and decreased waste generation. Thus, microflow photochemistry unambiguously has demonstrated its superiority over conventional reactor systems and its potential as green technology in synthesis processes.",
publisher = "Zagreb, Croatia : Faculty of Food Technology and Biotechnology,  University of Zagreb",
journal = "Book of abstracts - Natural resources, green technology and sustainable development - 4-GREEN2022, 14-16 September 2022, Zagreb, Croatia",
title = "Microreactor technology for green and sustainable photo– and organo– catalytic synthesis",
pages = "129-129",
url = "https://hdl.handle.net/21.15107/rcub_cer_7082"
}

Filipović, A., Džambaski, Z.,& Bondžić, B.. (2022). Microreactor technology for green and sustainable photo– and organo– catalytic synthesis. in Book of abstracts - Natural resources, green technology and sustainable development - 4-GREEN2022, 14-16 September 2022, Zagreb, Croatia
Zagreb, Croatia : Faculty of Food Technology and Biotechnology,  University of Zagreb., 129-129.
https://hdl.handle.net/21.15107/rcub_cer_7082

Filipović A, Džambaski Z, Bondžić B. Microreactor technology for green and sustainable photo– and organo– catalytic synthesis. in Book of abstracts - Natural resources, green technology and sustainable development - 4-GREEN2022, 14-16 September 2022, Zagreb, Croatia. 2022;:129-129.
https://hdl.handle.net/21.15107/rcub_cer_7082 .

Filipović, Ana, Džambaski, Zdravko, Bondžić, Bojan, "Microreactor technology for green and sustainable photo– and organo– catalytic synthesis" in Book of abstracts - Natural resources, green technology and sustainable development - 4-GREEN2022, 14-16 September 2022, Zagreb, Croatia (2022):129-129,
https://hdl.handle.net/21.15107/rcub_cer_7082 .

TY  - JOUR
AU  - Bondžić, Aleksandra
AU  - Lazarević Pašti, Tamara
AU  - Pasti, Igor
AU  - Bondžić, Bojan
AU  - Momčilović, Miloš D.
AU  - Loosen, Alexandra
AU  - Parac-Vogt Tatjana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5430
AB  - Organophosphate-based pesticides have remarkably contributed to the agriculture industry, but their toxicity has a large negative impact on the environment as well as on the health of humans and other living organisms. Most of the methods developed to remedy the organophosphate pesticide toxicity are very time-consuming and are based on their adsorption onto different materials and/or their degradation to nontoxic species. In this study, detoxification of three structurally different organophosphate pesticides was investigated using an NU-1000 metal-organic framework. We showed that NU-1000 is an excellent agent for fast (average time ≤ 3 min) and effective removal of organophosphate pesticides with an aromatic heterocyclic moiety. In particular, superior detoxification of chlorpyrifos solution after NU-1000 treatment was achieved after only 1 min. The combination of experimental and computational methods revealed that the synergic effects of sorption and hydrolysis are responsible for the superior removal of CHP by NU-1000. The sorption process occurs on the Zr node (chemisorption) and pyrene linkers (physisorption) following pseudo-first-order kinetics during the first minute, and a pseudo-second-order model fits the entire time range. The multilayer adsorption of chlorpyrifos or its hydrolyzed product, 3,5,6-trichloro-2-pyridinol, takes place on a pyrene linker, whereas the aliphatic part of the molecule remains chemisorbed on the Zr node. Such unique synergy between induced sorption and hydrolysis of chlorpyrifos by NU-1000 results in its fast and effective removal with rapid detoxification in non-buffered solutions.
PB  - USA : American Chemical Society
T2  - ACS Applied Nano Materials
T1  - Synergistic Effect of Sorption and Hydrolysis by NU-1000 Nanostructures for Removal and Detoxification of Chlorpyrifos
VL  - 5
IS  - 3
SP  - 3312
EP  - 3324
DO  - 10.1021/acsanm.1c03863
ER  - 

@article{
author = "Bondžić, Aleksandra and Lazarević Pašti, Tamara and Pasti, Igor and Bondžić, Bojan and Momčilović, Miloš D. and Loosen, Alexandra and Parac-Vogt Tatjana",
year = "2022",
abstract = "Organophosphate-based pesticides have remarkably contributed to the agriculture industry, but their toxicity has a large negative impact on the environment as well as on the health of humans and other living organisms. Most of the methods developed to remedy the organophosphate pesticide toxicity are very time-consuming and are based on their adsorption onto different materials and/or their degradation to nontoxic species. In this study, detoxification of three structurally different organophosphate pesticides was investigated using an NU-1000 metal-organic framework. We showed that NU-1000 is an excellent agent for fast (average time ≤ 3 min) and effective removal of organophosphate pesticides with an aromatic heterocyclic moiety. In particular, superior detoxification of chlorpyrifos solution after NU-1000 treatment was achieved after only 1 min. The combination of experimental and computational methods revealed that the synergic effects of sorption and hydrolysis are responsible for the superior removal of CHP by NU-1000. The sorption process occurs on the Zr node (chemisorption) and pyrene linkers (physisorption) following pseudo-first-order kinetics during the first minute, and a pseudo-second-order model fits the entire time range. The multilayer adsorption of chlorpyrifos or its hydrolyzed product, 3,5,6-trichloro-2-pyridinol, takes place on a pyrene linker, whereas the aliphatic part of the molecule remains chemisorbed on the Zr node. Such unique synergy between induced sorption and hydrolysis of chlorpyrifos by NU-1000 results in its fast and effective removal with rapid detoxification in non-buffered solutions.",
publisher = "USA : American Chemical Society",
journal = "ACS Applied Nano Materials",
title = "Synergistic Effect of Sorption and Hydrolysis by NU-1000 Nanostructures for Removal and Detoxification of Chlorpyrifos",
volume = "5",
number = "3",
pages = "3312-3324",
doi = "10.1021/acsanm.1c03863"
}

Bondžić, A., Lazarević Pašti, T., Pasti, I., Bondžić, B., Momčilović, M. D., Loosen, A.,& Parac-Vogt Tatjana. (2022). Synergistic Effect of Sorption and Hydrolysis by NU-1000 Nanostructures for Removal and Detoxification of Chlorpyrifos. in ACS Applied Nano Materials
USA : American Chemical Society., 5(3), 3312-3324.
https://doi.org/10.1021/acsanm.1c03863

Bondžić A, Lazarević Pašti T, Pasti I, Bondžić B, Momčilović MD, Loosen A, Parac-Vogt Tatjana. Synergistic Effect of Sorption and Hydrolysis by NU-1000 Nanostructures for Removal and Detoxification of Chlorpyrifos. in ACS Applied Nano Materials. 2022;5(3):3312-3324.
doi:10.1021/acsanm.1c03863 .

Bondžić, Aleksandra, Lazarević Pašti, Tamara, Pasti, Igor, Bondžić, Bojan, Momčilović, Miloš D., Loosen, Alexandra, Parac-Vogt Tatjana, "Synergistic Effect of Sorption and Hydrolysis by NU-1000 Nanostructures for Removal and Detoxification of Chlorpyrifos" in ACS Applied Nano Materials, 5, no. 3 (2022):3312-3324,
https://doi.org/10.1021/acsanm.1c03863 . .

TY  - JOUR
AU  - Bondžić, Bojan
AU  - Daskalakis, Konstantinos
AU  - Taniguchi, Tohru
AU  - Monde, Kenji
AU  - Hayashi, Yujiro
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5417
AB  - A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.
PB  - USA : American Chemical Society
T2  - Organic Letters
T1  - Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water
VL  - 24
IS  - 40
SP  - 7455
EP  - 7460
DO  - 10.1021/acs.orglett.2c03043
ER  - 

@article{
author = "Bondžić, Bojan and Daskalakis, Konstantinos and Taniguchi, Tohru and Monde, Kenji and Hayashi, Yujiro",
year = "2022",
abstract = "A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.",
publisher = "USA : American Chemical Society",
journal = "Organic Letters",
title = "Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water",
volume = "24",
number = "40",
pages = "7455-7460",
doi = "10.1021/acs.orglett.2c03043"
}

Bondžić, B., Daskalakis, K., Taniguchi, T., Monde, K.,& Hayashi, Y.. (2022). Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water. in Organic Letters
USA : American Chemical Society., 24(40), 7455-7460.
https://doi.org/10.1021/acs.orglett.2c03043

Bondžić B, Daskalakis K, Taniguchi T, Monde K, Hayashi Y. Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water. in Organic Letters. 2022;24(40):7455-7460.
doi:10.1021/acs.orglett.2c03043 .

