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  - 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  - Smiljanić, Milče M.
AU  - Radjenović, Branislav
AU  - Lazić, Žarko
AU  - Radmilović Radjenović, Marija
AU  - Rašljić Rafajilović, Milena
AU  - Cvetanović Zobenica, Katarina
AU  - Milinković, Evgenija
AU  - Filipović, Ana
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4453
AB  - In  this  paper,  fabrication  of  silicon  microchannels  with  integrated  obstacles  by  using  25 wt.% tetramethylammonium  hydroxide  (TMAH)  aqueous  solution  at  the  temperature  of  80 C  is presented  and  analysed.  We  studied  basic  island  patterns,  which present  union  of  two symmetrical parallelograms with the sides along predetermined crystallographic directions <n10> (2<n<8) and <100>. Acute angles of the parallelograms were smaller than 45o. We have derived analytical  relations  for  determining  dimensions  of  the  integrated  obstacles.  The  developed etching  technique  provides  reduction  of  the  distance  between  the  obstacles.  Before  the experiments, we performed simulations of pattern etching based on the level set method and presented  evolution  of  the  etched basic  patterns  for  the  predetermined  crystallographic directions  <n10>.  Combination  of  basic  patterns  with  sides  along  the  <610>  and  <100> crystallographic  directions  is  used  to  fabricate  a  matrix  of  two  row  of  silicon  obstacles  in  a microchannel.   We   obtained   a   good   agreement   between   the   experimental   results   and simulations.   Our   results   enable   simple  and   cost-effective  fabrication   of  various   complex microfluidic silicon platforms with integrated obstacles.
AB  - U ovom radu je prezentovana i analizirana izrada silicijumskih mikrokanala sa integrisanim preprekama u vodenom rastvoru 25 mas.% tetrametilamonijum hidroksida (TMAH) na temperaturi od 80 oC. Proučavani su osnovni oblici maski koji predstavljaju uniju dva simetrična ostrva u obliku paralelograma čije su stranice duž unapred određenih kristalografskih pravaca (2<n<8) i <100>. Oštri uglovi paralelograma su manji od 45˚. Izvedene su formule za izračunavanje dimenzija integrisanih prepreka. Razvijena je tehnika nagrizanja koja smanjuje rastojanje između prepreka. Pre eksperimenata izvršene su simulacije osnovnih oblika koje se baziraju na metodi implicitno definisanih nivoa (engl. level set method). Prezentovan je razvoj nagrizanih osnovnih oblika maski za unapred određene kristalografske pravce <n10>. Kombinacija osnovnih oblika maski čije su stranice duž kristalografskih pravaca <610> i <100> je iskorišćena za izradu dva reda matrice silicijumskih prepreka u mikrokanalu. Dobijeno je dobro slaganje između eksperimenata i simulacija. Dobijeni rezultati omogućavaju jednostavnu i jeftinu izradu različitih kompleksnih mikrofluidnih silicijumskih platformi sa integrisanim preprekama.
PB  - Association of Chemical Engeneers of Serbia
T2  - Hemijska industrija
T1  - Controllable arrangement of integrated obstacles in silicon microchannels etched in 25 wt % TMAH
T1  - Kontrolisan raspored integrisanih prepreka u silicijumskim mikrokanalima nagrizanim u 25 mas.% rastvoru tetrametilamonijum hidroksida
VL  - 75
IS  - 1
SP  - 15
EP  - 24
DO  - 10.2298/HEMIND200807005S
ER  - 

