TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Opsenica, Dejan M.
AU  - Milojković-Opsenica, Dušanka
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3686
AB  - Among widely used chromatographic methods modern thin-layer chromatography is not only the simplest to perform but is also considered as respectable analytical method in various phases of drug discovery and development processes such as monitoring of synthesis, identification of bioactive substances from various natural sources and their isolation and purification, determination of lipophilicity and other physico-chemical parameters, quantitative structure-activity relationship studies, bioautography, as well as qualitative and quantitative analysis of drugs and their metabolites. An overview of recently published papers dealing with application of thin-layer chromatography in medicinal chemistry is presented.
PB  - Taylor and Francis Inc.
T2  - Journal of Liquid Chromatography and Related Technologies
T1  - Thin-layer chromatography in medicinal chemistry
VL  - 42
IS  - 9-10
SP  - 238
EP  - 248
DO  - 10.1080/10826076.2019.1585615
ER  - 

@article{
author = "Šegan, Sandra B. and Opsenica, Dejan M. and Milojković-Opsenica, Dušanka",
year = "2019",
abstract = "Among widely used chromatographic methods modern thin-layer chromatography is not only the simplest to perform but is also considered as respectable analytical method in various phases of drug discovery and development processes such as monitoring of synthesis, identification of bioactive substances from various natural sources and their isolation and purification, determination of lipophilicity and other physico-chemical parameters, quantitative structure-activity relationship studies, bioautography, as well as qualitative and quantitative analysis of drugs and their metabolites. An overview of recently published papers dealing with application of thin-layer chromatography in medicinal chemistry is presented.",
publisher = "Taylor and Francis Inc.",
journal = "Journal of Liquid Chromatography and Related Technologies",
title = "Thin-layer chromatography in medicinal chemistry",
volume = "42",
number = "9-10",
pages = "238-248",
doi = "10.1080/10826076.2019.1585615"
}

Šegan, S. B., Opsenica, D. M.,& Milojković-Opsenica, D.. (2019). Thin-layer chromatography in medicinal chemistry. in Journal of Liquid Chromatography and Related Technologies
Taylor and Francis Inc.., 42(9-10), 238-248.
https://doi.org/10.1080/10826076.2019.1585615

Šegan SB, Opsenica DM, Milojković-Opsenica D. Thin-layer chromatography in medicinal chemistry. in Journal of Liquid Chromatography and Related Technologies. 2019;42(9-10):238-248.
doi:10.1080/10826076.2019.1585615 .

Šegan, Sandra B., Opsenica, Dejan M., Milojković-Opsenica, Dušanka, "Thin-layer chromatography in medicinal chemistry" in Journal of Liquid Chromatography and Related Technologies, 42, no. 9-10 (2019):238-248,
https://doi.org/10.1080/10826076.2019.1585615 . .

TY  - JOUR
AU  - Aleksic, Ivana
AU  - Jeremic, Jelena
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Opsenica, Dejan M.
AU  - Senerovic, Lidija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3771
AB  - Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.
PB  - American Chemical Society
T2  - ACS Chemical Biology
T1  - N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
DO  - 10.1021/acschembio.9b00682
ER  - 

@article{
author = "Aleksic, Ivana and Jeremic, Jelena and Milivojević, Dušan and Ilić-Tomić, Tatjana and Šegan, Sandra B. and Zlatović, Mario and Opsenica, Dejan M. and Senerovic, Lidija",
year = "2019",
abstract = "Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.",
publisher = "American Chemical Society",
journal = "ACS Chemical Biology",
title = "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa",
doi = "10.1021/acschembio.9b00682"
}

Aleksic, I., Jeremic, J., Milivojević, D., Ilić-Tomić, T., Šegan, S. B., Zlatović, M., Opsenica, D. M.,& Senerovic, L.. (2019). N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology
American Chemical Society..
https://doi.org/10.1021/acschembio.9b00682

Aleksic I, Jeremic J, Milivojević D, Ilić-Tomić T, Šegan SB, Zlatović M, Opsenica DM, Senerovic L. N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology. 2019;.
doi:10.1021/acschembio.9b00682 .

Aleksic, Ivana, Jeremic, Jelena, Milivojević, Dušan, Ilić-Tomić, Tatjana, Šegan, Sandra B., Zlatović, Mario, Opsenica, Dejan M., Senerovic, Lidija, "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" in ACS Chemical Biology (2019),
https://doi.org/10.1021/acschembio.9b00682 . .

TY  - JOUR
AU  - Aleksic, Ivana
AU  - Jeremic, Jelena
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Opsenica, Dejan M.
AU  - Senerovic, Lidija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3772
AB  - Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.
PB  - American Chemical Society
T2  - ACS Chemical Biology
T1  - N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
DO  - 10.1021/acschembio.9b00682
ER  - 

@article{
author = "Aleksic, Ivana and Jeremic, Jelena and Milivojević, Dušan and Ilić-Tomić, Tatjana and Šegan, Sandra B. and Zlatović, Mario and Opsenica, Dejan M. and Senerovic, Lidija",
year = "2019",
abstract = "Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.",
publisher = "American Chemical Society",
journal = "ACS Chemical Biology",
title = "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa",
doi = "10.1021/acschembio.9b00682"
}

Aleksic, I., Jeremic, J., Milivojević, D., Ilić-Tomić, T., Šegan, S. B., Zlatović, M., Opsenica, D. M.,& Senerovic, L.. (2019). N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology
American Chemical Society..
https://doi.org/10.1021/acschembio.9b00682

Aleksic I, Jeremic J, Milivojević D, Ilić-Tomić T, Šegan SB, Zlatović M, Opsenica DM, Senerovic L. N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology. 2019;.
doi:10.1021/acschembio.9b00682 .

Aleksic, Ivana, Jeremic, Jelena, Milivojević, Dušan, Ilić-Tomić, Tatjana, Šegan, Sandra B., Zlatović, Mario, Opsenica, Dejan M., Senerovic, Lidija, "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" in ACS Chemical Biology (2019),
https://doi.org/10.1021/acschembio.9b00682 . .

TY  - DATA
AU  - Aleksic, Ivana
AU  - Jeremic, Jelena
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Opsenica, Dejan M.
AU  - Senerovic, Lidija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3773
PB  - American Chemical Society
T2  - ACS Chemical Biology
T1  - Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3773
ER  - 

@misc{
author = "Aleksic, Ivana and Jeremic, Jelena and Milivojević, Dušan and Ilić-Tomić, Tatjana and Šegan, Sandra B. and Zlatović, Mario and Opsenica, Dejan M. and Senerovic, Lidija",
year = "2019",
publisher = "American Chemical Society",
journal = "ACS Chemical Biology",
title = "Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3773"
}

Aleksic, I., Jeremic, J., Milivojević, D., Ilić-Tomić, T., Šegan, S. B., Zlatović, M., Opsenica, D. M.,& Senerovic, L.. (2019). Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology
American Chemical Society..
https://hdl.handle.net/21.15107/rcub_cherry_3773

Aleksic I, Jeremic J, Milivojević D, Ilić-Tomić T, Šegan SB, Zlatović M, Opsenica DM, Senerovic L. Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3773 .

Aleksic, Ivana, Jeremic, Jelena, Milivojević, Dušan, Ilić-Tomić, Tatjana, Šegan, Sandra B., Zlatović, Mario, Opsenica, Dejan M., Senerovic, Lidija, "Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" in ACS Chemical Biology (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3773 .

TY  - JOUR
AU  - Janakiev, Tamara
AU  - Dimkić, Ivica
AU  - Unković, Nikola
AU  - Ljaljević-Grbić, Milica
AU  - Opsenica, Dejan M.
AU  - Gašić, Uroš M.
AU  - Stanković, Slaviša
AU  - Berić, Tanja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3729
AB  - European plum (Prunus domestica L.) is a significant commercial crop in Serbia in terms of total fruit production, and is traditionally processed into slivovitz brandy. The brown rot disease caused by Monilinia laxa drastically reduces plum yield almost every year. Fungal communities associated with leaves and fruits of four local Serbian plum cultivars (Požegača, Ranka, Čačanska Lepotica and Čačanska Rodna) were investigated in two phenological stages during early (May) and late (July) fruit maturation. Alpha diversity indices showed that fungal communities were heterogeneous and Beta diversity indicated that autochthonous fungal communities depended upon seasonal changes and the cultivars themselves. The phylum Ascomycota was the most abundant in all samples, with relative abundance (RA) between 46% in the Požegača cultivar (May) and 89% in the Lepotica cultivar (July). The most abundant genus for all plum cultivars in May was Aureobasidium, with RA from 19.27 to 33.69%, followed by Cryptococcus, with 4.8 to 48.80%. In July, besides Cryptococcus, different genera (Metschnikowia, Fusarium, and Hanseniaspora) were dominant on particular cultivars. Among all cultivable fungi, molecular identification of eleven M. laxa isolates from four plum cultivars was performed simultaneously. Bacterial isolates from the plum phyllosphere were tested for their potential antifungal activity against indigenous M. laxa isolates. The most potent antagonist P4/16_1, which significantly reduced mycelial growth of M. laxa, was identified as Pseudomonas synxantha. Further characterization of P4/16_1 revealed the production of volatile organic compounds and phenazine-1-carboxylic acid (PCA). Crude benzene extract of PCA exhibited 57–63% mycelial growth inhibition of M. laxa. LC/MS analysis of the crude extract confirmed the presence of phenazine derivatives amongst other compounds. Scanning electron microscopy revealed morpho-physiological changes in the hyphae of M. laxa isolates caused by the cell culture and the P. synxantha P4/16_1 crude benzene extract. This is the first report of antagonistic activity of P. synxantha against M. laxa induced by diffusible and volatile antifungal compounds, and it appears to be a promising candidate for further investigation for potential use as a biocontrol agent against brown rot-causing fungi.
PB  - Frontiers Media S.A.
T2  - Frontiers in Microbiology
T1  - Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas synxantha Against Monilinia laxa
VL  - 10
DO  - 10.3389/fmicb.2019.02287
ER  - 

