Selaković, Života

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orcid::0000-0003-0322-6884
  • Selaković, Života (13)
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Author's Bibliography

Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines

Nikolić, Andrea; Stanić, Jelena; Zlatar, Matija; Gruden, Maja; Anđelković, Boban; Selaković, Života; Ajdačić, Vladimir; Opsenica, Igor

(American Chemical Society (ACS), 2021)

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4358
AB  - The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines
VL  - 86
IS  - 6
SP  - 4794
EP  - 4803
DO  - 10.1021/acs.joc.1c00282
ER  - 
@article{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/4358",
abstract = "The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines",
volume = "86",
number = "6",
pages = "4794-4803",
doi = "10.1021/acs.joc.1c00282"
}
Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines.
The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282
Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković B, Selaković Ž, Ajdačić V, Opsenica I. Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry. 2021;86(6):4794-4803
Nikolić Andrea, Stanić Jelena, Zlatar Matija, Gruden Maja, Anđelković Boban, Selaković Života, Ajdačić Vladimir, Opsenica Igor, "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines" The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 .
9

Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines

Nikolić, Andrea; Stanić, Jelena; Zlatar, Matija; Gruden, Maja; Anđelković, Boban; Selaković, Života; Ajdačić, Vladimir; Opsenica, Igor

(American Chemical Society (ACS), 2021)

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4359
AB  - The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines
VL  - 86
IS  - 6
SP  - 4794
EP  - 4803
DO  - 10.1021/acs.joc.1c00282
ER  - 
@article{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/4359",
abstract = "The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines",
volume = "86",
number = "6",
pages = "4794-4803",
doi = "10.1021/acs.joc.1c00282"
}
Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines.
The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282
Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković B, Selaković Ž, Ajdačić V, Opsenica I. Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry. 2021;86(6):4794-4803
Nikolić Andrea, Stanić Jelena, Zlatar Matija, Gruden Maja, Anđelković Boban, Selaković Života, Ajdačić Vladimir, Opsenica Igor, "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines" The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 .
9

Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282

Nikolić, Andrea; Stanić, Jelena; Zlatar, Matija; Gruden, Maja; Anđelković, Boban; Selaković, Života; Ajdačić, Vladimir; Opsenica, Igor

(American Chemical Society (ACS), 2021)

TY  - BOOK
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4360
AB  - Copies of 1H and 13C NMR spectra for the synthesized compounds; Extended computational results, and total electronic energies, number of imaginary frequencies;  Cartesian coordinates of all structures.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282
DO  - 10.1021/acs.joc.1c00282.s001
ER  - 
@book{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/4360",
abstract = "Copies of 1H and 13C NMR spectra for the synthesized compounds; Extended computational results, and total electronic energies, number of imaginary frequencies;  Cartesian coordinates of all structures.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282",
doi = "10.1021/acs.joc.1c00282.s001"
}
Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282.
The Journal of Organic Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.joc.1c00282.s001
Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković B, Selaković Ž, Ajdačić V, Opsenica I. Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282. The Journal of Organic Chemistry. 2021;
Nikolić Andrea, Stanić Jelena, Zlatar Matija, Gruden Maja, Anđelković Boban, Selaković Života, Ajdačić Vladimir, Opsenica Igor, "Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282" The Journal of Organic Chemistry (2021),
https://doi.org/10.1021/acs.joc.1c00282.s001 .

One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles

Nikolić, Andrea M.; Živković, Filip; Selaković, Života; Wipf, Peter; Opsenica, Igor

(Wiley, 2020)

TY  - JOUR
AU  - Nikolić, Andrea M.
AU  - Živković, Filip
AU  - Selaković, Života
AU  - Wipf, Peter
AU  - Opsenica, Igor
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4294
AB  - An efficient one-pot, two step method for fusing two biologically active motifs, CF3-substituted pyrazoles and isochromenes, was developed. Selective O-benzylation of CF3-substituted pyrazolones and subsequent Pd-catalyzed direct C–H arylation generate a fused tricycle. For the synthesized compounds through-space 13C–19F spin–spin coupling was revealed. In addition, the synthesis of three thioisochromene analogues, and one isocoumarin derivative, was accomplished.
PB  - Wiley
T2  - European Journal of Organic Chemistry
T2  - 2-s2.0-85089311831
T1  - One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles
VL  - 2020
IS  - 34
SP  - 5616
EP  - 5619
DO  - https://doi.org/10.1002/ejoc.202000942
ER  - 
@article{
author = "Nikolić, Andrea M. and Živković, Filip and Selaković, Života and Wipf, Peter and Opsenica, Igor",
year = "2020",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/4294",
abstract = "An efficient one-pot, two step method for fusing two biologically active motifs, CF3-substituted pyrazoles and isochromenes, was developed. Selective O-benzylation of CF3-substituted pyrazolones and subsequent Pd-catalyzed direct C–H arylation generate a fused tricycle. For the synthesized compounds through-space 13C–19F spin–spin coupling was revealed. In addition, the synthesis of three thioisochromene analogues, and one isocoumarin derivative, was accomplished.",
publisher = "Wiley",
journal = "European Journal of Organic Chemistry, 2-s2.0-85089311831",
title = "One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles",
volume = "2020",
number = "34",
pages = "5616-5619",
doi = "https://doi.org/10.1002/ejoc.202000942"
}
Nikolić, A. M., Živković, F., Selaković, Ž., Wipf, P.,& Opsenica, I. (2020). One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles.
2-s2.0-85089311831
Wiley., 2020(34), 5616-5619.
https://doi.org/https://doi.org/10.1002/ejoc.202000942
Nikolić AM, Živković F, Selaković Ž, Wipf P, Opsenica I. One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles. 2-s2.0-85089311831. 2020;2020(34):5616-5619
Nikolić Andrea M., Živković Filip, Selaković Života, Wipf Peter, Opsenica Igor, "One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles" 2-s2.0-85089311831, 2020, no. 34 (2020):5616-5619,
https://doi.org/https://doi.org/10.1002/ejoc.202000942 .
1
1

Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole

Selaković, Života

(Универзитет у Београду, Хемијски факултет, 2019)

TY  - BOOK
AU  - Selaković, Života
PY  - 2019
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7017
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:20625/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51648783
UR  - http://nardus.mpn.gov.rs/123456789/11673
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3901
AB  - Ebolavirus je rod virusa iz familije Filoviridae, endemski prisutan u Subsaharskoj Africi. Vrste koje pripadaju ovom rodu uzročnici su smrtonosne hemoragijske groznice kod ljudi i primata, a otkrivene su, kao i njima srodni virusi marburga, u drugoj polovini 20. veka, kada su registrovani prvi slučajevi. U ovom trenutku ne postoji odobrena vakcina niti lek protiv ove opasne infekcije. Nekoliko imunoterapeutika, kao i složenih makromolekulskih formulacija, predstavlja obećavajuće kandidate za lek, a ostvaren je i napredak u istraživanjima sa malim molekulima. Oslanjajući se na ranija istraživanja u našoj istraživačkoj grupi, u okviru ove teze sintetisane su dve grupe jedinjenja za koje se pretpostavljalo da mogu imati antivirusnu aktivnost – derivati 4,10-diazahrizena i 1,5-naftiridina. Ukupno je testirano 29 jedinjenja, a po aktivnosti naročito su se istakla dva diazahrizenska derivata koji su imali veoma dobru in vitro aktivnost i štitili su 9/10, odnosno 10/10 inficiranih miševa pri dozi 10 mg/kg. Urađen je veći broj ogleda sa ciljem utvrđivanja mehanizma dejstva ova dva jedinjenja, pri čemu je otkriveno da ona inhibiraju ulazak virusa u ćeliju domaćina, na način koji se razlikuje od do sada poznatih inhibitora ulaska virusa. Dobijeni rezultati ukazuju da su molekuli razvijeni u ovoj tezi značajni i jedinstveni i da zavređuju dalja ispitivanja.
AB  - Ebolavirus is a genus of viruses from the Filoviridae family, endemic to Sub-Saharan Africa. Species from this genus cause a lethal hemorrhagic fewer in humans and non-human primates. Like the related Marburgviruses, they were discovered in the second half of the 20th century, when first cases were reported. Presently, there is no approved vaccine or other therapeutics to treat this dangerous infection. Several immunotherapeutics, as well as sophisticated macromolecular formulations, have shown promising results, and advances have also been made in small molecule research. Based on our previous results we developed two new chemotypes as possible antivirals – derivatives of 4,10-diazachrysene and 1,5-naphthyridine, respectively. A total of 29 compounds were tested, with two of them showing very good results: they had excellent in vitro activity and they protected 9/10 and 10/10 infected mice from a fatal Ebola challenge, respectively (10 mg/kg dose). A number of experiments were carried out to determine the mechanism of action of these two compounds, and it was discovered that they prevent viral entry into cells, albeit in a manner that differed from other known entry inhibitors. The results obtained in this thesis show that the developed compounds are unique and worthy of further examination
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole
ER  - 
@phdthesis{
author = "Selaković, Života",
year = "2019",
url = "http://eteze.bg.ac.rs/application/showtheses?thesesId=7017, https://fedorabg.bg.ac.rs/fedora/get/o:20625/bdef:Content/download, http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51648783, http://nardus.mpn.gov.rs/123456789/11673, http://cherry.chem.bg.ac.rs/handle/123456789/3901",
abstract = "Ebolavirus je rod virusa iz familije Filoviridae, endemski prisutan u Subsaharskoj Africi. Vrste koje pripadaju ovom rodu uzročnici su smrtonosne hemoragijske groznice kod ljudi i primata, a otkrivene su, kao i njima srodni virusi marburga, u drugoj polovini 20. veka, kada su registrovani prvi slučajevi. U ovom trenutku ne postoji odobrena vakcina niti lek protiv ove opasne infekcije. Nekoliko imunoterapeutika, kao i složenih makromolekulskih formulacija, predstavlja obećavajuće kandidate za lek, a ostvaren je i napredak u istraživanjima sa malim molekulima. Oslanjajući se na ranija istraživanja u našoj istraživačkoj grupi, u okviru ove teze sintetisane su dve grupe jedinjenja za koje se pretpostavljalo da mogu imati antivirusnu aktivnost – derivati 4,10-diazahrizena i 1,5-naftiridina. Ukupno je testirano 29 jedinjenja, a po aktivnosti naročito su se istakla dva diazahrizenska derivata koji su imali veoma dobru in vitro aktivnost i štitili su 9/10, odnosno 10/10 inficiranih miševa pri dozi 10 mg/kg. Urađen je veći broj ogleda sa ciljem utvrđivanja mehanizma dejstva ova dva jedinjenja, pri čemu je otkriveno da ona inhibiraju ulazak virusa u ćeliju domaćina, na način koji se razlikuje od do sada poznatih inhibitora ulaska virusa. Dobijeni rezultati ukazuju da su molekuli razvijeni u ovoj tezi značajni i jedinstveni i da zavređuju dalja ispitivanja., Ebolavirus is a genus of viruses from the Filoviridae family, endemic to Sub-Saharan Africa. Species from this genus cause a lethal hemorrhagic fewer in humans and non-human primates. Like the related Marburgviruses, they were discovered in the second half of the 20th century, when first cases were reported. Presently, there is no approved vaccine or other therapeutics to treat this dangerous infection. Several immunotherapeutics, as well as sophisticated macromolecular formulations, have shown promising results, and advances have also been made in small molecule research. Based on our previous results we developed two new chemotypes as possible antivirals – derivatives of 4,10-diazachrysene and 1,5-naphthyridine, respectively. A total of 29 compounds were tested, with two of them showing very good results: they had excellent in vitro activity and they protected 9/10 and 10/10 infected mice from a fatal Ebola challenge, respectively (10 mg/kg dose). A number of experiments were carried out to determine the mechanism of action of these two compounds, and it was discovered that they prevent viral entry into cells, albeit in a manner that differed from other known entry inhibitors. The results obtained in this thesis show that the developed compounds are unique and worthy of further examination",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole"
}
Selaković, Ž. (2019). Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole.
Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
Selaković Ž. Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole. Универзитет у Београду. 2019;
Selaković Života, "Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole" Универзитет у Београду (2019)

Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action

Selaković, Života; Tran, J.P.; Kota, K.P.; Lazić, Marija; Retterer, C.; Besh, R.; Panchal, R.G.; Soloveva, V.; Sean, V.A.; Jay, W.B.; Pavić, A.; Verbić, Tatjana; Vasiljević, Branka; Kuehl, K.; Duplantier, A.J.; Bavari, S.; Mudhasani, R.; Šolaja, Bogdan A.

(Elsevier, 2019)

TY  - JOUR
AU  - Selaković, Života
AU  - Tran, J.P.
AU  - Kota, K.P.
AU  - Lazić, Marija
AU  - Retterer, C.
AU  - Besh, R.
AU  - Panchal, R.G.
AU  - Soloveva, V.
AU  - Sean, V.A.
AU  - Jay, W.B.
AU  - Pavić, A.
AU  - Verbić, Tatjana
AU  - Vasiljević, Branka
AU  - Kuehl, K.
AU  - Duplantier, A.J.
AU  - Bavari, S.
AU  - Mudhasani, R.
AU  - Šolaja, Bogdan A.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2966
AB  - Ebola virus (EBOV) causes a deadly hemorrhagic fever in humans and non-human primates. There is currently no FDA-approved vaccine or medication to counter this disease. Here, we report on the design, synthesis and anti-viral activities of two classes of compounds which show high potency against EBOV in both in vitro cell culture assays and in vivo mouse models Ebola viral disease. These compounds incorporate the structural features of cationic amphiphilic drugs (CAD), i.e they possess both a hydrophobic domain and a hydrophilic domain consisting of an ionizable amine functional group. These structural features enable easily diffusion into cells but once inside an acidic compartment their amine groups became protonated, ionized and remain trapped inside the acidic compartments such as late endosomes and lysosomes. These compounds, by virtue of their lysomotrophic functions, blocked EBOV entry. However, unlike other drugs containing a CAD moiety including chloroquine and amodiaquine, compounds reported in this study display faster kinetics of accumulation in the lysosomes, robust expansion of late endosome/lysosomes, relatively more potent suppression of lysosome fusion with other vesicular compartments and inhibition of cathepsins activities, all of which play a vital role in anti-EBOV activity. Furthermore, the diazachrysene 2 (ZSML08) that showed most potent activity against EBOV in in vitro cell culture assays also showed significant survival benefit with 100% protection in mouse models of Ebola virus disease, at a low dose of 10 mg/kg/day. Lastly, toxicity studies in vivo using zebrafish models suggest no developmental defects or toxicity associated with these compounds. Overall, these studies describe two new pharmacophores that by virtue of being potent lysosomotrophs, display potent anti-EBOV activities both in vitro and in vivo animal models of EBOV disease. © 2018 Elsevier Masson SAS
PB  - Elsevier
T2  - European Journal of Medicinal Chemistry
T1  - Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action
VL  - 162
SP  - 32
EP  - 50
DO  - 10.1016/j.ejmech.2018.10.061
ER  - 
@article{
author = "Selaković, Života and Tran, J.P. and Kota, K.P. and Lazić, Marija and Retterer, C. and Besh, R. and Panchal, R.G. and Soloveva, V. and Sean, V.A. and Jay, W.B. and Pavić, A. and Verbić, Tatjana and Vasiljević, Branka and Kuehl, K. and Duplantier, A.J. and Bavari, S. and Mudhasani, R. and Šolaja, Bogdan A.",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2966",
abstract = "Ebola virus (EBOV) causes a deadly hemorrhagic fever in humans and non-human primates. There is currently no FDA-approved vaccine or medication to counter this disease. Here, we report on the design, synthesis and anti-viral activities of two classes of compounds which show high potency against EBOV in both in vitro cell culture assays and in vivo mouse models Ebola viral disease. These compounds incorporate the structural features of cationic amphiphilic drugs (CAD), i.e they possess both a hydrophobic domain and a hydrophilic domain consisting of an ionizable amine functional group. These structural features enable easily diffusion into cells but once inside an acidic compartment their amine groups became protonated, ionized and remain trapped inside the acidic compartments such as late endosomes and lysosomes. These compounds, by virtue of their lysomotrophic functions, blocked EBOV entry. However, unlike other drugs containing a CAD moiety including chloroquine and amodiaquine, compounds reported in this study display faster kinetics of accumulation in the lysosomes, robust expansion of late endosome/lysosomes, relatively more potent suppression of lysosome fusion with other vesicular compartments and inhibition of cathepsins activities, all of which play a vital role in anti-EBOV activity. Furthermore, the diazachrysene 2 (ZSML08) that showed most potent activity against EBOV in in vitro cell culture assays also showed significant survival benefit with 100% protection in mouse models of Ebola virus disease, at a low dose of 10 mg/kg/day. Lastly, toxicity studies in vivo using zebrafish models suggest no developmental defects or toxicity associated with these compounds. Overall, these studies describe two new pharmacophores that by virtue of being potent lysosomotrophs, display potent anti-EBOV activities both in vitro and in vivo animal models of EBOV disease. © 2018 Elsevier Masson SAS",
publisher = "Elsevier",
journal = "European Journal of Medicinal Chemistry",
title = "Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action",
volume = "162",
pages = "32-50",
doi = "10.1016/j.ejmech.2018.10.061"
}
Selaković, Ž., Tran, J.P., Kota, K.P., Lazić, M., Retterer, C., Besh, R., Panchal, R.G., Soloveva, V., Sean, V.A., Jay, W.B., Pavić, A., Verbić, T., Vasiljević, B., Kuehl, K., Duplantier, A.J., Bavari, S., Mudhasani, R.,& Šolaja, B. A. (2019). Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action.
European Journal of Medicinal Chemistry
Elsevier., 162, 32-50.
https://doi.org/10.1016/j.ejmech.2018.10.061
Selaković Ž, Tran J, Kota K, Lazić M, Retterer C, Besh R, Panchal R, Soloveva V, Sean V, Jay W, Pavić A, Verbić T, Vasiljević B, Kuehl K, Duplantier A, Bavari S, Mudhasani R, Šolaja BA. Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action. European Journal of Medicinal Chemistry. 2019;162:32-50
Selaković Života, Tran J.P., Kota K.P., Lazić Marija, Retterer C., Besh R., Panchal R.G., Soloveva V., Sean V.A., Jay W.B., Pavić A., Verbić Tatjana, Vasiljević Branka, Kuehl K., Duplantier A.J., Bavari S., Mudhasani R., Šolaja Bogdan A., "Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action" European Journal of Medicinal Chemistry, 162 (2019):32-50,
https://doi.org/10.1016/j.ejmech.2018.10.061 .
3
5
5
5

Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061

Selaković, Života; Tran, J.P.; Kota, K.P.; Lazić, Marija; Retterer, C.; Besh, R.; Panchal, R.G.; Soloveva, V.; Sean, V.A.; Jay, W.B.; Pavić, A.; Verbić, Tatjana; Vasiljević, Branka; Kuehl, K.; Duplantier, A.J.; Bavari, S.; Mudhasani, R.; Šolaja, Bogdan A.

(2019)

TY  - BOOK
AU  - Selaković, Života
AU  - Tran, J.P.
AU  - Kota, K.P.
AU  - Lazić, Marija
AU  - Retterer, C.
AU  - Besh, R.
AU  - Panchal, R.G.
AU  - Soloveva, V.
AU  - Sean, V.A.
AU  - Jay, W.B.
AU  - Pavić, A.
AU  - Verbić, Tatjana
AU  - Vasiljević, Branka
AU  - Kuehl, K.
AU  - Duplantier, A.J.
AU  - Bavari, S.
AU  - Mudhasani, R.
AU  - Šolaja, Bogdan A.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2967
T2  - European Journal of Medicinal Chemistry
T1  - Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061
ER  - 
@book{
author = "Selaković, Života and Tran, J.P. and Kota, K.P. and Lazić, Marija and Retterer, C. and Besh, R. and Panchal, R.G. and Soloveva, V. and Sean, V.A. and Jay, W.B. and Pavić, A. and Verbić, Tatjana and Vasiljević, Branka and Kuehl, K. and Duplantier, A.J. and Bavari, S. and Mudhasani, R. and Šolaja, Bogdan A.",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2967",
journal = "European Journal of Medicinal Chemistry",
title = "Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061"
}
Selaković, Ž., Tran, J.P., Kota, K.P., Lazić, M., Retterer, C., Besh, R., Panchal, R.G., Soloveva, V., Sean, V.A., Jay, W.B., Pavić, A., Verbić, T., Vasiljević, B., Kuehl, K., Duplantier, A.J., Bavari, S., Mudhasani, R.,& Šolaja, B. A. (2019). Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061.
European Journal of Medicinal Chemistry.
Selaković Ž, Tran J, Kota K, Lazić M, Retterer C, Besh R, Panchal R, Soloveva V, Sean V, Jay W, Pavić A, Verbić T, Vasiljević B, Kuehl K, Duplantier A, Bavari S, Mudhasani R, Šolaja BA. Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061. European Journal of Medicinal Chemistry. 2019;
Selaković Života, Tran J.P., Kota K.P., Lazić Marija, Retterer C., Besh R., Panchal R.G., Soloveva V., Sean V.A., Jay W.B., Pavić A., Verbić Tatjana, Vasiljević Branka, Kuehl K., Duplantier A.J., Bavari S., Mudhasani R., Šolaja Bogdan A., "Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061" European Journal of Medicinal Chemistry (2019)

Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action

Selaković, Života; Tran, J.P.; Kota, K.P.; Lazić, Marija; Retterer, C.; Besh, R.; Panchal, R.G.; Soloveva, V.; Sean, V.A.; Jay, W.B.; Pavić, A.; Verbić, Tatjana; Vasiljević, Branka; Kuehl, K.; Duplantier, A.J.; Bavari, S.; Mudhasani, R.; Šolaja, Bogdan A.

