Ajdačić, Vladimir

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Authority KeyName Variants
orcid::0000-0002-3423-0862
  • Ajdačić, Vladimir (22)
Projects
The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors Microbial diversity study and characterization of beneficial environmental microorganisms
Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research Serbian Academy of Sciences and Arts
European Society of Clinical Microbiology and Infectious Diseases (ESCMID) Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM)
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200168 (University of Belgrade, Faculty of Chemistry) Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200288 (Innovation Center of the Faculty of Chemistry)
Serbian Academy of Sciences and Arts (01-2019-F65) European Research Council (grant ERC-StG-678905 CoBABATI to J.D.D.)
European Unions Horizon research and innovation program under the Marie Sklodowska-Curie Grant [642095] OPATHY - From Omics to Patient: Improving Diagnostics of Pathogenic Yeasts
Molecular designing of nanoparticles with controlled morphological and physicochemical characteristics and functional materials based on them PHC French-Serbian partnership project Pavle Savić (451-03- 01963/2017-09/03)

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 ChemistryAmerican 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" 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 .
8

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 ChemistryAmerican 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" 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 .
8

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 ChemistryAmerican 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" (2021),
https://doi.org/10.1021/acs.joc.1c00282.s001 .

Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida

Ajdačić, Vladimir

(Универзитет у Београду, Хемијски факултет, 2019-11-08)

TY  - BOOK
AU  - Ajdačić, Vladimir
PY  - 2019-11-08
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7600
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:22540/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51816719
UR  - http://nardus.mpn.gov.rs/handle/123456789/17444
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4386
AB  - Sintetisan je i okarakterisan katalizator magnetnih osobina na bazi paladijuma (Pd/Fe2O3) kao i katalizator na bazi paladijuma gde je kao nosač upotrebljena bakterijska nanoceluloza (Pd/BNC) i ispitana je njihova primena u reakciji dekarbonilovanja aldehida. Optimizovani reakcioni uslovi primenjeni su na aromatičnim i heteroaromatičnim aldehidima i na alifatičnim aldehidima koji imaju vodonikove atome na α- i δ-ugljenikovim atomima. Istovremeno, određen je mehanizam reakcije dekarbonilovanja i ispitana je mogućnost reciklovanja katalizatora.Pored reakcije dekarbonilovanja sintetisani katalizator Pd/Fe2O3 upotrebljen je i u reakciji reduktivnog dehalogenovanja arilhalogenida.U nastavku istražena je i reakcije dekarbonilativnog bromovanja 5-ariltiofen-2-karbaldehida. Eksperimentalnim i računarskim metodama ispitan je mehanizam reakcije kao i njena primena u sintezi triarilsupstituisanih tiofena.
AB  - Palladium-based catalysts obtained by palladium immobilization on maghemite (Pd/ γ-Fe2O3) and bacterial nanocellulose (Pd/BNC) as solid supports were synthesized and characterized and their application in the decarbonylation reaction was investigated. Optimized reaction conditions were applied to a series of aromatic and heteroaromatic aldehydes as well as to several aldehydes having alpha and beta hydrogen atoms. The mechanism of the mentioned transformation as well as the possibility of catalyst recycling has also been investigated.In addition to the decarbonylation reaction, the synthesized catalyst Pd/γ-Fe2O3 was used in the reductive dehalogenation reaction of arylhalides.The decarbonylative bromination reaction of 5-arylthiophene-2-carbaldehydes was also investigated. By combining experimental and computational methods, the mechanism of this reaction was examined, as well as its application to the synthesis of triaryl-substituted thiophene derivatives.
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida
ER  - 
@phdthesis{
author = "Ajdačić, Vladimir",
year = "2019-11-08",
url = "http://eteze.bg.ac.rs/application/showtheses?thesesId=7600, https://fedorabg.bg.ac.rs/fedora/get/o:22540/bdef:Content/download, http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51816719, http://nardus.mpn.gov.rs/handle/123456789/17444, http://cherry.chem.bg.ac.rs/handle/123456789/4386",
abstract = "Sintetisan je i okarakterisan katalizator magnetnih osobina na bazi paladijuma (Pd/Fe2O3) kao i katalizator na bazi paladijuma gde je kao nosač upotrebljena bakterijska nanoceluloza (Pd/BNC) i ispitana je njihova primena u reakciji dekarbonilovanja aldehida. Optimizovani reakcioni uslovi primenjeni su na aromatičnim i heteroaromatičnim aldehidima i na alifatičnim aldehidima koji imaju vodonikove atome na α- i δ-ugljenikovim atomima. Istovremeno, određen je mehanizam reakcije dekarbonilovanja i ispitana je mogućnost reciklovanja katalizatora.Pored reakcije dekarbonilovanja sintetisani katalizator Pd/Fe2O3 upotrebljen je i u reakciji reduktivnog dehalogenovanja arilhalogenida.U nastavku istražena je i reakcije dekarbonilativnog bromovanja 5-ariltiofen-2-karbaldehida. Eksperimentalnim i računarskim metodama ispitan je mehanizam reakcije kao i njena primena u sintezi triarilsupstituisanih tiofena., Palladium-based catalysts obtained by palladium immobilization on maghemite (Pd/ γ-Fe2O3) and bacterial nanocellulose (Pd/BNC) as solid supports were synthesized and characterized and their application in the decarbonylation reaction was investigated. Optimized reaction conditions were applied to a series of aromatic and heteroaromatic aldehydes as well as to several aldehydes having alpha and beta hydrogen atoms. The mechanism of the mentioned transformation as well as the possibility of catalyst recycling has also been investigated.In addition to the decarbonylation reaction, the synthesized catalyst Pd/γ-Fe2O3 was used in the reductive dehalogenation reaction of arylhalides.The decarbonylative bromination reaction of 5-arylthiophene-2-carbaldehydes was also investigated. By combining experimental and computational methods, the mechanism of this reaction was examined, as well as its application to the synthesis of triaryl-substituted thiophene derivatives.",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida"
}
Ajdačić, V. (2019-11-08). Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida.
Универзитет у БеоградуУниверзитет у Београду, Хемијски факултет..
Ajdačić V. Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida. Универзитет у Београду. 2019;
Ajdačić Vladimir, "Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida" (2019-11-08)

Palladium-catalyzed N-Arylation of 1-substituted-1H-tetrazol-5-amines

Nikolić, Andrea M.; Ajdačić, Vladimir; Opsenica, Igor

(Elsevier, 2019)

TY  - JOUR
AU  - Nikolić, Andrea M.
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3787
PB  - Elsevier
T2  - Journal of Organometallic Chemistry
T1  - Palladium-catalyzed N-Arylation of 1-substituted-1H-tetrazol-5-amines
VL  - 880
SP  - 134
EP  - 142
DO  - 10.1016/j.jorganchem.2018.11.007
ER  - 
@article{
author = "Nikolić, Andrea M. and Ajdačić, Vladimir and Opsenica, Igor",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3787",
publisher = "Elsevier",
journal = "Journal of Organometallic Chemistry",
title = "Palladium-catalyzed N-Arylation of 1-substituted-1H-tetrazol-5-amines",
volume = "880",
pages = "134-142",
doi = "10.1016/j.jorganchem.2018.11.007"
}
Nikolić, A. M., Ajdačić, V.,& Opsenica, I. (2019). Palladium-catalyzed N-Arylation of 1-substituted-1H-tetrazol-5-amines.
Journal of Organometallic ChemistryElsevier., 880, 134-142.
https://doi.org/10.1016/j.jorganchem.2018.11.007
Nikolić AM, Ajdačić V, Opsenica I. Palladium-catalyzed N-Arylation of 1-substituted-1H-tetrazol-5-amines. Journal of Organometallic Chemistry. 2019;880:134-142
Nikolić Andrea M., Ajdačić Vladimir, Opsenica Igor, "Palladium-catalyzed N-Arylation of 1-substituted-1H-tetrazol-5-amines" 880 (2019):134-142,
https://doi.org/10.1016/j.jorganchem.2018.11.007 .
1
2
2
3

Supplementary data for article: Nikolić, A. M.; Ajdačić, V.; Opsenica, I. M. Palladium-Catalyzed N-Arylation of 1-Substituted-1H-Tetrazol-5-Amines. Journal of Organometallic Chemistry 2019, 880, 134–142. https://doi.org/10.1016/j.jorganchem.2018.11.007

Nikolić, Andrea M.; Ajdačić, Vladimir; Opsenica, Igor

(Elsevier, 2019)