@article{
author = "Smiljanić, Milče M. and Radjenović, Branislav and Lazić, Žarko and Radmilović Radjenović, Marija and Rašljić Rafajilović, Milena and Cvetanović Zobenica, Katarina and Milinković, Evgenija and Filipović, Ana",
year = "2021",
abstract = "In  this  paper,  fabrication  of  silicon  microchannels  with  integrated  obstacles  by  using  25 wt.% tetramethylammonium  hydroxide  (TMAH)  aqueous  solution  at  the  temperature  of  80 C  is presented  and  analysed.  We  studied  basic  island  patterns,  which present  union  of  two symmetrical parallelograms with the sides along predetermined crystallographic directions <n10> (2<n<8) and <100>. Acute angles of the parallelograms were smaller than 45o. We have derived analytical  relations  for  determining  dimensions  of  the  integrated  obstacles.  The  developed etching  technique  provides  reduction  of  the  distance  between  the  obstacles.  Before  the experiments, we performed simulations of pattern etching based on the level set method and presented  evolution  of  the  etched basic  patterns  for  the  predetermined  crystallographic directions  <n10>.  Combination  of  basic  patterns  with  sides  along  the  <610>  and  <100> crystallographic  directions  is  used  to  fabricate  a  matrix  of  two  row  of  silicon  obstacles  in  a microchannel.   We   obtained   a   good   agreement   between   the   experimental   results   and simulations.   Our   results   enable   simple  and   cost-effective  fabrication   of  various   complex microfluidic silicon platforms with integrated obstacles., U ovom radu je prezentovana i analizirana izrada silicijumskih mikrokanala sa integrisanim preprekama u vodenom rastvoru 25 mas.% tetrametilamonijum hidroksida (TMAH) na temperaturi od 80 oC. Proučavani su osnovni oblici maski koji predstavljaju uniju dva simetrična ostrva u obliku paralelograma čije su stranice duž unapred određenih kristalografskih pravaca (2<n<8) i <100>. Oštri uglovi paralelograma su manji od 45˚. Izvedene su formule za izračunavanje dimenzija integrisanih prepreka. Razvijena je tehnika nagrizanja koja smanjuje rastojanje između prepreka. Pre eksperimenata izvršene su simulacije osnovnih oblika koje se baziraju na metodi implicitno definisanih nivoa (engl. level set method). Prezentovan je razvoj nagrizanih osnovnih oblika maski za unapred određene kristalografske pravce <n10>. Kombinacija osnovnih oblika maski čije su stranice duž kristalografskih pravaca <610> i <100> je iskorišćena za izradu dva reda matrice silicijumskih prepreka u mikrokanalu. Dobijeno je dobro slaganje između eksperimenata i simulacija. Dobijeni rezultati omogućavaju jednostavnu i jeftinu izradu različitih kompleksnih mikrofluidnih silicijumskih platformi sa integrisanim preprekama.",
publisher = "Association of Chemical Engeneers of Serbia",
journal = "Hemijska industrija",
title = "Controllable arrangement of integrated obstacles in silicon microchannels etched in 25 wt % TMAH, Kontrolisan raspored integrisanih prepreka u silicijumskim mikrokanalima nagrizanim u 25 mas.% rastvoru tetrametilamonijum hidroksida",
volume = "75",
number = "1",
pages = "15-24",
doi = "10.2298/HEMIND200807005S"
}

Smiljanić, M. M., Radjenović, B., Lazić, Ž., Radmilović Radjenović, M., Rašljić Rafajilović, M., Cvetanović Zobenica, K., Milinković, E.,& Filipović, A.. (2021). Controllable arrangement of integrated obstacles in silicon microchannels etched in 25 wt % TMAH. in Hemijska industrija
Association of Chemical Engeneers of Serbia., 75(1), 15-24.
https://doi.org/10.2298/HEMIND200807005S

Smiljanić MM, Radjenović B, Lazić Ž, Radmilović Radjenović M, Rašljić Rafajilović M, Cvetanović Zobenica K, Milinković E, Filipović A. Controllable arrangement of integrated obstacles in silicon microchannels etched in 25 wt % TMAH. in Hemijska industrija. 2021;75(1):15-24.
doi:10.2298/HEMIND200807005S .

Smiljanić, Milče M., Radjenović, Branislav, Lazić, Žarko, Radmilović Radjenović, Marija, Rašljić Rafajilović, Milena, Cvetanović Zobenica, Katarina, Milinković, Evgenija, Filipović, Ana, "Controllable arrangement of integrated obstacles in silicon microchannels etched in 25 wt % TMAH" in Hemijska industrija, 75, no. 1 (2021):15-24,
https://doi.org/10.2298/HEMIND200807005S . .