@article{
author = "Janakiev, Tamara and Dimkić, Ivica and Unković, Nikola and Ljaljević-Grbić, Milica and Opsenica, Dejan M. and Gašić, Uroš M. and Stanković, Slaviša and Berić, Tanja",
year = "2019",
abstract = "European plum (Prunus domestica L.) is a significant commercial crop in Serbia in terms of total fruit production, and is traditionally processed into slivovitz brandy. The brown rot disease caused by Monilinia laxa drastically reduces plum yield almost every year. Fungal communities associated with leaves and fruits of four local Serbian plum cultivars (Požegača, Ranka, Čačanska Lepotica and Čačanska Rodna) were investigated in two phenological stages during early (May) and late (July) fruit maturation. Alpha diversity indices showed that fungal communities were heterogeneous and Beta diversity indicated that autochthonous fungal communities depended upon seasonal changes and the cultivars themselves. The phylum Ascomycota was the most abundant in all samples, with relative abundance (RA) between 46% in the Požegača cultivar (May) and 89% in the Lepotica cultivar (July). The most abundant genus for all plum cultivars in May was Aureobasidium, with RA from 19.27 to 33.69%, followed by Cryptococcus, with 4.8 to 48.80%. In July, besides Cryptococcus, different genera (Metschnikowia, Fusarium, and Hanseniaspora) were dominant on particular cultivars. Among all cultivable fungi, molecular identification of eleven M. laxa isolates from four plum cultivars was performed simultaneously. Bacterial isolates from the plum phyllosphere were tested for their potential antifungal activity against indigenous M. laxa isolates. The most potent antagonist P4/16_1, which significantly reduced mycelial growth of M. laxa, was identified as Pseudomonas synxantha. Further characterization of P4/16_1 revealed the production of volatile organic compounds and phenazine-1-carboxylic acid (PCA). Crude benzene extract of PCA exhibited 57–63% mycelial growth inhibition of M. laxa. LC/MS analysis of the crude extract confirmed the presence of phenazine derivatives amongst other compounds. Scanning electron microscopy revealed morpho-physiological changes in the hyphae of M. laxa isolates caused by the cell culture and the P. synxantha P4/16_1 crude benzene extract. This is the first report of antagonistic activity of P. synxantha against M. laxa induced by diffusible and volatile antifungal compounds, and it appears to be a promising candidate for further investigation for potential use as a biocontrol agent against brown rot-causing fungi.",
publisher = "Frontiers Media S.A.",
journal = "Frontiers in Microbiology",
title = "Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas synxantha Against Monilinia laxa",
volume = "10",
doi = "10.3389/fmicb.2019.02287"
}

Janakiev, T., Dimkić, I., Unković, N., Ljaljević-Grbić, M., Opsenica, D. M., Gašić, U. M., Stanković, S.,& Berić, T.. (2019). Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas synxantha Against Monilinia laxa. in Frontiers in Microbiology
Frontiers Media S.A.., 10.
https://doi.org/10.3389/fmicb.2019.02287

Janakiev T, Dimkić I, Unković N, Ljaljević-Grbić M, Opsenica DM, Gašić UM, Stanković S, Berić T. Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas synxantha Against Monilinia laxa. in Frontiers in Microbiology. 2019;10.
doi:10.3389/fmicb.2019.02287 .

Janakiev, Tamara, Dimkić, Ivica, Unković, Nikola, Ljaljević-Grbić, Milica, Opsenica, Dejan M., Gašić, Uroš M., Stanković, Slaviša, Berić, Tanja, "Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas synxantha Against Monilinia laxa" in Frontiers in Microbiology, 10 (2019),
https://doi.org/10.3389/fmicb.2019.02287 . .

TY  - DATA
AU  - Janakiev, Tamara
AU  - Dimkić, Ivica
AU  - Unković, Nikola
AU  - Ljaljević-Grbić, Milica
AU  - Opsenica, Dejan M.
AU  - Gašić, Uroš M.
AU  - Stanković, Slaviša
AU  - Berić, Tanja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3730
PB  - Frontiers Media S.A.
T2  - Frontiers in Microbiology
T1  - Supplementary data for the article: Janakiev, T.; Dimkić, I.; Unković, N.; Ljaljević Grbić, M.; Opsenica, D.; Gašić, U.; Stanković, S.; Berić, T. Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas Synxantha Against Monilinia Laxa. Frontiers in Microbiology 2019, 10. https://doi.org/10.3389/fmicb.2019.02287
VL  - 10
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3730
ER  - 

@misc{
author = "Janakiev, Tamara and Dimkić, Ivica and Unković, Nikola and Ljaljević-Grbić, Milica and Opsenica, Dejan M. and Gašić, Uroš M. and Stanković, Slaviša and Berić, Tanja",
year = "2019",
publisher = "Frontiers Media S.A.",
journal = "Frontiers in Microbiology",
title = "Supplementary data for the article: Janakiev, T.; Dimkić, I.; Unković, N.; Ljaljević Grbić, M.; Opsenica, D.; Gašić, U.; Stanković, S.; Berić, T. Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas Synxantha Against Monilinia Laxa. Frontiers in Microbiology 2019, 10. https://doi.org/10.3389/fmicb.2019.02287",
volume = "10",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3730"
}

Janakiev, T., Dimkić, I., Unković, N., Ljaljević-Grbić, M., Opsenica, D. M., Gašić, U. M., Stanković, S.,& Berić, T.. (2019). Supplementary data for the article: Janakiev, T.; Dimkić, I.; Unković, N.; Ljaljević Grbić, M.; Opsenica, D.; Gašić, U.; Stanković, S.; Berić, T. Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas Synxantha Against Monilinia Laxa. Frontiers in Microbiology 2019, 10. https://doi.org/10.3389/fmicb.2019.02287. in Frontiers in Microbiology
Frontiers Media S.A.., 10.
https://hdl.handle.net/21.15107/rcub_cherry_3730

Janakiev T, Dimkić I, Unković N, Ljaljević-Grbić M, Opsenica DM, Gašić UM, Stanković S, Berić T. Supplementary data for the article: Janakiev, T.; Dimkić, I.; Unković, N.; Ljaljević Grbić, M.; Opsenica, D.; Gašić, U.; Stanković, S.; Berić, T. Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas Synxantha Against Monilinia Laxa. Frontiers in Microbiology 2019, 10. https://doi.org/10.3389/fmicb.2019.02287. in Frontiers in Microbiology. 2019;10.
https://hdl.handle.net/21.15107/rcub_cherry_3730 .

Janakiev, Tamara, Dimkić, Ivica, Unković, Nikola, Ljaljević-Grbić, Milica, Opsenica, Dejan M., Gašić, Uroš M., Stanković, Slaviša, Berić, Tanja, "Supplementary data for the article: Janakiev, T.; Dimkić, I.; Unković, N.; Ljaljević Grbić, M.; Opsenica, D.; Gašić, U.; Stanković, S.; Berić, T. Phyllosphere Fungal Communities of Plum and Antifungal Activity of Indigenous Phenazine-Producing Pseudomonas Synxantha Against Monilinia Laxa. Frontiers in Microbiology 2019, 10. https://doi.org/10.3389/fmicb.2019.02287" in Frontiers in Microbiology, 10 (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3730 .

TY  - CHAP
AU  - Senerovic, Lidija
AU  - Opsenica, Dejan M.
AU  - Moric, Ivana
AU  - Aleksic, Ivana
AU  - Spasić, Marta
AU  - Vasiljević, Branka
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4274
AB  - Infective diseases have become health threat ofa global proportion due to appearance andspread of microorganisms resistant to majorityof therapeutics currently used for their treatment.Therefore, there is a constant need fordevelopment of new antimicrobial agents, aswell as novel therapeutic strategies.Quinolines and quinolones, isolated fromplants, animals, and microorganisms, havedemonstrated numerous biological activitiessuch as antimicrobial, insecticidal, antiinflammatory,antiplatelet, and antitumor. Formore than two centuries quinoline/quinolonemoiety has been used as a scaffold for drugdevelopment and even today it represents aninexhaustible inspiration for design and developmentof novel semi-synthetic or syntheticagents exhibiting broad spectrum ofbioactivities. The structural diversity ofsynthetized compounds provides high andselective activity attained through differentmechanisms of action, as well as low toxicityon human cells. This review describes quinolineand quinolone derivatives withantibacterial, antifungal, anti-virulent,antiviral, and anti-parasitic activities with thefocus on the last 10 years literature.
PB  - Springer Nature
T2  - Advances in Experimental Medicine and Biology - Advances in Microbiology, Infectious Diseases and Public Health
T1  - Quinolines and Quinolones as Antibacterial, Antifungal, Antivirulence, Antiviral and Anti-parasitic Agents
DO  - 10.1007/5584_2019_428
ER  - 

@inbook{
author = "Senerovic, Lidija and Opsenica, Dejan M. and Moric, Ivana and Aleksic, Ivana and Spasić, Marta and Vasiljević, Branka",
year = "2019",
abstract = "Infective diseases have become health threat ofa global proportion due to appearance andspread of microorganisms resistant to majorityof therapeutics currently used for their treatment.Therefore, there is a constant need fordevelopment of new antimicrobial agents, aswell as novel therapeutic strategies.Quinolines and quinolones, isolated fromplants, animals, and microorganisms, havedemonstrated numerous biological activitiessuch as antimicrobial, insecticidal, antiinflammatory,antiplatelet, and antitumor. Formore than two centuries quinoline/quinolonemoiety has been used as a scaffold for drugdevelopment and even today it represents aninexhaustible inspiration for design and developmentof novel semi-synthetic or syntheticagents exhibiting broad spectrum ofbioactivities. The structural diversity ofsynthetized compounds provides high andselective activity attained through differentmechanisms of action, as well as low toxicityon human cells. This review describes quinolineand quinolone derivatives withantibacterial, antifungal, anti-virulent,antiviral, and anti-parasitic activities with thefocus on the last 10 years literature.",
publisher = "Springer Nature",
journal = "Advances in Experimental Medicine and Biology - Advances in Microbiology, Infectious Diseases and Public Health",
booktitle = "Quinolines and Quinolones as Antibacterial, Antifungal, Antivirulence, Antiviral and Anti-parasitic Agents",
doi = "10.1007/5584_2019_428"
}

Senerovic, L., Opsenica, D. M., Moric, I., Aleksic, I., Spasić, M.,& Vasiljević, B.. (2019). Quinolines and Quinolones as Antibacterial, Antifungal, Antivirulence, Antiviral and Anti-parasitic Agents. in Advances in Experimental Medicine and Biology - Advances in Microbiology, Infectious Diseases and Public Health
Springer Nature..
https://doi.org/10.1007/5584_2019_428

Senerovic L, Opsenica DM, Moric I, Aleksic I, Spasić M, Vasiljević B. Quinolines and Quinolones as Antibacterial, Antifungal, Antivirulence, Antiviral and Anti-parasitic Agents. in Advances in Experimental Medicine and Biology - Advances in Microbiology, Infectious Diseases and Public Health. 2019;.
doi:10.1007/5584_2019_428 .

