TY  - JOUR
AU  - Andrić, Deana B.
AU  - Dukić-Stefanović, Slađana
AU  - Krunić, Mihajlo J.
AU  - Jevtić, Ivana I.
AU  - Penjišević, Jelena Z.
AU  - Šukalović, Vladimir B.
AU  - Kostić-Rajačić, Slađana
PY  - 2024
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6472
AB  - Serotonin, or 5-hydroxytryptamine (5-HT), is a biogenic amine most
noted as a neurotransmitter, an activator of the utmost subtype family of G-protein-
coupled receptors (GPCR). Drugs targeting 5-HT1A and other 5-HT receptors
treat central nervous system diseases such as schizophrenia and depression.
Recent advances in serotonin receptor structure research gave us several
crystal 5-HT1A receptor structures, most notably 5-HT1A bound to the antipsychotic
drug aripiprazole (Abilify®). This discovery prompted us to evaluate
a series of newly synthesized ligands for serotonergic activity since those arylpiperazine
derivatives share minimal general structure with aripiprazole. The
results of molecular docking analysis of unsubstituted starting substances
encouraged us to propound further modifications of the tail and head parts of
the parent molecules to maximize receptor binding affinity. Intrigued by the
results of molecular analysis, all foreseen derivatives were synthesized. The
pharmacological activity of all nine (5a and 6a are synthesized previously)
compounds was assessed by the in vitro tests and in silico pharmacokinetics
predictions for the most promising candidates. All tested ligands have improved
affinity compering to parent compounds (10a and 11a), 8b and 9b expressed
the best pharmacological profile with an improved binding affinity
toward serotonin 5-HT1A receptors (Ki 12.1 and 4.8 nM, respectively).
PB  - Belgrade : Serbian Chemical Society
T2  - J. Serb. Chem. Soc.
T1  - Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides
VL  - 89
IS  - 3
SP  - 291
EP  - 303
DO  - 10.2298/JSC230906076A
ER  - 

@article{
author = "Andrić, Deana B. and Dukić-Stefanović, Slađana and Krunić, Mihajlo J. and Jevtić, Ivana I. and Penjišević, Jelena Z. and Šukalović, Vladimir B. and Kostić-Rajačić, Slađana",
year = "2024",
abstract = "Serotonin, or 5-hydroxytryptamine (5-HT), is a biogenic amine most
noted as a neurotransmitter, an activator of the utmost subtype family of G-protein-
coupled receptors (GPCR). Drugs targeting 5-HT1A and other 5-HT receptors
treat central nervous system diseases such as schizophrenia and depression.
Recent advances in serotonin receptor structure research gave us several
crystal 5-HT1A receptor structures, most notably 5-HT1A bound to the antipsychotic
drug aripiprazole (Abilify®). This discovery prompted us to evaluate
a series of newly synthesized ligands for serotonergic activity since those arylpiperazine
derivatives share minimal general structure with aripiprazole. The
results of molecular docking analysis of unsubstituted starting substances
encouraged us to propound further modifications of the tail and head parts of
the parent molecules to maximize receptor binding affinity. Intrigued by the
results of molecular analysis, all foreseen derivatives were synthesized. The
pharmacological activity of all nine (5a and 6a are synthesized previously)
compounds was assessed by the in vitro tests and in silico pharmacokinetics
predictions for the most promising candidates. All tested ligands have improved
affinity compering to parent compounds (10a and 11a), 8b and 9b expressed
the best pharmacological profile with an improved binding affinity
toward serotonin 5-HT1A receptors (Ki 12.1 and 4.8 nM, respectively).",
publisher = "Belgrade : Serbian Chemical Society",
journal = "J. Serb. Chem. Soc.",
title = "Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides",
volume = "89",
number = "3",
pages = "291-303",
doi = "10.2298/JSC230906076A"
}

Andrić, D. B., Dukić-Stefanović, S., Krunić, M. J., Jevtić, I. I., Penjišević, J. Z., Šukalović, V. B.,& Kostić-Rajačić, S.. (2024). Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides. in J. Serb. Chem. Soc.
Belgrade : Serbian Chemical Society., 89(3), 291-303.
https://doi.org/10.2298/JSC230906076A

Andrić DB, Dukić-Stefanović S, Krunić MJ, Jevtić II, Penjišević JZ, Šukalović VB, Kostić-Rajačić S. Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides. in J. Serb. Chem. Soc.. 2024;89(3):291-303.
doi:10.2298/JSC230906076A .

