TY  - JOUR
AU  - Ferjancic, Zorana
AU  - Bihelovic, Filip
AU  - Vulovic, Bojan
AU  - Matovic, Radomir
AU  - Trmcic, Milena
AU  - Jankovic, Aleksandar
AU  - Pavlovic, Milos
AU  - Djurkovic, Filip
AU  - Prodanovic, Radivoje
AU  - Djurdjevic Djelmas, Aleksandra
AU  - Kalicanin, Nevena
AU  - Zlatovic, Mario
AU  - Sladic, Dusan
AU  - Vallet, Thomas
AU  - Vignuzzi, Marco
AU  - Saicic, Radomir N.
PY  - 2024
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6475
AB  - We developed new iminosugar-based glycosidase inhibitors against SARS-CoV-2. Known drugs (miglustat, migalastat, miglitol, and swainsonine) were chosen as lead compounds to develop three classes of glycosidase inhibitors (α-glucosidase, α-galactosidase, and mannosidase). Molecular modelling of the lead compounds, synthesis of the compounds with the highest docking scores, enzyme inhibition tests, and in vitro antiviral assays afforded rationally designed inhibitors. Two highly active α-glucosidase inhibitors were discovered, where one of them is the most potent iminosugar-based anti-SARS-CoV-2 agent to date (EC90 = 1.94 µM in A549-ACE2 cells against Omicron BA.1 strain). However, galactosidase inhibitors did not exhibit antiviral activity, whereas mannosidase inhibitors were both active and cytotoxic. As our iminosugar-based drug candidates act by a host-directed mechanism, they should be more resilient to drug resistance. Moreover, this strategy could be extended to identify potential drug candidates for other viral infections.
PB  - Taylor and Francis Group
T2  - Journal of Enzyme Inhibition and Medicinal Chemistry
T1  - Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies
VL  - 39
IS  - 1
SP  - 2289007
DO  - 10.1080/14756366.2023.2289007
ER  - 

@article{
author = "Ferjancic, Zorana and Bihelovic, Filip and Vulovic, Bojan and Matovic, Radomir and Trmcic, Milena and Jankovic, Aleksandar and Pavlovic, Milos and Djurkovic, Filip and Prodanovic, Radivoje and Djurdjevic Djelmas, Aleksandra and Kalicanin, Nevena and Zlatovic, Mario and Sladic, Dusan and Vallet, Thomas and Vignuzzi, Marco and Saicic, Radomir N.",
year = "2024",
abstract = "We developed new iminosugar-based glycosidase inhibitors against SARS-CoV-2. Known drugs (miglustat, migalastat, miglitol, and swainsonine) were chosen as lead compounds to develop three classes of glycosidase inhibitors (α-glucosidase, α-galactosidase, and mannosidase). Molecular modelling of the lead compounds, synthesis of the compounds with the highest docking scores, enzyme inhibition tests, and in vitro antiviral assays afforded rationally designed inhibitors. Two highly active α-glucosidase inhibitors were discovered, where one of them is the most potent iminosugar-based anti-SARS-CoV-2 agent to date (EC90 = 1.94 µM in A549-ACE2 cells against Omicron BA.1 strain). However, galactosidase inhibitors did not exhibit antiviral activity, whereas mannosidase inhibitors were both active and cytotoxic. As our iminosugar-based drug candidates act by a host-directed mechanism, they should be more resilient to drug resistance. Moreover, this strategy could be extended to identify potential drug candidates for other viral infections.",
publisher = "Taylor and Francis Group",
journal = "Journal of Enzyme Inhibition and Medicinal Chemistry",
title = "Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies",
volume = "39",
number = "1",
pages = "2289007",
doi = "10.1080/14756366.2023.2289007"
}

Ferjancic, Z., Bihelovic, F., Vulovic, B., Matovic, R., Trmcic, M., Jankovic, A., Pavlovic, M., Djurkovic, F., Prodanovic, R., Djurdjevic Djelmas, A., Kalicanin, N., Zlatovic, M., Sladic, D., Vallet, T., Vignuzzi, M.,& Saicic, R. N.. (2024). Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies. in Journal of Enzyme Inhibition and Medicinal Chemistry
Taylor and Francis Group., 39(1), 2289007.
https://doi.org/10.1080/14756366.2023.2289007

Ferjancic Z, Bihelovic F, Vulovic B, Matovic R, Trmcic M, Jankovic A, Pavlovic M, Djurkovic F, Prodanovic R, Djurdjevic Djelmas A, Kalicanin N, Zlatovic M, Sladic D, Vallet T, Vignuzzi M, Saicic RN. Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies. in Journal of Enzyme Inhibition and Medicinal Chemistry. 2024;39(1):2289007.
doi:10.1080/14756366.2023.2289007 .

Ferjancic, Zorana, Bihelovic, Filip, Vulovic, Bojan, Matovic, Radomir, Trmcic, Milena, Jankovic, Aleksandar, Pavlovic, Milos, Djurkovic, Filip, Prodanovic, Radivoje, Djurdjevic Djelmas, Aleksandra, Kalicanin, Nevena, Zlatovic, Mario, Sladic, Dusan, Vallet, Thomas, Vignuzzi, Marco, Saicic, Radomir N., "Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies" in Journal of Enzyme Inhibition and Medicinal Chemistry, 39, no. 1 (2024):2289007,
https://doi.org/10.1080/14756366.2023.2289007 . .