Senerovic, Lidija, Opsenica, Dejan M., Moric, Ivana, Aleksic, Ivana, Spasić, Marta, Vasiljević, Branka, "Quinolines and Quinolones as Antibacterial, Antifungal, Antivirulence, Antiviral and Anti-parasitic Agents" in Advances in Experimental Medicine and Biology - Advances in Microbiology, Infectious Diseases and Public Health (2019),
https://doi.org/10.1007/5584_2019_428 . .

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Ristivojević, Petar
AU  - Pavić, Aleksandar
AU  - Radojević, Ivana
AU  - Čomić, Ljiljana R.
AU  - Vasiljević, Branka
AU  - Opsenica, Dejan M.
AU  - Milojković-Opsenica, Dušanka
AU  - Šenerović, Lidija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2166
AB  - Ethnopharmacological relevance: Trapa natans L. (water chestnut or water caltrop) is a widespread aquatic plant, which has been cultivated for food and traditional medicine since ancient times. Pharmacological studies showed that water chestnut exhibits the wide range of biological activities, such as antimicrobial, antioxidative, analgesic, anti-inflammatory, as well as antiulcer. Aim of the study: Evaluation of anti-virulence potential and toxicity of T. natans methanol (TnM), acetone (TnA) and ethyl acetate (TnEA) leaf extracts. Materials and methods: The anti-quorum sensing activity of Tn extracts was addressed by measuring their effects on biofilm formation, swarming motility and pyocyanin and elastase production in Pseudomonas aeruginosa. Specific P. aeruginosa biosensors were used to identify which of the signaling pathways were affected. The lethal and developmental toxicity of extracts were addressed in vivo using the zebrafish (Danio rerio) model system. The phenolic composition of T. natans leafs extracts was analyzed by a linear ion trap-OrbiTrap hybrid mass spectrometer (LTQ OrbiTrapMS) and UHPLC system configured with a diode array detector (DAD) hyphenated with the triple quadrupole mass spectrometer. Results: Subinhibitory concentrations of Tn leaf extracts (0.2 MIC) inhibited pyocyanin and elastase production up to 50% and 60%, respectively, and reduced swarming zones, comparing to non-treated P. aeruginosa. TnA inhibited biofilm formation by 15%, TnM showed a stimulatory effect on biofilm formation up to 20%, while TnEA showed no effect. The bioactive concentrations of TnM and TnA were not toxic in the zebrafish model system. Twenty-two phenolic compounds were tentatively identified in TnM, where thirteen of them were identified in T. natans for the first time. Tn extracts, as well as their major components, ellagic and ferulic acids, demonstrated the ability to interfere with P. aeruginosa Las and PQS signaling pathways. Conclusions: This study demonstrates anti-virulence potential of Tn leaf extracts against medically important pathogen P. aeruginosa and confirms the ethnopharmacological application of this plant against microbial infections.
PB  - Elsevier Ireland Ltd, Clare
T2  - Journal of Ethnopharmacology
T1  - Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts
VL  - 222
SP  - 148
EP  - 158
DO  - 10.1016/j.jep.2018.05.005
ER  - 

@article{
author = "Aleksić, Ivana and Ristivojević, Petar and Pavić, Aleksandar and Radojević, Ivana and Čomić, Ljiljana R. and Vasiljević, Branka and Opsenica, Dejan M. and Milojković-Opsenica, Dušanka and Šenerović, Lidija",
year = "2018",
abstract = "Ethnopharmacological relevance: Trapa natans L. (water chestnut or water caltrop) is a widespread aquatic plant, which has been cultivated for food and traditional medicine since ancient times. Pharmacological studies showed that water chestnut exhibits the wide range of biological activities, such as antimicrobial, antioxidative, analgesic, anti-inflammatory, as well as antiulcer. Aim of the study: Evaluation of anti-virulence potential and toxicity of T. natans methanol (TnM), acetone (TnA) and ethyl acetate (TnEA) leaf extracts. Materials and methods: The anti-quorum sensing activity of Tn extracts was addressed by measuring their effects on biofilm formation, swarming motility and pyocyanin and elastase production in Pseudomonas aeruginosa. Specific P. aeruginosa biosensors were used to identify which of the signaling pathways were affected. The lethal and developmental toxicity of extracts were addressed in vivo using the zebrafish (Danio rerio) model system. The phenolic composition of T. natans leafs extracts was analyzed by a linear ion trap-OrbiTrap hybrid mass spectrometer (LTQ OrbiTrapMS) and UHPLC system configured with a diode array detector (DAD) hyphenated with the triple quadrupole mass spectrometer. Results: Subinhibitory concentrations of Tn leaf extracts (0.2 MIC) inhibited pyocyanin and elastase production up to 50% and 60%, respectively, and reduced swarming zones, comparing to non-treated P. aeruginosa. TnA inhibited biofilm formation by 15%, TnM showed a stimulatory effect on biofilm formation up to 20%, while TnEA showed no effect. The bioactive concentrations of TnM and TnA were not toxic in the zebrafish model system. Twenty-two phenolic compounds were tentatively identified in TnM, where thirteen of them were identified in T. natans for the first time. Tn extracts, as well as their major components, ellagic and ferulic acids, demonstrated the ability to interfere with P. aeruginosa Las and PQS signaling pathways. Conclusions: This study demonstrates anti-virulence potential of Tn leaf extracts against medically important pathogen P. aeruginosa and confirms the ethnopharmacological application of this plant against microbial infections.",
publisher = "Elsevier Ireland Ltd, Clare",
journal = "Journal of Ethnopharmacology",
title = "Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts",
volume = "222",
pages = "148-158",
doi = "10.1016/j.jep.2018.05.005"
}

Aleksić, I., Ristivojević, P., Pavić, A., Radojević, I., Čomić, L. R., Vasiljević, B., Opsenica, D. M., Milojković-Opsenica, D.,& Šenerović, L.. (2018). Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts. in Journal of Ethnopharmacology
Elsevier Ireland Ltd, Clare., 222, 148-158.
https://doi.org/10.1016/j.jep.2018.05.005

Aleksić I, Ristivojević P, Pavić A, Radojević I, Čomić LR, Vasiljević B, Opsenica DM, Milojković-Opsenica D, Šenerović L. Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts. in Journal of Ethnopharmacology. 2018;222:148-158.
doi:10.1016/j.jep.2018.05.005 .

Aleksić, Ivana, Ristivojević, Petar, Pavić, Aleksandar, Radojević, Ivana, Čomić, Ljiljana R., Vasiljević, Branka, Opsenica, Dejan M., Milojković-Opsenica, Dušanka, Šenerović, Lidija, "Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts" in Journal of Ethnopharmacology, 222 (2018):148-158,
https://doi.org/10.1016/j.jep.2018.05.005 . .

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Ristivojević, Petar
AU  - Pavić, Aleksandar
AU  - Radojević, Ivana
AU  - Čomić, Ljiljana R.
AU  - Vasiljević, Branka
AU  - Opsenica, Dejan M.
AU  - Milojković-Opsenica, Dušanka
AU  - Šenerović, Lidija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2932
AB  - Ethnopharmacological relevance: Trapa natans L. (water chestnut or water caltrop) is a widespread aquatic plant, which has been cultivated for food and traditional medicine since ancient times. Pharmacological studies showed that water chestnut exhibits the wide range of biological activities, such as antimicrobial, antioxidative, analgesic, anti-inflammatory, as well as antiulcer. Aim of the study: Evaluation of anti-virulence potential and toxicity of T. natans methanol (TnM), acetone (TnA) and ethyl acetate (TnEA) leaf extracts. Materials and methods: The anti-quorum sensing activity of Tn extracts was addressed by measuring their effects on biofilm formation, swarming motility and pyocyanin and elastase production in Pseudomonas aeruginosa. Specific P. aeruginosa biosensors were used to identify which of the signaling pathways were affected. The lethal and developmental toxicity of extracts were addressed in vivo using the zebrafish (Danio rerio) model system. The phenolic composition of T. natans leafs extracts was analyzed by a linear ion trap-OrbiTrap hybrid mass spectrometer (LTQ OrbiTrapMS) and UHPLC system configured with a diode array detector (DAD) hyphenated with the triple quadrupole mass spectrometer. Results: Subinhibitory concentrations of Tn leaf extracts (0.2 MIC) inhibited pyocyanin and elastase production up to 50% and 60%, respectively, and reduced swarming zones, comparing to non-treated P. aeruginosa. TnA inhibited biofilm formation by 15%, TnM showed a stimulatory effect on biofilm formation up to 20%, while TnEA showed no effect. The bioactive concentrations of TnM and TnA were not toxic in the zebrafish model system. Twenty-two phenolic compounds were tentatively identified in TnM, where thirteen of them were identified in T. natans for the first time. Tn extracts, as well as their major components, ellagic and ferulic acids, demonstrated the ability to interfere with P. aeruginosa Las and PQS signaling pathways. Conclusions: This study demonstrates anti-virulence potential of Tn leaf extracts against medically important pathogen P. aeruginosa and confirms the ethnopharmacological application of this plant against microbial infections.
PB  - Elsevier Ireland Ltd, Clare
T2  - Journal of Ethnopharmacology
T1  - Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts
VL  - 222
SP  - 148
EP  - 158
DO  - 10.1016/j.jep.2018.05.005
ER  - 

@article{
author = "Aleksić, Ivana and Ristivojević, Petar and Pavić, Aleksandar and Radojević, Ivana and Čomić, Ljiljana R. and Vasiljević, Branka and Opsenica, Dejan M. and Milojković-Opsenica, Dušanka and Šenerović, Lidija",
year = "2018",
abstract = "Ethnopharmacological relevance: Trapa natans L. (water chestnut or water caltrop) is a widespread aquatic plant, which has been cultivated for food and traditional medicine since ancient times. Pharmacological studies showed that water chestnut exhibits the wide range of biological activities, such as antimicrobial, antioxidative, analgesic, anti-inflammatory, as well as antiulcer. Aim of the study: Evaluation of anti-virulence potential and toxicity of T. natans methanol (TnM), acetone (TnA) and ethyl acetate (TnEA) leaf extracts. Materials and methods: The anti-quorum sensing activity of Tn extracts was addressed by measuring their effects on biofilm formation, swarming motility and pyocyanin and elastase production in Pseudomonas aeruginosa. Specific P. aeruginosa biosensors were used to identify which of the signaling pathways were affected. The lethal and developmental toxicity of extracts were addressed in vivo using the zebrafish (Danio rerio) model system. The phenolic composition of T. natans leafs extracts was analyzed by a linear ion trap-OrbiTrap hybrid mass spectrometer (LTQ OrbiTrapMS) and UHPLC system configured with a diode array detector (DAD) hyphenated with the triple quadrupole mass spectrometer. Results: Subinhibitory concentrations of Tn leaf extracts (0.2 MIC) inhibited pyocyanin and elastase production up to 50% and 60%, respectively, and reduced swarming zones, comparing to non-treated P. aeruginosa. TnA inhibited biofilm formation by 15%, TnM showed a stimulatory effect on biofilm formation up to 20%, while TnEA showed no effect. The bioactive concentrations of TnM and TnA were not toxic in the zebrafish model system. Twenty-two phenolic compounds were tentatively identified in TnM, where thirteen of them were identified in T. natans for the first time. Tn extracts, as well as their major components, ellagic and ferulic acids, demonstrated the ability to interfere with P. aeruginosa Las and PQS signaling pathways. Conclusions: This study demonstrates anti-virulence potential of Tn leaf extracts against medically important pathogen P. aeruginosa and confirms the ethnopharmacological application of this plant against microbial infections.",
publisher = "Elsevier Ireland Ltd, Clare",
journal = "Journal of Ethnopharmacology",
title = "Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts",
volume = "222",
pages = "148-158",
doi = "10.1016/j.jep.2018.05.005"
}