(2019)

TY  - JOUR
AU  - Selaković, Života
AU  - Tran, J.P.
AU  - Kota, K.P.
AU  - Lazić, Marija
AU  - Retterer, C.
AU  - Besh, R.
AU  - Panchal, R.G.
AU  - Soloveva, V.
AU  - Sean, V.A.
AU  - Jay, W.B.
AU  - Pavić, A.
AU  - Verbić, Tatjana
AU  - Vasiljević, Branka
AU  - Kuehl, K.
AU  - Duplantier, A.J.
AU  - Bavari, S.
AU  - Mudhasani, R.
AU  - Šolaja, Bogdan A.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/360
AB  - Ebola virus (EBOV) causes a deadly hemorrhagic fever in humans and non-human primates. There is currently no FDA-approved vaccine or medication to counter this disease. Here, we report on the design, synthesis and anti-viral activities of two classes of compounds which show high potency against EBOV in both in vitro cell culture assays and in vivo mouse models Ebola viral disease. These compounds incorporate the structural features of cationic amphiphilic drugs (CAD), i.e they possess both a hydrophobic domain and a hydrophilic domain consisting of an ionizable amine functional group. These structural features enable easily diffusion into cells but once inside an acidic compartment their amine groups became protonated, ionized and remain trapped inside the acidic compartments such as late endosomes and lysosomes. These compounds, by virtue of their lysomotrophic functions, blocked EBOV entry. However, unlike other drugs containing a CAD moiety including chloroquine and amodiaquine, compounds reported in this study display faster kinetics of accumulation in the lysosomes, robust expansion of late endosome/lysosomes, relatively more potent suppression of lysosome fusion with other vesicular compartments and inhibition of cathepsins activities, all of which play a vital role in anti-EBOV activity. Furthermore, the diazachrysene 2 (ZSML08) that showed most potent activity against EBOV in in vitro cell culture assays also showed significant survival benefit with 100% protection in mouse models of Ebola virus disease, at a low dose of 10 mg/kg/day. Lastly, toxicity studies in vivo using zebrafish models suggest no developmental defects or toxicity associated with these compounds. Overall, these studies describe two new pharmacophores that by virtue of being potent lysosomotrophs, display potent anti-EBOV activities both in vitro and in vivo animal models of EBOV disease. © 2018 Elsevier Masson SAS
T2  - European Journal of Medicinal Chemistry
T1  - Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action
VL  - 162
SP  - 32
EP  - 50
DO  - 10.1016/j.ejmech.2018.10.061
ER  - 
@article{
author = "Selaković, Života and Tran, J.P. and Kota, K.P. and Lazić, Marija and Retterer, C. and Besh, R. and Panchal, R.G. and Soloveva, V. and Sean, V.A. and Jay, W.B. and Pavić, A. and Verbić, Tatjana and Vasiljević, Branka and Kuehl, K. and Duplantier, A.J. and Bavari, S. and Mudhasani, R. and Šolaja, Bogdan A.",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/360",
abstract = "Ebola virus (EBOV) causes a deadly hemorrhagic fever in humans and non-human primates. There is currently no FDA-approved vaccine or medication to counter this disease. Here, we report on the design, synthesis and anti-viral activities of two classes of compounds which show high potency against EBOV in both in vitro cell culture assays and in vivo mouse models Ebola viral disease. These compounds incorporate the structural features of cationic amphiphilic drugs (CAD), i.e they possess both a hydrophobic domain and a hydrophilic domain consisting of an ionizable amine functional group. These structural features enable easily diffusion into cells but once inside an acidic compartment their amine groups became protonated, ionized and remain trapped inside the acidic compartments such as late endosomes and lysosomes. These compounds, by virtue of their lysomotrophic functions, blocked EBOV entry. However, unlike other drugs containing a CAD moiety including chloroquine and amodiaquine, compounds reported in this study display faster kinetics of accumulation in the lysosomes, robust expansion of late endosome/lysosomes, relatively more potent suppression of lysosome fusion with other vesicular compartments and inhibition of cathepsins activities, all of which play a vital role in anti-EBOV activity. Furthermore, the diazachrysene 2 (ZSML08) that showed most potent activity against EBOV in in vitro cell culture assays also showed significant survival benefit with 100% protection in mouse models of Ebola virus disease, at a low dose of 10 mg/kg/day. Lastly, toxicity studies in vivo using zebrafish models suggest no developmental defects or toxicity associated with these compounds. Overall, these studies describe two new pharmacophores that by virtue of being potent lysosomotrophs, display potent anti-EBOV activities both in vitro and in vivo animal models of EBOV disease. © 2018 Elsevier Masson SAS",
journal = "European Journal of Medicinal Chemistry",
title = "Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action",
volume = "162",
pages = "32-50",
doi = "10.1016/j.ejmech.2018.10.061"
}
Selaković, Ž., Tran, J.P., Kota, K.P., Lazić, M., Retterer, C., Besh, R., Panchal, R.G., Soloveva, V., Sean, V.A., Jay, W.B., Pavić, A., Verbić, T., Vasiljević, B., Kuehl, K., Duplantier, A.J., Bavari, S., Mudhasani, R.,& Šolaja, B. A. (2019). Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action.
European Journal of Medicinal Chemistry, 162, 32-50.
https://doi.org/10.1016/j.ejmech.2018.10.061
Selaković Ž, Tran J, Kota K, Lazić M, Retterer C, Besh R, Panchal R, Soloveva V, Sean V, Jay W, Pavić A, Verbić T, Vasiljević B, Kuehl K, Duplantier A, Bavari S, Mudhasani R, Šolaja BA. Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action. European Journal of Medicinal Chemistry. 2019;162:32-50
Selaković Života, Tran J.P., Kota K.P., Lazić Marija, Retterer C., Besh R., Panchal R.G., Soloveva V., Sean V.A., Jay W.B., Pavić A., Verbić Tatjana, Vasiljević Branka, Kuehl K., Duplantier A.J., Bavari S., Mudhasani R., Šolaja Bogdan A., "Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action" European Journal of Medicinal Chemistry, 162 (2019):32-50,
https://doi.org/10.1016/j.ejmech.2018.10.061 .
3
5
5
5

Supplementary data for the article: Selaković, Z.; Soloveva, V.; Gharaibeh, D. N.; Wells, J.; Šegan, S.; Panchal, R. G.; Šolaja, B. A. Anti-Ebola Activity of Diazachrysene Small Molecules. ACS Infectious Diseases 2016, 1 (6), 264–271. https://doi.org/10.1021/acsinfecdis.5b00028