TY  - BOOK
AU  - Nikolić, Andrea M.
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3788
PB  - Elsevier
T2  - Journal of Organometallic Chemistry
T1  - Supplementary data for article: Nikolić, A. M.; Ajdačić, V.; Opsenica, I. M. Palladium-Catalyzed N-Arylation of 1-Substituted-1H-Tetrazol-5-Amines. Journal of Organometallic Chemistry 2019, 880, 134–142. https://doi.org/10.1016/j.jorganchem.2018.11.007
DO  - 10.1016/j.jorganchem.2018.11.007
ER  - 
@book{
author = "Nikolić, Andrea M. and Ajdačić, Vladimir and Opsenica, Igor",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3788",
publisher = "Elsevier",
journal = "Journal of Organometallic Chemistry",
title = "Supplementary data for article: Nikolić, A. M.; Ajdačić, V.; Opsenica, I. M. Palladium-Catalyzed N-Arylation of 1-Substituted-1H-Tetrazol-5-Amines. Journal of Organometallic Chemistry 2019, 880, 134–142. https://doi.org/10.1016/j.jorganchem.2018.11.007",
doi = "10.1016/j.jorganchem.2018.11.007"
}
Nikolić, A. M., Ajdačić, V.,& Opsenica, I. (2019). Supplementary data for article: Nikolić, A. M.; Ajdačić, V.; Opsenica, I. M. Palladium-Catalyzed N-Arylation of 1-Substituted-1H-Tetrazol-5-Amines. Journal of Organometallic Chemistry 2019, 880, 134–142. https://doi.org/10.1016/j.jorganchem.2018.11.007.
Journal of Organometallic ChemistryElsevier..
https://doi.org/10.1016/j.jorganchem.2018.11.007
Nikolić AM, Ajdačić V, Opsenica I. Supplementary data for article: Nikolić, A. M.; Ajdačić, V.; Opsenica, I. M. Palladium-Catalyzed N-Arylation of 1-Substituted-1H-Tetrazol-5-Amines. Journal of Organometallic Chemistry 2019, 880, 134–142. https://doi.org/10.1016/j.jorganchem.2018.11.007. Journal of Organometallic Chemistry. 2019;
Nikolić Andrea M., Ajdačić Vladimir, Opsenica Igor, "Supplementary data for article: Nikolić, A. M.; Ajdačić, V.; Opsenica, I. M. Palladium-Catalyzed N-Arylation of 1-Substituted-1H-Tetrazol-5-Amines. Journal of Organometallic Chemistry 2019, 880, 134–142. https://doi.org/10.1016/j.jorganchem.2018.11.007" (2019),
https://doi.org/10.1016/j.jorganchem.2018.11.007 .
1
2
2
3

Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity

Božinović, Nina S.; Ajdačić, Vladimir; Lazić, Jelena O.; Lecerf, Maxime; Daventure, Victoria; Nikodinović-Runić, Jasmina; Opsenica, Igor; Dimitrov, Jordan D.

(American Chemical Society, 2019)

TY  - JOUR
AU  - Božinović, Nina S.
AU  - Ajdačić, Vladimir
AU  - Lazić, Jelena O.
AU  - Lecerf, Maxime
AU  - Daventure, Victoria
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
AU  - Dimitrov, Jordan D.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3793
AB  - In a healthy immune repertoire, there exists a fraction of polyreactive antibodies that can bind to a variety of unrelated self- and foreign antigens. Apart from naturally polyreactive antibodies, in every healthy individual, there is a fraction of antibody that can gain polyreactivity upon exposure to porphyrin cofactor heme. Molecular mechanisms and biological significance of the appearance of cryptic polyreactivity are not well understood. It is believed that heme acts as an interfacial cofactor between the antibody and the newly recognized antigens. To further test this claim and gain insight into the types of interactions involved in heme binding, we herein investigated the influence of a group of aromatic guanylhydrazone molecules on the heme-induced antibody polyreactivity. From the analysis of SAR and the results of UV-vis absorbance spectroscopy, it was concluded that the most probable mechanism by which the studied molecules inhibit heme-mediated polyreactivity of the antibody is the direct binding to heme, thus preventing heme from binding to antibody and/or antigen. The inhibitory capacity of the most potent compounds was substantially higher than that of chloroquine, a well-known heme binder. Some of the guanylhydrazone molecules were able to induce polyreactivity of the studied antibody themselves, possibly by a mechanism similar to heme. Results described here point to the conclusion that heme indeed must bind to an antibody to induce its polyreactivity, and that both π-stacking interactions and iron coordination contribute to the binding affinity, while certain structures, such as guanylhydrazones, can interfere with these processes.
PB  - American Chemical Society
T2  - ACS Omega
T1  - Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity
VL  - 4
IS  - 24
SP  - 20450
EP  - 20458
DO  - 10.1021/acsomega.9b01548
ER  - 
@article{
author = "Božinović, Nina S. and Ajdačić, Vladimir and Lazić, Jelena O. and Lecerf, Maxime and Daventure, Victoria and Nikodinović-Runić, Jasmina and Opsenica, Igor and Dimitrov, Jordan D.",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3793",
abstract = "In a healthy immune repertoire, there exists a fraction of polyreactive antibodies that can bind to a variety of unrelated self- and foreign antigens. Apart from naturally polyreactive antibodies, in every healthy individual, there is a fraction of antibody that can gain polyreactivity upon exposure to porphyrin cofactor heme. Molecular mechanisms and biological significance of the appearance of cryptic polyreactivity are not well understood. It is believed that heme acts as an interfacial cofactor between the antibody and the newly recognized antigens. To further test this claim and gain insight into the types of interactions involved in heme binding, we herein investigated the influence of a group of aromatic guanylhydrazone molecules on the heme-induced antibody polyreactivity. From the analysis of SAR and the results of UV-vis absorbance spectroscopy, it was concluded that the most probable mechanism by which the studied molecules inhibit heme-mediated polyreactivity of the antibody is the direct binding to heme, thus preventing heme from binding to antibody and/or antigen. The inhibitory capacity of the most potent compounds was substantially higher than that of chloroquine, a well-known heme binder. Some of the guanylhydrazone molecules were able to induce polyreactivity of the studied antibody themselves, possibly by a mechanism similar to heme. Results described here point to the conclusion that heme indeed must bind to an antibody to induce its polyreactivity, and that both π-stacking interactions and iron coordination contribute to the binding affinity, while certain structures, such as guanylhydrazones, can interfere with these processes.",
publisher = "American Chemical Society",
journal = "ACS Omega",
title = "Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity",
volume = "4",
number = "24",
pages = "20450-20458",
doi = "10.1021/acsomega.9b01548"
}
Božinović, N. S., Ajdačić, V., Lazić, J. O., Lecerf, M., Daventure, V., Nikodinović-Runić, J., Opsenica, I.,& Dimitrov, J. D. (2019). Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity.
ACS OmegaAmerican Chemical Society., 4(24), 20450-20458.
https://doi.org/10.1021/acsomega.9b01548
Božinović NS, Ajdačić V, Lazić JO, Lecerf M, Daventure V, Nikodinović-Runić J, Opsenica I, Dimitrov JD. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega. 2019;4(24):20450-20458
Božinović Nina S., Ajdačić Vladimir, Lazić Jelena O., Lecerf Maxime, Daventure Victoria, Nikodinović-Runić Jasmina, Opsenica Igor, Dimitrov Jordan D., "Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity" 4, no. 24 (2019):20450-20458,
https://doi.org/10.1021/acsomega.9b01548 .
1

Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548

Božinović, Nina S.; Ajdačić, Vladimir; Lazić, Jelena O.; Lecerf, Maxime; Daventure, Victoria; Nikodinović-Runić, Jasmina; Opsenica, Igor; Dimitrov, Jordan D.