Aleksić, I., Ristivojević, P., Pavić, A., Radojević, I., Čomić, L. R., Vasiljević, B., Opsenica, D. M., Milojković-Opsenica, D.,& Šenerović, L.. (2018). Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts. in Journal of Ethnopharmacology
Elsevier Ireland Ltd, Clare., 222, 148-158.
https://doi.org/10.1016/j.jep.2018.05.005

Aleksić I, Ristivojević P, Pavić A, Radojević I, Čomić LR, Vasiljević B, Opsenica DM, Milojković-Opsenica D, Šenerović L. Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts. in Journal of Ethnopharmacology. 2018;222:148-158.
doi:10.1016/j.jep.2018.05.005 .

Aleksić, Ivana, Ristivojević, Petar, Pavić, Aleksandar, Radojević, Ivana, Čomić, Ljiljana R., Vasiljević, Branka, Opsenica, Dejan M., Milojković-Opsenica, Dušanka, Šenerović, Lidija, "Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts" in Journal of Ethnopharmacology, 222 (2018):148-158,
https://doi.org/10.1016/j.jep.2018.05.005 . .

TY  - DATA
AU  - Aleksić, Ivana
AU  - Ristivojević, Petar
AU  - Pavić, Aleksandar
AU  - Radojević, Ivana
AU  - Čomić, Ljiljana R.
AU  - Vasiljević, Branka
AU  - Opsenica, Dejan M.
AU  - Milojković-Opsenica, Dušanka
AU  - Šenerović, Lidija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2933
PB  - Elsevier Ireland Ltd, Clare
T2  - Journal of Ethnopharmacology
T1  - Supplementary data for the article: Aleksic, I.; Ristivojevic, P.; Pavic, A.; Radojević, I.; Čomić, L. R.; Vasiljevic, B.; Opsenica, D.; Milojković-Opsenica, D.; Senerovic, L. Anti-Quorum Sensing Activity, Toxicity in Zebrafish (Danio Rerio) Embryos and Phytochemical Characterization of Trapa Natans Leaf Extracts. Journal of Ethnopharmacology 2018, 222, 148–158. https://doi.org/10.1016/j.jep.2018.05.005
DO  - 10.1016/j.jep.2018.05.005
ER  - 

@misc{
author = "Aleksić, Ivana and Ristivojević, Petar and Pavić, Aleksandar and Radojević, Ivana and Čomić, Ljiljana R. and Vasiljević, Branka and Opsenica, Dejan M. and Milojković-Opsenica, Dušanka and Šenerović, Lidija",
year = "2018",
publisher = "Elsevier Ireland Ltd, Clare",
journal = "Journal of Ethnopharmacology",
title = "Supplementary data for the article: Aleksic, I.; Ristivojevic, P.; Pavic, A.; Radojević, I.; Čomić, L. R.; Vasiljevic, B.; Opsenica, D.; Milojković-Opsenica, D.; Senerovic, L. Anti-Quorum Sensing Activity, Toxicity in Zebrafish (Danio Rerio) Embryos and Phytochemical Characterization of Trapa Natans Leaf Extracts. Journal of Ethnopharmacology 2018, 222, 148–158. https://doi.org/10.1016/j.jep.2018.05.005",
doi = "10.1016/j.jep.2018.05.005"
}

Aleksić, I., Ristivojević, P., Pavić, A., Radojević, I., Čomić, L. R., Vasiljević, B., Opsenica, D. M., Milojković-Opsenica, D.,& Šenerović, L.. (2018). Supplementary data for the article: Aleksic, I.; Ristivojevic, P.; Pavic, A.; Radojević, I.; Čomić, L. R.; Vasiljevic, B.; Opsenica, D.; Milojković-Opsenica, D.; Senerovic, L. Anti-Quorum Sensing Activity, Toxicity in Zebrafish (Danio Rerio) Embryos and Phytochemical Characterization of Trapa Natans Leaf Extracts. Journal of Ethnopharmacology 2018, 222, 148–158. https://doi.org/10.1016/j.jep.2018.05.005. in Journal of Ethnopharmacology
Elsevier Ireland Ltd, Clare..
https://doi.org/10.1016/j.jep.2018.05.005

Aleksić I, Ristivojević P, Pavić A, Radojević I, Čomić LR, Vasiljević B, Opsenica DM, Milojković-Opsenica D, Šenerović L. Supplementary data for the article: Aleksic, I.; Ristivojevic, P.; Pavic, A.; Radojević, I.; Čomić, L. R.; Vasiljevic, B.; Opsenica, D.; Milojković-Opsenica, D.; Senerovic, L. Anti-Quorum Sensing Activity, Toxicity in Zebrafish (Danio Rerio) Embryos and Phytochemical Characterization of Trapa Natans Leaf Extracts. Journal of Ethnopharmacology 2018, 222, 148–158. https://doi.org/10.1016/j.jep.2018.05.005. in Journal of Ethnopharmacology. 2018;.
doi:10.1016/j.jep.2018.05.005 .

Aleksić, Ivana, Ristivojević, Petar, Pavić, Aleksandar, Radojević, Ivana, Čomić, Ljiljana R., Vasiljević, Branka, Opsenica, Dejan M., Milojković-Opsenica, Dušanka, Šenerović, Lidija, "Supplementary data for the article: Aleksic, I.; Ristivojevic, P.; Pavic, A.; Radojević, I.; Čomić, L. R.; Vasiljevic, B.; Opsenica, D.; Milojković-Opsenica, D.; Senerovic, L. Anti-Quorum Sensing Activity, Toxicity in Zebrafish (Danio Rerio) Embryos and Phytochemical Characterization of Trapa Natans Leaf Extracts. Journal of Ethnopharmacology 2018, 222, 148–158. https://doi.org/10.1016/j.jep.2018.05.005" in Journal of Ethnopharmacology (2018),
https://doi.org/10.1016/j.jep.2018.05.005 . .

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Šegan, Sandra B.
AU  - Andrić, Filip
AU  - Zlatović, Mario
AU  - Morić, Ivana
AU  - Opsenica, Dejan M.
AU  - Šenerović, Lidija
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2461
AB  - Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC)  gt  400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.
PB  - Amer Chemical Soc, Washington
T2  - ACS Chemical Biology
T1  - Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa
VL  - 12
IS  - 5
SP  - 1425
EP  - 1434
DO  - 10.1021/acschembio.6b01149
ER  - 

@article{
author = "Aleksić, Ivana and Šegan, Sandra B. and Andrić, Filip and Zlatović, Mario and Morić, Ivana and Opsenica, Dejan M. and Šenerović, Lidija",
year = "2017",
abstract = "Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC)  gt  400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS Chemical Biology",
title = "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa",
volume = "12",
number = "5",
pages = "1425-1434",
doi = "10.1021/acschembio.6b01149"
}

Aleksić, I., Šegan, S. B., Andrić, F., Zlatović, M., Morić, I., Opsenica, D. M.,& Šenerović, L.. (2017). Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in ACS Chemical Biology
Amer Chemical Soc, Washington., 12(5), 1425-1434.
https://doi.org/10.1021/acschembio.6b01149

Aleksić I, Šegan SB, Andrić F, Zlatović M, Morić I, Opsenica DM, Šenerović L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in ACS Chemical Biology. 2017;12(5):1425-1434.
doi:10.1021/acschembio.6b01149 .

Aleksić, Ivana, Šegan, Sandra B., Andrić, Filip, Zlatović, Mario, Morić, Ivana, Opsenica, Dejan M., Šenerović, Lidija, "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa" in ACS Chemical Biology, 12, no. 5 (2017):1425-1434,
https://doi.org/10.1021/acschembio.6b01149 . .

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Šegan, Sandra B.
AU  - Andrić, Filip
AU  - Zlatović, Mario
AU  - Morić, Ivana
AU  - Opsenica, Dejan M.
AU  - Šenerović, Lidija
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3089
AB  - Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC)  gt  400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.
PB  - Amer Chemical Soc, Washington
T2  - ACS Chemical Biology
T1  - Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa
VL  - 12
IS  - 5
SP  - 1425
EP  - 1434
DO  - 10.1021/acschembio.6b01149
ER  - 

@article{
author = "Aleksić, Ivana and Šegan, Sandra B. and Andrić, Filip and Zlatović, Mario and Morić, Ivana and Opsenica, Dejan M. and Šenerović, Lidija",
year = "2017",
abstract = "Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC)  gt  400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS Chemical Biology",
title = "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa",
volume = "12",
number = "5",
pages = "1425-1434",
doi = "10.1021/acschembio.6b01149"
}

Aleksić, I., Šegan, S. B., Andrić, F., Zlatović, M., Morić, I., Opsenica, D. M.,& Šenerović, L.. (2017). Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in ACS Chemical Biology
Amer Chemical Soc, Washington., 12(5), 1425-1434.
https://doi.org/10.1021/acschembio.6b01149

Aleksić I, Šegan SB, Andrić F, Zlatović M, Morić I, Opsenica DM, Šenerović L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in ACS Chemical Biology. 2017;12(5):1425-1434.
doi:10.1021/acschembio.6b01149 .

Aleksić, Ivana, Šegan, Sandra B., Andrić, Filip, Zlatović, Mario, Morić, Ivana, Opsenica, Dejan M., Šenerović, Lidija, "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa" in ACS Chemical Biology, 12, no. 5 (2017):1425-1434,
https://doi.org/10.1021/acschembio.6b01149 . .