Andrić, Deana B., Dukić-Stefanović, Slađana, Krunić, Mihajlo J., Jevtić, Ivana I., Penjišević, Jelena Z., Šukalović, Vladimir B., Kostić-Rajačić, Slađana, "Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides" in J. Serb. Chem. Soc., 89, no. 3 (2024):291-303,
https://doi.org/10.2298/JSC230906076A . .

TY  - JOUR
AU  - Penjišević, Jelena 
AU  - Šukalović, Vladimir 
AU  - Dukić-Stefanović, Slađana
AU  - Deuther-Conrad, Winnie
AU  - Andrić, Deana 
AU  - Kostić-Rajačić, Slađana
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5819
AB  - Serotonin receptors modulate numerous behavioral and neuropsychological processes. Therefore, they are the target for the action of many drugs, such as antipsychotics, antidepressants, antiemetics, migraine remedies, and many others. The 5-HT1A receptors have been involved in the pathogenesis and treatment of anxiety and depression and represent a promising target for new drugs with reduced extrapyramidal side effects. In most antidepressants, a piperazine-based structural motif can be identified as a common moiety. Here we describe the synthesis, pharmacological, and in silico characterization of a novel arylpiperazines series with excellent 5-HT1A affinity. The final compounds, 4a, 8a, and 8b, were selected according to predictions of in silico pharmacokinetics, docking analysis, and molecular dynamics in conjunction with physical properties, and metabolic stability. The accentuated molecules could serve as a lead compound for developing 5-HT1A drug-like molecules for depression treatment.
PB  - Elsevier
T2  - Arabian Journal of Chemistry
T1  - Synthesis of novel 5-HT1A arylpiperazine ligands: Binding data and computer-aided analysis of pharmacological potency
VL  - 16
IS  - 4
SP  - 104636
DO  - 10.1016/j.arabjc.2023.104636
ER  - 

@article{
author = "Penjišević, Jelena  and Šukalović, Vladimir  and Dukić-Stefanović, Slađana and Deuther-Conrad, Winnie and Andrić, Deana  and Kostić-Rajačić, Slađana",
year = "2023",
abstract = "Serotonin receptors modulate numerous behavioral and neuropsychological processes. Therefore, they are the target for the action of many drugs, such as antipsychotics, antidepressants, antiemetics, migraine remedies, and many others. The 5-HT1A receptors have been involved in the pathogenesis and treatment of anxiety and depression and represent a promising target for new drugs with reduced extrapyramidal side effects. In most antidepressants, a piperazine-based structural motif can be identified as a common moiety. Here we describe the synthesis, pharmacological, and in silico characterization of a novel arylpiperazines series with excellent 5-HT1A affinity. The final compounds, 4a, 8a, and 8b, were selected according to predictions of in silico pharmacokinetics, docking analysis, and molecular dynamics in conjunction with physical properties, and metabolic stability. The accentuated molecules could serve as a lead compound for developing 5-HT1A drug-like molecules for depression treatment.",
publisher = "Elsevier",
journal = "Arabian Journal of Chemistry",
title = "Synthesis of novel 5-HT1A arylpiperazine ligands: Binding data and computer-aided analysis of pharmacological potency",
volume = "16",
number = "4",
pages = "104636",
doi = "10.1016/j.arabjc.2023.104636"
}

Penjišević, J., Šukalović, V., Dukić-Stefanović, S., Deuther-Conrad, W., Andrić, D.,& Kostić-Rajačić, S.. (2023). Synthesis of novel 5-HT1A arylpiperazine ligands: Binding data and computer-aided analysis of pharmacological potency. in Arabian Journal of Chemistry
Elsevier., 16(4), 104636.
https://doi.org/10.1016/j.arabjc.2023.104636

Penjišević J, Šukalović V, Dukić-Stefanović S, Deuther-Conrad W, Andrić D, Kostić-Rajačić S. Synthesis of novel 5-HT1A arylpiperazine ligands: Binding data and computer-aided analysis of pharmacological potency. in Arabian Journal of Chemistry. 2023;16(4):104636.
doi:10.1016/j.arabjc.2023.104636 .

Penjišević, Jelena , Šukalović, Vladimir , Dukić-Stefanović, Slađana, Deuther-Conrad, Winnie, Andrić, Deana , Kostić-Rajačić, Slađana, "Synthesis of novel 5-HT1A arylpiperazine ligands: Binding data and computer-aided analysis of pharmacological potency" in Arabian Journal of Chemistry, 16, no. 4 (2023):104636,
https://doi.org/10.1016/j.arabjc.2023.104636 . .