Selaković, Života; Soloveva, Veronica; Gharaibeh, Dima N.; Wells, Jay; Šegan, Sandra B.; Panchal, Rekha G.; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2015)

TY  - BOOK
AU  - Selaković, Života
AU  - Soloveva, Veronica
AU  - Gharaibeh, Dima N.
AU  - Wells, Jay
AU  - Šegan, Sandra B.
AU  - Panchal, Rekha G.
AU  - Šolaja, Bogdan A.
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3339
PB  - Amer Chemical Soc, Washington
T2  - ACS INFECTIOUS DISEASES
T1  - Supplementary data for the article: Selaković, Z.; Soloveva, V.; Gharaibeh, D. N.; Wells, J.; Šegan, S.; Panchal, R. G.; Šolaja, B. A. Anti-Ebola Activity of Diazachrysene Small Molecules. ACS Infectious Diseases 2016, 1 (6), 264–271. https://doi.org/10.1021/acsinfecdis.5b00028
ER  - 
@book{
author = "Selaković, Života and Soloveva, Veronica and Gharaibeh, Dima N. and Wells, Jay and Šegan, Sandra B. and Panchal, Rekha G. and Šolaja, Bogdan A.",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3339",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS INFECTIOUS DISEASES",
title = "Supplementary data for the article: Selaković, Z.; Soloveva, V.; Gharaibeh, D. N.; Wells, J.; Šegan, S.; Panchal, R. G.; Šolaja, B. A. Anti-Ebola Activity of Diazachrysene Small Molecules. ACS Infectious Diseases 2016, 1 (6), 264–271. https://doi.org/10.1021/acsinfecdis.5b00028"
}
Selaković, Ž., Soloveva, V., Gharaibeh, D. N., Wells, J., Šegan, S. B., Panchal, R. G.,& Šolaja, B. A. (2015). Supplementary data for the article: Selaković, Z.; Soloveva, V.; Gharaibeh, D. N.; Wells, J.; Šegan, S.; Panchal, R. G.; Šolaja, B. A. Anti-Ebola Activity of Diazachrysene Small Molecules. ACS Infectious Diseases 2016, 1 (6), 264–271. https://doi.org/10.1021/acsinfecdis.5b00028.
ACS INFECTIOUS DISEASES
Amer Chemical Soc, Washington..
Selaković Ž, Soloveva V, Gharaibeh DN, Wells J, Šegan SB, Panchal RG, Šolaja BA. Supplementary data for the article: Selaković, Z.; Soloveva, V.; Gharaibeh, D. N.; Wells, J.; Šegan, S.; Panchal, R. G.; Šolaja, B. A. Anti-Ebola Activity of Diazachrysene Small Molecules. ACS Infectious Diseases 2016, 1 (6), 264–271. https://doi.org/10.1021/acsinfecdis.5b00028. ACS INFECTIOUS DISEASES. 2015;
Selaković Života, Soloveva Veronica, Gharaibeh Dima N., Wells Jay, Šegan Sandra B., Panchal Rekha G., Šolaja Bogdan A., "Supplementary data for the article: Selaković, Z.; Soloveva, V.; Gharaibeh, D. N.; Wells, J.; Šegan, S.; Panchal, R. G.; Šolaja, B. A. Anti-Ebola Activity of Diazachrysene Small Molecules. ACS Infectious Diseases 2016, 1 (6), 264–271. https://doi.org/10.1021/acsinfecdis.5b00028" ACS INFECTIOUS DISEASES (2015)

Anti-Ebola Activity of Diazachrysene Small Molecules

Selaković, Života; Soloveva, Veronica; Gharaibeh, Dima N.; Wells, Jay; Šegan, Sandra B.; Panchal, Rekha G.; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2015)

TY  - JOUR
AU  - Selaković, Života
AU  - Soloveva, Veronica
AU  - Gharaibeh, Dima N.
AU  - Wells, Jay
AU  - Šegan, Sandra B.
AU  - Panchal, Rekha G.
AU  - Šolaja, Bogdan A.
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2035
AB  - Herein we report on a diazachrysene class of small molecules that exhibit potent antiviral activity against the Ebola (EBOV) virus. The antiviral compounds are easily synthesized, and the most active compounds have excellent in vitro activity (0.34-0.70 mu M) and are significantly less lipophilic than their predecessors. The three most potent diazachrysene antivirals do not exhibit any toxicity in vivo and protected 70-90% of the mice at 10 mg/kg following EBOV challenge. Together, these studies suggest that diazachrysenes are a promising class of compounds for hit to lead optimization and as potential Ebola therapeutics.
PB  - Amer Chemical Soc, Washington
T2  - ACS INFECTIOUS DISEASES
T1  - Anti-Ebola Activity of Diazachrysene Small Molecules
VL  - 1
IS  - 6
SP  - 264
EP  - 271
DO  - 10.1021/acsinfecdis.5b00028
ER  - 
@article{
author = "Selaković, Života and Soloveva, Veronica and Gharaibeh, Dima N. and Wells, Jay and Šegan, Sandra B. and Panchal, Rekha G. and Šolaja, Bogdan A.",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2035",
abstract = "Herein we report on a diazachrysene class of small molecules that exhibit potent antiviral activity against the Ebola (EBOV) virus. The antiviral compounds are easily synthesized, and the most active compounds have excellent in vitro activity (0.34-0.70 mu M) and are significantly less lipophilic than their predecessors. The three most potent diazachrysene antivirals do not exhibit any toxicity in vivo and protected 70-90% of the mice at 10 mg/kg following EBOV challenge. Together, these studies suggest that diazachrysenes are a promising class of compounds for hit to lead optimization and as potential Ebola therapeutics.",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS INFECTIOUS DISEASES",
title = "Anti-Ebola Activity of Diazachrysene Small Molecules",
volume = "1",
number = "6",
pages = "264-271",
doi = "10.1021/acsinfecdis.5b00028"
}
Selaković, Ž., Soloveva, V., Gharaibeh, D. N., Wells, J., Šegan, S. B., Panchal, R. G.,& Šolaja, B. A. (2015). Anti-Ebola Activity of Diazachrysene Small Molecules.
ACS INFECTIOUS DISEASES
Amer Chemical Soc, Washington., 1(6), 264-271.
https://doi.org/10.1021/acsinfecdis.5b00028
Selaković Ž, Soloveva V, Gharaibeh DN, Wells J, Šegan SB, Panchal RG, Šolaja BA. Anti-Ebola Activity of Diazachrysene Small Molecules. ACS INFECTIOUS DISEASES. 2015;1(6):264-271
Selaković Života, Soloveva Veronica, Gharaibeh Dima N., Wells Jay, Šegan Sandra B., Panchal Rekha G., Šolaja Bogdan A., "Anti-Ebola Activity of Diazachrysene Small Molecules" ACS INFECTIOUS DISEASES, 1, no. 6 (2015):264-271,
https://doi.org/10.1021/acsinfecdis.5b00028 .
24
4
5
5

Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria

Selaković, Milica; Opsenica, Dejan M.; Burnett, James C.; Gomba, Laura; Nuss, Jonathan E.; Selaković, Života; Konstantinović, Jelena M.; Krstić-Ristivojević, Maja; Šegan, Sandra B.; Zlatović, Mario; Sciotti, Richard J.; Bavari, Sina; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2014)

TY  - JOUR
AU  - Selaković, Milica
AU  - Opsenica, Dejan M.
AU  - Burnett, James C.
AU  - Gomba, Laura
AU  - Nuss, Jonathan E.
AU  - Selaković, Života
AU  - Konstantinović, Jelena M.
AU  - Krstić-Ristivojević, Maja
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Sciotti, Richard J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan A.
PY  - 2014
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1781
AB  - Significantly more potent second generation 4-amino-7-chloroquinoline (4,7-ACQ) based inhibitors of the botulinum neurotoxin serotype A (BoNT/A) light chain were synthesized. Introducing an amino group at the C(3) position of the cholate component markedly increased potency (IC50 values for such derivatives ranged from 0.81 to 2.27 mu M). Two additional subclasses were prepared: bis(steroidal)-4,7-ACQ derivatives and bis(4,7-ACQ)cholate derivatives; both classes provided inhibitors with nanomolar-range potencies (e.g., the K-i of compound 67 is 0.10 mu M). During BoNT/A challenge using primary neurons, select derivatives protected SNAP-25 by up to 89%. Docking simulations were performed to rationalize the compounds' in vitro potencies. In addition to specific residue contacts, coordination of the enzyme's catalytic zinc and expulsion of the enzyme's catalytic water were a consistent theme. With respect to antimalarial activity, the compounds provided better IC90 activities against chloroquine resistant (CQR) malaria than CQ, and seven compounds were more active than mefloquine against CQR strain W2.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria
VL  - 57
IS  - 10
SP  - 4134
EP  - 4153
DO  - 10.1021/jm500033r
ER  - 
@article{
author = "Selaković, Milica and Opsenica, Dejan M. and Burnett, James C. and Gomba, Laura and Nuss, Jonathan E. and Selaković, Života and Konstantinović, Jelena M. and Krstić-Ristivojević, Maja and Šegan, Sandra B. and Zlatović, Mario and Sciotti, Richard J. and Bavari, Sina and Šolaja, Bogdan A.",
year = "2014",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1781",
abstract = "Significantly more potent second generation 4-amino-7-chloroquinoline (4,7-ACQ) based inhibitors of the botulinum neurotoxin serotype A (BoNT/A) light chain were synthesized. Introducing an amino group at the C(3) position of the cholate component markedly increased potency (IC50 values for such derivatives ranged from 0.81 to 2.27 mu M). Two additional subclasses were prepared: bis(steroidal)-4,7-ACQ derivatives and bis(4,7-ACQ)cholate derivatives; both classes provided inhibitors with nanomolar-range potencies (e.g., the K-i of compound 67 is 0.10 mu M). During BoNT/A challenge using primary neurons, select derivatives protected SNAP-25 by up to 89%. Docking simulations were performed to rationalize the compounds' in vitro potencies. In addition to specific residue contacts, coordination of the enzyme's catalytic zinc and expulsion of the enzyme's catalytic water were a consistent theme. With respect to antimalarial activity, the compounds provided better IC90 activities against chloroquine resistant (CQR) malaria than CQ, and seven compounds were more active than mefloquine against CQR strain W2.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria",
volume = "57",
number = "10",
pages = "4134-4153",
doi = "10.1021/jm500033r"
}
Selaković, M., Opsenica, D. M., Burnett, J. C., Gomba, L., Nuss, J. E., Selaković, Ž., Konstantinović, J. M., Krstić-Ristivojević, M., Šegan, S. B., Zlatović, M., Sciotti, R. J., Bavari, S.,& Šolaja, B. A. (2014). Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria.
Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 57(10), 4134-4153.
https://doi.org/10.1021/jm500033r
Selaković M, Opsenica DM, Burnett JC, Gomba L, Nuss JE, Selaković Ž, Konstantinović JM, Krstić-Ristivojević M, Šegan SB, Zlatović M, Sciotti RJ, Bavari S, Šolaja BA. Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria. Journal of Medicinal Chemistry. 2014;57(10):4134-4153
Selaković Milica, Opsenica Dejan M., Burnett James C., Gomba Laura, Nuss Jonathan E., Selaković Života, Konstantinović Jelena M., Krstić-Ristivojević Maja, Šegan Sandra B., Zlatović Mario, Sciotti Richard J., Bavari Sina, Šolaja Bogdan A., "Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria" Journal of Medicinal Chemistry, 57, no. 10 (2014):4134-4153,
https://doi.org/10.1021/jm500033r .
3
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A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor

Selaković, Života; Opsenica, Dejan M.; Eaton, Brett; Retterer, Cary; Bavari, Sina; Burnett, James C.; Šolaja, Bogdan A.; Panchal, Rekha G.

