TY  - JOUR
AU  - Knežević, Sara
AU  - Jovanović, Nataša Terzić
AU  - Vlahović, Filip
AU  - Ajdačić, Vladimir
AU  - Costache, Vlad
AU  - Vidić, Jasmina
AU  - Opsenica, Igor
AU  - Stanković, Dalibor
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6348
AB  - Covalent organic frameworks (COFs) are emerging as promising sensing materials due to their controllable structure and function properties, as well as excellent physicochemical characteristics. Here, specific interactions between a triazine-based COF and a mass-used herbicide – glyphosate (GLY) have been utilized to design a disposable sensing platform for GLY detection. This herbicide has been extensively used for decades, however, its harmful environmental impact and toxicity to humans have been recently proven, conditioning the necessity for the strict control and monitoring of its use and its presence in soil, water, and food. Glyphosate is an organophosphorus compound, and its detection in complex matrices usually requires laborious pretreatment. Here, we developed a direct, miniaturized, robust, and green approach for disposable electrochemical sensing of glyphosate, utilizing COF's ability to selectively capture and concentrate negatively charged glyphosate molecules inside its nanopores. This process generates the concentration gradient of GLY, accelerating its diffusion towards the electrode surface. Simultaneously, specific COF-glyphosate binding catalyses the oxidative cleavage of the C–P bond and, together with pore nanoconfinement, enables sensitive glyphosate detection. Detailed sensing principles and selectiveness were scrutinized using DFT-based modelling. The proposed electrochemical method has a linear working range from 0.1 μM to 10 μM, a low limit of detection of 96 nM, and a limit of quantification of 320 nM. The elaborated sensing approach is viable for use in real sample matrices and tested for GLY determination in soil and water samples, without pretreatment, preparation, or purification. The results showed the practical usefulness of the sensor in the real sample analysis and suggested its suitability for possible out-of-laboratory sensing.
PB  - Elsevier
T2  - Chemosphere
T1  - Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle
VL  - 341
SP  - 139930
DO  - 10.1016/j.chemosphere.2023.139930
ER  - 

@article{
author = "Knežević, Sara and Jovanović, Nataša Terzić and Vlahović, Filip and Ajdačić, Vladimir and Costache, Vlad and Vidić, Jasmina and Opsenica, Igor and Stanković, Dalibor",
year = "2023",
abstract = "Covalent organic frameworks (COFs) are emerging as promising sensing materials due to their controllable structure and function properties, as well as excellent physicochemical characteristics. Here, specific interactions between a triazine-based COF and a mass-used herbicide – glyphosate (GLY) have been utilized to design a disposable sensing platform for GLY detection. This herbicide has been extensively used for decades, however, its harmful environmental impact and toxicity to humans have been recently proven, conditioning the necessity for the strict control and monitoring of its use and its presence in soil, water, and food. Glyphosate is an organophosphorus compound, and its detection in complex matrices usually requires laborious pretreatment. Here, we developed a direct, miniaturized, robust, and green approach for disposable electrochemical sensing of glyphosate, utilizing COF's ability to selectively capture and concentrate negatively charged glyphosate molecules inside its nanopores. This process generates the concentration gradient of GLY, accelerating its diffusion towards the electrode surface. Simultaneously, specific COF-glyphosate binding catalyses the oxidative cleavage of the C–P bond and, together with pore nanoconfinement, enables sensitive glyphosate detection. Detailed sensing principles and selectiveness were scrutinized using DFT-based modelling. The proposed electrochemical method has a linear working range from 0.1 μM to 10 μM, a low limit of detection of 96 nM, and a limit of quantification of 320 nM. The elaborated sensing approach is viable for use in real sample matrices and tested for GLY determination in soil and water samples, without pretreatment, preparation, or purification. The results showed the practical usefulness of the sensor in the real sample analysis and suggested its suitability for possible out-of-laboratory sensing.",
publisher = "Elsevier",
journal = "Chemosphere",
title = "Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle",
volume = "341",
pages = "139930",
doi = "10.1016/j.chemosphere.2023.139930"
}

Knežević, S., Jovanović, N. T., Vlahović, F., Ajdačić, V., Costache, V., Vidić, J., Opsenica, I.,& Stanković, D.. (2023). Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle. in Chemosphere
Elsevier., 341, 139930.
https://doi.org/10.1016/j.chemosphere.2023.139930

Knežević S, Jovanović NT, Vlahović F, Ajdačić V, Costache V, Vidić J, Opsenica I, Stanković D. Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle. in Chemosphere. 2023;341:139930.
doi:10.1016/j.chemosphere.2023.139930 .