TY  - DATA
AU  - Aleksić, Ivana
AU  - Šegan, Sandra B.
AU  - Andrić, Filip
AU  - Zlatović, Mario
AU  - Morić, Ivana
AU  - Opsenica, Dejan M.
AU  - Šenerović, Lidija
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3090
PB  - Amer Chemical Soc, Washington
T2  - ACS Chemical Biology
T1  - Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3090
ER  - 

@misc{
author = "Aleksić, Ivana and Šegan, Sandra B. and Andrić, Filip and Zlatović, Mario and Morić, Ivana and Opsenica, Dejan M. and Šenerović, Lidija",
year = "2017",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS Chemical Biology",
title = "Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3090"
}

Aleksić, I., Šegan, S. B., Andrić, F., Zlatović, M., Morić, I., Opsenica, D. M.,& Šenerović, L.. (2017). Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149. in ACS Chemical Biology
Amer Chemical Soc, Washington..
https://hdl.handle.net/21.15107/rcub_cherry_3090

Aleksić I, Šegan SB, Andrić F, Zlatović M, Morić I, Opsenica DM, Šenerović L. Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149. in ACS Chemical Biology. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3090 .

Aleksić, Ivana, Šegan, Sandra B., Andrić, Filip, Zlatović, Mario, Morić, Ivana, Opsenica, Dejan M., Šenerović, Lidija, "Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149" in ACS Chemical Biology (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3090 .

TY  - DATA
AU  - Nikolić, Stefan
AU  - Opsenica, Dejan M.
AU  - Filipović, Vuk
AU  - Dojčinović, Biljana P.
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3429
PB  - Amer Chemical Soc, Washington
T2  - Organometallics
T1  - Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3429
ER  - 

@misc{
author = "Nikolić, Stefan and Opsenica, Dejan M. and Filipović, Vuk and Dojčinović, Biljana P. and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2015",
publisher = "Amer Chemical Soc, Washington",
journal = "Organometallics",
title = "Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3429"
}

Nikolić, S., Opsenica, D. M., Filipović, V., Dojčinović, B. P., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S.. (2015). Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041. in Organometallics
Amer Chemical Soc, Washington..
https://hdl.handle.net/21.15107/rcub_cherry_3429

Nikolić S, Opsenica DM, Filipović V, Dojčinović BP, Aranđelović S, Radulović S, Grgurić-Šipka S. Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041. in Organometallics. 2015;.
https://hdl.handle.net/21.15107/rcub_cherry_3429 .

Nikolić, Stefan, Opsenica, Dejan M., Filipović, Vuk, Dojčinović, Biljana P., Aranđelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, "Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041" in Organometallics (2015),
https://hdl.handle.net/21.15107/rcub_cherry_3429 .

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Opsenica, Dejan M.
AU  - Filipović, Vuk
AU  - Dojčinović, Biljana P.
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1746
AB  - Two p-cymenerutheniumchlorido complexes with thiourea derivative of 7-chloroquinoline (C1) and pyridine-3-imidazole (C2) were synthesized starting from [(eta(6)-p-cymene)RuCl2](2) and corresponding ligands. The structures of complexes were determined with elemental analysis and IR, ESIMS, H-1 and C-13{H-1} NMR, and 2D H-1-N-15 correlation NMR spectroscopy. Cytotoxic activities examined by the MTT assay were performed in five human neoplastic cell lines (HeLa, K562, A549, MDA-MB-231, EA.hy926) and one nontumor human fetal lung fibroblast cell line (MRC-5). Tested complexes exhibited low micromolar activities with IC50 in the range 11.03-56.45 mu M, while ligands L1 and L2 were significantly less active. Complex C1 showed cytoselective activity toward the K562 cell line (IC50 = 11.03 +/- 1.39 mu M) and was 3 times less active against the nontumor MRC-5 cell line. Flow cytometry analysis indicated that complexes C1 and C2 after 24 h treatment caused a concentration-dependent increase of the apoptotic sub-G1 fraction (up to 18.4%), comparable to cis-diamminedichloridoplatinum(II) (cisplatin, CDDP), although without other substantial alterations of the cell cycle. A drug-accumulation and DNA-binding study performed by ICP-MS in the K562 cell line revealed that complex C1 had a high intracellular uptake (1.38 mu g Ru/10 (6) cells), which significantly exceeded the intracellular uptake levels of CDDP (0.29 mu g Pt/10 (6) cells) and C2 (0.08 mu g Ru/10 (6) cells). However, both ruthenium complexes C1 and C2 bind to cellular DNA less efficiently in comparison to CDDP. The structure-activity relationship clearly suggested that introduction of a 7-chloroquinoline moiety in the ruthenium(II)-p-cymene complex significantly contributed to the intracellular uptake of C1 and higher cytotoxicity and cytoselectivity.
PB  - Amer Chemical Soc, Washington
T2  - Organometallics
T1  - Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes
VL  - 34
IS  - 14
SP  - 3464
EP  - 3473
DO  - 10.1021/acs.organomet.5b00041
ER  - 

@article{
author = "Nikolić, Stefan and Opsenica, Dejan M. and Filipović, Vuk and Dojčinović, Biljana P. and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2015",
abstract = "Two p-cymenerutheniumchlorido complexes with thiourea derivative of 7-chloroquinoline (C1) and pyridine-3-imidazole (C2) were synthesized starting from [(eta(6)-p-cymene)RuCl2](2) and corresponding ligands. The structures of complexes were determined with elemental analysis and IR, ESIMS, H-1 and C-13{H-1} NMR, and 2D H-1-N-15 correlation NMR spectroscopy. Cytotoxic activities examined by the MTT assay were performed in five human neoplastic cell lines (HeLa, K562, A549, MDA-MB-231, EA.hy926) and one nontumor human fetal lung fibroblast cell line (MRC-5). Tested complexes exhibited low micromolar activities with IC50 in the range 11.03-56.45 mu M, while ligands L1 and L2 were significantly less active. Complex C1 showed cytoselective activity toward the K562 cell line (IC50 = 11.03 +/- 1.39 mu M) and was 3 times less active against the nontumor MRC-5 cell line. Flow cytometry analysis indicated that complexes C1 and C2 after 24 h treatment caused a concentration-dependent increase of the apoptotic sub-G1 fraction (up to 18.4%), comparable to cis-diamminedichloridoplatinum(II) (cisplatin, CDDP), although without other substantial alterations of the cell cycle. A drug-accumulation and DNA-binding study performed by ICP-MS in the K562 cell line revealed that complex C1 had a high intracellular uptake (1.38 mu g Ru/10 (6) cells), which significantly exceeded the intracellular uptake levels of CDDP (0.29 mu g Pt/10 (6) cells) and C2 (0.08 mu g Ru/10 (6) cells). However, both ruthenium complexes C1 and C2 bind to cellular DNA less efficiently in comparison to CDDP. The structure-activity relationship clearly suggested that introduction of a 7-chloroquinoline moiety in the ruthenium(II)-p-cymene complex significantly contributed to the intracellular uptake of C1 and higher cytotoxicity and cytoselectivity.",
publisher = "Amer Chemical Soc, Washington",
journal = "Organometallics",
title = "Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes",
volume = "34",
number = "14",
pages = "3464-3473",
doi = "10.1021/acs.organomet.5b00041"
}

Nikolić, S., Opsenica, D. M., Filipović, V., Dojčinović, B. P., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S.. (2015). Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. in Organometallics
Amer Chemical Soc, Washington., 34(14), 3464-3473.
https://doi.org/10.1021/acs.organomet.5b00041

Nikolić S, Opsenica DM, Filipović V, Dojčinović BP, Aranđelović S, Radulović S, Grgurić-Šipka S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. in Organometallics. 2015;34(14):3464-3473.
doi:10.1021/acs.organomet.5b00041 .

Nikolić, Stefan, Opsenica, Dejan M., Filipović, Vuk, Dojčinović, Biljana P., Aranđelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, "Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes" in Organometallics, 34, no. 14 (2015):3464-3473,
https://doi.org/10.1021/acs.organomet.5b00041 . .

TY  - JOUR
AU  - Opsenica, Dejan M.
AU  - Radivojević, Jelena
AU  - Matić, Ivana Z.
AU  - Štajner, Tijana
AU  - Knezevic-Usaj, Slavica
AU  - Đurković-Đaković, Olgica
AU  - Šolaja, Bogdan A.
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2010
AB  - New cyclohexylidene 1,2,4,5-tetraoxanes with polar guanidine and urea based groups were synthesized and evaluated for their antimalarial activity against chloroquine resistant and susceptible Plasmodium falciparum strains. The derivatives showed moderate, nM range antimalarial activities and low cytotoxicity. The N-phenylurea derivative 24 exhibited the best resistance indices (RIW2 = 0.44, RITM91C235 = 0.80) and was not toxic against human normal peripheral blood mononuclear cells (IC50  gt  200 mu M). Seven derivatives were tested in vitro against four human cancer cell lines and they demonstrated high selectivity toward leukaemia K562 cells. One compound, derivative 21 with a primary amino group, was the first tetraoxane tested in vivo against Toxoplasma gondii as another apicomplexan parasite. Subcutaneous administration at a dose of 10 mg kg(-1) day(-1) for 8 days allowed the survival of 20 % of infected mice, thus demonstrating the high potential of tetraoxanes for the treatment of apicomplexan parasites.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules
VL  - 80
IS  - 11
SP  - 1339
DO  - 10.2298/JSC150430063O
ER  - 

@article{
author = "Opsenica, Dejan M. and Radivojević, Jelena and Matić, Ivana Z. and Štajner, Tijana and Knezevic-Usaj, Slavica and Đurković-Đaković, Olgica and Šolaja, Bogdan A.",
year = "2015",
abstract = "New cyclohexylidene 1,2,4,5-tetraoxanes with polar guanidine and urea based groups were synthesized and evaluated for their antimalarial activity against chloroquine resistant and susceptible Plasmodium falciparum strains. The derivatives showed moderate, nM range antimalarial activities and low cytotoxicity. The N-phenylurea derivative 24 exhibited the best resistance indices (RIW2 = 0.44, RITM91C235 = 0.80) and was not toxic against human normal peripheral blood mononuclear cells (IC50  gt  200 mu M). Seven derivatives were tested in vitro against four human cancer cell lines and they demonstrated high selectivity toward leukaemia K562 cells. One compound, derivative 21 with a primary amino group, was the first tetraoxane tested in vivo against Toxoplasma gondii as another apicomplexan parasite. Subcutaneous administration at a dose of 10 mg kg(-1) day(-1) for 8 days allowed the survival of 20 % of infected mice, thus demonstrating the high potential of tetraoxanes for the treatment of apicomplexan parasites.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules",
volume = "80",
number = "11",
pages = "1339",
doi = "10.2298/JSC150430063O"
}

Opsenica, D. M., Radivojević, J., Matić, I. Z., Štajner, T., Knezevic-Usaj, S., Đurković-Đaković, O.,& Šolaja, B. A.. (2015). Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 80(11), 1339.
https://doi.org/10.2298/JSC150430063O

Opsenica DM, Radivojević J, Matić IZ, Štajner T, Knezevic-Usaj S, Đurković-Đaković O, Šolaja BA. Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules. in Journal of the Serbian Chemical Society. 2015;80(11):1339.
doi:10.2298/JSC150430063O .