TY  - JOUR
AU  - Trajković, Miloš D.
AU  - Pavlović, Miloš
AU  - Bihelović, Filip
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2022
UR  - https://doi.org/10.1177/1934578X221091672
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5179
AB  - A tactical combination of either (S)- or (R)-proline catalyzed aldol reaction followed by intramolecular reductive amination enabled the synthesis of a chiral pyrrolidine derivative with 3 contiguous stereocenters in only 2 synthetic steps, starting from achiral precursors. This product, obtainable in both enantiomeric forms, was further exploited as a common intermediate in total syntheses of the biologically active iminosugars: ( + )-swainsonine, (–)-swainsonine, ( + )-8-epi-swainsonine, and ( + )-dideoxy-imino-lyxitol.
PB  - SAGE Publications
T2  - Natural Product Communications
T2  - Natural Product CommunicationsNatural Product Communications
T1  - Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence
VL  - 17
IS  - 4
DO  - 10.1177/1934578X221091672
ER  - 

@article{
author = "Trajković, Miloš D. and Pavlović, Miloš and Bihelović, Filip and Ferjančić, Zorana and Saičić, Radomir",
year = "2022",
abstract = "A tactical combination of either (S)- or (R)-proline catalyzed aldol reaction followed by intramolecular reductive amination enabled the synthesis of a chiral pyrrolidine derivative with 3 contiguous stereocenters in only 2 synthetic steps, starting from achiral precursors. This product, obtainable in both enantiomeric forms, was further exploited as a common intermediate in total syntheses of the biologically active iminosugars: ( + )-swainsonine, (–)-swainsonine, ( + )-8-epi-swainsonine, and ( + )-dideoxy-imino-lyxitol.",
publisher = "SAGE Publications",
journal = "Natural Product Communications, Natural Product CommunicationsNatural Product Communications",
title = "Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence",
volume = "17",
number = "4",
doi = "10.1177/1934578X221091672"
}

Trajković, M. D., Pavlović, M., Bihelović, F., Ferjančić, Z.,& Saičić, R.. (2022). Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence. in Natural Product Communications
SAGE Publications., 17(4).
https://doi.org/10.1177/1934578X221091672

Trajković MD, Pavlović M, Bihelović F, Ferjančić Z, Saičić R. Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence. in Natural Product Communications. 2022;17(4).
doi:10.1177/1934578X221091672 .

Trajković, Miloš D., Pavlović, Miloš, Bihelović, Filip, Ferjančić, Zorana, Saičić, Radomir, "Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence" in Natural Product Communications, 17, no. 4 (2022),
https://doi.org/10.1177/1934578X221091672 . .

TY  - THES
AU  - Petrić, Rajo
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4728
AB  - Iminošećeri su raznovrsna grupa polihidroksilovanih heterocikličnih jedinjenja, od kojih su mnoga medicinski zančajna. Najpoznatije jedinjenje ovog tipa je 1 ̶ deoksinodžirimicin (DNJ), čiji N ̶ alkilovani derivati su našli primjenu u medicini, zahvaljujući tome što djeluju kao inhibitori α- glukozidaze i ispoljavaju antidijabetička, antiviralna i druga svojstva. Spektar upotrebe ovih jedinjenja bi mogao da se proširi, jer su se neka pokazala kao inhibitori replikacije SARS ̶ CoV ̶ 19 virusa, pa su iminošećeri potencijalni lijekovi za bolest izazvanu ovim virusom. Cilj ovog rada je bila sinteza DNJ i dva njegova N ̶ alkilovana derivata (N ̶ butil i N ̶ nonil), kako bi se oni dalje koristili za ispitivanje njihovih antiviralnih svojstava.
T1  - Sinteza iminošećera 1 ̶ deoksinodžirimicina i njegovih N ̶ alkilovanih derivata kao potencijalnih terapeutika za COVID ̶ 19
SP  - 1
EP  - 60
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4728
ER  - 

@misc{
author = "Petrić, Rajo",
year = "2021",
abstract = "Iminošećeri su raznovrsna grupa polihidroksilovanih heterocikličnih jedinjenja, od kojih su mnoga medicinski zančajna. Najpoznatije jedinjenje ovog tipa je 1 ̶ deoksinodžirimicin (DNJ), čiji N ̶ alkilovani derivati su našli primjenu u medicini, zahvaljujući tome što djeluju kao inhibitori α- glukozidaze i ispoljavaju antidijabetička, antiviralna i druga svojstva. Spektar upotrebe ovih jedinjenja bi mogao da se proširi, jer su se neka pokazala kao inhibitori replikacije SARS ̶ CoV ̶ 19 virusa, pa su iminošećeri potencijalni lijekovi za bolest izazvanu ovim virusom. Cilj ovog rada je bila sinteza DNJ i dva njegova N ̶ alkilovana derivata (N ̶ butil i N ̶ nonil), kako bi se oni dalje koristili za ispitivanje njihovih antiviralnih svojstava.",
title = "Sinteza iminošećera 1 ̶ deoksinodžirimicina i njegovih N ̶ alkilovanih derivata kao potencijalnih terapeutika za COVID ̶ 19",
pages = "1-60",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4728"
}

Petrić, R.. (2021). Sinteza iminošećera 1 ̶ deoksinodžirimicina i njegovih N ̶ alkilovanih derivata kao potencijalnih terapeutika za COVID ̶ 19. , 1-60.
https://hdl.handle.net/21.15107/rcub_cherry_4728

Petrić R. Sinteza iminošećera 1 ̶ deoksinodžirimicina i njegovih N ̶ alkilovanih derivata kao potencijalnih terapeutika za COVID ̶ 19. 2021;:1-60.
https://hdl.handle.net/21.15107/rcub_cherry_4728 .

Petrić, Rajo, "Sinteza iminošećera 1 ̶ deoksinodžirimicina i njegovih N ̶ alkilovanih derivata kao potencijalnih terapeutika za COVID ̶ 19" (2021):1-60,
https://hdl.handle.net/21.15107/rcub_cherry_4728 .