Knežević, Sara, Jovanović, Nataša Terzić, Vlahović, Filip, Ajdačić, Vladimir, Costache, Vlad, Vidić, Jasmina, Opsenica, Igor, Stanković, Dalibor, "Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle" in Chemosphere, 341 (2023):139930,
https://doi.org/10.1016/j.chemosphere.2023.139930 . .

TY  - JOUR
AU  - Kokanović, Andrija
AU  - Ajdačić, Vladimir
AU  - Terzić-Jovanović, Natasa
AU  - Stankić, Slavica
AU  - Opsenica, Igor
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6282
AB  - Herein, we report the synthesis and application of a highly active and
versatile Pd/chemical vapor synthesis-ZnO (Pd/CVS-ZnO) catalytic system. The twostep
preparation of the catalyst includes chemical vapor synthesis (CVS) of ultrapure
ZnO nanotetrapods, followed by the liquid-phase in situ reduction of a Pd precursor
and deposition of polycrystalline Pd nanoparticles (∼6 nm). The as-synthesized catalyst
was characterized using standard instrumental techniques. The catalyst was successfully
applied in four chemical reactions: Suzuki−Miyaura cross-coupling, reduction of
nitroarenes, decarbonylation, and hydrodebromination of aromatic compounds, of
which, the latter two are reported for the first time for the Pd/ZnO catalytic system.
The catalyst showed excellent activity within a wide range of substrates, delivering the products in high yields (70−99%). The
recyclability of the Pd/CVS-ZnO catalyst was tested through two different approaches. First, the catalyst recyclability was examined
in all four reactions, reusing the catalyst up to four times in the Suzuki−Miyaura cross-coupling reaction, as well as the reduction of
4-nitrobenzonitrile, without a significant loss of yield. Furthermore, the catalyst was successively used in three different reactions,
showing a high degree of stability and delivering excellent product yields in all cases. In addition to its excellent activity, versatility,
and stability, the Pd/CVS-ZnO catalytic system also exhibits excellent recyclability over consecutive runs, which makes it a
promising candidate for future application in complex industrial processes.
PB  - American Chemical Society
T2  - ACS Applied Nano Materials
T1  - Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts
VL  - 6
IS  - 17
SP  - 15820
EP  - 15828
DO  - 10.1021/acsanm.3c02743
ER  - 

@article{
author = "Kokanović, Andrija and Ajdačić, Vladimir and Terzić-Jovanović, Natasa and Stankić, Slavica and Opsenica, Igor",
year = "2023",
abstract = "Herein, we report the synthesis and application of a highly active and
versatile Pd/chemical vapor synthesis-ZnO (Pd/CVS-ZnO) catalytic system. The twostep
preparation of the catalyst includes chemical vapor synthesis (CVS) of ultrapure
ZnO nanotetrapods, followed by the liquid-phase in situ reduction of a Pd precursor
and deposition of polycrystalline Pd nanoparticles (∼6 nm). The as-synthesized catalyst
was characterized using standard instrumental techniques. The catalyst was successfully
applied in four chemical reactions: Suzuki−Miyaura cross-coupling, reduction of
nitroarenes, decarbonylation, and hydrodebromination of aromatic compounds, of
which, the latter two are reported for the first time for the Pd/ZnO catalytic system.
The catalyst showed excellent activity within a wide range of substrates, delivering the products in high yields (70−99%). The
recyclability of the Pd/CVS-ZnO catalyst was tested through two different approaches. First, the catalyst recyclability was examined
in all four reactions, reusing the catalyst up to four times in the Suzuki−Miyaura cross-coupling reaction, as well as the reduction of
4-nitrobenzonitrile, without a significant loss of yield. Furthermore, the catalyst was successively used in three different reactions,
showing a high degree of stability and delivering excellent product yields in all cases. In addition to its excellent activity, versatility,
and stability, the Pd/CVS-ZnO catalytic system also exhibits excellent recyclability over consecutive runs, which makes it a
promising candidate for future application in complex industrial processes.",
publisher = "American Chemical Society",
journal = "ACS Applied Nano Materials",
title = "Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts",
volume = "6",
number = "17",
pages = "15820-15828",
doi = "10.1021/acsanm.3c02743"
}