(American Chemical Society, 2019)

TY  - BOOK
AU  - Božinović, Nina S.
AU  - Ajdačić, Vladimir
AU  - Lazić, Jelena O.
AU  - Lecerf, Maxime
AU  - Daventure, Victoria
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
AU  - Dimitrov, Jordan D.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3794
PB  - American Chemical Society
T2  - ACS Omega
T1  - Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548
ER  - 
@book{
author = "Božinović, Nina S. and Ajdačić, Vladimir and Lazić, Jelena O. and Lecerf, Maxime and Daventure, Victoria and Nikodinović-Runić, Jasmina and Opsenica, Igor and Dimitrov, Jordan D.",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3794",
publisher = "American Chemical Society",
journal = "ACS Omega",
title = "Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548"
}
Božinović, N. S., Ajdačić, V., Lazić, J. O., Lecerf, M., Daventure, V., Nikodinović-Runić, J., Opsenica, I.,& Dimitrov, J. D. (2019). Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548.
ACS OmegaAmerican Chemical Society..
Božinović NS, Ajdačić V, Lazić JO, Lecerf M, Daventure V, Nikodinović-Runić J, Opsenica I, Dimitrov JD. Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548. ACS Omega. 2019;
Božinović Nina S., Ajdačić Vladimir, Lazić Jelena O., Lecerf Maxime, Daventure Victoria, Nikodinović-Runić Jasmina, Opsenica Igor, Dimitrov Jordan D., "Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548" (2019)

Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions

Jeremić, Sanja; Đokić, Lidija; Ajdačić, Vladimir; Božinović, Nina S.; Pavlović, Vladimir D.; Manojlović, Dragan D.; Babu, Ramesh P.; Senthamaraikannan, Ramsankar; Rojas, Orlando; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Elsevier, 2019)

TY  - JOUR
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Ajdačić, Vladimir
AU  - Božinović, Nina S.
AU  - Pavlović, Vladimir D.
AU  - Manojlović, Dragan D.
AU  - Babu, Ramesh P.
AU  - Senthamaraikannan, Ramsankar
AU  - Rojas, Orlando
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2850
AB  - Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions
VL  - 129
SP  - 351
EP  - 360
DO  - 10.1016/j.ijbiomac.2019.01.154
ER  - 
@article{
author = "Jeremić, Sanja and Đokić, Lidija and Ajdačić, Vladimir and Božinović, Nina S. and Pavlović, Vladimir D. and Manojlović, Dragan D. and Babu, Ramesh P. and Senthamaraikannan, Ramsankar and Rojas, Orlando and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2850",
abstract = "Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions",
volume = "129",
pages = "351-360",
doi = "10.1016/j.ijbiomac.2019.01.154"
}
Jeremić, S., Đokić, L., Ajdačić, V., Božinović, N. S., Pavlović, V. D., Manojlović, D. D., Babu, R. P., Senthamaraikannan, R., Rojas, O., Opsenica, I.,& Nikodinović-Runić, J. (2019). Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions.
International Journal of Biological MacromoleculesElsevier., 129, 351-360.
https://doi.org/10.1016/j.ijbiomac.2019.01.154
Jeremić S, Đokić L, Ajdačić V, Božinović NS, Pavlović VD, Manojlović DD, Babu RP, Senthamaraikannan R, Rojas O, Opsenica I, Nikodinović-Runić J. Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. International Journal of Biological Macromolecules. 2019;129:351-360
Jeremić Sanja, Đokić Lidija, Ajdačić Vladimir, Božinović Nina S., Pavlović Vladimir D., Manojlović Dragan D., Babu Ramesh P., Senthamaraikannan Ramsankar, Rojas Orlando, Opsenica Igor, Nikodinović-Runić Jasmina, "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions" 129 (2019):351-360,
https://doi.org/10.1016/j.ijbiomac.2019.01.154 .
8
7
10

Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions

Jeremić, Sanja; Đokić, Lidija; Ajdačić, Vladimir; Božinović, Nina S.; Pavlović, Vladimir D.; Manojlović, Dragan D.; Babu, Ramesh P.; Senthamaraikannan, Ramsankar; Rojas, Orlando; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Elsevier, 2019)

TY  - JOUR
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Ajdačić, Vladimir
AU  - Božinović, Nina S.
AU  - Pavlović, Vladimir D.
AU  - Manojlović, Dragan D.
AU  - Babu, Ramesh P.
AU  - Senthamaraikannan, Ramsankar
AU  - Rojas, Orlando
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2866
AB  - Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions
VL  - 129
SP  - 351
EP  - 360
DO  - 10.1016/j.ijbiomac.2019.01.154
ER  - 
@article{
author = "Jeremić, Sanja and Đokić, Lidija and Ajdačić, Vladimir and Božinović, Nina S. and Pavlović, Vladimir D. and Manojlović, Dragan D. and Babu, Ramesh P. and Senthamaraikannan, Ramsankar and Rojas, Orlando and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2866",
abstract = "Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions",
volume = "129",
pages = "351-360",
doi = "10.1016/j.ijbiomac.2019.01.154"
}
Jeremić, S., Đokić, L., Ajdačić, V., Božinović, N. S., Pavlović, V. D., Manojlović, D. D., Babu, R. P., Senthamaraikannan, R., Rojas, O., Opsenica, I.,& Nikodinović-Runić, J. (2019). Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions.
International Journal of Biological MacromoleculesElsevier., 129, 351-360.
https://doi.org/10.1016/j.ijbiomac.2019.01.154
Jeremić S, Đokić L, Ajdačić V, Božinović NS, Pavlović VD, Manojlović DD, Babu RP, Senthamaraikannan R, Rojas O, Opsenica I, Nikodinović-Runić J. Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. International Journal of Biological Macromolecules. 2019;129:351-360
Jeremić Sanja, Đokić Lidija, Ajdačić Vladimir, Božinović Nina S., Pavlović Vladimir D., Manojlović Dragan D., Babu Ramesh P., Senthamaraikannan Ramsankar, Rojas Orlando, Opsenica Igor, Nikodinović-Runić Jasmina, "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions" 129 (2019):351-360,
https://doi.org/10.1016/j.ijbiomac.2019.01.154 .
8
7
10

Supplementary data for the article: Ajdačić, V.; Nikolić, A.; Simić, S.; Manojlović, D.; Stojanović, Z.; Nikodinovic-Runic, J.; Opsenica, I. M. Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst. Synthesis (Germany) 2018, 50 (1), 119–126. https://doi.org/10.1055/s-0036-1590892

Ajdačić, Vladimir; Nikolić, Andrea; Simić, Stefan; Manojlović, Dragan D.; Stojanović, Zoran; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Georg Thieme Verlag Kg, Stuttgart, 2018)

TY  - BOOK
AU  - Ajdačić, Vladimir
AU  - Nikolić, Andrea
AU  - Simić, Stefan
AU  - Manojlović, Dragan D.
AU  - Stojanović, Zoran
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2995
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis, Stuttgart
T1  - Supplementary data for the article:
Ajdačić, V.; Nikolić, A.; Simić, S.; Manojlović, D.; Stojanović, Z.; Nikodinovic-Runic, J.; Opsenica, I. M. Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst. Synthesis (Germany) 2018, 50 (1), 119–126. https://doi.org/10.1055/s-0036-1590892
ER  - 
@book{
author = "Ajdačić, Vladimir and Nikolić, Andrea and Simić, Stefan and Manojlović, Dragan D. and Stojanović, Zoran and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2995",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis, Stuttgart",
title = "Supplementary data for the article:
Ajdačić, V.; Nikolić, A.; Simić, S.; Manojlović, D.; Stojanović, Z.; Nikodinovic-Runic, J.; Opsenica, I. M. Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst. Synthesis (Germany) 2018, 50 (1), 119–126. https://doi.org/10.1055/s-0036-1590892"
}
Ajdačić, V., Nikolić, A., Simić, S., Manojlović, D. D., Stojanović, Z., Nikodinović-Runić, J.,& Opsenica, I. (2018). Supplementary data for the article:
Ajdačić, V.; Nikolić, A.; Simić, S.; Manojlović, D.; Stojanović, Z.; Nikodinovic-Runic, J.; Opsenica, I. M. Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst. Synthesis (Germany) 2018, 50 (1), 119–126. https://doi.org/10.1055/s-0036-1590892.
Synthesis, StuttgartGeorg Thieme Verlag Kg, Stuttgart..
Ajdačić V, Nikolić A, Simić S, Manojlović DD, Stojanović Z, Nikodinović-Runić J, Opsenica I. Supplementary data for the article:
Ajdačić, V.; Nikolić, A.; Simić, S.; Manojlović, D.; Stojanović, Z.; Nikodinovic-Runic, J.; Opsenica, I. M. Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst. Synthesis (Germany) 2018, 50 (1), 119–126. https://doi.org/10.1055/s-0036-1590892. Synthesis, Stuttgart. 2018;
Ajdačić Vladimir, Nikolić Andrea, Simić Stefan, Manojlović Dragan D., Stojanović Zoran, Nikodinović-Runić Jasmina, Opsenica Igor, "Supplementary data for the article:
Ajdačić, V.; Nikolić, A.; Simić, S.; Manojlović, D.; Stojanović, Z.; Nikodinovic-Runic, J.; Opsenica, I. M. Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst. Synthesis (Germany) 2018, 50 (1), 119–126. https://doi.org/10.1055/s-0036-1590892" (2018)