TY  - CONF
AU  - Jevtić, Ivana I.
AU  - Andrić, Deana
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Dukić-Stefanović, Slađana
AU  - Kostić-Rajačić, Slađana
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5866
PB  - EFMC-YMCS
C3  - EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France
T1  - Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands
SP  - 66
EP  - 66
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5866
ER  - 

@conference{
author = "Jevtić, Ivana I. and Andrić, Deana and Penjišević, Jelena and Šukalović, Vladimir and Dukić-Stefanović, Slađana and Kostić-Rajačić, Slađana",
year = "2022",
publisher = "EFMC-YMCS",
journal = "EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France",
title = "Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands",
pages = "66-66",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5866"
}

Jevtić, I. I., Andrić, D., Penjišević, J., Šukalović, V., Dukić-Stefanović, S.,& Kostić-Rajačić, S.. (2022). Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands. in EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France
EFMC-YMCS., 66-66.
https://hdl.handle.net/21.15107/rcub_cherry_5866

Jevtić II, Andrić D, Penjišević J, Šukalović V, Dukić-Stefanović S, Kostić-Rajačić S. Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands. in EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France. 2022;:66-66.
https://hdl.handle.net/21.15107/rcub_cherry_5866 .

Jevtić, Ivana I., Andrić, Deana, Penjišević, Jelena, Šukalović, Vladimir, Dukić-Stefanović, Slađana, Kostić-Rajačić, Slađana, "Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands" in EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France (2022):66-66,
https://hdl.handle.net/21.15107/rcub_cherry_5866 .

TY  - JOUR
AU  - Dukić-Stefanović, Slađana
AU  - Hang Lai, Thu
AU  - Toussaint, Magali
AU  - Clauß, Oliver
AU  - Jevtić, Ivana I.
AU  - Penjišević, Jelena
AU  - Andrić, Deana
AU  - Ludwig, Friedrich-Alexander
AU  - Gündel, Daniel
AU  - Deuther-Conrad, Winnie
AU  - Kostić-Rajačić, Slađana
AU  - Brust, Peter
AU  - Teodoro, Rodrigo
PY  - 2021
UR  - https://www.sciencedirect.com/science/article/pii/S0960894X21004819
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4591
AB  - Monoamine oxidases (MAOs) play a key role in the metabolism of major monoamine neurotransmitters. In particular, the upregulation of MAO-B in Parkinson’s disease, Alzheimer’s disease and cancer augmented the development of selective MAO-B inhibitors for diagnostic and therapeutic purposes, such as the anti-parkinsonian MAO-B irreversible binder l-deprenyl (Selegiline®). Herein we report on the synthesis of novel fluorinated indanone derivatives for PET imaging of MAO-B in the brain. Out of our series, the derivatives 6, 8, 9 and 13 are amongst the most affine and selective ligands for MAO-B reported so far. For the derivative 6-((3-fluorobenzyl)oxy)-2,3-dihydro-1H-inden-1-one (6) exhibiting an outstanding affinity (Ki MAO-B = 6 nM), an automated copper-mediated radiofluorination starting from the pinacol boronic ester 17 is described. An in vitro screening in different species revealed a MAO-B region-specific accumulation of [18F]6 in rats and piglets in comparison to L-[3H]deprenyl. The pre-clinical in vivo assessment of [18F]6 in mice demonstrated the potential of indanones to readily cross the blood–brain barrier. Nonetheless, parallel in vivo metabolism studies indicated the presence of blood–brain barrier metabolites, thus arguing for further structural modifications. With the matching analytical profiles of the radiometabolite analysis from the in vitro liver microsome studies and the in vivo evaluation, the structure’s elucidation of the blood–brain barrier penetrant radiometabolites is possible and will serve as basis for the development of new indanone derivatives suitable for the PET imaging of MAO-B.
PB  - Elsevier
T2  - Bioorganic & Medicinal Chemistry Letters
T1  - In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain
VL  - 48
SP  - 128254
DO  - 10.1016/j.bmcl.2021.128254
ER  - 