Opsenica, Dejan M., Radivojević, Jelena, Matić, Ivana Z., Štajner, Tijana, Knezevic-Usaj, Slavica, Đurković-Đaković, Olgica, Šolaja, Bogdan A., "Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules" in Journal of the Serbian Chemical Society, 80, no. 11 (2015):1339,
https://doi.org/10.2298/JSC150430063O . .

TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Terzić-Jovanović, Nataša
AU  - Milojković-Opsenica, Dušanka
AU  - Trifković, Jelena
AU  - Šolaja, Bogdan A.
AU  - Opsenica, Dejan M.
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1795
AB  - The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO). (c) 2014 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters
VL  - 97
SP  - 178
EP  - 183
DO  - 10.1016/j.jpba.2014.04.029
ER  - 

@article{
author = "Šegan, Sandra B. and Terzić-Jovanović, Nataša and Milojković-Opsenica, Dušanka and Trifković, Jelena and Šolaja, Bogdan A. and Opsenica, Dejan M.",
year = "2014",
abstract = "The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO). (c) 2014 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters",
volume = "97",
pages = "178-183",
doi = "10.1016/j.jpba.2014.04.029"
}

Šegan, S. B., Terzić-Jovanović, N., Milojković-Opsenica, D., Trifković, J., Šolaja, B. A.,& Opsenica, D. M.. (2014). Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier Science Bv, Amsterdam., 97, 178-183.
https://doi.org/10.1016/j.jpba.2014.04.029

Šegan SB, Terzić-Jovanović N, Milojković-Opsenica D, Trifković J, Šolaja BA, Opsenica DM. Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. in Journal of Pharmaceutical and Biomedical Analysis. 2014;97:178-183.
doi:10.1016/j.jpba.2014.04.029 .

Šegan, Sandra B., Terzić-Jovanović, Nataša, Milojković-Opsenica, Dušanka, Trifković, Jelena, Šolaja, Bogdan A., Opsenica, Dejan M., "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters" in Journal of Pharmaceutical and Biomedical Analysis, 97 (2014):178-183,
https://doi.org/10.1016/j.jpba.2014.04.029 . .

TY  - JOUR
AU  - Videnović, Milica
AU  - Opsenica, Dejan M.
AU  - Burnett, James C.
AU  - Gomba, Laura
AU  - Nuss, Jonathan E.
AU  - Selaković, Života
AU  - Konstantinović, Jelena M.
AU  - Krstić-Ristivojević, Maja
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Sciotti, Richard J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan A.
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1781
AB  - Significantly more potent second generation 4-amino-7-chloroquinoline (4,7-ACQ) based inhibitors of the botulinum neurotoxin serotype A (BoNT/A) light chain were synthesized. Introducing an amino group at the C(3) position of the cholate component markedly increased potency (IC50 values for such derivatives ranged from 0.81 to 2.27 mu M). Two additional subclasses were prepared: bis(steroidal)-4,7-ACQ derivatives and bis(4,7-ACQ)cholate derivatives; both classes provided inhibitors with nanomolar-range potencies (e.g., the K-i of compound 67 is 0.10 mu M). During BoNT/A challenge using primary neurons, select derivatives protected SNAP-25 by up to 89%. Docking simulations were performed to rationalize the compounds' in vitro potencies. In addition to specific residue contacts, coordination of the enzyme's catalytic zinc and expulsion of the enzyme's catalytic water were a consistent theme. With respect to antimalarial activity, the compounds provided better IC90 activities against chloroquine resistant (CQR) malaria than CQ, and seven compounds were more active than mefloquine against CQR strain W2.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria
VL  - 57
IS  - 10
SP  - 4134
EP  - 4153
DO  - 10.1021/jm500033r
ER  - 

@article{
author = "Videnović, Milica and Opsenica, Dejan M. and Burnett, James C. and Gomba, Laura and Nuss, Jonathan E. and Selaković, Života and Konstantinović, Jelena M. and Krstić-Ristivojević, Maja and Šegan, Sandra B. and Zlatović, Mario and Sciotti, Richard J. and Bavari, Sina and Šolaja, Bogdan A.",
year = "2014",
abstract = "Significantly more potent second generation 4-amino-7-chloroquinoline (4,7-ACQ) based inhibitors of the botulinum neurotoxin serotype A (BoNT/A) light chain were synthesized. Introducing an amino group at the C(3) position of the cholate component markedly increased potency (IC50 values for such derivatives ranged from 0.81 to 2.27 mu M). Two additional subclasses were prepared: bis(steroidal)-4,7-ACQ derivatives and bis(4,7-ACQ)cholate derivatives; both classes provided inhibitors with nanomolar-range potencies (e.g., the K-i of compound 67 is 0.10 mu M). During BoNT/A challenge using primary neurons, select derivatives protected SNAP-25 by up to 89%. Docking simulations were performed to rationalize the compounds' in vitro potencies. In addition to specific residue contacts, coordination of the enzyme's catalytic zinc and expulsion of the enzyme's catalytic water were a consistent theme. With respect to antimalarial activity, the compounds provided better IC90 activities against chloroquine resistant (CQR) malaria than CQ, and seven compounds were more active than mefloquine against CQR strain W2.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria",
volume = "57",
number = "10",
pages = "4134-4153",
doi = "10.1021/jm500033r"
}

Videnović, M., Opsenica, D. M., Burnett, J. C., Gomba, L., Nuss, J. E., Selaković, Ž., Konstantinović, J. M., Krstić-Ristivojević, M., Šegan, S. B., Zlatović, M., Sciotti, R. J., Bavari, S.,& Šolaja, B. A.. (2014). Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria. in Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 57(10), 4134-4153.
https://doi.org/10.1021/jm500033r

Videnović M, Opsenica DM, Burnett JC, Gomba L, Nuss JE, Selaković Ž, Konstantinović JM, Krstić-Ristivojević M, Šegan SB, Zlatović M, Sciotti RJ, Bavari S, Šolaja BA. Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria. in Journal of Medicinal Chemistry. 2014;57(10):4134-4153.
doi:10.1021/jm500033r .

Videnović, Milica, Opsenica, Dejan M., Burnett, James C., Gomba, Laura, Nuss, Jonathan E., Selaković, Života, Konstantinović, Jelena M., Krstić-Ristivojević, Maja, Šegan, Sandra B., Zlatović, Mario, Sciotti, Richard J., Bavari, Sina, Šolaja, Bogdan A., "Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria" in Journal of Medicinal Chemistry, 57, no. 10 (2014):4134-4153,
https://doi.org/10.1021/jm500033r . .

TY  - JOUR
AU  - Reljic, Zorica
AU  - Zlatović, Mario
AU  - Savic-Radojevic, Ana
AU  - Pekmezovic, Tatjana
AU  - Djukanovic, Ljubica
AU  - Matic, Marija
AU  - Pljesa-Ercegovac, Marija
AU  - Mimic-Oka, Jasmina
AU  - Opsenica, Dejan M.
AU  - Simić, Tatjana
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1842
AB  - Although recent data suggest aristolochic acid as a putative cause of Balkan endemic nephropathy (BEN), evidence also exists in favor of ochratoxin A (OTA) exposure as risk factor for the disease. The potential role of xenobiotic metabolizing enzymes, such as the glutathione transferases (GSTs), in OTA biotransformation is based on OTA glutathione adducts (OTHQ-SG and OTB-SG) in blood and urine of BEN patients. We aimed to analyze the association between common GSTA1, GSTM1, GSTT1, and GSTP1 polymorphisms and BEN susceptibility, and thereafter performed an in silico simulation of particular GST enzymes potentially involved in OTA transformations. GSTA1, GSTM1, GSTT1 and GSTP1 genotypes were determined in 207 BEN patients and 138 non-BEN healthy individuals from endemic regions by polymerase chain reaction (PCR). Molecular modeling in silico was performed for GSTA1 protein. Among the GST polymorphisms tested, only GSTA1 was significantly associated with a higher risk of BEN. Namely, carriers of the GSTA1*B gene variant, associated with lower transcriptional activation, were at a 1.6-fold higher BEN risk than those carrying the homozygous GSTA1*A/*A genotype (OR = 1.6; p = 0.037). In in silico modeling, we found four structures, two OTB-SG and two OTHQ-SG, bound in a GSTA1 monomer. We found that GSTA1 polymorphism was associated with increased risk of BEN, and suggested, according to the in silico simulation, that GSTA1-1 might be involved in catalyzing the formation of OTHQ-SG and OTB-SG conjugates.
PB  - Mdpi Ag, Basel
T2  - Toxins
T1  - Is Increased Susceptibility to Balkan Endemic Nephropathy in Carriers of Common GSTA1 (*A/*B) Polymorphism Linked with the Catalytic Role of GSTA1 in Ochratoxin A Biotransformation? Serbian Case Control Study and In Silico Analysis
VL  - 6
IS  - 8
SP  - 2348
EP  - 2362
DO  - 10.3390/toxins6082348
ER  - 