Supplementary material for the article: Lazić, J.; Ajdačić, V.; Vojnovic, S.; Zlatović, M.; Pekmezovic, M.; Mogavero, S.; Opsenica, I.; Nikodinovic-Runic, J. Bis-Guanylhydrazones as Efficient Anti-Candida Compounds through DNA Interaction. Appl Microbiol Biotechnol 2018, 102 (4), 1889–1901. https://doi.org/10.1007/s00253-018-8749-3

Lazić, Jelena O.; Ajdačić, Vladimir; Vojnović, Sandra; Zlatović, Mario; Pekmezović, Marina; Mogavero, Selene; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Springer, New York, 2018)

TY  - BOOK
AU  - Lazić, Jelena O.
AU  - Ajdačić, Vladimir
AU  - Vojnović, Sandra
AU  - Zlatović, Mario
AU  - Pekmezović, Marina
AU  - Mogavero, Selene
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3176
PB  - Springer, New York
T2  - Applied Microbiology and Biotechnology
T1  - Supplementary material for the article: Lazić, J.; Ajdačić, V.; Vojnovic, S.; Zlatović, M.; Pekmezovic, M.; Mogavero, S.; Opsenica,  I.; Nikodinovic-Runic, J. Bis-Guanylhydrazones as Efficient Anti-Candida Compounds  through DNA Interaction. Appl Microbiol Biotechnol 2018, 102 (4), 1889–1901.  https://doi.org/10.1007/s00253-018-8749-3
ER  - 
@book{
author = "Lazić, Jelena O. and Ajdačić, Vladimir and Vojnović, Sandra and Zlatović, Mario and Pekmezović, Marina and Mogavero, Selene and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3176",
publisher = "Springer, New York",
journal = "Applied Microbiology and Biotechnology",
title = "Supplementary material for the article: Lazić, J.; Ajdačić, V.; Vojnovic, S.; Zlatović, M.; Pekmezovic, M.; Mogavero, S.; Opsenica,  I.; Nikodinovic-Runic, J. Bis-Guanylhydrazones as Efficient Anti-Candida Compounds  through DNA Interaction. Appl Microbiol Biotechnol 2018, 102 (4), 1889–1901.  https://doi.org/10.1007/s00253-018-8749-3"
}
Lazić, J. O., Ajdačić, V., Vojnović, S., Zlatović, M., Pekmezović, M., Mogavero, S., Opsenica, I.,& Nikodinović-Runić, J. (2018). Supplementary material for the article: Lazić, J.; Ajdačić, V.; Vojnovic, S.; Zlatović, M.; Pekmezovic, M.; Mogavero, S.; Opsenica,  I.; Nikodinovic-Runic, J. Bis-Guanylhydrazones as Efficient Anti-Candida Compounds  through DNA Interaction. Appl Microbiol Biotechnol 2018, 102 (4), 1889–1901.  https://doi.org/10.1007/s00253-018-8749-3.
Applied Microbiology and BiotechnologySpringer, New York..
Lazić JO, Ajdačić V, Vojnović S, Zlatović M, Pekmezović M, Mogavero S, Opsenica I, Nikodinović-Runić J. Supplementary material for the article: Lazić, J.; Ajdačić, V.; Vojnovic, S.; Zlatović, M.; Pekmezovic, M.; Mogavero, S.; Opsenica,  I.; Nikodinovic-Runic, J. Bis-Guanylhydrazones as Efficient Anti-Candida Compounds  through DNA Interaction. Appl Microbiol Biotechnol 2018, 102 (4), 1889–1901.  https://doi.org/10.1007/s00253-018-8749-3. Applied Microbiology and Biotechnology. 2018;
Lazić Jelena O., Ajdačić Vladimir, Vojnović Sandra, Zlatović Mario, Pekmezović Marina, Mogavero Selene, Opsenica Igor, Nikodinović-Runić Jasmina, "Supplementary material for the article: Lazić, J.; Ajdačić, V.; Vojnovic, S.; Zlatović, M.; Pekmezovic, M.; Mogavero, S.; Opsenica,  I.; Nikodinovic-Runic, J. Bis-Guanylhydrazones as Efficient Anti-Candida Compounds  through DNA Interaction. Appl Microbiol Biotechnol 2018, 102 (4), 1889–1901.  https://doi.org/10.1007/s00253-018-8749-3" (2018)

Supplementary material for the article: Ajdačić, V.; Nikolić, A.; Kerner, M.; Wipf, P.; Opsenica, I. M. Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes. Synlett 2018, 29 (13), 1781–1785. https://doi.org/10.1055/s-0037-1610433

Ajdačić, Vladimir; Nikolić, Andrea; Kerner, Michael; Wipf, Peter; Opsenica, Igor

(Georg Thieme Verlag Kg, Stuttgart, 2018)

TY  - BOOK
AU  - Ajdačić, Vladimir
AU  - Nikolić, Andrea
AU  - Kerner, Michael
AU  - Wipf, Peter
AU  - Opsenica, Igor
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3252
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synlett
T1  - Supplementary material for the article: Ajdačić, V.; Nikolić, A.; Kerner, M.; Wipf, P.; Opsenica, I. M. Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes. Synlett 2018, 29 (13), 1781–1785. https://doi.org/10.1055/s-0037-1610433
ER  - 
@book{
author = "Ajdačić, Vladimir and Nikolić, Andrea and Kerner, Michael and Wipf, Peter and Opsenica, Igor",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3252",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synlett",
title = "Supplementary material for the article: Ajdačić, V.; Nikolić, A.; Kerner, M.; Wipf, P.; Opsenica, I. M. Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes. Synlett 2018, 29 (13), 1781–1785. https://doi.org/10.1055/s-0037-1610433"
}
Ajdačić, V., Nikolić, A., Kerner, M., Wipf, P.,& Opsenica, I. (2018). Supplementary material for the article: Ajdačić, V.; Nikolić, A.; Kerner, M.; Wipf, P.; Opsenica, I. M. Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes. Synlett 2018, 29 (13), 1781–1785. https://doi.org/10.1055/s-0037-1610433.
SynlettGeorg Thieme Verlag Kg, Stuttgart..
Ajdačić V, Nikolić A, Kerner M, Wipf P, Opsenica I. Supplementary material for the article: Ajdačić, V.; Nikolić, A.; Kerner, M.; Wipf, P.; Opsenica, I. M. Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes. Synlett 2018, 29 (13), 1781–1785. https://doi.org/10.1055/s-0037-1610433. Synlett. 2018;
Ajdačić Vladimir, Nikolić Andrea, Kerner Michael, Wipf Peter, Opsenica Igor, "Supplementary material for the article: Ajdačić, V.; Nikolić, A.; Kerner, M.; Wipf, P.; Opsenica, I. M. Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes. Synlett 2018, 29 (13), 1781–1785. https://doi.org/10.1055/s-0037-1610433" (2018)

Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes

Ajdačić, Vladimir; Nikolić, Andrea; Kerner, Michael; Wipf, Peter; Opsenica, Igor

(Georg Thieme Verlag Kg, Stuttgart, 2018)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Nikolić, Andrea
AU  - Kerner, Michael
AU  - Wipf, Peter
AU  - Opsenica, Igor
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2192
AB  - An improved method for the decarbonylation of aliphatic aldehydes by using a commercially available Pd/C catalyst is described. The reaction conditions are suitable for linear, cyclic, or sterically demanding substrates, as they afford the corresponding alkanes in yields of up to 99%. In addition, this Pd/C-catalyzed method exhibits good functional-group tolerance. A comparison of previously reported methods with the present one showed that the reaction conditions play a crucial role in the outcome of the reaction. The method can also be applied in a two-step reaction sequence for the synthesis of industrially important compounds.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synlett
T1  - Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes
VL  - 29
IS  - 13
SP  - 1781
EP  - 1785
DO  - 10.1055/s-0037-1610433
ER  - 
@article{
author = "Ajdačić, Vladimir and Nikolić, Andrea and Kerner, Michael and Wipf, Peter and Opsenica, Igor",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2192",
abstract = "An improved method for the decarbonylation of aliphatic aldehydes by using a commercially available Pd/C catalyst is described. The reaction conditions are suitable for linear, cyclic, or sterically demanding substrates, as they afford the corresponding alkanes in yields of up to 99%. In addition, this Pd/C-catalyzed method exhibits good functional-group tolerance. A comparison of previously reported methods with the present one showed that the reaction conditions play a crucial role in the outcome of the reaction. The method can also be applied in a two-step reaction sequence for the synthesis of industrially important compounds.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synlett",
title = "Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes",
volume = "29",
number = "13",
pages = "1781-1785",
doi = "10.1055/s-0037-1610433"
}
Ajdačić, V., Nikolić, A., Kerner, M., Wipf, P.,& Opsenica, I. (2018). Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes.
SynlettGeorg Thieme Verlag Kg, Stuttgart., 29(13), 1781-1785.
https://doi.org/10.1055/s-0037-1610433
Ajdačić V, Nikolić A, Kerner M, Wipf P, Opsenica I. Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes. Synlett. 2018;29(13):1781-1785
Ajdačić Vladimir, Nikolić Andrea, Kerner Michael, Wipf Peter, Opsenica Igor, "Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes" 29, no. 13 (2018):1781-1785,
https://doi.org/10.1055/s-0037-1610433 .
1
3
2
2

Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst

Ajdačić, Vladimir; Nikolić, Andrea; Simić, Stefan; Manojlović, Dragan D.; Stojanović, Zoran; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Georg Thieme Verlag Kg, Stuttgart, 2018)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Nikolić, Andrea
AU  - Simić, Stefan
AU  - Manojlović, Dragan D.
AU  - Stojanović, Zoran
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2569
AB  - A facile decarbonylation reaction of a variety of aromatic and heteroaromatic aldehydes using maghemite-supported palladium catalyst has been developed. The magnetic properties of catalyst facilitated an easy and efficient recovery of the catalyst from the reaction mixture using an external magnet. It was found that the catalyst could be reused up to four consecutive catalytic runs without a significant change in activity. In addition, the catalyst was also very effective in the dehalogenation of aryl halides. This is the first report on efficient utilization of directly immobilized Pd on maghemite in decarbonylation and dehalogenation reactions.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis, Stuttgart
T1  - Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst
VL  - 50
IS  - 1
SP  - 119
EP  - 126
DO  - 10.1055/s-0036-1590892
ER  - 
@article{
author = "Ajdačić, Vladimir and Nikolić, Andrea and Simić, Stefan and Manojlović, Dragan D. and Stojanović, Zoran and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2569",
abstract = "A facile decarbonylation reaction of a variety of aromatic and heteroaromatic aldehydes using maghemite-supported palladium catalyst has been developed. The magnetic properties of catalyst facilitated an easy and efficient recovery of the catalyst from the reaction mixture using an external magnet. It was found that the catalyst could be reused up to four consecutive catalytic runs without a significant change in activity. In addition, the catalyst was also very effective in the dehalogenation of aryl halides. This is the first report on efficient utilization of directly immobilized Pd on maghemite in decarbonylation and dehalogenation reactions.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis, Stuttgart",
title = "Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst",
volume = "50",
number = "1",
pages = "119-126",
doi = "10.1055/s-0036-1590892"
}
Ajdačić, V., Nikolić, A., Simić, S., Manojlović, D. D., Stojanović, Z., Nikodinović-Runić, J.,& Opsenica, I. (2018). Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst.
Synthesis, StuttgartGeorg Thieme Verlag Kg, Stuttgart., 50(1), 119-126.
https://doi.org/10.1055/s-0036-1590892
Ajdačić V, Nikolić A, Simić S, Manojlović DD, Stojanović Z, Nikodinović-Runić J, Opsenica I. Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst. Synthesis, Stuttgart. 2018;50(1):119-126
Ajdačić Vladimir, Nikolić Andrea, Simić Stefan, Manojlović Dragan D., Stojanović Zoran, Nikodinović-Runić Jasmina, Opsenica Igor, "Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst" 50, no. 1 (2018):119-126,
https://doi.org/10.1055/s-0036-1590892 .
4
5
6

Bis-guanylhydrazones as efficient anti-Candida compounds through DNA interaction

Lazić, Jelena O.; Ajdačić, Vladimir; Vojnović, Sandra; Zlatović, Mario; Pekmezović, Marina; Mogavero, Selene; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Springer, New York, 2018)

TY  - JOUR
AU  - Lazić, Jelena O.
AU  - Ajdačić, Vladimir
AU  - Vojnović, Sandra
AU  - Zlatović, Mario
AU  - Pekmezović, Marina
AU  - Mogavero, Selene
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2078
AB  - Candida spp. are leading causes of opportunistic mycoses, including life-threatening hospital-borne infections, and novel antifungals, preferably aiming targets that have not been used before, are constantly needed. Hydrazone-and guanidinecontaining molecules have shown a wide range of biological activities, including recently described excellent antifungal properties. In this study, four bis-guanylhydrazone derivatives (BG1-4) were generated following a previously developed synthetic route. Anti-Candida (two C. albicans, C. glabrata, and C. parapsilosis) minimal inhibitory concentrations (MICs) of bisguanylhydrazones were between 2 and 15.6 mu g/mL. They were also effective against preformed 48-h-old C. albicans biofilms. In vitroDNA interaction, circular dichroism, and molecular docking analysis showed the great ability of these compounds to bind fungal DNA. Competition with DNA-binding stain, exposure of phosphatidylserine at the outer layer of the cytoplasmic membrane, and activation of metacaspases were shown for BG3. This pro-apoptotic effect of BG3 was only partially due to the accumulation of reactive oxygen species in C. albicans, as only twofold MIC and higher concentrations of BG3 caused depolarization of mitochondrial membrane which was accompanied by the decrease of the activity of fungal mitochondrial dehydrogenases, while the activity of oxidative stress response enzymes glutathione reductase and catalase was not significantly affected. BG3 showed synergistic activity with amphotericin B with a fractional inhibitory concentration index of 0.5. It also exerted low cytotoxicity and the ability to inhibit epithelial cell (TR146) invasion and damage by virulent C. albicans SC5314. With further developments, BG3 may further progress in the antifungal pipeline as a DNA-targeting agent.
PB  - Springer, New York
T2  - Applied Microbiology and Biotechnology
T1  - Bis-guanylhydrazones as efficient anti-Candida compounds through DNA interaction
VL  - 102
IS  - 4
SP  - 1889
EP  - 1901
DO  - 10.1007/s00253-018-8749-3
ER  - 
@article{
author = "Lazić, Jelena O. and Ajdačić, Vladimir and Vojnović, Sandra and Zlatović, Mario and Pekmezović, Marina and Mogavero, Selene and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2078",
abstract = "Candida spp. are leading causes of opportunistic mycoses, including life-threatening hospital-borne infections, and novel antifungals, preferably aiming targets that have not been used before, are constantly needed. Hydrazone-and guanidinecontaining molecules have shown a wide range of biological activities, including recently described excellent antifungal properties. In this study, four bis-guanylhydrazone derivatives (BG1-4) were generated following a previously developed synthetic route. Anti-Candida (two C. albicans, C. glabrata, and C. parapsilosis) minimal inhibitory concentrations (MICs) of bisguanylhydrazones were between 2 and 15.6 mu g/mL. They were also effective against preformed 48-h-old C. albicans biofilms. In vitroDNA interaction, circular dichroism, and molecular docking analysis showed the great ability of these compounds to bind fungal DNA. Competition with DNA-binding stain, exposure of phosphatidylserine at the outer layer of the cytoplasmic membrane, and activation of metacaspases were shown for BG3. This pro-apoptotic effect of BG3 was only partially due to the accumulation of reactive oxygen species in C. albicans, as only twofold MIC and higher concentrations of BG3 caused depolarization of mitochondrial membrane which was accompanied by the decrease of the activity of fungal mitochondrial dehydrogenases, while the activity of oxidative stress response enzymes glutathione reductase and catalase was not significantly affected. BG3 showed synergistic activity with amphotericin B with a fractional inhibitory concentration index of 0.5. It also exerted low cytotoxicity and the ability to inhibit epithelial cell (TR146) invasion and damage by virulent C. albicans SC5314. With further developments, BG3 may further progress in the antifungal pipeline as a DNA-targeting agent.",
publisher = "Springer, New York",
journal = "Applied Microbiology and Biotechnology",
title = "Bis-guanylhydrazones as efficient anti-Candida compounds through DNA interaction",
volume = "102",
number = "4",
pages = "1889-1901",
doi = "10.1007/s00253-018-8749-3"
}
Lazić, J. O., Ajdačić, V., Vojnović, S., Zlatović, M., Pekmezović, M., Mogavero, S., Opsenica, I.,& Nikodinović-Runić, J. (2018). Bis-guanylhydrazones as efficient anti-Candida compounds through DNA interaction.
Applied Microbiology and BiotechnologySpringer, New York., 102(4), 1889-1901.
https://doi.org/10.1007/s00253-018-8749-3
Lazić JO, Ajdačić V, Vojnović S, Zlatović M, Pekmezović M, Mogavero S, Opsenica I, Nikodinović-Runić J. Bis-guanylhydrazones as efficient anti-Candida compounds through DNA interaction. Applied Microbiology and Biotechnology. 2018;102(4):1889-1901
Lazić Jelena O., Ajdačić Vladimir, Vojnović Sandra, Zlatović Mario, Pekmezović Marina, Mogavero Selene, Opsenica Igor, Nikodinović-Runić Jasmina, "Bis-guanylhydrazones as efficient anti-Candida compounds through DNA interaction" 102, no. 4 (2018):1889-1901,
https://doi.org/10.1007/s00253-018-8749-3 .
1
6
6
7