Bondžić, Bojan, Daskalakis, Konstantinos, Taniguchi, Tohru, Monde, Kenji, Hayashi, Yujiro, "Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water" in Organic Letters, 24, no. 40 (2022):7455-7460,
https://doi.org/10.1021/acs.orglett.2c03043 . .

TY  - JOUR
AU  - Gajić, Mihajlo
AU  - Ilić, Budimir S.
AU  - Bondžić, Bojan
AU  - Džambaski, Zdravko
AU  - Filipović, Ana
AU  - Kocić, Gordana
AU  - Šmelcerović, Andrija
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6939
AB  - Xanthine oxidase (XO) is a versatile metalloflavoprotein enzyme that is best known for its rate-limiting role in the purine degradation pathway. Therapeutic inhibition of XO is based on its role in a variety of diseases that is attributed either to the hyperproduction of uric acid, or the hyperproduction of reactive oxygen species. Herein, we report the assessment of XO inhibitory properties of 24 1,2,3,4-tetrahydroisoquinoline derivatives, among which compound 
16 exhibited IC50 value of 135.72 ± 2.71 µM. The interaction of compound 16 with XO enzyme was simulated using the Site Finder module, molecular docking and molecular dynamics. Molecular modeling suggests that interactions with Met 1038, Gln 1040, Thr 1077, Gln 1194 and Val 1259 are an important factor for inhibitor affinity toward the XO enzyme. Our proposed binding model might be beneficial for the discovery of new active 1,2,3,4-tetrahydroisoquinoline-based inhibitors of XO enzyme.
AB  - Ksantin oksidaza (XO) je metaloflavoproteinski enzim, koji je najpoznatiji po svojoj ulozi ograničavanja brzine razgradnje purinskih nukleotida. Terapijska inhibicija XO zasniva se na njenoj ulozi u brojnim bolestima, koje su povezane bilo sa hiperprodukcijom mokraćne kiseline ili hiperprodukcijom reaktivnih kiseoničnih vrsta. U ovom radu izvršeno je ispitivanje sposobnosti inhibicije XO 24 derivata 1,2,3,4-tetrahidroizohinolina, od kojih je jedinjenje 16 pokazalo IC50 vrednost od 135,72 µM ± 2,71 µM. Interakcija jedinjenja 16 sa XO enzimom simulirana je korišćenjem Site Finder modula molekularnog dokinga i molekularne dinamike. Molekulsko modelovanje ukazuje na to da su interakcije sa Met 1038, Gln 1040, Thr 1077, Gln 1194 i Val 1259 važan faktor postojanja afiniteta inhibitora prema XO enzimu. Naš predloženi model vezivanja mogao bi biti od značaja za razvoj novih aktivnih inhibitora XO zasnovanih na 1,2,3,4-tetrahidroizohinolinskom heterociklusu.
PB  - Acta Medica Medianae
T2  - Acta Medica Medianae
T1  - Xanthine Oxidase Inhibitory Properties of 1,2,3,4–Tetrahydroisoquinoline Derivatives
T1  - Inhibicija ksantin oksidaze derivatima 1,2,3,4-tetrahidroizohinolina
VL  - 60
IS  - 1
SP  - 48
EP  - 55
DO  - 10.5633/amm.2021.0106
ER  - 

@article{
author = "Gajić, Mihajlo and Ilić, Budimir S. and Bondžić, Bojan and Džambaski, Zdravko and Filipović, Ana and Kocić, Gordana and Šmelcerović, Andrija",
year = "2021",
abstract = "Xanthine oxidase (XO) is a versatile metalloflavoprotein enzyme that is best known for its rate-limiting role in the purine degradation pathway. Therapeutic inhibition of XO is based on its role in a variety of diseases that is attributed either to the hyperproduction of uric acid, or the hyperproduction of reactive oxygen species. Herein, we report the assessment of XO inhibitory properties of 24 1,2,3,4-tetrahydroisoquinoline derivatives, among which compound 
16 exhibited IC50 value of 135.72 ± 2.71 µM. The interaction of compound 16 with XO enzyme was simulated using the Site Finder module, molecular docking and molecular dynamics. Molecular modeling suggests that interactions with Met 1038, Gln 1040, Thr 1077, Gln 1194 and Val 1259 are an important factor for inhibitor affinity toward the XO enzyme. Our proposed binding model might be beneficial for the discovery of new active 1,2,3,4-tetrahydroisoquinoline-based inhibitors of XO enzyme., Ksantin oksidaza (XO) je metaloflavoproteinski enzim, koji je najpoznatiji po svojoj ulozi ograničavanja brzine razgradnje purinskih nukleotida. Terapijska inhibicija XO zasniva se na njenoj ulozi u brojnim bolestima, koje su povezane bilo sa hiperprodukcijom mokraćne kiseline ili hiperprodukcijom reaktivnih kiseoničnih vrsta. U ovom radu izvršeno je ispitivanje sposobnosti inhibicije XO 24 derivata 1,2,3,4-tetrahidroizohinolina, od kojih je jedinjenje 16 pokazalo IC50 vrednost od 135,72 µM ± 2,71 µM. Interakcija jedinjenja 16 sa XO enzimom simulirana je korišćenjem Site Finder modula molekularnog dokinga i molekularne dinamike. Molekulsko modelovanje ukazuje na to da su interakcije sa Met 1038, Gln 1040, Thr 1077, Gln 1194 i Val 1259 važan faktor postojanja afiniteta inhibitora prema XO enzimu. Naš predloženi model vezivanja mogao bi biti od značaja za razvoj novih aktivnih inhibitora XO zasnovanih na 1,2,3,4-tetrahidroizohinolinskom heterociklusu.",
publisher = "Acta Medica Medianae",
journal = "Acta Medica Medianae",
title = "Xanthine Oxidase Inhibitory Properties of 1,2,3,4–Tetrahydroisoquinoline Derivatives, Inhibicija ksantin oksidaze derivatima 1,2,3,4-tetrahidroizohinolina",
volume = "60",
number = "1",
pages = "48-55",
doi = "10.5633/amm.2021.0106"
}

Gajić, M., Ilić, B. S., Bondžić, B., Džambaski, Z., Filipović, A., Kocić, G.,& Šmelcerović, A.. (2021). Xanthine Oxidase Inhibitory Properties of 1,2,3,4–Tetrahydroisoquinoline Derivatives. in Acta Medica Medianae
Acta Medica Medianae., 60(1), 48-55.
https://doi.org/10.5633/amm.2021.0106

Gajić M, Ilić BS, Bondžić B, Džambaski Z, Filipović A, Kocić G, Šmelcerović A. Xanthine Oxidase Inhibitory Properties of 1,2,3,4–Tetrahydroisoquinoline Derivatives. in Acta Medica Medianae. 2021;60(1):48-55.
doi:10.5633/amm.2021.0106 .

Gajić, Mihajlo, Ilić, Budimir S., Bondžić, Bojan, Džambaski, Zdravko, Filipović, Ana, Kocić, Gordana, Šmelcerović, Andrija, "Xanthine Oxidase Inhibitory Properties of 1,2,3,4–Tetrahydroisoquinoline Derivatives" in Acta Medica Medianae, 60, no. 1 (2021):48-55,
https://doi.org/10.5633/amm.2021.0106 . .