@article{
author = "Reljic, Zorica and Zlatović, Mario and Savic-Radojevic, Ana and Pekmezovic, Tatjana and Djukanovic, Ljubica and Matic, Marija and Pljesa-Ercegovac, Marija and Mimic-Oka, Jasmina and Opsenica, Dejan M. and Simić, Tatjana",
year = "2014",
abstract = "Although recent data suggest aristolochic acid as a putative cause of Balkan endemic nephropathy (BEN), evidence also exists in favor of ochratoxin A (OTA) exposure as risk factor for the disease. The potential role of xenobiotic metabolizing enzymes, such as the glutathione transferases (GSTs), in OTA biotransformation is based on OTA glutathione adducts (OTHQ-SG and OTB-SG) in blood and urine of BEN patients. We aimed to analyze the association between common GSTA1, GSTM1, GSTT1, and GSTP1 polymorphisms and BEN susceptibility, and thereafter performed an in silico simulation of particular GST enzymes potentially involved in OTA transformations. GSTA1, GSTM1, GSTT1 and GSTP1 genotypes were determined in 207 BEN patients and 138 non-BEN healthy individuals from endemic regions by polymerase chain reaction (PCR). Molecular modeling in silico was performed for GSTA1 protein. Among the GST polymorphisms tested, only GSTA1 was significantly associated with a higher risk of BEN. Namely, carriers of the GSTA1*B gene variant, associated with lower transcriptional activation, were at a 1.6-fold higher BEN risk than those carrying the homozygous GSTA1*A/*A genotype (OR = 1.6; p = 0.037). In in silico modeling, we found four structures, two OTB-SG and two OTHQ-SG, bound in a GSTA1 monomer. We found that GSTA1 polymorphism was associated with increased risk of BEN, and suggested, according to the in silico simulation, that GSTA1-1 might be involved in catalyzing the formation of OTHQ-SG and OTB-SG conjugates.",
publisher = "Mdpi Ag, Basel",
journal = "Toxins",
title = "Is Increased Susceptibility to Balkan Endemic Nephropathy in Carriers of Common GSTA1 (*A/*B) Polymorphism Linked with the Catalytic Role of GSTA1 in Ochratoxin A Biotransformation? Serbian Case Control Study and In Silico Analysis",
volume = "6",
number = "8",
pages = "2348-2362",
doi = "10.3390/toxins6082348"
}

Reljic, Z., Zlatović, M., Savic-Radojevic, A., Pekmezovic, T., Djukanovic, L., Matic, M., Pljesa-Ercegovac, M., Mimic-Oka, J., Opsenica, D. M.,& Simić, T.. (2014). Is Increased Susceptibility to Balkan Endemic Nephropathy in Carriers of Common GSTA1 (*A/*B) Polymorphism Linked with the Catalytic Role of GSTA1 in Ochratoxin A Biotransformation? Serbian Case Control Study and In Silico Analysis. in Toxins
Mdpi Ag, Basel., 6(8), 2348-2362.
https://doi.org/10.3390/toxins6082348

Reljic Z, Zlatović M, Savic-Radojevic A, Pekmezovic T, Djukanovic L, Matic M, Pljesa-Ercegovac M, Mimic-Oka J, Opsenica DM, Simić T. Is Increased Susceptibility to Balkan Endemic Nephropathy in Carriers of Common GSTA1 (*A/*B) Polymorphism Linked with the Catalytic Role of GSTA1 in Ochratoxin A Biotransformation? Serbian Case Control Study and In Silico Analysis. in Toxins. 2014;6(8):2348-2362.
doi:10.3390/toxins6082348 .

Reljic, Zorica, Zlatović, Mario, Savic-Radojevic, Ana, Pekmezovic, Tatjana, Djukanovic, Ljubica, Matic, Marija, Pljesa-Ercegovac, Marija, Mimic-Oka, Jasmina, Opsenica, Dejan M., Simić, Tatjana, "Is Increased Susceptibility to Balkan Endemic Nephropathy in Carriers of Common GSTA1 (*A/*B) Polymorphism Linked with the Catalytic Role of GSTA1 in Ochratoxin A Biotransformation? Serbian Case Control Study and In Silico Analysis" in Toxins, 6, no. 8 (2014):2348-2362,
https://doi.org/10.3390/toxins6082348 . .

TY  - DATA
AU  - Šegan, Sandra B.
AU  - Trifković, Jelena
AU  - Verbić, Tatjana
AU  - Opsenica, Dejan M.
AU  - Zlatović, Mario
AU  - Burnett, James
AU  - Šolaja, Bogdan A.
AU  - Milojković-Opsenica, Dušanka
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3477
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Supplementary data for article: Šegan, S. B.; Trifković, J.; Verbić, T.; Opsenica, D. M.; Zlatović, M.; Burnett, J.; Šolaja, B. A.; Milojković-Opsenica, D. Correlation between Structure, Retention, Property, and Activity of Biologically Relevant 1,7-Bis(Aminoalkyl)Diazachrysene Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2013, 72, 231–239. https://doi.org/10.1016/j.jpba.2012.08.025
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3477
ER  - 

@misc{
author = "Šegan, Sandra B. and Trifković, Jelena and Verbić, Tatjana and Opsenica, Dejan M. and Zlatović, Mario and Burnett, James and Šolaja, Bogdan A. and Milojković-Opsenica, Dušanka",
year = "2013",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Supplementary data for article: Šegan, S. B.; Trifković, J.; Verbić, T.; Opsenica, D. M.; Zlatović, M.; Burnett, J.; Šolaja, B. A.; Milojković-Opsenica, D. Correlation between Structure, Retention, Property, and Activity of Biologically Relevant 1,7-Bis(Aminoalkyl)Diazachrysene Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2013, 72, 231–239. https://doi.org/10.1016/j.jpba.2012.08.025",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3477"
}

Šegan, S. B., Trifković, J., Verbić, T., Opsenica, D. M., Zlatović, M., Burnett, J., Šolaja, B. A.,& Milojković-Opsenica, D.. (2013). Supplementary data for article: Šegan, S. B.; Trifković, J.; Verbić, T.; Opsenica, D. M.; Zlatović, M.; Burnett, J.; Šolaja, B. A.; Milojković-Opsenica, D. Correlation between Structure, Retention, Property, and Activity of Biologically Relevant 1,7-Bis(Aminoalkyl)Diazachrysene Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2013, 72, 231–239. https://doi.org/10.1016/j.jpba.2012.08.025. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier Science Bv, Amsterdam..
https://hdl.handle.net/21.15107/rcub_cherry_3477

Šegan SB, Trifković J, Verbić T, Opsenica DM, Zlatović M, Burnett J, Šolaja BA, Milojković-Opsenica D. Supplementary data for article: Šegan, S. B.; Trifković, J.; Verbić, T.; Opsenica, D. M.; Zlatović, M.; Burnett, J.; Šolaja, B. A.; Milojković-Opsenica, D. Correlation between Structure, Retention, Property, and Activity of Biologically Relevant 1,7-Bis(Aminoalkyl)Diazachrysene Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2013, 72, 231–239. https://doi.org/10.1016/j.jpba.2012.08.025. in Journal of Pharmaceutical and Biomedical Analysis. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3477 .

Šegan, Sandra B., Trifković, Jelena, Verbić, Tatjana, Opsenica, Dejan M., Zlatović, Mario, Burnett, James, Šolaja, Bogdan A., Milojković-Opsenica, Dušanka, "Supplementary data for article: Šegan, S. B.; Trifković, J.; Verbić, T.; Opsenica, D. M.; Zlatović, M.; Burnett, J.; Šolaja, B. A.; Milojković-Opsenica, D. Correlation between Structure, Retention, Property, and Activity of Biologically Relevant 1,7-Bis(Aminoalkyl)Diazachrysene Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2013, 72, 231–239. https://doi.org/10.1016/j.jpba.2012.08.025" in Journal of Pharmaceutical and Biomedical Analysis (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3477 .

TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Trifković, Jelena
AU  - Verbić, Tatjana
AU  - Opsenica, Dejan M.
AU  - Zlatović, Mario
AU  - Burnett, James C.
AU  - Šolaja, Bogdan A.
AU  - Milojković-Opsenica, Dušanka
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1555
AB  - The physicochemical properties, retention parameters (R-M(0)), partition coefficients (log P-OW), and pK(a) values for a series of thirteen 1,7-bis(aminoalkyl) diazachrysene (1,7-DAAC) derivatives were determined in order to reveal the characteristics responsible for their biological behavior. The investigated compounds inhibit three unrelated pathogens (the Botulinum neurotoxin serotype A light chain (BoNT/A LC), Plasmodium falciparum malaria, and Ebola filovirus) via three different mechanisms of action. To determine the most influential factors governing the retention and activities of the investigated diazachrysenes, R-M(0), log P-OW, and biological activity values were correlated with 2D and 3D molecular descriptors, using a partial least squares regression. The resulting quantitative structure-retention (property) relationships indicate the importance of descriptors related to the hydrophobicity of the molecules (e.g., predicted partition coefficients and hydrophobic surface area). Quantitative structure-activity relationship models for describing biological activity against the BoNT/A LC and malarial strains also include overall compound polarity, electron density distribution, and proton donor/acceptor potential. Furthermore, models for Ebola filovirus inhibition are presented qualitatively to provide insights into parameters that may contribute to the compounds' antiviral activities. Overall, the models form the basis for selecting structural features that significantly affect the compound's absorption, distribution, metabolism, excretion, and toxicity profiles.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives
VL  - 72
SP  - 231
EP  - 239
DO  - 10.1016/j.jpba.2012.08.025
ER  - 

@article{
author = "Šegan, Sandra B. and Trifković, Jelena and Verbić, Tatjana and Opsenica, Dejan M. and Zlatović, Mario and Burnett, James C. and Šolaja, Bogdan A. and Milojković-Opsenica, Dušanka",
year = "2013",
abstract = "The physicochemical properties, retention parameters (R-M(0)), partition coefficients (log P-OW), and pK(a) values for a series of thirteen 1,7-bis(aminoalkyl) diazachrysene (1,7-DAAC) derivatives were determined in order to reveal the characteristics responsible for their biological behavior. The investigated compounds inhibit three unrelated pathogens (the Botulinum neurotoxin serotype A light chain (BoNT/A LC), Plasmodium falciparum malaria, and Ebola filovirus) via three different mechanisms of action. To determine the most influential factors governing the retention and activities of the investigated diazachrysenes, R-M(0), log P-OW, and biological activity values were correlated with 2D and 3D molecular descriptors, using a partial least squares regression. The resulting quantitative structure-retention (property) relationships indicate the importance of descriptors related to the hydrophobicity of the molecules (e.g., predicted partition coefficients and hydrophobic surface area). Quantitative structure-activity relationship models for describing biological activity against the BoNT/A LC and malarial strains also include overall compound polarity, electron density distribution, and proton donor/acceptor potential. Furthermore, models for Ebola filovirus inhibition are presented qualitatively to provide insights into parameters that may contribute to the compounds' antiviral activities. Overall, the models form the basis for selecting structural features that significantly affect the compound's absorption, distribution, metabolism, excretion, and toxicity profiles.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives",
volume = "72",
pages = "231-239",
doi = "10.1016/j.jpba.2012.08.025"
}

Šegan, S. B., Trifković, J., Verbić, T., Opsenica, D. M., Zlatović, M., Burnett, J. C., Šolaja, B. A.,& Milojković-Opsenica, D.. (2013). Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier Science Bv, Amsterdam., 72, 231-239.
https://doi.org/10.1016/j.jpba.2012.08.025

Šegan SB, Trifković J, Verbić T, Opsenica DM, Zlatović M, Burnett JC, Šolaja BA, Milojković-Opsenica D. Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives. in Journal of Pharmaceutical and Biomedical Analysis. 2013;72:231-239.
doi:10.1016/j.jpba.2012.08.025 .