Kokanović, A., Ajdačić, V., Terzić-Jovanović, N., Stankić, S.,& Opsenica, I.. (2023). Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts. in ACS Applied Nano Materials
American Chemical Society., 6(17), 15820-15828.
https://doi.org/10.1021/acsanm.3c02743

Kokanović A, Ajdačić V, Terzić-Jovanović N, Stankić S, Opsenica I. Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts. in ACS Applied Nano Materials. 2023;6(17):15820-15828.
doi:10.1021/acsanm.3c02743 .

Kokanović, Andrija, Ajdačić, Vladimir, Terzić-Jovanović, Natasa, Stankić, Slavica, Opsenica, Igor, "Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts" in ACS Applied Nano Materials, 6, no. 17 (2023):15820-15828,
https://doi.org/10.1021/acsanm.3c02743 . .

TY  - JOUR
AU  - Kokić, Branislav
AU  - Vulović, Bojan
AU  - Jović, Miloš
AU  - Andrijević, Ana
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6299
AB  - Прегледни чланак о до сад објављеним методама за кобалтом-катализовану адицију угљеничних електрофила на карбонилну и иминску функцију.
AB  - The addition of carbon electrophiles to carbonyls and imines has emerged as a valuable strategy for the construction of C−C bonds. The merger of this concept with sustainable cobalt catalysis has yielded numerous innovative methodologies. Remarkable functional group tolerance and selectivity have been observed in many cases, providing reliable methods for bond construction. The cobalt-catalyzed additions of carbon electrophiles to carbonyls, imines and carboxylic acid derivatives described in this review include the earliest reports, such as Takai-Utimoto Co/Cr co-catalyzed additions and their progression, as well as modern variants, exemplified by recent Co/photoredox co-catalyzed protocols. The systematic appraisal of this modern strategy provides a clearer perspective and inspiration for its further development.
PB  - Wiley
T2  - European Journal of Organic Chemistry
T1  - Strategies for Carbon Electrophile Addition to Carbonyls and Imines by Cobalt Catalysis
VL  - 26
IS  - 45
SP  - e202300997
DO  - 10.1002/ejoc.202300997
ER  - 

@article{
author = "Kokić, Branislav and Vulović, Bojan and Jović, Miloš and Andrijević, Ana and Ajdačić, Vladimir and Opsenica, Igor",
year = "2023",
abstract = "Прегледни чланак о до сад објављеним методама за кобалтом-катализовану адицију угљеничних електрофила на карбонилну и иминску функцију., The addition of carbon electrophiles to carbonyls and imines has emerged as a valuable strategy for the construction of C−C bonds. The merger of this concept with sustainable cobalt catalysis has yielded numerous innovative methodologies. Remarkable functional group tolerance and selectivity have been observed in many cases, providing reliable methods for bond construction. The cobalt-catalyzed additions of carbon electrophiles to carbonyls, imines and carboxylic acid derivatives described in this review include the earliest reports, such as Takai-Utimoto Co/Cr co-catalyzed additions and their progression, as well as modern variants, exemplified by recent Co/photoredox co-catalyzed protocols. The systematic appraisal of this modern strategy provides a clearer perspective and inspiration for its further development.",
publisher = "Wiley",
journal = "European Journal of Organic Chemistry",
title = "Strategies for Carbon Electrophile Addition to Carbonyls and Imines by Cobalt Catalysis",
volume = "26",
number = "45",
pages = "e202300997",
doi = "10.1002/ejoc.202300997"
}

Kokić, B., Vulović, B., Jović, M., Andrijević, A., Ajdačić, V.,& Opsenica, I.. (2023). Strategies for Carbon Electrophile Addition to Carbonyls and Imines by Cobalt Catalysis. in European Journal of Organic Chemistry
Wiley., 26(45), e202300997.
https://doi.org/10.1002/ejoc.202300997

Kokić B, Vulović B, Jović M, Andrijević A, Ajdačić V, Opsenica I. Strategies for Carbon Electrophile Addition to Carbonyls and Imines by Cobalt Catalysis. in European Journal of Organic Chemistry. 2023;26(45):e202300997.
doi:10.1002/ejoc.202300997 .