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  - Smiljanić, Milče M.
AU  - Lazić, Žarko
AU  - Rašljić Rafajilović, Milena
AU  - Cvetanović Zobenica, Katarina
AU  - Milinković, Evgenija
AU  - Filipović, Ana
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4002
AB  - In this study, Y-bifurcated microchannels fabricated from a {100} silicon in 25 wt% tetramethylammonium hydroxide water solution at the temperature of 80 °C have been presented and analysed. We studied the etching of acute angles with sides along the <n10> crystallographic directions in the masking layer where 1 < n < 8. We considered symmetrical acute corners in the masking layer with respect to the <100> crystallographic directions. The angles between the appropriate <n10> and <100> crystallographic directions were smaller than 45°. Moreover, we observed asymmetrical acute corners formed by the <n10> and <m10> crystallographic directions, where m ≠ n. We found that the obtained convex corners were not distorted during etching. Consequently, it is not necessary to apply convex corner compensation. These fabricated undistorted convex corners represent the angles of the bifurcations. The sidewalls of the microchannels are defined by etched planes of the {n11} and {100} families. Analytical relations were derived for the widths of the microchannels. The results enable simple and cost-effective fabrication of various complex silicon microfluidic platforms.
PB  - IOP Publishing
T2  - Journal of Micromechanics and Microengineering
T1  - Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution
VL  - 31
SP  - 017001
DO  - 10.1088/1361-6439/abcb67
ER  - 

@article{
author = "Smiljanić, Milče M. and Lazić, Žarko and Rašljić Rafajilović, Milena and Cvetanović Zobenica, Katarina and Milinković, Evgenija and Filipović, Ana",
year = "2020",
abstract = "In this study, Y-bifurcated microchannels fabricated from a {100} silicon in 25 wt% tetramethylammonium hydroxide water solution at the temperature of 80 °C have been presented and analysed. We studied the etching of acute angles with sides along the <n10> crystallographic directions in the masking layer where 1 < n < 8. We considered symmetrical acute corners in the masking layer with respect to the <100> crystallographic directions. The angles between the appropriate <n10> and <100> crystallographic directions were smaller than 45°. Moreover, we observed asymmetrical acute corners formed by the <n10> and <m10> crystallographic directions, where m ≠ n. We found that the obtained convex corners were not distorted during etching. Consequently, it is not necessary to apply convex corner compensation. These fabricated undistorted convex corners represent the angles of the bifurcations. The sidewalls of the microchannels are defined by etched planes of the {n11} and {100} families. Analytical relations were derived for the widths of the microchannels. The results enable simple and cost-effective fabrication of various complex silicon microfluidic platforms.",
publisher = "IOP Publishing",
journal = "Journal of Micromechanics and Microengineering",
title = "Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution",
volume = "31",
pages = "017001",
doi = "10.1088/1361-6439/abcb67"
}

Smiljanić, M. M., Lazić, Ž., Rašljić Rafajilović, M., Cvetanović Zobenica, K., Milinković, E.,& Filipović, A.. (2020). Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution. in Journal of Micromechanics and Microengineering
IOP Publishing., 31, 017001.
https://doi.org/10.1088/1361-6439/abcb67

Smiljanić MM, Lazić Ž, Rašljić Rafajilović M, Cvetanović Zobenica K, Milinković E, Filipović A. Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution. in Journal of Micromechanics and Microengineering. 2020;31:017001.
doi:10.1088/1361-6439/abcb67 .

Smiljanić, Milče M., Lazić, Žarko, Rašljić Rafajilović, Milena, Cvetanović Zobenica, Katarina, Milinković, Evgenija, Filipović, Ana, "Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution" in Journal of Micromechanics and Microengineering, 31 (2020):017001,
https://doi.org/10.1088/1361-6439/abcb67 . .