@article{
author = "Dukić-Stefanović, Slađana and Hang Lai, Thu and Toussaint, Magali and Clauß, Oliver and Jevtić, Ivana I. and Penjišević, Jelena and Andrić, Deana and Ludwig, Friedrich-Alexander and Gündel, Daniel and Deuther-Conrad, Winnie and Kostić-Rajačić, Slađana and Brust, Peter and Teodoro, Rodrigo",
year = "2021",
abstract = "Monoamine oxidases (MAOs) play a key role in the metabolism of major monoamine neurotransmitters. In particular, the upregulation of MAO-B in Parkinson’s disease, Alzheimer’s disease and cancer augmented the development of selective MAO-B inhibitors for diagnostic and therapeutic purposes, such as the anti-parkinsonian MAO-B irreversible binder l-deprenyl (Selegiline®). Herein we report on the synthesis of novel fluorinated indanone derivatives for PET imaging of MAO-B in the brain. Out of our series, the derivatives 6, 8, 9 and 13 are amongst the most affine and selective ligands for MAO-B reported so far. For the derivative 6-((3-fluorobenzyl)oxy)-2,3-dihydro-1H-inden-1-one (6) exhibiting an outstanding affinity (Ki MAO-B = 6 nM), an automated copper-mediated radiofluorination starting from the pinacol boronic ester 17 is described. An in vitro screening in different species revealed a MAO-B region-specific accumulation of [18F]6 in rats and piglets in comparison to L-[3H]deprenyl. The pre-clinical in vivo assessment of [18F]6 in mice demonstrated the potential of indanones to readily cross the blood–brain barrier. Nonetheless, parallel in vivo metabolism studies indicated the presence of blood–brain barrier metabolites, thus arguing for further structural modifications. With the matching analytical profiles of the radiometabolite analysis from the in vitro liver microsome studies and the in vivo evaluation, the structure’s elucidation of the blood–brain barrier penetrant radiometabolites is possible and will serve as basis for the development of new indanone derivatives suitable for the PET imaging of MAO-B.",
publisher = "Elsevier",
journal = "Bioorganic & Medicinal Chemistry Letters",
title = "In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain",
volume = "48",
pages = "128254",
doi = "10.1016/j.bmcl.2021.128254"
}

Dukić-Stefanović, S., Hang Lai, T., Toussaint, M., Clauß, O., Jevtić, I. I., Penjišević, J., Andrić, D., Ludwig, F., Gündel, D., Deuther-Conrad, W., Kostić-Rajačić, S., Brust, P.,& Teodoro, R.. (2021). In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain. in Bioorganic & Medicinal Chemistry Letters
Elsevier., 48, 128254.
https://doi.org/10.1016/j.bmcl.2021.128254

Dukić-Stefanović S, Hang Lai T, Toussaint M, Clauß O, Jevtić II, Penjišević J, Andrić D, Ludwig F, Gündel D, Deuther-Conrad W, Kostić-Rajačić S, Brust P, Teodoro R. In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain. in Bioorganic & Medicinal Chemistry Letters. 2021;48:128254.
doi:10.1016/j.bmcl.2021.128254 .

Dukić-Stefanović, Slađana, Hang Lai, Thu, Toussaint, Magali, Clauß, Oliver, Jevtić, Ivana I., Penjišević, Jelena, Andrić, Deana, Ludwig, Friedrich-Alexander, Gündel, Daniel, Deuther-Conrad, Winnie, Kostić-Rajačić, Slađana, Brust, Peter, Teodoro, Rodrigo, "In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain" in Bioorganic & Medicinal Chemistry Letters, 48 (2021):128254,
https://doi.org/10.1016/j.bmcl.2021.128254 . .

TY  - DATA
AU  - Dukić-Stefanović, Slađana
AU  - Hang Lai, Thu
AU  - Toussaint, Magali
AU  - Clauß, Oliver
AU  - Jevtić, Ivana I.
AU  - Penjišević, Jelena
AU  - Andrić, Deana
AU  - Ludwig, Friedrich-Alexander
AU  - Gündel, Daniel
AU  - Deuther-Conrad, Winnie
AU  - Kostić-Rajačić, Slađana
AU  - Brust, Peter
AU  - Teodoro, Rodrigo
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4592
PB  - Elsevier
T2  - Bioorganic & Medicinal Chemistry Letters
T1  - Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254.
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4592
ER  - 

@misc{
author = "Dukić-Stefanović, Slađana and Hang Lai, Thu and Toussaint, Magali and Clauß, Oliver and Jevtić, Ivana I. and Penjišević, Jelena and Andrić, Deana and Ludwig, Friedrich-Alexander and Gündel, Daniel and Deuther-Conrad, Winnie and Kostić-Rajačić, Slađana and Brust, Peter and Teodoro, Rodrigo",
year = "2021",
publisher = "Elsevier",
journal = "Bioorganic & Medicinal Chemistry Letters",
title = "Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254.",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4592"
}

Dukić-Stefanović, S., Hang Lai, T., Toussaint, M., Clauß, O., Jevtić, I. I., Penjišević, J., Andrić, D., Ludwig, F., Gündel, D., Deuther-Conrad, W., Kostić-Rajačić, S., Brust, P.,& Teodoro, R.. (2021). Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254.. in Bioorganic & Medicinal Chemistry Letters
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_4592

Dukić-Stefanović S, Hang Lai T, Toussaint M, Clauß O, Jevtić II, Penjišević J, Andrić D, Ludwig F, Gündel D, Deuther-Conrad W, Kostić-Rajačić S, Brust P, Teodoro R. Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254.. in Bioorganic & Medicinal Chemistry Letters. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_4592 .