Kokić, Branislav, Vulović, Bojan, Jović, Miloš, Andrijević, Ana, Ajdačić, Vladimir, Opsenica, Igor, "Strategies for Carbon Electrophile Addition to Carbonyls and Imines by Cobalt Catalysis" in European Journal of Organic Chemistry, 26, no. 45 (2023):e202300997,
https://doi.org/10.1002/ejoc.202300997 . .

TY  - JOUR
AU  - Kokić, Branislav
AU  - Selaković, Života
AU  - Nikolić, Andrea M.
AU  - Andrijević, Ana
AU  - Anđelković, Boban D.
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5680
AB  - Herein, we report a low-valent cobalt-catalyzed deprotection of allyloxyarenes. The method displays a broad substrate scope and good functional group tolerance, granting its utilization on more complex substrates, including O-allylated derivatives of natural products and drugs. Based on comprehensive experiments, a plausible mechanistic pathway for the low-valent cobalt-catalyzed O-deallylation of allyloxyarenes is proposed.
PB  - Wiley
T2  - European Journal of Organic Chemistry
T1  - Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes
VL  - 43
SP  - e202201112
DO  - 10.1002/ejoc.202201112
ER  - 

@article{
author = "Kokić, Branislav and Selaković, Života and Nikolić, Andrea M. and Andrijević, Ana and Anđelković, Boban D. and Ajdačić, Vladimir and Opsenica, Igor",
year = "2022",
abstract = "Herein, we report a low-valent cobalt-catalyzed deprotection of allyloxyarenes. The method displays a broad substrate scope and good functional group tolerance, granting its utilization on more complex substrates, including O-allylated derivatives of natural products and drugs. Based on comprehensive experiments, a plausible mechanistic pathway for the low-valent cobalt-catalyzed O-deallylation of allyloxyarenes is proposed.",
publisher = "Wiley",
journal = "European Journal of Organic Chemistry",
title = "Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes",
volume = "43",
pages = "e202201112",
doi = "10.1002/ejoc.202201112"
}

Kokić, B., Selaković, Ž., Nikolić, A. M., Andrijević, A., Anđelković, B. D., Ajdačić, V.,& Opsenica, I.. (2022). Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes. in European Journal of Organic Chemistry
Wiley., 43, e202201112.
https://doi.org/10.1002/ejoc.202201112

Kokić B, Selaković Ž, Nikolić AM, Andrijević A, Anđelković BD, Ajdačić V, Opsenica I. Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes. in European Journal of Organic Chemistry. 2022;43:e202201112.
doi:10.1002/ejoc.202201112 .

Kokić, Branislav, Selaković, Života, Nikolić, Andrea M., Andrijević, Ana, Anđelković, Boban D., Ajdačić, Vladimir, Opsenica, Igor, "Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes" in European Journal of Organic Chemistry, 43 (2022):e202201112,
https://doi.org/10.1002/ejoc.202201112 . .

TY  - DATA
AU  - Kokić, Branislav
AU  - Selaković, Života
AU  - Nikolić, Andrea M.
AU  - Andrijević, Ana
AU  - Anđelković, Boban D.
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5706
AB  - Herein, we report a low-valent cobalt-catalyzed deprotection of allyloxyarenes. The method displays a broad substrate scope and good functional group tolerance, granting its utilization on more complex substrates, including O-allylated derivatives of natural products and drugs. Based on comprehensive experiments, a plausible mechanistic pathway for the low-valent cobalt-catalyzed O-deallylation of allyloxyarenes is proposed.
PB  - Wiley
T2  - European Journal of Organic Chemistry
T1  - Supplementary material for: Kokić, B., Selaković, Ž., Nikolić, A. M., Andrijević, A., Anđelković, B. D., Ajdačić, V., & Opsenica, I. (2022). Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes. European Journal of Organic Chemistry, 43, e202201112. https://doi.org/10.1002/ejoc.202201112
VL  - 43
SP  - e202201112
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5706
ER  - 