TY  - DATA
AU  - Filipović, Ana
AU  - Džambaski, Zdravko
AU  - Vasiljević-Radović, Dana
AU  - Bondžić, Bojan
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4495
AB  - Full characterization data for all compounds.
PB  - Royal Society  of Chemistry
T2  - Organic and Biomolecular Chemistry
T1  - Supplementary material for: "Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4495
ER  - 

@misc{
author = "Filipović, Ana and Džambaski, Zdravko and Vasiljević-Radović, Dana and Bondžić, Bojan",
year = "2021",
abstract = "Full characterization data for all compounds.",
publisher = "Royal Society  of Chemistry",
journal = "Organic and Biomolecular Chemistry",
title = "Supplementary material for: "Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4495"
}

Filipović, A., Džambaski, Z., Vasiljević-Radović, D.,& Bondžić, B.. (2021). Supplementary material for: "Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow". in Organic and Biomolecular Chemistry
Royal Society  of Chemistry..
https://hdl.handle.net/21.15107/rcub_cer_4495

Filipović A, Džambaski Z, Vasiljević-Radović D, Bondžić B. Supplementary material for: "Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow". in Organic and Biomolecular Chemistry. 2021;.
https://hdl.handle.net/21.15107/rcub_cer_4495 .

Filipović, Ana, Džambaski, Zdravko, Vasiljević-Radović, Dana, Bondžić, Bojan, "Supplementary material for: "Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow"" in Organic and Biomolecular Chemistry (2021),
https://hdl.handle.net/21.15107/rcub_cer_4495 .

TY  - JOUR
AU  - Filipović, Ana
AU  - Džambaski, Zdravko
AU  - Vasiljević-Radović, Dana
AU  - Bondžić, Bojan
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4494
AB  - A merger of organocatalysis and visible light photoredox catalysis performed in flow allowed access to a wide range of functionalizedN-aryl-substituted tetrahydroisoquinolines (THIQs) in a formal C-H oxidation/Mannich reaction. Strecker type functionalization and copper-catalyzed alkynylation of severalN-aryl-substituted THIQs were also successfully performed in flow, giving valuable products with high efficiencies. The use of custom-made porous polymeric type microreactors proved to be crucial regarding the C-H oxidation step and overall reaction performance.
PB  - Royal Society  of Chemistry
T2  - Organic and Biomolecular Chemistry
T1  - Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow
VL  - 19
IS  - 12
SP  - 2668
EP  - 2675
DO  - 10.1039/d0ob02582h
ER  - 

@article{
author = "Filipović, Ana and Džambaski, Zdravko and Vasiljević-Radović, Dana and Bondžić, Bojan",
year = "2021",
abstract = "A merger of organocatalysis and visible light photoredox catalysis performed in flow allowed access to a wide range of functionalizedN-aryl-substituted tetrahydroisoquinolines (THIQs) in a formal C-H oxidation/Mannich reaction. Strecker type functionalization and copper-catalyzed alkynylation of severalN-aryl-substituted THIQs were also successfully performed in flow, giving valuable products with high efficiencies. The use of custom-made porous polymeric type microreactors proved to be crucial regarding the C-H oxidation step and overall reaction performance.",
publisher = "Royal Society  of Chemistry",
journal = "Organic and Biomolecular Chemistry",
title = "Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow",
volume = "19",
number = "12",
pages = "2668-2675",
doi = "10.1039/d0ob02582h"
}

Filipović, A., Džambaski, Z., Vasiljević-Radović, D.,& Bondžić, B.. (2021). Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow. in Organic and Biomolecular Chemistry
Royal Society  of Chemistry., 19(12), 2668-2675.
https://doi.org/10.1039/d0ob02582h

Filipović A, Džambaski Z, Vasiljević-Radović D, Bondžić B. Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow. in Organic and Biomolecular Chemistry. 2021;19(12):2668-2675.
doi:10.1039/d0ob02582h .

Filipović, Ana, Džambaski, Zdravko, Vasiljević-Radović, Dana, Bondžić, Bojan, "Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow" in Organic and Biomolecular Chemistry, 19, no. 12 (2021):2668-2675,
https://doi.org/10.1039/d0ob02582h . .

TY  - JOUR
AU  - Ilić, Budimir S.
AU  - Gajić, Mihajlo
AU  - Bondžić, Bojan
AU  - Džambaski, Zdravko
AU  - Kocić, Gordana
AU  - Šmelcerović, Andrija
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4498
AB  - Deoxyribonuclease I (DNase I) inhibitory properties of two 1-(pyrrolidin-2-yl)propan-2-one derivatives were examined in vitro. Determined IC50 values of 1-[1-(4-methoxyphenyl)pyrrolidin-2-yl]propan-2-one (1) (192.13±16.95 μM) and 1-[1-(3,4,5-trimethoxyphenyl)pyrrolidin-2-yl]propan-2-one (2) (132.62±9.92 μM) exceed IC50 value of crystal violet, used as a positive control, 1.89- and 2.73-times, respectively. Compounds are predicted to be nontoxic and to have favorable pharmacokinetic profiles, with high gastrointestinal absorption and blood-brain barrier permeability. Molecular docking and molecular dynamics simulations suggest that interactions with Glu 39, Glu 78, Arg 111, Pro 137, Asp 251 and His 252 are an important factor for inhibitors affinity toward the DNase I. Determined inhibitory properties along with predicted ADMET profiles and observed interactions would be beneficial for the discovery of new active 1-(pyrrolidin-2-yl)propan-2-one-based inhibitors of DNase I.
PB  - Switzerland :Wiley-Blackwell
T2  - Chemistry and Biodisversity
T1  - Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives
VL  - 18
IS  - 3
SP  - e2000996
DO  - 10.1002/cbdv.202000996
ER  - 

@article{
author = "Ilić, Budimir S. and Gajić, Mihajlo and Bondžić, Bojan and Džambaski, Zdravko and Kocić, Gordana and Šmelcerović, Andrija",
year = "2021",
abstract = "Deoxyribonuclease I (DNase I) inhibitory properties of two 1-(pyrrolidin-2-yl)propan-2-one derivatives were examined in vitro. Determined IC50 values of 1-[1-(4-methoxyphenyl)pyrrolidin-2-yl]propan-2-one (1) (192.13±16.95 μM) and 1-[1-(3,4,5-trimethoxyphenyl)pyrrolidin-2-yl]propan-2-one (2) (132.62±9.92 μM) exceed IC50 value of crystal violet, used as a positive control, 1.89- and 2.73-times, respectively. Compounds are predicted to be nontoxic and to have favorable pharmacokinetic profiles, with high gastrointestinal absorption and blood-brain barrier permeability. Molecular docking and molecular dynamics simulations suggest that interactions with Glu 39, Glu 78, Arg 111, Pro 137, Asp 251 and His 252 are an important factor for inhibitors affinity toward the DNase I. Determined inhibitory properties along with predicted ADMET profiles and observed interactions would be beneficial for the discovery of new active 1-(pyrrolidin-2-yl)propan-2-one-based inhibitors of DNase I.",
publisher = "Switzerland :Wiley-Blackwell",
journal = "Chemistry and Biodisversity",
title = "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives",
volume = "18",
number = "3",
pages = "e2000996",
doi = "10.1002/cbdv.202000996"
}

Ilić, B. S., Gajić, M., Bondžić, B., Džambaski, Z., Kocić, G.,& Šmelcerović, A.. (2021). Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives. in Chemistry and Biodisversity
Switzerland :Wiley-Blackwell., 18(3), e2000996.
https://doi.org/10.1002/cbdv.202000996

Ilić BS, Gajić M, Bondžić B, Džambaski Z, Kocić G, Šmelcerović A. Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives. in Chemistry and Biodisversity. 2021;18(3):e2000996.
doi:10.1002/cbdv.202000996 .

Ilić, Budimir S., Gajić, Mihajlo, Bondžić, Bojan, Džambaski, Zdravko, Kocić, Gordana, Šmelcerović, Andrija, "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives" in Chemistry and Biodisversity, 18, no. 3 (2021):e2000996,
https://doi.org/10.1002/cbdv.202000996 . .