Antibacterial and antifungal properties of guanylhydrazones

Ajdačić, Vladimir; Lazić, Jelena O.; Mojicevic, Marija; Šegan, Sandra B.; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Serbian Chemical Soc, Belgrade, 2017)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Lazić, Jelena O.
AU  - Mojicevic, Marija
AU  - Šegan, Sandra B.
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2508
AB  - A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Antibacterial and antifungal properties of guanylhydrazones
VL  - 82
IS  - 6
SP  - 641
EP  - 649
DO  - 10.2298/JSC170213033A
ER  - 
@article{
author = "Ajdačić, Vladimir and Lazić, Jelena O. and Mojicevic, Marija and Šegan, Sandra B. and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2508",
abstract = "A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Antibacterial and antifungal properties of guanylhydrazones",
volume = "82",
number = "6",
pages = "641-649",
doi = "10.2298/JSC170213033A"
}
Ajdačić, V., Lazić, J. O., Mojicevic, M., Šegan, S. B., Nikodinović-Runić, J.,& Opsenica, I. (2017). Antibacterial and antifungal properties of guanylhydrazones.
Journal of the Serbian Chemical SocietySerbian Chemical Soc, Belgrade., 82(6), 641-649.
https://doi.org/10.2298/JSC170213033A
Ajdačić V, Lazić JO, Mojicevic M, Šegan SB, Nikodinović-Runić J, Opsenica I. Antibacterial and antifungal properties of guanylhydrazones. Journal of the Serbian Chemical Society. 2017;82(6):641-649
Ajdačić Vladimir, Lazić Jelena O., Mojicevic Marija, Šegan Sandra B., Nikodinović-Runić Jasmina, Opsenica Igor, "Antibacterial and antifungal properties of guanylhydrazones" 82, no. 6 (2017):641-649,
https://doi.org/10.2298/JSC170213033A .
3
3
3

Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates

Ajdačić, Vladimir; Šenerović, Lidija; Vranić, Marija; Pekmezović, Marina; Arsić-Arsnijević, Valentina; Veselinović, Aleksandar; Veselinović, Jovana; Šolaja, Bogdan A.; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Pergamon-Elsevier Science Ltd, Oxford, 2016)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Šenerović, Lidija
AU  - Vranić, Marija
AU  - Pekmezović, Marina
AU  - Arsić-Arsnijević, Valentina
AU  - Veselinović, Aleksandar
AU  - Veselinović, Jovana
AU  - Šolaja, Bogdan A.
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3627
AB  - A series of new thiophene-based guanylhydrazones (iminoguanidines) were synthesized in high yields using a straightforward two-step procedure. The antifungal activity of compounds was evaluated against a wide range of medicaly important fungal strains including yeasts, molds, and dermatophytes in comparison to clinically used drug voriconazole. Cytotoxic properties of compounds were also determined using human lung fibroblast cell line and hemolysis assay. All guanylhydrazones showed significant activity against broad spectrum of clinically important species of Candida spp., Aspergillus fumigatus, Fusarium oxysporum, Microsporum canis and Trichophyton mentagrophytes, which was in some cases comparable or better than activity of voriconazole. More importantly, compounds 10, 11, 13, 14, 18 and 21 exhibited excellent activity against voriconazole-resistant Candida albicans CA5 with very low minimal inhibitory concentration (MIC) values  lt 2 mu g mL(-1). Derivative 14, bearing bromine on the phenyl ring, was the most effective compound with MICs ranging from 0.25 to 6.25 g mL(-1). However, bis-guanylhydrazone 18 showed better selectivity in terms of therapeutic index values. In vivo embryotoxicity on zebrafish (Danio rerio) showed improved toxicity profile of 11, 14 and 18 in comparison to that of voriconazole. Most guanylhydrazones also inhibited C albicans yeast to hyphal transition, essential for its biofilm formation, while 11 and 18 were able to disperse preformed Candida biofilms. All guanylhydrazones showed the equal potential to interact with genomic DNA of C albicans in vitro, thus indicating a possible mechanism of their action, as well as possible mechanism of observed cytotoxic effects. Tested compounds did not have significant hemolytic effect and caused low liposome leakage, which excluded the cell membrane as a primary target. On the basis of computational docking experiments using both human and cytochrome P450 from Candida it was concluded that the most active guanylhydrazones had minimal structural prerequisites to interact with the cytochrome P450 14a-demethylase (CYP51). Promising guanylhydrazone derivatives also showed satisfactory pharmacokinetic profile based on molecular calculations. (C) 2016 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry
T1  - Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates
VL  - 24
IS  - 6
SP  - 1277
EP  - 1291
DO  - 10.1016/j.bmc.2016.01.058
ER  - 
@article{
author = "Ajdačić, Vladimir and Šenerović, Lidija and Vranić, Marija and Pekmezović, Marina and Arsić-Arsnijević, Valentina and Veselinović, Aleksandar and Veselinović, Jovana and Šolaja, Bogdan A. and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3627",
abstract = "A series of new thiophene-based guanylhydrazones (iminoguanidines) were synthesized in high yields using a straightforward two-step procedure. The antifungal activity of compounds was evaluated against a wide range of medicaly important fungal strains including yeasts, molds, and dermatophytes in comparison to clinically used drug voriconazole. Cytotoxic properties of compounds were also determined using human lung fibroblast cell line and hemolysis assay. All guanylhydrazones showed significant activity against broad spectrum of clinically important species of Candida spp., Aspergillus fumigatus, Fusarium oxysporum, Microsporum canis and Trichophyton mentagrophytes, which was in some cases comparable or better than activity of voriconazole. More importantly, compounds 10, 11, 13, 14, 18 and 21 exhibited excellent activity against voriconazole-resistant Candida albicans CA5 with very low minimal inhibitory concentration (MIC) values  lt 2 mu g mL(-1). Derivative 14, bearing bromine on the phenyl ring, was the most effective compound with MICs ranging from 0.25 to 6.25 g mL(-1). However, bis-guanylhydrazone 18 showed better selectivity in terms of therapeutic index values. In vivo embryotoxicity on zebrafish (Danio rerio) showed improved toxicity profile of 11, 14 and 18 in comparison to that of voriconazole. Most guanylhydrazones also inhibited C albicans yeast to hyphal transition, essential for its biofilm formation, while 11 and 18 were able to disperse preformed Candida biofilms. All guanylhydrazones showed the equal potential to interact with genomic DNA of C albicans in vitro, thus indicating a possible mechanism of their action, as well as possible mechanism of observed cytotoxic effects. Tested compounds did not have significant hemolytic effect and caused low liposome leakage, which excluded the cell membrane as a primary target. On the basis of computational docking experiments using both human and cytochrome P450 from Candida it was concluded that the most active guanylhydrazones had minimal structural prerequisites to interact with the cytochrome P450 14a-demethylase (CYP51). Promising guanylhydrazone derivatives also showed satisfactory pharmacokinetic profile based on molecular calculations. (C) 2016 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry",
title = "Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates",
volume = "24",
number = "6",
pages = "1277-1291",
doi = "10.1016/j.bmc.2016.01.058"
}
Ajdačić, V., Šenerović, L., Vranić, M., Pekmezović, M., Arsić-Arsnijević, V., Veselinović, A., Veselinović, J., Šolaja, B. A., Nikodinović-Runić, J.,& Opsenica, I. (2016). Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates.
Bioorganic and Medicinal ChemistryPergamon-Elsevier Science Ltd, Oxford., 24(6), 1277-1291.
https://doi.org/10.1016/j.bmc.2016.01.058
Ajdačić V, Šenerović L, Vranić M, Pekmezović M, Arsić-Arsnijević V, Veselinović A, Veselinović J, Šolaja BA, Nikodinović-Runić J, Opsenica I. Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates. Bioorganic and Medicinal Chemistry. 2016;24(6):1277-1291
Ajdačić Vladimir, Šenerović Lidija, Vranić Marija, Pekmezović Marina, Arsić-Arsnijević Valentina, Veselinović Aleksandar, Veselinović Jovana, Šolaja Bogdan A., Nikodinović-Runić Jasmina, Opsenica Igor, "Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates" 24, no. 6 (2016):1277-1291,
https://doi.org/10.1016/j.bmc.2016.01.058 .
1
19
24
25