@misc{
author = "Kokić, Branislav and Selaković, Života and Nikolić, Andrea M. and Andrijević, Ana and Anđelković, Boban D. and Ajdačić, Vladimir and Opsenica, Igor",
year = "2022",
abstract = "Herein, we report a low-valent cobalt-catalyzed deprotection of allyloxyarenes. The method displays a broad substrate scope and good functional group tolerance, granting its utilization on more complex substrates, including O-allylated derivatives of natural products and drugs. Based on comprehensive experiments, a plausible mechanistic pathway for the low-valent cobalt-catalyzed O-deallylation of allyloxyarenes is proposed.",
publisher = "Wiley",
journal = "European Journal of Organic Chemistry",
title = "Supplementary material for: Kokić, B., Selaković, Ž., Nikolić, A. M., Andrijević, A., Anđelković, B. D., Ajdačić, V., & Opsenica, I. (2022). Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes. European Journal of Organic Chemistry, 43, e202201112. https://doi.org/10.1002/ejoc.202201112",
volume = "43",
pages = "e202201112",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5706"
}

Kokić, B., Selaković, Ž., Nikolić, A. M., Andrijević, A., Anđelković, B. D., Ajdačić, V.,& Opsenica, I.. (2022). Supplementary material for: Kokić, B., Selaković, Ž., Nikolić, A. M., Andrijević, A., Anđelković, B. D., Ajdačić, V., & Opsenica, I. (2022). Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes. European Journal of Organic Chemistry, 43, e202201112. https://doi.org/10.1002/ejoc.202201112. in European Journal of Organic Chemistry
Wiley., 43, e202201112.
https://hdl.handle.net/21.15107/rcub_cherry_5706

Kokić B, Selaković Ž, Nikolić AM, Andrijević A, Anđelković BD, Ajdačić V, Opsenica I. Supplementary material for: Kokić, B., Selaković, Ž., Nikolić, A. M., Andrijević, A., Anđelković, B. D., Ajdačić, V., & Opsenica, I. (2022). Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes. European Journal of Organic Chemistry, 43, e202201112. https://doi.org/10.1002/ejoc.202201112. in European Journal of Organic Chemistry. 2022;43:e202201112.
https://hdl.handle.net/21.15107/rcub_cherry_5706 .

Kokić, Branislav, Selaković, Života, Nikolić, Andrea M., Andrijević, Ana, Anđelković, Boban D., Ajdačić, Vladimir, Opsenica, Igor, "Supplementary material for: Kokić, B., Selaković, Ž., Nikolić, A. M., Andrijević, A., Anđelković, B. D., Ajdačić, V., & Opsenica, I. (2022). Low-Valent Cobalt-Catalyzed Deprotection of Allyloxyarenes. European Journal of Organic Chemistry, 43, e202201112. https://doi.org/10.1002/ejoc.202201112" in European Journal of Organic Chemistry, 43 (2022):e202201112,
https://hdl.handle.net/21.15107/rcub_cherry_5706 .

TY  - JOUR
AU  - Selaković, Života
AU  - Nikolić, Andrea
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4871
AB  - Decarbonylation is an invaluable reaction, utilized by nature and chemists alike. In different life forms, such as prokaryotes, plants and animals, this transformation is catalyzed by aldehyde decarbonylases. In the laboratory, the transition metal-catalyzed (TMC) decarbonylation, which was first achieved in 1959, is by and large the dominant way for conducting this reaction. The carbon-carbon bond cleavage is most often made possible by RhCl(PPh3)3 i. e. Wilkinson's catalyst, but other metals are also used, both in academia and in industry. In this review, we chose to present the applications of TMC decarbonylation in the synthesis of natural products and their derivatives. More than 30 examples are showcased and categorized into three categories based on the essence of the role of the aldehyde group in the synthesis. A short outlook is given in the end, listing the different advantages and disadvantages of Wilkinson's catalyst, as well as offering a brief prospect for the future.
PB  - Wiley
T2  - European Journal of Organic Chemistry
T1  - Application of Transition Metal-Catalyzed Decarbonylation of Aldehydes in the Total Synthesis of Natural Products
VL  - 2022
IS  - 1
SP  - e202101265
DO  - 10.1002/ejoc.202101265
ER  - 