TY  - DATA
AU  - Ilić, Budimir S.
AU  - Gajić, Mihajlo
AU  - Bondžić, Bojan
AU  - Džambaski, Zdravko
AU  - Kocić, Gordana
AU  - Šmelcerović, Andrija
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4499
AB  - Experimental Section: 1.1. Chemicals. 1.2. Compounds. 1.3. Evaluation of deoxyribonuclease I inhibition. 1.4. In silico molecular and ADMET properties. 1.5. In silico PAINS and promiscuity assessment. 1.6. Molecular docking. 1.6.1. Ligand preparation. 1.6.2. Receptor preparation  1.6.3. Binding site selection 1.6.4. Docking protocol 1.7. Molecular dynamics simulation . Table S1. Summary of the top five inhibitor-binding sites in DNase I. Additional references.
PB  - Switzerland : Wiley-Blackwell
T2  - Chemistry and Biodisversity
T1  - Supporting information for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4499
ER  - 

@misc{
author = "Ilić, Budimir S. and Gajić, Mihajlo and Bondžić, Bojan and Džambaski, Zdravko and Kocić, Gordana and Šmelcerović, Andrija",
year = "2021",
abstract = "Experimental Section: 1.1. Chemicals. 1.2. Compounds. 1.3. Evaluation of deoxyribonuclease I inhibition. 1.4. In silico molecular and ADMET properties. 1.5. In silico PAINS and promiscuity assessment. 1.6. Molecular docking. 1.6.1. Ligand preparation. 1.6.2. Receptor preparation  1.6.3. Binding site selection 1.6.4. Docking protocol 1.7. Molecular dynamics simulation . Table S1. Summary of the top five inhibitor-binding sites in DNase I. Additional references.",
publisher = "Switzerland : Wiley-Blackwell",
journal = "Chemistry and Biodisversity",
title = "Supporting information for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4499"
}

Ilić, B. S., Gajić, M., Bondžić, B., Džambaski, Z., Kocić, G.,& Šmelcerović, A.. (2021). Supporting information for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". in Chemistry and Biodisversity
Switzerland : Wiley-Blackwell..
https://hdl.handle.net/21.15107/rcub_cer_4499

Ilić BS, Gajić M, Bondžić B, Džambaski Z, Kocić G, Šmelcerović A. Supporting information for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". in Chemistry and Biodisversity. 2021;.
https://hdl.handle.net/21.15107/rcub_cer_4499 .

Ilić, Budimir S., Gajić, Mihajlo, Bondžić, Bojan, Džambaski, Zdravko, Kocić, Gordana, Šmelcerović, Andrija, "Supporting information for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives"" in Chemistry and Biodisversity (2021),
https://hdl.handle.net/21.15107/rcub_cer_4499 .

TY  - DATA
AU  - Ilić, Budimir S.
AU  - Gajić, Mihajlo
AU  - Bondžić, Bojan
AU  - Džambaski, Zdravko
AU  - Kocić, Gordana
AU  - Šmelcerović, Andrija
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4500
AB  - Animation of molecular dynamics simulations: 1‐[1‐(4‐methoxyphenyl)pyrrolidin‐2‐yl]propan‐2‐one / DNase I
PB  - Switzerland : Wiley-Blackwell
T2  - Chemistry and Biodisversity
T1  - Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations I.
UR  - https://hdl.handle.net/21.15107/rcub_cer_4500
ER  - 

@misc{
author = "Ilić, Budimir S. and Gajić, Mihajlo and Bondžić, Bojan and Džambaski, Zdravko and Kocić, Gordana and Šmelcerović, Andrija",
year = "2021",
abstract = "Animation of molecular dynamics simulations: 1‐[1‐(4‐methoxyphenyl)pyrrolidin‐2‐yl]propan‐2‐one / DNase I",
publisher = "Switzerland : Wiley-Blackwell",
journal = "Chemistry and Biodisversity",
title = "Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations I.",
url = "https://hdl.handle.net/21.15107/rcub_cer_4500"
}

Ilić, B. S., Gajić, M., Bondžić, B., Džambaski, Z., Kocić, G.,& Šmelcerović, A.. (2021). Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations I.. in Chemistry and Biodisversity
Switzerland : Wiley-Blackwell..
https://hdl.handle.net/21.15107/rcub_cer_4500

Ilić BS, Gajić M, Bondžić B, Džambaski Z, Kocić G, Šmelcerović A. Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations I.. in Chemistry and Biodisversity. 2021;.
https://hdl.handle.net/21.15107/rcub_cer_4500 .

Ilić, Budimir S., Gajić, Mihajlo, Bondžić, Bojan, Džambaski, Zdravko, Kocić, Gordana, Šmelcerović, Andrija, "Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations I." in Chemistry and Biodisversity (2021),
https://hdl.handle.net/21.15107/rcub_cer_4500 .

TY  - DATA
AU  - Ilić, Budimir S.
AU  - Gajić, Mihajlo
AU  - Bondžić, Bojan
AU  - Džambaski, Zdravko
AU  - Kocić, Gordana
AU  - Šmelcerović, Andrija
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4501
AB  - Animation of molecular dynamics simulations: 1‐[1‐(3,4,5‐trimethoxyphenyl)pyrrolidin‐2‐yl]propan‐2‐one / DNase I
PB  - Switzerland : Wiley-Blackwell
T2  - Chemistry and Biodisversity
T1  - Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations II.
UR  - https://hdl.handle.net/21.15107/rcub_cer_4501
ER  - 

@misc{
author = "Ilić, Budimir S. and Gajić, Mihajlo and Bondžić, Bojan and Džambaski, Zdravko and Kocić, Gordana and Šmelcerović, Andrija",
year = "2021",
abstract = "Animation of molecular dynamics simulations: 1‐[1‐(3,4,5‐trimethoxyphenyl)pyrrolidin‐2‐yl]propan‐2‐one / DNase I",
publisher = "Switzerland : Wiley-Blackwell",
journal = "Chemistry and Biodisversity",
title = "Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations II.",
url = "https://hdl.handle.net/21.15107/rcub_cer_4501"
}

Ilić, B. S., Gajić, M., Bondžić, B., Džambaski, Z., Kocić, G.,& Šmelcerović, A.. (2021). Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations II.. in Chemistry and Biodisversity
Switzerland : Wiley-Blackwell..
https://hdl.handle.net/21.15107/rcub_cer_4501

Ilić BS, Gajić M, Bondžić B, Džambaski Z, Kocić G, Šmelcerović A. Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations II.. in Chemistry and Biodisversity. 2021;.
https://hdl.handle.net/21.15107/rcub_cer_4501 .

Ilić, Budimir S., Gajić, Mihajlo, Bondžić, Bojan, Džambaski, Zdravko, Kocić, Gordana, Šmelcerović, Andrija, "Supporting data for: "Deoxyribonuclease I Inhibitory Properties, Molecular Docking and Molecular Dynamics Simulations of 1-(Pyrrolidin-2-yl)propan-2-one Derivatives". Animation of molecular dynamics simulations II." in Chemistry and Biodisversity (2021),
https://hdl.handle.net/21.15107/rcub_cer_4501 .