(Mdpi Ag, Basel, 2012)

TY  - JOUR
AU  - Selaković, Života
AU  - Opsenica, Dejan M.
AU  - Eaton, Brett
AU  - Retterer, Cary
AU  - Bavari, Sina
AU  - Burnett, James C.
AU  - Šolaja, Bogdan A.
AU  - Panchal, Rekha G.
PY  - 2012
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1528
AB  - Ebola (EBOV) and Marburg (MARV) filoviruses are highly infectious pathogens causing deadly hemorrhagic fever in humans and non-human primates. Promising vaccine candidates providing immunity against filoviruses have been reported. However, the sporadic nature and swift progression of filovirus disease underlines the need for the development of small molecule therapeutics providing immediate antiviral effects. Herein we describe a brief structural exploration of two previously reported diazachrysene (DAAC)-based EBOV inhibitors. Specifically, three analogs were prepared to examine how slight substituent modifications would affect inhibitory efficacy and inhibitor-mediated toxicity during not only EBOV, but also MARV cellular infection. Of the three analogs, one was highly efficacious, providing IC50 values of 0.696 mu M +/- 0.13 mu M and 2.76 mu M +/- 0.21 mu M against EBOV and MARV infection, respectively, with little or no associated cellular toxicity. Overall, the structure-activity and structure-toxicity results from this study provide a framework for the future development of DAAC-based filovirus inhibitors that will be both active and non-toxic in vivo.
PB  - Mdpi Ag, Basel
T2  - Viruses
T1  - A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor
VL  - 4
IS  - 8
SP  - 1279
EP  - 1288
DO  - 10.3390/v4081279
ER  - 
@article{
author = "Selaković, Života and Opsenica, Dejan M. and Eaton, Brett and Retterer, Cary and Bavari, Sina and Burnett, James C. and Šolaja, Bogdan A. and Panchal, Rekha G.",
year = "2012",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1528",
abstract = "Ebola (EBOV) and Marburg (MARV) filoviruses are highly infectious pathogens causing deadly hemorrhagic fever in humans and non-human primates. Promising vaccine candidates providing immunity against filoviruses have been reported. However, the sporadic nature and swift progression of filovirus disease underlines the need for the development of small molecule therapeutics providing immediate antiviral effects. Herein we describe a brief structural exploration of two previously reported diazachrysene (DAAC)-based EBOV inhibitors. Specifically, three analogs were prepared to examine how slight substituent modifications would affect inhibitory efficacy and inhibitor-mediated toxicity during not only EBOV, but also MARV cellular infection. Of the three analogs, one was highly efficacious, providing IC50 values of 0.696 mu M +/- 0.13 mu M and 2.76 mu M +/- 0.21 mu M against EBOV and MARV infection, respectively, with little or no associated cellular toxicity. Overall, the structure-activity and structure-toxicity results from this study provide a framework for the future development of DAAC-based filovirus inhibitors that will be both active and non-toxic in vivo.",
publisher = "Mdpi Ag, Basel",
journal = "Viruses",
title = "A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor",
volume = "4",
number = "8",
pages = "1279-1288",
doi = "10.3390/v4081279"
}
Selaković, Ž., Opsenica, D. M., Eaton, B., Retterer, C., Bavari, S., Burnett, J. C., Šolaja, B. A.,& Panchal, R. G. (2012). A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor.
Viruses
Mdpi Ag, Basel., 4(8), 1279-1288.
https://doi.org/10.3390/v4081279
Selaković Ž, Opsenica DM, Eaton B, Retterer C, Bavari S, Burnett JC, Šolaja BA, Panchal RG. A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor. Viruses. 2012;4(8):1279-1288
Selaković Života, Opsenica Dejan M., Eaton Brett, Retterer Cary, Bavari Sina, Burnett James C., Šolaja Bogdan A., Panchal Rekha G., "A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor" Viruses, 4, no. 8 (2012):1279-1288,
https://doi.org/10.3390/v4081279 .
1
9
7
11

Nobelova nagrada za hemiju 2010

Kolarski, Dušan; Milić, Jovana; Selaković, Života; Filipović, Vuk

(2011)

TY  - JOUR
AU  - Kolarski, Dušan
AU  - Milić, Jovana
AU  - Selaković, Života
AU  - Filipović, Vuk
PY  - 2011
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/278
T2  - Hemijski pregled
T1  - Nobelova nagrada za hemiju 2010
VL  - 52
IS  - 1
SP  - 3
EP  - 11
ER  - 
@article{
author = "Kolarski, Dušan and Milić, Jovana and Selaković, Života and Filipović, Vuk",
year = "2011",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/278",
journal = "Hemijski pregled",
title = "Nobelova nagrada za hemiju 2010",
volume = "52",
number = "1",
pages = "3-11"
}
Kolarski, D., Milić, J., Selaković, Ž.,& Filipović, V. (2011). Nobelova nagrada za hemiju 2010.
Hemijski pregled, 52(1), 3-11.
Kolarski D, Milić J, Selaković Ž, Filipović V. Nobelova nagrada za hemiju 2010. Hemijski pregled. 2011;52(1):3-11
Kolarski Dušan, Milić Jovana, Selaković Života, Filipović Vuk, "Nobelova nagrada za hemiju 2010" Hemijski pregled, 52, no. 1 (2011):3-11