@article{
author = "Selaković, Života and Nikolić, Andrea and Ajdačić, Vladimir and Opsenica, Igor",
year = "2022",
abstract = "Decarbonylation is an invaluable reaction, utilized by nature and chemists alike. In different life forms, such as prokaryotes, plants and animals, this transformation is catalyzed by aldehyde decarbonylases. In the laboratory, the transition metal-catalyzed (TMC) decarbonylation, which was first achieved in 1959, is by and large the dominant way for conducting this reaction. The carbon-carbon bond cleavage is most often made possible by RhCl(PPh3)3 i. e. Wilkinson's catalyst, but other metals are also used, both in academia and in industry. In this review, we chose to present the applications of TMC decarbonylation in the synthesis of natural products and their derivatives. More than 30 examples are showcased and categorized into three categories based on the essence of the role of the aldehyde group in the synthesis. A short outlook is given in the end, listing the different advantages and disadvantages of Wilkinson's catalyst, as well as offering a brief prospect for the future.",
publisher = "Wiley",
journal = "European Journal of Organic Chemistry",
title = "Application of Transition Metal-Catalyzed Decarbonylation of Aldehydes in the Total Synthesis of Natural Products",
volume = "2022",
number = "1",
pages = "e202101265",
doi = "10.1002/ejoc.202101265"
}

Selaković, Ž., Nikolić, A., Ajdačić, V.,& Opsenica, I.. (2022). Application of Transition Metal-Catalyzed Decarbonylation of Aldehydes in the Total Synthesis of Natural Products. in European Journal of Organic Chemistry
Wiley., 2022(1), e202101265.
https://doi.org/10.1002/ejoc.202101265

Selaković Ž, Nikolić A, Ajdačić V, Opsenica I. Application of Transition Metal-Catalyzed Decarbonylation of Aldehydes in the Total Synthesis of Natural Products. in European Journal of Organic Chemistry. 2022;2022(1):e202101265.
doi:10.1002/ejoc.202101265 .

Selaković, Života, Nikolić, Andrea, Ajdačić, Vladimir, Opsenica, Igor, "Application of Transition Metal-Catalyzed Decarbonylation of Aldehydes in the Total Synthesis of Natural Products" in European Journal of Organic Chemistry, 2022, no. 1 (2022):e202101265,
https://doi.org/10.1002/ejoc.202101265 . .

TY  - JOUR
AU  - Terzić-Jovanović, Nataša
AU  - Ajdačić, Vladimir
PY  - 2022
UR  - https://www.shd-pub.org.rs/index.php/JSCS/article/view/11599
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5982
AB  - A simple methodology for the decarbonylation of aldehydes catal­ysed by commercially available palladium on carbon in a green two-solvent system is reported. Various aromatic, aliphatic and heteroaromatic aldehydes were transformed to the corresponding decarbonylated products in good yields. Pro­duct isolation from the reaction mixture is simple in practice, and the cat­alyst can be reused three times.
T2  - Journal of the Serbian Chemical Society
T1  - Palladium on carbon in PEG-400/cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes: Scientific paper
VL  - 87
IS  - 6
SP  - 669
EP  - 675
DO  - 10.2298/JSC220128024T
ER  - 

@article{
author = "Terzić-Jovanović, Nataša and Ajdačić, Vladimir",
year = "2022",
abstract = "A simple methodology for the decarbonylation of aldehydes catal­ysed by commercially available palladium on carbon in a green two-solvent system is reported. Various aromatic, aliphatic and heteroaromatic aldehydes were transformed to the corresponding decarbonylated products in good yields. Pro­duct isolation from the reaction mixture is simple in practice, and the cat­alyst can be reused three times.",
journal = "Journal of the Serbian Chemical Society",
title = "Palladium on carbon in PEG-400/cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes: Scientific paper",
volume = "87",
number = "6",
pages = "669-675",
doi = "10.2298/JSC220128024T"
}

Terzić-Jovanović, N.,& Ajdačić, V.. (2022). Palladium on carbon in PEG-400/cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes: Scientific paper. in Journal of the Serbian Chemical Society, 87(6), 669-675.
https://doi.org/10.2298/JSC220128024T

Terzić-Jovanović N, Ajdačić V. Palladium on carbon in PEG-400/cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes: Scientific paper. in Journal of the Serbian Chemical Society. 2022;87(6):669-675.
doi:10.2298/JSC220128024T .

Terzić-Jovanović, Nataša, Ajdačić, Vladimir, "Palladium on carbon in PEG-400/cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes: Scientific paper" in Journal of the Serbian Chemical Society, 87, no. 6 (2022):669-675,
https://doi.org/10.2298/JSC220128024T . .