TY  - JOUR
AU  - Gajić, Mihajlo
AU  - Džambaski, Zdravko
AU  - Ilić, Budimir S.
AU  - Kocić, Gordana
AU  - Bondžić, Bojan
AU  - Šmelcerović, Andrija
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4729
AB  - In this study, seven new 4-oxothiazolidine derivatives were synthesized and assayed, along 7 known derivatives, for inhibitory properties against deoxyribonuclease I (DNase I) and xanthine oxidase (XO) in vitro. Among tested compounds, (5Z)-Ethyl-2-(2-(cyanomethylene)-4-oxothiazolidin-5-yliden)acetate (6) exhibited inhibitory activity against both enzymes (DNase I IC50 = 67.94 ± 5.99 μM; XO IC50 = 98.98 ± 13.47 μM), therefore being the first reported dual inhibitor of DNase I and XO. Observed DNase I inhibition qualifies compound 6 as the most potent small organic DNase I inhibitor reported so far. Derivatives of 2-alkyliden-4-oxothiazolidinone (1) inhibited DNase I below 200 μM, while the other tested 4-oxothiazolidine derivatives remained inactive against both enzymes. The molecular docking and molecular dynamics simulations into the binding sites of DNase I and XO enzyme allowed us to clarify the binding modes of this 4-oxothiazolidine derivative, which might aid future development of dual DNase I and XO.
PB  - Elsevier
T2  - Chemico-Biological Interactions
T1  - Synthesis and analysis of 4-oxothiazolidines as potential dual inhibitors of deoxyribonuclease I and xanthine oxidase
VL  - 345
SP  - 109536
DO  - 10.1016/j.cbi.2021.109536
ER  - 

@article{
author = "Gajić, Mihajlo and Džambaski, Zdravko and Ilić, Budimir S. and Kocić, Gordana and Bondžić, Bojan and Šmelcerović, Andrija",
year = "2021",
abstract = "In this study, seven new 4-oxothiazolidine derivatives were synthesized and assayed, along 7 known derivatives, for inhibitory properties against deoxyribonuclease I (DNase I) and xanthine oxidase (XO) in vitro. Among tested compounds, (5Z)-Ethyl-2-(2-(cyanomethylene)-4-oxothiazolidin-5-yliden)acetate (6) exhibited inhibitory activity against both enzymes (DNase I IC50 = 67.94 ± 5.99 μM; XO IC50 = 98.98 ± 13.47 μM), therefore being the first reported dual inhibitor of DNase I and XO. Observed DNase I inhibition qualifies compound 6 as the most potent small organic DNase I inhibitor reported so far. Derivatives of 2-alkyliden-4-oxothiazolidinone (1) inhibited DNase I below 200 μM, while the other tested 4-oxothiazolidine derivatives remained inactive against both enzymes. The molecular docking and molecular dynamics simulations into the binding sites of DNase I and XO enzyme allowed us to clarify the binding modes of this 4-oxothiazolidine derivative, which might aid future development of dual DNase I and XO.",
publisher = "Elsevier",
journal = "Chemico-Biological Interactions",
title = "Synthesis and analysis of 4-oxothiazolidines as potential dual inhibitors of deoxyribonuclease I and xanthine oxidase",
volume = "345",
pages = "109536",
doi = "10.1016/j.cbi.2021.109536"
}

Gajić, M., Džambaski, Z., Ilić, B. S., Kocić, G., Bondžić, B.,& Šmelcerović, A.. (2021). Synthesis and analysis of 4-oxothiazolidines as potential dual inhibitors of deoxyribonuclease I and xanthine oxidase. in Chemico-Biological Interactions
Elsevier., 345, 109536.
https://doi.org/10.1016/j.cbi.2021.109536

Gajić M, Džambaski Z, Ilić BS, Kocić G, Bondžić B, Šmelcerović A. Synthesis and analysis of 4-oxothiazolidines as potential dual inhibitors of deoxyribonuclease I and xanthine oxidase. in Chemico-Biological Interactions. 2021;345:109536.
doi:10.1016/j.cbi.2021.109536 .

Gajić, Mihajlo, Džambaski, Zdravko, Ilić, Budimir S., Kocić, Gordana, Bondžić, Bojan, Šmelcerović, Andrija, "Synthesis and analysis of 4-oxothiazolidines as potential dual inhibitors of deoxyribonuclease I and xanthine oxidase" in Chemico-Biological Interactions, 345 (2021):109536,
https://doi.org/10.1016/j.cbi.2021.109536 . .

TY  - JOUR
AU  - Gajić, Mihajlo
AU  - Ilić, Budimir S.
AU  - Bondžić, Bojan
AU  - Džambaski, Zdravko
AU  - Kojić, Vesna V.
AU  - Jakimov, Dimitar S.
AU  - Kocić, Gordana
AU  - Šmelcerović, Andrija
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4815
AB  - Herein we report an assessment of 24 1,2,3,4-tetrahydroisoquinoline derivatives for potential DNase I (deoxyribonuclease I) inhibitory properties in vitro. Four of them inhibited DNase I with IC50 values below 200 μM. The most potent was 1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one (2) (IC50=134.35±11.38 μM) exhibiting slightly better IC50 value compared to three other active compounds, 2-[2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]-1-phenylethan-1-one (15) (IC50=147.51±14.87 μM), 2-[2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]cyclohexan-1-one (18) (IC50=149.07±2.98 μM) and 2-[6,7-dimethoxy-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]cyclohexan-1-one (22) (IC50=148.31±2.96 μM). Cytotoxicity assessment of the active DNase I inhibitors revealed a lack of toxic effects on the healthy cell lines MRC-5. Molecular docking and molecular dynamics simulations suggest that interactions with Glu 39, His 134, Asn 170, Tyr 211, Asp 251 and His 252 are an important factor for inhibitors affinity toward the DNase I. Observed interactions would be beneficial for the discovery of new active 1,2,3,4-tetrahydroisoquinoline-based inhibitors of DNase I, but might also encourage researchers to further explore and utilize potential therapeutic application of DNase I inhibitors, based on a versatile role of DNase I during apoptotic cell death.
PB  - Wiley
T2  - Chemistry and Biodisversity
T1  - 1,2,3,4-Tetrahydroisoquinoline Derivatives as a Novel Deoxyribonuclease I Inhibitors
VL  - 18
IS  - 8
SP  - e2100261
DO  - 10.1002/cbdv.202100261
ER  - 

@article{
author = "Gajić, Mihajlo and Ilić, Budimir S. and Bondžić, Bojan and Džambaski, Zdravko and Kojić, Vesna V. and Jakimov, Dimitar S. and Kocić, Gordana and Šmelcerović, Andrija",
year = "2021",
abstract = "Herein we report an assessment of 24 1,2,3,4-tetrahydroisoquinoline derivatives for potential DNase I (deoxyribonuclease I) inhibitory properties in vitro. Four of them inhibited DNase I with IC50 values below 200 μM. The most potent was 1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one (2) (IC50=134.35±11.38 μM) exhibiting slightly better IC50 value compared to three other active compounds, 2-[2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]-1-phenylethan-1-one (15) (IC50=147.51±14.87 μM), 2-[2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]cyclohexan-1-one (18) (IC50=149.07±2.98 μM) and 2-[6,7-dimethoxy-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]cyclohexan-1-one (22) (IC50=148.31±2.96 μM). Cytotoxicity assessment of the active DNase I inhibitors revealed a lack of toxic effects on the healthy cell lines MRC-5. Molecular docking and molecular dynamics simulations suggest that interactions with Glu 39, His 134, Asn 170, Tyr 211, Asp 251 and His 252 are an important factor for inhibitors affinity toward the DNase I. Observed interactions would be beneficial for the discovery of new active 1,2,3,4-tetrahydroisoquinoline-based inhibitors of DNase I, but might also encourage researchers to further explore and utilize potential therapeutic application of DNase I inhibitors, based on a versatile role of DNase I during apoptotic cell death.",
publisher = "Wiley",
journal = "Chemistry and Biodisversity",
title = "1,2,3,4-Tetrahydroisoquinoline Derivatives as a Novel Deoxyribonuclease I Inhibitors",
volume = "18",
number = "8",
pages = "e2100261",
doi = "10.1002/cbdv.202100261"
}

Gajić, M., Ilić, B. S., Bondžić, B., Džambaski, Z., Kojić, V. V., Jakimov, D. S., Kocić, G.,& Šmelcerović, A.. (2021). 1,2,3,4-Tetrahydroisoquinoline Derivatives as a Novel Deoxyribonuclease I Inhibitors. in Chemistry and Biodisversity
Wiley., 18(8), e2100261.
https://doi.org/10.1002/cbdv.202100261

Gajić M, Ilić BS, Bondžić B, Džambaski Z, Kojić VV, Jakimov DS, Kocić G, Šmelcerović A. 1,2,3,4-Tetrahydroisoquinoline Derivatives as a Novel Deoxyribonuclease I Inhibitors. in Chemistry and Biodisversity. 2021;18(8):e2100261.
doi:10.1002/cbdv.202100261 .