Dukić-Stefanović, Slađana, Hang Lai, Thu, Toussaint, Magali, Clauß, Oliver, Jevtić, Ivana I., Penjišević, Jelena, Andrić, Deana, Ludwig, Friedrich-Alexander, Gündel, Daniel, Deuther-Conrad, Winnie, Kostić-Rajačić, Slađana, Brust, Peter, Teodoro, Rodrigo, "Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254." in Bioorganic & Medicinal Chemistry Letters (2021),
https://hdl.handle.net/21.15107/rcub_cherry_4592 .

TY  - JOUR
AU  - Jevtić, Ivana I.
AU  - Lai, Thu Hang
AU  - Penjišević, Jelena
AU  - Dukić-Stefanović, Slađana
AU  - Andrić, Deana
AU  - Brust, Peter
AU  - Kostić-Rajačić, Slađana
AU  - Teodoro, Rodrigo
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4272
AB  - Herein, we report on the synthesis and pharmacological evaluation of ten novel fluorinated cinnamylpiperazines as potential monoamine oxidase B (MAO-B) ligands. The designed derivatives consist of either cinnamyl or 2-fluorocinnamyl moieties connected to 2-fluoropyridylpiperazines. The three-step synthesis starting from commercially available piperazine afforded the final products in overall yields between 9% and 29%. An in vitro competitive binding assay using l-[3H]Deprenyl as radioligand was developed and the MAO-B binding affinities of the synthesized derivatives were assessed. Docking studies revealed that the compounds 8–17 were stabilized in both MAO-B entrance and substrate cavities, thus resembling the binding pose of l-Deprenyl. Although our results revealed that the novel fluorinated cinnamylpiperazines 8–17 do not possess sufficient MAO-B binding affinity to be eligible as positron emission tomography (PET) agents, the herein developed binding assay and the insights gained within our docking studies will certainly pave the way for further development of MAO-B ligands.
PB  - MDPI
T2  - Molecules
T1  - Newly Synthesized Fluorinated Cinnamylpiperazines Possessing Low In Vitro MAO-B Binding
VL  - 25
IS  - 21
SP  - 4941
DO  - 10.3390/molecules25214941
ER  - 

@article{
author = "Jevtić, Ivana I. and Lai, Thu Hang and Penjišević, Jelena and Dukić-Stefanović, Slađana and Andrić, Deana and Brust, Peter and Kostić-Rajačić, Slađana and Teodoro, Rodrigo",
year = "2020",
abstract = "Herein, we report on the synthesis and pharmacological evaluation of ten novel fluorinated cinnamylpiperazines as potential monoamine oxidase B (MAO-B) ligands. The designed derivatives consist of either cinnamyl or 2-fluorocinnamyl moieties connected to 2-fluoropyridylpiperazines. The three-step synthesis starting from commercially available piperazine afforded the final products in overall yields between 9% and 29%. An in vitro competitive binding assay using l-[3H]Deprenyl as radioligand was developed and the MAO-B binding affinities of the synthesized derivatives were assessed. Docking studies revealed that the compounds 8–17 were stabilized in both MAO-B entrance and substrate cavities, thus resembling the binding pose of l-Deprenyl. Although our results revealed that the novel fluorinated cinnamylpiperazines 8–17 do not possess sufficient MAO-B binding affinity to be eligible as positron emission tomography (PET) agents, the herein developed binding assay and the insights gained within our docking studies will certainly pave the way for further development of MAO-B ligands.",
publisher = "MDPI",
journal = "Molecules",
title = "Newly Synthesized Fluorinated Cinnamylpiperazines Possessing Low In Vitro MAO-B Binding",
volume = "25",
number = "21",
pages = "4941",
doi = "10.3390/molecules25214941"
}

Jevtić, I. I., Lai, T. H., Penjišević, J., Dukić-Stefanović, S., Andrić, D., Brust, P., Kostić-Rajačić, S.,& Teodoro, R.. (2020). Newly Synthesized Fluorinated Cinnamylpiperazines Possessing Low In Vitro MAO-B Binding. in Molecules
MDPI., 25(21), 4941.
https://doi.org/10.3390/molecules25214941

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