Supplementary data for the article: Ajdačić, V.; Senerovic, L.; Vranić, M.; Pekmezovic, M.; Arsic-Arsnijevic, V.; Veselinovic, A.; Veselinovic, J.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Evaluation of Thiophene-Based Guanylhydrazones (Iminoguanidines) Efficient against Panel of Voriconazole-Resistant Fungal Isolates. Bioorganic and Medicinal Chemistry 2016, 24 (6), 1277–1291. https://doi.org/10.1016/j.bmc.2016.01.058

Ajdačić, Vladimir; Šenerović, Lidija; Vranić, Marija; Pekmezović, Marina; Arsić-Arsnijević, Valentina; Veselinović, Aleksandar; Veselinović, Jovana; Šolaja, Bogdan A.; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Pergamon-Elsevier Science Ltd, Oxford, 2016)

TY  - BOOK
AU  - Ajdačić, Vladimir
AU  - Šenerović, Lidija
AU  - Vranić, Marija
AU  - Pekmezović, Marina
AU  - Arsić-Arsnijević, Valentina
AU  - Veselinović, Aleksandar
AU  - Veselinović, Jovana
AU  - Šolaja, Bogdan A.
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3628
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry
T1  - Supplementary data for the article: Ajdačić, V.; Senerovic, L.; Vranić, M.; Pekmezovic, M.; Arsic-Arsnijevic, V.; Veselinovic, A.; Veselinovic, J.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Evaluation of Thiophene-Based Guanylhydrazones (Iminoguanidines) Efficient against Panel of Voriconazole-Resistant Fungal Isolates. Bioorganic and Medicinal Chemistry 2016, 24 (6), 1277–1291. https://doi.org/10.1016/j.bmc.2016.01.058
ER  - 
@book{
author = "Ajdačić, Vladimir and Šenerović, Lidija and Vranić, Marija and Pekmezović, Marina and Arsić-Arsnijević, Valentina and Veselinović, Aleksandar and Veselinović, Jovana and Šolaja, Bogdan A. and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3628",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry",
title = "Supplementary data for the article: Ajdačić, V.; Senerovic, L.; Vranić, M.; Pekmezovic, M.; Arsic-Arsnijevic, V.; Veselinovic, A.; Veselinovic, J.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Evaluation of Thiophene-Based Guanylhydrazones (Iminoguanidines) Efficient against Panel of Voriconazole-Resistant Fungal Isolates. Bioorganic and Medicinal Chemistry 2016, 24 (6), 1277–1291. https://doi.org/10.1016/j.bmc.2016.01.058"
}
Ajdačić, V., Šenerović, L., Vranić, M., Pekmezović, M., Arsić-Arsnijević, V., Veselinović, A., Veselinović, J., Šolaja, B. A., Nikodinović-Runić, J.,& Opsenica, I. (2016). Supplementary data for the article: Ajdačić, V.; Senerovic, L.; Vranić, M.; Pekmezovic, M.; Arsic-Arsnijevic, V.; Veselinovic, A.; Veselinovic, J.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Evaluation of Thiophene-Based Guanylhydrazones (Iminoguanidines) Efficient against Panel of Voriconazole-Resistant Fungal Isolates. Bioorganic and Medicinal Chemistry 2016, 24 (6), 1277–1291. https://doi.org/10.1016/j.bmc.2016.01.058.
Bioorganic and Medicinal ChemistryPergamon-Elsevier Science Ltd, Oxford..
Ajdačić V, Šenerović L, Vranić M, Pekmezović M, Arsić-Arsnijević V, Veselinović A, Veselinović J, Šolaja BA, Nikodinović-Runić J, Opsenica I. Supplementary data for the article: Ajdačić, V.; Senerovic, L.; Vranić, M.; Pekmezovic, M.; Arsic-Arsnijevic, V.; Veselinovic, A.; Veselinovic, J.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Evaluation of Thiophene-Based Guanylhydrazones (Iminoguanidines) Efficient against Panel of Voriconazole-Resistant Fungal Isolates. Bioorganic and Medicinal Chemistry 2016, 24 (6), 1277–1291. https://doi.org/10.1016/j.bmc.2016.01.058. Bioorganic and Medicinal Chemistry. 2016;
Ajdačić Vladimir, Šenerović Lidija, Vranić Marija, Pekmezović Marina, Arsić-Arsnijević Valentina, Veselinović Aleksandar, Veselinović Jovana, Šolaja Bogdan A., Nikodinović-Runić Jasmina, Opsenica Igor, "Supplementary data for the article: Ajdačić, V.; Senerovic, L.; Vranić, M.; Pekmezovic, M.; Arsic-Arsnijevic, V.; Veselinovic, A.; Veselinovic, J.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Evaluation of Thiophene-Based Guanylhydrazones (Iminoguanidines) Efficient against Panel of Voriconazole-Resistant Fungal Isolates. Bioorganic and Medicinal Chemistry 2016, 24 (6), 1277–1291. https://doi.org/10.1016/j.bmc.2016.01.058" (2016)

Supplementary material for the article: Ajdačić, V.; Stepanović, S.; Zlatović, M.; Gruden, M.; Opsenica, I. M. Decarbonylative Dibromination of 5-Phenylthiophene-2-Carbaldehyde with Bromine. Synthesis (Germany) 2016, 48 (24), 4423–4430. https://doi.org/10.1055/s-0035-1562615

Ajdačić, Vladimir; Stepanović, Stepan; Zlatović, Mario; Gruden-Pavlović, Maja; Opsenica, Igor

(Georg Thieme Verlag Kg, Stuttgart, 2016)

TY  - BOOK
AU  - Ajdačić, Vladimir
AU  - Stepanović, Stepan
AU  - Zlatović, Mario
AU  - Gruden-Pavlović, Maja
AU  - Opsenica, Igor
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3435
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis, Stuttgart
T1  - Supplementary material for the article: Ajdačić, V.; Stepanović, S.; Zlatović, M.; Gruden, M.; Opsenica, I. M. Decarbonylative Dibromination of 5-Phenylthiophene-2-Carbaldehyde with Bromine. Synthesis (Germany) 2016, 48 (24), 4423–4430. https://doi.org/10.1055/s-0035-1562615
ER  - 
@book{
author = "Ajdačić, Vladimir and Stepanović, Stepan and Zlatović, Mario and Gruden-Pavlović, Maja and Opsenica, Igor",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3435",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis, Stuttgart",
title = "Supplementary material for the article: Ajdačić, V.; Stepanović, S.; Zlatović, M.; Gruden, M.; Opsenica, I. M. Decarbonylative Dibromination of 5-Phenylthiophene-2-Carbaldehyde with Bromine. Synthesis (Germany) 2016, 48 (24), 4423–4430. https://doi.org/10.1055/s-0035-1562615"
}
Ajdačić, V., Stepanović, S., Zlatović, M., Gruden-Pavlović, M.,& Opsenica, I. (2016). Supplementary material for the article: Ajdačić, V.; Stepanović, S.; Zlatović, M.; Gruden, M.; Opsenica, I. M. Decarbonylative Dibromination of 5-Phenylthiophene-2-Carbaldehyde with Bromine. Synthesis (Germany) 2016, 48 (24), 4423–4430. https://doi.org/10.1055/s-0035-1562615.
Synthesis, StuttgartGeorg Thieme Verlag Kg, Stuttgart..
Ajdačić V, Stepanović S, Zlatović M, Gruden-Pavlović M, Opsenica I. Supplementary material for the article: Ajdačić, V.; Stepanović, S.; Zlatović, M.; Gruden, M.; Opsenica, I. M. Decarbonylative Dibromination of 5-Phenylthiophene-2-Carbaldehyde with Bromine. Synthesis (Germany) 2016, 48 (24), 4423–4430. https://doi.org/10.1055/s-0035-1562615. Synthesis, Stuttgart. 2016;
Ajdačić Vladimir, Stepanović Stepan, Zlatović Mario, Gruden-Pavlović Maja, Opsenica Igor, "Supplementary material for the article: Ajdačić, V.; Stepanović, S.; Zlatović, M.; Gruden, M.; Opsenica, I. M. Decarbonylative Dibromination of 5-Phenylthiophene-2-Carbaldehyde with Bromine. Synthesis (Germany) 2016, 48 (24), 4423–4430. https://doi.org/10.1055/s-0035-1562615" (2016)

Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine

Ajdačić, Vladimir; Stepanović, Stepan; Zlatović, Mario; Gruden-Pavlović, Maja; Opsenica, Igor