Gajić, Mihajlo, Ilić, Budimir S., Bondžić, Bojan, Džambaski, Zdravko, Kojić, Vesna V., Jakimov, Dimitar S., Kocić, Gordana, Šmelcerović, Andrija, "1,2,3,4-Tetrahydroisoquinoline Derivatives as a Novel Deoxyribonuclease I Inhibitors" in Chemistry and Biodisversity, 18, no. 8 (2021):e2100261,
https://doi.org/10.1002/cbdv.202100261 . .

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Bondžić, Aleksandra M.
AU  - Triandafillidi, Ierasia
AU  - Kokotos, Christoforos G.
AU  - Bondžić, Bojan
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4823
AB  - Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes. (Figure presented.).
PB  - Wiley
T2  - Advanced Synthesis and Catalysis
T1  - Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction
VL  - 363
IS  - 16
SP  - 4002
EP  - 4008
DO  - 10.1002/adsc.202100630
ER  - 

@article{
author = "Džambaski, Zdravko and Bondžić, Aleksandra M. and Triandafillidi, Ierasia and Kokotos, Christoforos G. and Bondžić, Bojan",
year = "2021",
abstract = "Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes. (Figure presented.).",
publisher = "Wiley",
journal = "Advanced Synthesis and Catalysis",
title = "Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction",
volume = "363",
number = "16",
pages = "4002-4008",
doi = "10.1002/adsc.202100630"
}

Džambaski, Z., Bondžić, A. M., Triandafillidi, I., Kokotos, C. G.,& Bondžić, B.. (2021). Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction. in Advanced Synthesis and Catalysis
Wiley., 363(16), 4002-4008.
https://doi.org/10.1002/adsc.202100630

Džambaski Z, Bondžić AM, Triandafillidi I, Kokotos CG, Bondžić B. Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction. in Advanced Synthesis and Catalysis. 2021;363(16):4002-4008.
doi:10.1002/adsc.202100630 .

Džambaski, Zdravko, Bondžić, Aleksandra M., Triandafillidi, Ierasia, Kokotos, Christoforos G., Bondžić, Bojan, "Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction" in Advanced Synthesis and Catalysis, 363, no. 16 (2021):4002-4008,
https://doi.org/10.1002/adsc.202100630 . .

TY  - JOUR
AU  - Bondžić, Aleksandra
AU  - Senćanski, Milan
AU  - Vujačić Nikezić, Ana V.
AU  - Kirillova, Marina V.
AU  - André, Vânia
AU  - Kirillov, Alexander M.
AU  - Bondžić, Bojan
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3958
AB  - Three coordination compounds featuring different types of tetracopper(II) cores, namely
[O⊂Cu4{N(CH2CH2O)3}4(BOH)4][BF4]2 (1), [Cu4(μ4-H2edte)(μ5-H2edte)(sal)2]n·7nH2O, (H4edte=N,N,N′,
N′-tetrakis(2-hydroxyethyl)ethylenediamine, H2sal=salicylic acid) (2), and [{Cu4(μ3-Hbes)4(μ-hba)}K
(H2O)3]n, H3bes=N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (3), were assayed for their potency to
inhibit the acetyl (AChE) and butyrylcholinesterase (BuChE) enzymes aiming to test these compounds as potential
dual inhibitors in the treatment of Alzheimer's disease. All the investigated compounds showed a strong
inhibitory potency toward both enzymes with IC50 values in micromolar range of concentration; compound 1
displayed the most potent inhibitory behaviour toward both enzymes. The mechanism of the AChE and BuChE
inhibition was examined by enzyme kinetic measurements. The obtained kinetic parameters, Vmax and Km indicated
an uncompetitive type of inhibition of both enzymes by compound 1. For the other two compounds a
non-competitive inhibition mode was observed. To get further insight into the mechanism of action and to
elucidate binding modes in details we examined the interactions of 1–3 with acetylcholinesterase, using molecular
docking approach. Grid based docking studies indicated that these compounds can bind to peripheral
anionic site (PAS) of the AChE with Ki values in micromolar range. Moreover, blind docking revealed the
capability of investigated compounds to bind to new allosteric site (i.e. binding site II) distinct from PAS.
Showing that these Cu-based compounds can act as new allosteric inhibitors of AChE and identifying novel
allosteric binding site on AChE represents a significant contribution toward the design of novel and more
effective inhibitors of AChE.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action
VL  - 205
SP  - 110990
DO  - 10.1016/j.jinorgbio.2019.110990
ER  - 

@article{
author = "Bondžić, Aleksandra and Senćanski, Milan and Vujačić Nikezić, Ana V. and Kirillova, Marina V. and André, Vânia and Kirillov, Alexander M. and Bondžić, Bojan",
year = "2020",
abstract = "Three coordination compounds featuring different types of tetracopper(II) cores, namely
[O⊂Cu4{N(CH2CH2O)3}4(BOH)4][BF4]2 (1), [Cu4(μ4-H2edte)(μ5-H2edte)(sal)2]n·7nH2O, (H4edte=N,N,N′,
N′-tetrakis(2-hydroxyethyl)ethylenediamine, H2sal=salicylic acid) (2), and [{Cu4(μ3-Hbes)4(μ-hba)}K
(H2O)3]n, H3bes=N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (3), were assayed for their potency to
inhibit the acetyl (AChE) and butyrylcholinesterase (BuChE) enzymes aiming to test these compounds as potential
dual inhibitors in the treatment of Alzheimer's disease. All the investigated compounds showed a strong
inhibitory potency toward both enzymes with IC50 values in micromolar range of concentration; compound 1
displayed the most potent inhibitory behaviour toward both enzymes. The mechanism of the AChE and BuChE
inhibition was examined by enzyme kinetic measurements. The obtained kinetic parameters, Vmax and Km indicated
an uncompetitive type of inhibition of both enzymes by compound 1. For the other two compounds a
non-competitive inhibition mode was observed. To get further insight into the mechanism of action and to
elucidate binding modes in details we examined the interactions of 1–3 with acetylcholinesterase, using molecular
docking approach. Grid based docking studies indicated that these compounds can bind to peripheral
anionic site (PAS) of the AChE with Ki values in micromolar range. Moreover, blind docking revealed the
capability of investigated compounds to bind to new allosteric site (i.e. binding site II) distinct from PAS.
Showing that these Cu-based compounds can act as new allosteric inhibitors of AChE and identifying novel
allosteric binding site on AChE represents a significant contribution toward the design of novel and more
effective inhibitors of AChE.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action",
volume = "205",
pages = "110990",
doi = "10.1016/j.jinorgbio.2019.110990"
}

Bondžić, A., Senćanski, M., Vujačić Nikezić, A. V., Kirillova, M. V., André, V., Kirillov, A. M.,& Bondžić, B.. (2020). Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action. in Journal of Inorganic Biochemistry
Elsevier., 205, 110990.
https://doi.org/10.1016/j.jinorgbio.2019.110990

Bondžić A, Senćanski M, Vujačić Nikezić AV, Kirillova MV, André V, Kirillov AM, Bondžić B. Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action. in Journal of Inorganic Biochemistry. 2020;205:110990.
doi:10.1016/j.jinorgbio.2019.110990 .

Bondžić, Aleksandra, Senćanski, Milan, Vujačić Nikezić, Ana V., Kirillova, Marina V., André, Vânia, Kirillov, Alexander M., Bondžić, Bojan, "Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action" in Journal of Inorganic Biochemistry, 205 (2020):110990,
https://doi.org/10.1016/j.jinorgbio.2019.110990 . .