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban D.
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://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 D. and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
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. D., 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. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282

Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković BD, 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. in The Journal of Organic Chemistry. 2021;86(6):4794-4803.
doi:10.1021/acs.joc.1c00282 .

Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban D., 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" in The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 . .

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban D.
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://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 D. and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
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. D., 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. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282

Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković BD, 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. in The Journal of Organic Chemistry. 2021;86(6):4794-4803.
doi:10.1021/acs.joc.1c00282 .

Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban D., 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" in The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 . .

TY  - DATA
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban D.
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://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  - 

@misc{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban D. and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
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. D., 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. in The Journal of Organic Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.joc.1c00282.s001

Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković BD, 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. in The Journal of Organic Chemistry. 2021;.
doi:10.1021/acs.joc.1c00282.s001 .

Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban D., 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" in The Journal of Organic Chemistry (2021),
https://doi.org/10.1021/acs.joc.1c00282.s001 . .

TY  - DATA
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  - https://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
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3794
ER  - 

@misc{
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",
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",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3794"
}

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. in ACS Omega
American Chemical Society..
https://hdl.handle.net/21.15107/rcub_cherry_3794

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. in ACS Omega. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3794 .

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" in ACS Omega (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3794 .

TY  - THES
AU  - Ajdačić, Vladimir
PY  - 2019
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  - https://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
UR  - https://hdl.handle.net/21.15107/rcub_nardus_17444
ER  - 

@phdthesis{
author = "Ajdačić, Vladimir",
year = "2019",
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",
url = "https://hdl.handle.net/21.15107/rcub_nardus_17444"
}

Ajdačić, V.. (2019). Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_17444

Ajdačić V. Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida. in Универзитет у Београду. 2019;.
https://hdl.handle.net/21.15107/rcub_nardus_17444 .

Ajdačić, Vladimir, "Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida" in Универзитет у Београду (2019),
https://hdl.handle.net/21.15107/rcub_nardus_17444 .

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  - https://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",
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. in International Journal of Biological Macromolecules
Elsevier., 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. in International Journal of Biological Macromolecules. 2019;129:351-360.
doi:10.1016/j.ijbiomac.2019.01.154 .

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" in International Journal of Biological Macromolecules, 129 (2019):351-360,
https://doi.org/10.1016/j.ijbiomac.2019.01.154 . .

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  - https://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",
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. in International Journal of Biological Macromolecules
Elsevier., 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. in International Journal of Biological Macromolecules. 2019;129:351-360.
doi:10.1016/j.ijbiomac.2019.01.154 .

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" in International Journal of Biological Macromolecules, 129 (2019):351-360,
https://doi.org/10.1016/j.ijbiomac.2019.01.154 . .

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2019
UR  - https://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 and Ajdačić, Vladimir and Opsenica, Igor",
year = "2019",
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., Ajdačić, V.,& Opsenica, I.. (2019). Palladium-catalyzed N-Arylation of 1-substituted-1H-tetrazol-5-amines. in Journal of Organometallic Chemistry
Elsevier., 880, 134-142.
https://doi.org/10.1016/j.jorganchem.2018.11.007

Nikolić A, Ajdačić V, Opsenica I. Palladium-catalyzed N-Arylation of 1-substituted-1H-tetrazol-5-amines. in Journal of Organometallic Chemistry. 2019;880:134-142.
doi:10.1016/j.jorganchem.2018.11.007 .

Nikolić, Andrea, Ajdačić, Vladimir, Opsenica, Igor, "Palladium-catalyzed N-Arylation of 1-substituted-1H-tetrazol-5-amines" in Journal of Organometallic Chemistry, 880 (2019):134-142,
https://doi.org/10.1016/j.jorganchem.2018.11.007 . .

TY  - DATA
AU  - Nikolić, Andrea
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2019
UR  - https://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  - 

@misc{
author = "Nikolić, Andrea and Ajdačić, Vladimir and Opsenica, Igor",
year = "2019",
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., 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. in Journal of Organometallic Chemistry
Elsevier..
https://doi.org/10.1016/j.jorganchem.2018.11.007

Nikolić A, 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. in Journal of Organometallic Chemistry. 2019;.
doi:10.1016/j.jorganchem.2018.11.007 .