TY  - JOUR
AU  - Smiljanić, Milče M.
AU  - Lazić, Žarko
AU  - Rašljić Rafajilović, Milena
AU  - Cvetanović Zobenica, Katarina
AU  - Milinković, Evgenija
AU  - Filipović, Ana
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4003
AB  - In this study, Y-bifurcated microchannels fabricated from a {100} silicon in 25 wt% tetramethylammonium hydroxide water solution at the temperature of 80 °C have been presented and analysed. We studied the etching of acute angles with sides along the <n10> crystallographic directions in the masking layer where 1 < n < 8. We considered symmetrical acute corners in the masking layer with respect to the <100> crystallographic directions. The angles between the appropriate <n10> and <100> crystallographic directions were smaller than 45°. Moreover, we observed asymmetrical acute corners formed by the <n10> and <m10> crystallographic directions, where m ≠ n. We found that the obtained convex corners were not distorted during etching. Consequently, it is not necessary to apply convex corner compensation. These fabricated undistorted convex corners represent the angles of the bifurcations. The sidewalls of the microchannels are defined by etched planes of the {n11} and {100} families. Analytical relations were derived for the widths of the microchannels. The results enable simple and cost-effective fabrication of various complex silicon microfluidic platforms.
PB  - IOP Publishing
T2  - Journal of Micromechanics and Microengineering
T1  - Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution
VL  - 31
SP  - 017001
DO  - 10.1088/1361-6439/abcb67
ER  - 

@article{
author = "Smiljanić, Milče M. and Lazić, Žarko and Rašljić Rafajilović, Milena and Cvetanović Zobenica, Katarina and Milinković, Evgenija and Filipović, Ana",
year = "2020",
abstract = "In this study, Y-bifurcated microchannels fabricated from a {100} silicon in 25 wt% tetramethylammonium hydroxide water solution at the temperature of 80 °C have been presented and analysed. We studied the etching of acute angles with sides along the <n10> crystallographic directions in the masking layer where 1 < n < 8. We considered symmetrical acute corners in the masking layer with respect to the <100> crystallographic directions. The angles between the appropriate <n10> and <100> crystallographic directions were smaller than 45°. Moreover, we observed asymmetrical acute corners formed by the <n10> and <m10> crystallographic directions, where m ≠ n. We found that the obtained convex corners were not distorted during etching. Consequently, it is not necessary to apply convex corner compensation. These fabricated undistorted convex corners represent the angles of the bifurcations. The sidewalls of the microchannels are defined by etched planes of the {n11} and {100} families. Analytical relations were derived for the widths of the microchannels. The results enable simple and cost-effective fabrication of various complex silicon microfluidic platforms.",
publisher = "IOP Publishing",
journal = "Journal of Micromechanics and Microengineering",
title = "Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution",
volume = "31",
pages = "017001",
doi = "10.1088/1361-6439/abcb67"
}

Smiljanić, M. M., Lazić, Ž., Rašljić Rafajilović, M., Cvetanović Zobenica, K., Milinković, E.,& Filipović, A.. (2020). Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution. in Journal of Micromechanics and Microengineering
IOP Publishing., 31, 017001.
https://doi.org/10.1088/1361-6439/abcb67

Smiljanić MM, Lazić Ž, Rašljić Rafajilović M, Cvetanović Zobenica K, Milinković E, Filipović A. Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution. in Journal of Micromechanics and Microengineering. 2020;31:017001.
doi:10.1088/1361-6439/abcb67 .

Smiljanić, Milče M., Lazić, Žarko, Rašljić Rafajilović, Milena, Cvetanović Zobenica, Katarina, Milinković, Evgenija, Filipović, Ana, "Silicon Y-bifurcated microchannels etched in 25 wt% TMAH water solution" in Journal of Micromechanics and Microengineering, 31 (2020):017001,
https://doi.org/10.1088/1361-6439/abcb67 . .