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Tzaras, Dimitrios‐Ioannis
AU  - Lee, Sunggi
AU  - Kokotos, Christoforos G.
AU  - Bondžić, Bojan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2953
AB  - α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.
PB  - Wiley
T2  - Advanced Synthesis & Catalysis
T1  - Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction
VL  - 361
IS  - 8
SP  - 1792
EP  - 1797
DO  - 10.1002/adsc.201900061
ER  - 

@article{
author = "Džambaski, Zdravko and Tzaras, Dimitrios‐Ioannis and Lee, Sunggi and Kokotos, Christoforos G. and Bondžić, Bojan",
year = "2019",
abstract = "α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.",
publisher = "Wiley",
journal = "Advanced Synthesis & Catalysis",
title = "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction",
volume = "361",
number = "8",
pages = "1792-1797",
doi = "10.1002/adsc.201900061"
}

Džambaski, Z., Tzaras, D., Lee, S., Kokotos, C. G.,& Bondžić, B.. (2019). Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis
Wiley., 361(8), 1792-1797.
https://doi.org/10.1002/adsc.201900061

Džambaski Z, Tzaras D, Lee S, Kokotos CG, Bondžić B. Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis. 2019;361(8):1792-1797.
doi:10.1002/adsc.201900061 .

Džambaski, Zdravko, Tzaras, Dimitrios‐Ioannis, Lee, Sunggi, Kokotos, Christoforos G., Bondžić, Bojan, "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction" in Advanced Synthesis & Catalysis, 361, no. 8 (2019):1792-1797,
https://doi.org/10.1002/adsc.201900061 . .

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Tzaras, Dimitrios‐Ioannis
AU  - Lee, Sunggi
AU  - Kokotos, Christoforos G.
AU  - Bondžić, Bojan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2954
AB  - α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.
PB  - Wiley
T2  - Advanced Synthesis & Catalysis
T1  - Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction
VL  - 361
IS  - 8
SP  - 1792
EP  - 1797
DO  - 10.1002/adsc.201900061
ER  - 

@article{
author = "Džambaski, Zdravko and Tzaras, Dimitrios‐Ioannis and Lee, Sunggi and Kokotos, Christoforos G. and Bondžić, Bojan",
year = "2019",
abstract = "α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.",
publisher = "Wiley",
journal = "Advanced Synthesis & Catalysis",
title = "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction",
volume = "361",
number = "8",
pages = "1792-1797",
doi = "10.1002/adsc.201900061"
}

Džambaski, Z., Tzaras, D., Lee, S., Kokotos, C. G.,& Bondžić, B.. (2019). Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis
Wiley., 361(8), 1792-1797.
https://doi.org/10.1002/adsc.201900061

Džambaski Z, Tzaras D, Lee S, Kokotos CG, Bondžić B. Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis. 2019;361(8):1792-1797.
doi:10.1002/adsc.201900061 .

Džambaski, Zdravko, Tzaras, Dimitrios‐Ioannis, Lee, Sunggi, Kokotos, Christoforos G., Bondžić, Bojan, "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction" in Advanced Synthesis & Catalysis, 361, no. 8 (2019):1792-1797,
https://doi.org/10.1002/adsc.201900061 . .

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Bondžić, Bojan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3063
AB  - The organocatalyzed Mannich reaction of unsubstituted and N-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several N-aryl-substituted THIQs through dehydrogenative C(sp3)–H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C–H oxidation/Mannich reaction of less reactive N-aryl substituted pyrrolidines is achieved via metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.
PB  - Royal Society of Chemistry (RSC)
T2  - Organic & Biomolecular Chemistry
T1  - Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions
VL  - 17
IS  - 26
SP  - 6420
EP  - 6425
DO  - 10.1039/C9OB01090D
ER  - 

@article{
author = "Džambaski, Zdravko and Bondžić, Bojan",
year = "2019",
abstract = "The organocatalyzed Mannich reaction of unsubstituted and N-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several N-aryl-substituted THIQs through dehydrogenative C(sp3)–H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C–H oxidation/Mannich reaction of less reactive N-aryl substituted pyrrolidines is achieved via metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Organic & Biomolecular Chemistry",
title = "Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions",
volume = "17",
number = "26",
pages = "6420-6425",
doi = "10.1039/C9OB01090D"
}

Džambaski, Z.,& Bondžić, B.. (2019). Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions. in Organic & Biomolecular Chemistry
Royal Society of Chemistry (RSC)., 17(26), 6420-6425.
https://doi.org/10.1039/C9OB01090D

Džambaski Z, Bondžić B. Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions. in Organic & Biomolecular Chemistry. 2019;17(26):6420-6425.
doi:10.1039/C9OB01090D .

Džambaski, Zdravko, Bondžić, Bojan, "Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions" in Organic & Biomolecular Chemistry, 17, no. 26 (2019):6420-6425,
https://doi.org/10.1039/C9OB01090D . .

TY  - JOUR
AU  - Bondžić, Bojan
AU  - Džambaski, Zdravko
AU  - Kolarević, Ana
AU  - Đorđević, Aleksandra
AU  - Anderluh, Marko
AU  - Šmelcerović, Andrija
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3957
AB  - Eight new benzocyclobutane-2,5-diones (1a–1h) were synthesized, and their inhibitory properties
against bovine pancreatic DNase I were examined in vitro. Methods & results: Compounds 1a–1h
were synthesized using photocycloaddition of duroquinone with various phenyl-substituted ethylenes
in the presence of 18W compact fluorescent lamp (visible light). Two compounds, 1,3,4,6-tetramethyl-7-
phenylbicyclo[4.2.0]oct-3-ene-2,5-dione (1a) and 1,3,4,6-tetramethyl-7-p-tolylbicyclo[4.2.0]oct-3-ene-2,5-
dione (1b) inhibited DNase I in a noncompetitive manner with IC50 values below 150 μM and showed to
be more potent DNase I inhibitors than crystal violet, used as a positive control. In order to analyze potential
binding sites for the studied compounds with DNase I, molecular docking study was performed.
Conclusion: The studied benzocyclobutane-2,5-diones offer a good starting point for a design of new
DNase I inhibitors.
PB  - Future Medicine Ltd.
T2  - Future Medicinal Chemistry
T1  - Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones
VL  - 11
VL  - 2426
IS  - 18
SP  - 2415
DO  - 10.4155/fmc-2019-0032
ER  - 

@article{
author = "Bondžić, Bojan and Džambaski, Zdravko and Kolarević, Ana and Đorđević, Aleksandra and Anderluh, Marko and Šmelcerović, Andrija",
year = "2019",
abstract = "Eight new benzocyclobutane-2,5-diones (1a–1h) were synthesized, and their inhibitory properties
against bovine pancreatic DNase I were examined in vitro. Methods & results: Compounds 1a–1h
were synthesized using photocycloaddition of duroquinone with various phenyl-substituted ethylenes
in the presence of 18W compact fluorescent lamp (visible light). Two compounds, 1,3,4,6-tetramethyl-7-
phenylbicyclo[4.2.0]oct-3-ene-2,5-dione (1a) and 1,3,4,6-tetramethyl-7-p-tolylbicyclo[4.2.0]oct-3-ene-2,5-
dione (1b) inhibited DNase I in a noncompetitive manner with IC50 values below 150 μM and showed to
be more potent DNase I inhibitors than crystal violet, used as a positive control. In order to analyze potential
binding sites for the studied compounds with DNase I, molecular docking study was performed.
Conclusion: The studied benzocyclobutane-2,5-diones offer a good starting point for a design of new
DNase I inhibitors.",
publisher = "Future Medicine Ltd.",
journal = "Future Medicinal Chemistry",
title = "Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones",
volume = "11, 2426",
number = "18",
pages = "2415",
doi = "10.4155/fmc-2019-0032"
}

Bondžić, B., Džambaski, Z., Kolarević, A., Đorđević, A., Anderluh, M.,& Šmelcerović, A.. (2019). Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones. in Future Medicinal Chemistry
Future Medicine Ltd.., 11(18), 2415.
https://doi.org/10.4155/fmc-2019-0032

Bondžić B, Džambaski Z, Kolarević A, Đorđević A, Anderluh M, Šmelcerović A. Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones. in Future Medicinal Chemistry. 2019;11(18):2415.
doi:10.4155/fmc-2019-0032 .