Nikolić, Andrea, 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" in Journal of Organometallic Chemistry (2019),
https://doi.org/10.1016/j.jorganchem.2018.11.007 . .

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  - https://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",
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. in ACS Omega
American 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. in ACS Omega. 2019;4(24):20450-20458.
doi:10.1021/acsomega.9b01548 .

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" in ACS Omega, 4, no. 24 (2019):20450-20458,
https://doi.org/10.1021/acsomega.9b01548 . .

TY  - DATA
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  - https://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
UR  - https://hdl.handle.net/21.15107/rcub_cherry_2995
ER  - 

@misc{
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",
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",
url = "https://hdl.handle.net/21.15107/rcub_cherry_2995"
}

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. in Synthesis, Stuttgart
Georg Thieme Verlag Kg, Stuttgart..
https://hdl.handle.net/21.15107/rcub_cherry_2995

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. in Synthesis, Stuttgart. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_2995 .

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" in Synthesis, Stuttgart (2018),
https://hdl.handle.net/21.15107/rcub_cherry_2995 .

TY  - DATA
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  - https://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
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3176
ER  - 

@misc{
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",
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",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3176"
}

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. in Applied Microbiology and Biotechnology
Springer, New York..
https://hdl.handle.net/21.15107/rcub_cherry_3176

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. in Applied Microbiology and Biotechnology. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3176 .

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" in Applied Microbiology and Biotechnology (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3176 .

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  - https://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",
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. in Applied Microbiology and Biotechnology
Springer, 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. in Applied Microbiology and Biotechnology. 2018;102(4):1889-1901.
doi:10.1007/s00253-018-8749-3 .

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" in Applied Microbiology and Biotechnology, 102, no. 4 (2018):1889-1901,
https://doi.org/10.1007/s00253-018-8749-3 . .

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Nikolić, Andrea
AU  - Kerner, Michael
AU  - Wipf, Peter
AU  - Opsenica, Igor
PY  - 2018
UR  - https://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",
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. in Synlett
Georg 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. in Synlett. 2018;29(13):1781-1785.
doi:10.1055/s-0037-1610433 .

Ajdačić, Vladimir, Nikolić, Andrea, Kerner, Michael, Wipf, Peter, Opsenica, Igor, "Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes" in Synlett, 29, no. 13 (2018):1781-1785,
https://doi.org/10.1055/s-0037-1610433 . .

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  - https://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",
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. in Synthesis, Stuttgart
Georg 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. in Synthesis, Stuttgart. 2018;50(1):119-126.
doi:10.1055/s-0036-1590892 .

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" in Synthesis, Stuttgart, 50, no. 1 (2018):119-126,
https://doi.org/10.1055/s-0036-1590892 . .

TY  - DATA
AU  - Ajdačić, Vladimir
AU  - Nikolić, Andrea
AU  - Kerner, Michael
AU  - Wipf, Peter
AU  - Opsenica, Igor
PY  - 2018
UR  - https://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
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3252
ER  - 

@misc{
author = "Ajdačić, Vladimir and Nikolić, Andrea and Kerner, Michael and Wipf, Peter and Opsenica, Igor",
year = "2018",
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",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3252"
}

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. in Synlett
Georg Thieme Verlag Kg, Stuttgart..
https://hdl.handle.net/21.15107/rcub_cherry_3252

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. in Synlett. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3252 .

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" in Synlett (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3252 .

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  - https://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",
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. in Journal of the Serbian Chemical Society
Serbian 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. in Journal of the Serbian Chemical Society. 2017;82(6):641-649.
doi:10.2298/JSC170213033A .

Ajdačić, Vladimir, Lazić, Jelena O., Mojicevic, Marija, Šegan, Sandra B., Nikodinović-Runić, Jasmina, Opsenica, Igor, "Antibacterial and antifungal properties of guanylhydrazones" in Journal of the Serbian Chemical Society, 82, no. 6 (2017):641-649,
https://doi.org/10.2298/JSC170213033A . .

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  - https://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",
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. in Bioorganic and Medicinal Chemistry
Pergamon-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. in Bioorganic and Medicinal Chemistry. 2016;24(6):1277-1291.
doi: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, "Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates" in Bioorganic and Medicinal Chemistry, 24, no. 6 (2016):1277-1291,
https://doi.org/10.1016/j.bmc.2016.01.058 . .