TY  - CONF
AU  - Smiljanić, Milče M.
AU  - Lazić, Žarko
AU  - Radjenović, Branislav
AU  - Radjenović-Radmilović, Marija
AU  - Jović, Vesna
AU  - Rašljić, Milena
AU  - Cvetanović, Katarina
AU  - Filipović, Ana
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5771
AB  - In this paper, we present and analyze etching of 
parallelogram patterns in the masking layer on a (100) silicon in 
25 wt % TMAH water solution at the temperature of 80 0C. Sides 
of parallelogram islands in the masking layer are designed along 
<n10> and <100> crystallographic directions. A 3D simulation of 
the profile evolution from these patterns during etching of silicon 
using the level set method is also presented. We determined all
crystallographic planes that appear during etching in the 
experiment and obtained simulated etching profiles of these 3D 
structures. A good agreement between dominant 
crystallographic planes through experiments and simulations is 
obtained.
PB  - Society for Electronics, Telecommunications, Computers, Automatic Control and Nuclear Engineering
C3  - Proceedings - 6th International Conference on Electrical, Electronic and Computing Engineering, IcETRAN 2019, June 03 – 06, 2019, Silver Lake, Serbia
T1  - Etched Parallelogram Patterns with Sides Along <100> and <n10> Directions in 25 wt % TMAH
SP  - 584
EP  - 589
UR  - https://hdl.handle.net/21.15107/rcub_cer_5771
ER  - 

@conference{
author = "Smiljanić, Milče M. and Lazić, Žarko and Radjenović, Branislav and Radjenović-Radmilović, Marija and Jović, Vesna and Rašljić, Milena and Cvetanović, Katarina and Filipović, Ana",
year = "2019",
abstract = "In this paper, we present and analyze etching of 
parallelogram patterns in the masking layer on a (100) silicon in 
25 wt % TMAH water solution at the temperature of 80 0C. Sides 
of parallelogram islands in the masking layer are designed along 
<n10> and <100> crystallographic directions. A 3D simulation of 
the profile evolution from these patterns during etching of silicon 
using the level set method is also presented. We determined all
crystallographic planes that appear during etching in the 
experiment and obtained simulated etching profiles of these 3D 
structures. A good agreement between dominant 
crystallographic planes through experiments and simulations is 
obtained.",
publisher = "Society for Electronics, Telecommunications, Computers, Automatic Control and Nuclear Engineering",
journal = "Proceedings - 6th International Conference on Electrical, Electronic and Computing Engineering, IcETRAN 2019, June 03 – 06, 2019, Silver Lake, Serbia",
title = "Etched Parallelogram Patterns with Sides Along <100> and <n10> Directions in 25 wt % TMAH",
pages = "584-589",
url = "https://hdl.handle.net/21.15107/rcub_cer_5771"
}

Smiljanić, M. M., Lazić, Ž., Radjenović, B., Radjenović-Radmilović, M., Jović, V., Rašljić, M., Cvetanović, K.,& Filipović, A.. (2019). Etched Parallelogram Patterns with Sides Along <100> and <n10> Directions in 25 wt % TMAH. in Proceedings - 6th International Conference on Electrical, Electronic and Computing Engineering, IcETRAN 2019, June 03 – 06, 2019, Silver Lake, Serbia
Society for Electronics, Telecommunications, Computers, Automatic Control and Nuclear Engineering., 584-589.
https://hdl.handle.net/21.15107/rcub_cer_5771

Smiljanić MM, Lazić Ž, Radjenović B, Radjenović-Radmilović M, Jović V, Rašljić M, Cvetanović K, Filipović A. Etched Parallelogram Patterns with Sides Along <100> and <n10> Directions in 25 wt % TMAH. in Proceedings - 6th International Conference on Electrical, Electronic and Computing Engineering, IcETRAN 2019, June 03 – 06, 2019, Silver Lake, Serbia. 2019;:584-589.
https://hdl.handle.net/21.15107/rcub_cer_5771 .

Smiljanić, Milče M., Lazić, Žarko, Radjenović, Branislav, Radjenović-Radmilović, Marija, Jović, Vesna, Rašljić, Milena, Cvetanović, Katarina, Filipović, Ana, "Etched Parallelogram Patterns with Sides Along <100> and <n10> Directions in 25 wt % TMAH" in Proceedings - 6th International Conference on Electrical, Electronic and Computing Engineering, IcETRAN 2019, June 03 – 06, 2019, Silver Lake, Serbia (2019):584-589,
https://hdl.handle.net/21.15107/rcub_cer_5771 .