(Georg Thieme Verlag Kg, Stuttgart, 2016)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Stepanović, Stepan
AU  - Zlatović, Mario
AU  - Gruden-Pavlović, Maja
AU  - Opsenica, Igor
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2361
AB  - The decarbonylative dibromination of 2-thiophenecarboxaldehyde derivatives with bromine under mild conditions is developed. The mechanism for the decarbonylation is investigated by experimental and instrumental techniques and is extended by a computational study. Alongside removal of the formyl group, this method enables functionalization of the starting compounds in a single reaction step, which can be further exploited for the synthesis of 2,5-diaryl-3-bromothiophenes and 2,3,5-triarylthiophenes.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis, Stuttgart
T1  - Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine
VL  - 48
IS  - 24
SP  - 4423
EP  - 4430
DO  - 10.1055/s-0035-1562615
ER  - 
@article{
author = "Ajdačić, Vladimir and Stepanović, Stepan and Zlatović, Mario and Gruden-Pavlović, Maja and Opsenica, Igor",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2361",
abstract = "The decarbonylative dibromination of 2-thiophenecarboxaldehyde derivatives with bromine under mild conditions is developed. The mechanism for the decarbonylation is investigated by experimental and instrumental techniques and is extended by a computational study. Alongside removal of the formyl group, this method enables functionalization of the starting compounds in a single reaction step, which can be further exploited for the synthesis of 2,5-diaryl-3-bromothiophenes and 2,3,5-triarylthiophenes.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis, Stuttgart",
title = "Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine",
volume = "48",
number = "24",
pages = "4423-4430",
doi = "10.1055/s-0035-1562615"
}
Ajdačić, V., Stepanović, S., Zlatović, M., Gruden-Pavlović, M.,& Opsenica, I. (2016). Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine.
Synthesis, StuttgartGeorg Thieme Verlag Kg, Stuttgart., 48(24), 4423-4430.
https://doi.org/10.1055/s-0035-1562615
Ajdačić V, Stepanović S, Zlatović M, Gruden-Pavlović M, Opsenica I. Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine. Synthesis, Stuttgart. 2016;48(24):4423-4430
Ajdačić Vladimir, Stepanović Stepan, Zlatović Mario, Gruden-Pavlović Maja, Opsenica Igor, "Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine" 48, no. 24 (2016):4423-4430,
https://doi.org/10.1055/s-0035-1562615 .
1
2
2

Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates

Ajdačić, Vladimir; Šenerović, Lidija; Vranić, Marija; Pekmezović, Marina; Arsić-Arsnijević, Valentina; Veselinović, Aleksandar; Veselinović, Jovana; Šolaja, Bogdan A.; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Pergamon-Elsevier Science Ltd, Oxford, 2016)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Šenerović, Lidija
AU  - Vranić, Marija
AU  - Pekmezović, Marina
AU  - Arsić-Arsnijević, Valentina
AU  - Veselinović, Aleksandar
AU  - Veselinović, Jovana
AU  - Šolaja, Bogdan A.
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2058
AB  - A series of new thiophene-based guanylhydrazones (iminoguanidines) were synthesized in high yields using a straightforward two-step procedure. The antifungal activity of compounds was evaluated against a wide range of medicaly important fungal strains including yeasts, molds, and dermatophytes in comparison to clinically used drug voriconazole. Cytotoxic properties of compounds were also determined using human lung fibroblast cell line and hemolysis assay. All guanylhydrazones showed significant activity against broad spectrum of clinically important species of Candida spp., Aspergillus fumigatus, Fusarium oxysporum, Microsporum canis and Trichophyton mentagrophytes, which was in some cases comparable or better than activity of voriconazole. More importantly, compounds 10, 11, 13, 14, 18 and 21 exhibited excellent activity against voriconazole-resistant Candida albicans CA5 with very low minimal inhibitory concentration (MIC) values  lt 2 mu g mL(-1). Derivative 14, bearing bromine on the phenyl ring, was the most effective compound with MICs ranging from 0.25 to 6.25 g mL(-1). However, bis-guanylhydrazone 18 showed better selectivity in terms of therapeutic index values. In vivo embryotoxicity on zebrafish (Danio rerio) showed improved toxicity profile of 11, 14 and 18 in comparison to that of voriconazole. Most guanylhydrazones also inhibited C albicans yeast to hyphal transition, essential for its biofilm formation, while 11 and 18 were able to disperse preformed Candida biofilms. All guanylhydrazones showed the equal potential to interact with genomic DNA of C albicans in vitro, thus indicating a possible mechanism of their action, as well as possible mechanism of observed cytotoxic effects. Tested compounds did not have significant hemolytic effect and caused low liposome leakage, which excluded the cell membrane as a primary target. On the basis of computational docking experiments using both human and cytochrome P450 from Candida it was concluded that the most active guanylhydrazones had minimal structural prerequisites to interact with the cytochrome P450 14a-demethylase (CYP51). Promising guanylhydrazone derivatives also showed satisfactory pharmacokinetic profile based on molecular calculations. (C) 2016 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry
T1  - Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates
VL  - 24
IS  - 6
SP  - 1277
EP  - 1291
DO  - 10.1016/j.bmc.2016.01.058
ER  - 
@article{
author = "Ajdačić, Vladimir and Šenerović, Lidija and Vranić, Marija and Pekmezović, Marina and Arsić-Arsnijević, Valentina and Veselinović, Aleksandar and Veselinović, Jovana and Šolaja, Bogdan A. and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2058",
abstract = "A series of new thiophene-based guanylhydrazones (iminoguanidines) were synthesized in high yields using a straightforward two-step procedure. The antifungal activity of compounds was evaluated against a wide range of medicaly important fungal strains including yeasts, molds, and dermatophytes in comparison to clinically used drug voriconazole. Cytotoxic properties of compounds were also determined using human lung fibroblast cell line and hemolysis assay. All guanylhydrazones showed significant activity against broad spectrum of clinically important species of Candida spp., Aspergillus fumigatus, Fusarium oxysporum, Microsporum canis and Trichophyton mentagrophytes, which was in some cases comparable or better than activity of voriconazole. More importantly, compounds 10, 11, 13, 14, 18 and 21 exhibited excellent activity against voriconazole-resistant Candida albicans CA5 with very low minimal inhibitory concentration (MIC) values  lt 2 mu g mL(-1). Derivative 14, bearing bromine on the phenyl ring, was the most effective compound with MICs ranging from 0.25 to 6.25 g mL(-1). However, bis-guanylhydrazone 18 showed better selectivity in terms of therapeutic index values. In vivo embryotoxicity on zebrafish (Danio rerio) showed improved toxicity profile of 11, 14 and 18 in comparison to that of voriconazole. Most guanylhydrazones also inhibited C albicans yeast to hyphal transition, essential for its biofilm formation, while 11 and 18 were able to disperse preformed Candida biofilms. All guanylhydrazones showed the equal potential to interact with genomic DNA of C albicans in vitro, thus indicating a possible mechanism of their action, as well as possible mechanism of observed cytotoxic effects. Tested compounds did not have significant hemolytic effect and caused low liposome leakage, which excluded the cell membrane as a primary target. On the basis of computational docking experiments using both human and cytochrome P450 from Candida it was concluded that the most active guanylhydrazones had minimal structural prerequisites to interact with the cytochrome P450 14a-demethylase (CYP51). Promising guanylhydrazone derivatives also showed satisfactory pharmacokinetic profile based on molecular calculations. (C) 2016 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry",
title = "Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates",
volume = "24",
number = "6",
pages = "1277-1291",
doi = "10.1016/j.bmc.2016.01.058"
}
Ajdačić, V., Šenerović, L., Vranić, M., Pekmezović, M., Arsić-Arsnijević, V., Veselinović, A., Veselinović, J., Šolaja, B. A., Nikodinović-Runić, J.,& Opsenica, I. (2016). Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates.
Bioorganic and Medicinal ChemistryPergamon-Elsevier Science Ltd, Oxford., 24(6), 1277-1291.
https://doi.org/10.1016/j.bmc.2016.01.058
Ajdačić V, Šenerović L, Vranić M, Pekmezović M, Arsić-Arsnijević V, Veselinović A, Veselinović J, Šolaja BA, Nikodinović-Runić J, Opsenica I. Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates. Bioorganic and Medicinal Chemistry. 2016;24(6):1277-1291
Ajdačić Vladimir, Šenerović Lidija, Vranić Marija, Pekmezović Marina, Arsić-Arsnijević Valentina, Veselinović Aleksandar, Veselinović Jovana, Šolaja Bogdan A., Nikodinović-Runić Jasmina, Opsenica Igor, "Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates" 24, no. 6 (2016):1277-1291,
https://doi.org/10.1016/j.bmc.2016.01.058 .
1
19
24
25