Bondžić, Bojan, Džambaski, Zdravko, Kolarević, Ana, Đorđević, Aleksandra, Anderluh, Marko, Šmelcerović, Andrija, "Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones" in Future Medicinal Chemistry, 11, no. 18 (2019):2415,
https://doi.org/10.4155/fmc-2019-0032 . .

TY  - JOUR
AU  - Kolarević, Ana
AU  - Ilić, Budimir S.
AU  - Kocić, Gordana
AU  - Džambaski, Zdravko
AU  - Šmelcerović, Andrija
AU  - Bondžić, Bojan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2998
AB  - Twelve new thiazolidinones were synthesized and, together with 41 previously
synthesized thiazolidinones, evaluated for inhibitory activity against deoxyribonuclease I (DNase I) in vitro. Ten compounds inhibited commercial bovine pancreatic DNase I with an IC50 below 200 μM and showed to be more potent DNase I inhibitors than crystal violet (IC50 = 365.90 ± 47.33 μM), used as a positive control. Moreover, three compounds were active against DNase I in rat
liver homogenate, having an IC50 below 200 μM. (3‐Methyl‐1,4‐dioxothiazolidin‐2‐ylidene)‐N‐(2‐phenylethyl)ethanamide (41) exhibited the most potent DNase I inhibition against both commercial and rat liver DNase I with IC50 values of 115.96 ± 11.70 and 151.36 ± 15.85 μM, respectively. Site Finder and molecular docking defined the thiazolidinones interactions with the most important catalytic residues of DNase I, including the H‐acceptor interaction with residues His 134 and His 252 and/or H‐donor interaction with residues Glu 39 and Asp 168. The three most active compounds against both commercial and rat liver DNase I (31, 38, and 41) exhibited favorable physico‐chemical, pharmacokinetic, and toxicological properties. These observations could be
utilized to guide the rational design and optimization of novel thiazolidinone inhibitors. Thiazolidinones as novel DNase I inhibitors could have potential therapeutic applications due to the significant involvement of DNase I in the pathophysiology of many disease conditions.
PB  - Wiley
T2  - Journal of Cellular Biochemistry
T1  - Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives
VL  - 120
IS  - 1
SP  - 264
EP  - 274
DO  - 10.1002/jcb.27339
ER  - 

@article{
author = "Kolarević, Ana and Ilić, Budimir S. and Kocić, Gordana and Džambaski, Zdravko and Šmelcerović, Andrija and Bondžić, Bojan",
year = "2018",
abstract = "Twelve new thiazolidinones were synthesized and, together with 41 previously
synthesized thiazolidinones, evaluated for inhibitory activity against deoxyribonuclease I (DNase I) in vitro. Ten compounds inhibited commercial bovine pancreatic DNase I with an IC50 below 200 μM and showed to be more potent DNase I inhibitors than crystal violet (IC50 = 365.90 ± 47.33 μM), used as a positive control. Moreover, three compounds were active against DNase I in rat
liver homogenate, having an IC50 below 200 μM. (3‐Methyl‐1,4‐dioxothiazolidin‐2‐ylidene)‐N‐(2‐phenylethyl)ethanamide (41) exhibited the most potent DNase I inhibition against both commercial and rat liver DNase I with IC50 values of 115.96 ± 11.70 and 151.36 ± 15.85 μM, respectively. Site Finder and molecular docking defined the thiazolidinones interactions with the most important catalytic residues of DNase I, including the H‐acceptor interaction with residues His 134 and His 252 and/or H‐donor interaction with residues Glu 39 and Asp 168. The three most active compounds against both commercial and rat liver DNase I (31, 38, and 41) exhibited favorable physico‐chemical, pharmacokinetic, and toxicological properties. These observations could be
utilized to guide the rational design and optimization of novel thiazolidinone inhibitors. Thiazolidinones as novel DNase I inhibitors could have potential therapeutic applications due to the significant involvement of DNase I in the pathophysiology of many disease conditions.",
publisher = "Wiley",
journal = "Journal of Cellular Biochemistry",
title = "Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives",
volume = "120",
number = "1",
pages = "264-274",
doi = "10.1002/jcb.27339"
}

Kolarević, A., Ilić, B. S., Kocić, G., Džambaski, Z., Šmelcerović, A.,& Bondžić, B.. (2018). Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives. in Journal of Cellular Biochemistry
Wiley., 120(1), 264-274.
https://doi.org/10.1002/jcb.27339

Kolarević A, Ilić BS, Kocić G, Džambaski Z, Šmelcerović A, Bondžić B. Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives. in Journal of Cellular Biochemistry. 2018;120(1):264-274.
doi:10.1002/jcb.27339 .

Kolarević, Ana, Ilić, Budimir S., Kocić, Gordana, Džambaski, Zdravko, Šmelcerović, Andrija, Bondžić, Bojan, "Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives" in Journal of Cellular Biochemistry, 120, no. 1 (2018):264-274,
https://doi.org/10.1002/jcb.27339 . .

TY  - JOUR
AU  - Bondžić, Bojan
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3186
AB  - The hydroformylation reaction represents one of the most important metal catalyzed bulk chemical manufacturing processes today. However, tremendous progress towards more complex molecules using tandem hydroformylation has been achieved during the past decade. Different approaches towards indoles and other nitrogen containing heterocycles, alkaloids, and other biologically active compounds are steadily turning hydroformylation into one of the methods to be considered even in the complex syntheses of natural products and other fine chemicals. The application of organocatalyzed processes coupled with formation of aldehydes through hydroformylation reaction in the synthesis of enantioenriched fine chemicals is another turning point in the application of this reaction. Vast number of other new reaction sequences under hydroformylation conditions have been developed turning tandem and one pot sequences under hydroformylation conditions into a method of choice for organic chemistry and catalysis practitioners.
PB  - Elsevier
T2  - Journal of Molecular Catalysis A: Chemical
T1  - Rh catalyzed multicomponent tandem and one-pot reactions under hydroformylation conditions
VL  - 408
SP  - 310
EP  - 334
DO  - 10.1016/j.molcata.2015.07.026
ER  - 

@article{
author = "Bondžić, Bojan",
year = "2015",
abstract = "The hydroformylation reaction represents one of the most important metal catalyzed bulk chemical manufacturing processes today. However, tremendous progress towards more complex molecules using tandem hydroformylation has been achieved during the past decade. Different approaches towards indoles and other nitrogen containing heterocycles, alkaloids, and other biologically active compounds are steadily turning hydroformylation into one of the methods to be considered even in the complex syntheses of natural products and other fine chemicals. The application of organocatalyzed processes coupled with formation of aldehydes through hydroformylation reaction in the synthesis of enantioenriched fine chemicals is another turning point in the application of this reaction. Vast number of other new reaction sequences under hydroformylation conditions have been developed turning tandem and one pot sequences under hydroformylation conditions into a method of choice for organic chemistry and catalysis practitioners.",
publisher = "Elsevier",
journal = "Journal of Molecular Catalysis A: Chemical",
title = "Rh catalyzed multicomponent tandem and one-pot reactions under hydroformylation conditions",
volume = "408",
pages = "310-334",
doi = "10.1016/j.molcata.2015.07.026"
}

Bondžić, B.. (2015). Rh catalyzed multicomponent tandem and one-pot reactions under hydroformylation conditions. in Journal of Molecular Catalysis A: Chemical
Elsevier., 408, 310-334.
https://doi.org/10.1016/j.molcata.2015.07.026

Bondžić B. Rh catalyzed multicomponent tandem and one-pot reactions under hydroformylation conditions. in Journal of Molecular Catalysis A: Chemical. 2015;408:310-334.
doi:10.1016/j.molcata.2015.07.026 .

Bondžić, Bojan, "Rh catalyzed multicomponent tandem and one-pot reactions under hydroformylation conditions" in Journal of Molecular Catalysis A: Chemical, 408 (2015):310-334,
https://doi.org/10.1016/j.molcata.2015.07.026 . .