TY  - GEN
AU  - Rašljić, Milena
AU  - Smiljanić, Milče M.
AU  - Lazić, Žarko
AU  - Cvetanović Zobenica, Katarina
AU  - Filipović, Ana
AU  - Sarajlić, Milija
AU  - Vasiljević-Radović, Dana
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3976
AB  - Vlažnim hemijskim nagrizanjem u vodenom rastvoru HF (49%) se mogu napraviti i
različite 3D strukture od Pyrex stakla koje daju još jedan stepen slobode u projektovanju senzora i aktuatora. Ovaj tehnološki proces omogućava dobijanje otvora, jama i kanala mikrometarskih dimenzija kvalitetnih ivica i površine boljeg kvaliteta na pločici od Pyrex stakla. U IHTM-CMT je razvijen tehnološki postupak za nagrizanje Pyrex pločice sa jedne strane. Ovo tehničko rešenje predstavlja razvijanje tehnološkog postupka koji omogućava nagrizanje pločica sa obe strane, kako istovremeno, tako i jednu po jednu stranu. Novim tehnološkim postupkom će se izrađivati hemijski mikroreaktori i biološke platforme u okviru IHTM-CMT.
PB  - Belgrade : University of Belgrade - Institute of Chemistry, Technology and Metallurgy
T1  - Dvostrano vlažno hemijsko nagrizanje Pyrex stakla
UR  - https://hdl.handle.net/21.15107/rcub_cer_3976
ER  - 

@misc{
author = "Rašljić, Milena and Smiljanić, Milče M. and Lazić, Žarko and Cvetanović Zobenica, Katarina and Filipović, Ana and Sarajlić, Milija and Vasiljević-Radović, Dana",
year = "2019",
abstract = "Vlažnim hemijskim nagrizanjem u vodenom rastvoru HF (49%) se mogu napraviti i
različite 3D strukture od Pyrex stakla koje daju još jedan stepen slobode u projektovanju senzora i aktuatora. Ovaj tehnološki proces omogućava dobijanje otvora, jama i kanala mikrometarskih dimenzija kvalitetnih ivica i površine boljeg kvaliteta na pločici od Pyrex stakla. U IHTM-CMT je razvijen tehnološki postupak za nagrizanje Pyrex pločice sa jedne strane. Ovo tehničko rešenje predstavlja razvijanje tehnološkog postupka koji omogućava nagrizanje pločica sa obe strane, kako istovremeno, tako i jednu po jednu stranu. Novim tehnološkim postupkom će se izrađivati hemijski mikroreaktori i biološke platforme u okviru IHTM-CMT.",
publisher = "Belgrade : University of Belgrade - Institute of Chemistry, Technology and Metallurgy",
title = "Dvostrano vlažno hemijsko nagrizanje Pyrex stakla",
url = "https://hdl.handle.net/21.15107/rcub_cer_3976"
}

Rašljić, M., Smiljanić, M. M., Lazić, Ž., Cvetanović Zobenica, K., Filipović, A., Sarajlić, M.,& Vasiljević-Radović, D.. (2019). Dvostrano vlažno hemijsko nagrizanje Pyrex stakla. 
Belgrade : University of Belgrade - Institute of Chemistry, Technology and Metallurgy..
https://hdl.handle.net/21.15107/rcub_cer_3976

Rašljić M, Smiljanić MM, Lazić Ž, Cvetanović Zobenica K, Filipović A, Sarajlić M, Vasiljević-Radović D. Dvostrano vlažno hemijsko nagrizanje Pyrex stakla. 2019;.
https://hdl.handle.net/21.15107/rcub_cer_3976 .

Rašljić, Milena, Smiljanić, Milče M., Lazić, Žarko, Cvetanović Zobenica, Katarina, Filipović, Ana, Sarajlić, Milija, Vasiljević-Radović, Dana, "Dvostrano vlažno hemijsko nagrizanje Pyrex stakla" (2019),
https://hdl.handle.net/21.15107/rcub_cer_3976 .