Šegan, Sandra B., Trifković, Jelena, Verbić, Tatjana, Opsenica, Dejan M., Zlatović, Mario, Burnett, James C., Šolaja, Bogdan A., Milojković-Opsenica, Dušanka, "Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives" in Journal of Pharmaceutical and Biomedical Analysis, 72 (2013):231-239,
https://doi.org/10.1016/j.jpba.2012.08.025 . .

TY  - JOUR
AU  - Tot, Mikloš
AU  - Opsenica, Dejan M.
AU  - Mitric, Milena
AU  - Burnett, James C.
AU  - Gomba, Laura
AU  - Bavari, Sina
AU  - Šolaja, Bogdan A.
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1461
AB  - Steroidal and adamantane aminoacridine derivatives were prepared and tested as both botulinum neurotoxin (BoNT) inhibitors and antimalarials.. Steroid-bound acridines provided good potency against both the BoNT/A and BoNT/B light chains (LCs). The observed inhibition of the BoNT/B LC by ca. 50 % is the highest attained inhibitory activity against this serotype by acridine-based compounds to date. With respect to the antimalarial activity, the adamantane acridines were the most potent derivatives (IC50 = 6-9 nM, SI gt 326), indicating that an adamantyl group is a better carrier than a steroidal motif for this indication.
AB  - Sintetisani su derivati steroidnih i adamantil-akridina i ispitana je njihova inhibitorna aktivnost prema botulinum neurotoksinima (BoNT) i parazitu malarije. Steroidni akridini pokazuju dobru inhibiciju prema kratkom nizu (LCs) BoNT/A i BoNT/B. Ostvarena inhibicija BoNT/B LC od oko 50% je najviša postignuta vrednost akridinskih derivata prema ovom serotipu. Adamantil-akridinski derivati su pokazali najveću antimalarijsku aktivnost (IC50 u opsegu 6-9 nM, SI  gt  326), pokazujući da je adamantil-grupa bolji nosač farmakofore u poređenju sa steroidnim, prema ovoj indikaciji. .
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - New 9-aminoacridine derivatives as inhibitors of botulinum neurotoxins and P. falciparum malaria
T1  - Novi derivati 9-aminoakridina kao inhibitori botulinum neurotoksina i P. falciparum parazita malarije
VL  - 78
IS  - 12
SP  - 1847
EP  - 1864
DO  - 10.2298/JSC130924112T
ER  - 

@article{
author = "Tot, Mikloš and Opsenica, Dejan M. and Mitric, Milena and Burnett, James C. and Gomba, Laura and Bavari, Sina and Šolaja, Bogdan A.",
year = "2013",
abstract = "Steroidal and adamantane aminoacridine derivatives were prepared and tested as both botulinum neurotoxin (BoNT) inhibitors and antimalarials.. Steroid-bound acridines provided good potency against both the BoNT/A and BoNT/B light chains (LCs). The observed inhibition of the BoNT/B LC by ca. 50 % is the highest attained inhibitory activity against this serotype by acridine-based compounds to date. With respect to the antimalarial activity, the adamantane acridines were the most potent derivatives (IC50 = 6-9 nM, SI gt 326), indicating that an adamantyl group is a better carrier than a steroidal motif for this indication., Sintetisani su derivati steroidnih i adamantil-akridina i ispitana je njihova inhibitorna aktivnost prema botulinum neurotoksinima (BoNT) i parazitu malarije. Steroidni akridini pokazuju dobru inhibiciju prema kratkom nizu (LCs) BoNT/A i BoNT/B. Ostvarena inhibicija BoNT/B LC od oko 50% je najviša postignuta vrednost akridinskih derivata prema ovom serotipu. Adamantil-akridinski derivati su pokazali najveću antimalarijsku aktivnost (IC50 u opsegu 6-9 nM, SI  gt  326), pokazujući da je adamantil-grupa bolji nosač farmakofore u poređenju sa steroidnim, prema ovoj indikaciji. .",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "New 9-aminoacridine derivatives as inhibitors of botulinum neurotoxins and P. falciparum malaria, Novi derivati 9-aminoakridina kao inhibitori botulinum neurotoksina i P. falciparum parazita malarije",
volume = "78",
number = "12",
pages = "1847-1864",
doi = "10.2298/JSC130924112T"
}

Tot, M., Opsenica, D. M., Mitric, M., Burnett, J. C., Gomba, L., Bavari, S.,& Šolaja, B. A.. (2013). New 9-aminoacridine derivatives as inhibitors of botulinum neurotoxins and P. falciparum malaria. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 78(12), 1847-1864.
https://doi.org/10.2298/JSC130924112T

Tot M, Opsenica DM, Mitric M, Burnett JC, Gomba L, Bavari S, Šolaja BA. New 9-aminoacridine derivatives as inhibitors of botulinum neurotoxins and P. falciparum malaria. in Journal of the Serbian Chemical Society. 2013;78(12):1847-1864.
doi:10.2298/JSC130924112T .

Tot, Mikloš, Opsenica, Dejan M., Mitric, Milena, Burnett, James C., Gomba, Laura, Bavari, Sina, Šolaja, Bogdan A., "New 9-aminoacridine derivatives as inhibitors of botulinum neurotoxins and P. falciparum malaria" in Journal of the Serbian Chemical Society, 78, no. 12 (2013):1847-1864,
https://doi.org/10.2298/JSC130924112T . .

TY  - JOUR
AU  - Opsenica, Igor
AU  - Filipović, Vuk
AU  - Nuss, Jon E.
AU  - Gomba, Laura M.
AU  - Opsenica, Dejan M.
AU  - Burnett, James C.
AU  - Gussio, Rick
AU  - Šolaja, Bogdan A.
AU  - Bavari, Sina
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1314
AB  - Botulinum neurotoxins (BoNTs), composed of a family of seven serotypes (categorized A-G), are the deadliest of known biological toxins. The activity of the metalloprotease, light chain (LC) component of the toxins is responsible for causing the life-threatening paralysis associated with the disease botulism. Herein we report significantly more potent analogs of novel, lead BoNT serotype A LC inhibitor 2,5-bis(4-amidinophenyl)thiophene (K-i = 10.881 mu M +/- 0.90 mu M). Specifically, synthetic modifications involved simultaneously replacing the lead inhibitor's terminal bis-amidines with secondary amines and the systematic tethering of 4-amino-7-chloroquinoline substituents to provide derivatives with K-i values ranging from 0.302 mu M (+/- 0.03 mu M) to 0.889 mu M (+/- 0.11 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease
VL  - 53
SP  - 374
EP  - 379
DO  - 10.1016/j.ejmech.2012.03.043
ER  - 

@article{
author = "Opsenica, Igor and Filipović, Vuk and Nuss, Jon E. and Gomba, Laura M. and Opsenica, Dejan M. and Burnett, James C. and Gussio, Rick and Šolaja, Bogdan A. and Bavari, Sina",
year = "2012",
abstract = "Botulinum neurotoxins (BoNTs), composed of a family of seven serotypes (categorized A-G), are the deadliest of known biological toxins. The activity of the metalloprotease, light chain (LC) component of the toxins is responsible for causing the life-threatening paralysis associated with the disease botulism. Herein we report significantly more potent analogs of novel, lead BoNT serotype A LC inhibitor 2,5-bis(4-amidinophenyl)thiophene (K-i = 10.881 mu M +/- 0.90 mu M). Specifically, synthetic modifications involved simultaneously replacing the lead inhibitor's terminal bis-amidines with secondary amines and the systematic tethering of 4-amino-7-chloroquinoline substituents to provide derivatives with K-i values ranging from 0.302 mu M (+/- 0.03 mu M) to 0.889 mu M (+/- 0.11 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease",
volume = "53",
pages = "374-379",
doi = "10.1016/j.ejmech.2012.03.043"
}

Opsenica, I., Filipović, V., Nuss, J. E., Gomba, L. M., Opsenica, D. M., Burnett, J. C., Gussio, R., Šolaja, B. A.,& Bavari, S.. (2012). The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 53, 374-379.
https://doi.org/10.1016/j.ejmech.2012.03.043

Opsenica I, Filipović V, Nuss JE, Gomba LM, Opsenica DM, Burnett JC, Gussio R, Šolaja BA, Bavari S. The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease. in European Journal of Medicinal Chemistry. 2012;53:374-379.
doi:10.1016/j.ejmech.2012.03.043 .

Opsenica, Igor, Filipović, Vuk, Nuss, Jon E., Gomba, Laura M., Opsenica, Dejan M., Burnett, James C., Gussio, Rick, Šolaja, Bogdan A., Bavari, Sina, "The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease" in European Journal of Medicinal Chemistry, 53 (2012):374-379,
https://doi.org/10.1016/j.ejmech.2012.03.043 . .

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

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

Selaković, Ž., Opsenica, D. M., Eaton, B., Retterer, C., Bavari, S., Burnett, J. C., Šolaja, B. A.,& Panchal, R. G.. (2012). A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor. in Viruses
Mdpi Ag, Basel., 4(8), 1279-1288.
https://doi.org/10.3390/v4081279

Selaković Ž, Opsenica DM, Eaton B, Retterer C, Bavari S, Burnett JC, Šolaja BA, Panchal RG. A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor. in Viruses. 2012;4(8):1279-1288.
doi:10.3390/v4081279 .

Selaković, Života, Opsenica, Dejan M., Eaton, Brett, Retterer, Cary, Bavari, Sina, Burnett, James C., Šolaja, Bogdan A., Panchal, Rekha G., "A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor" in Viruses, 4, no. 8 (2012):1279-1288,
https://doi.org/10.3390/v4081279 . .

TY  - CONF
AU  - Žižak, Željko S.
AU  - Opsenica, Dejan M.
AU  - Šolaja, Bogdan A.
AU  - Juranić, Z.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1572
PB  - Elsevier Sci Ltd, Oxford
C3  - European Journal of Cancer / EJC
T1  - Investigation of Some Small Heterocyclic Compounds as Potential Antitumor Agents
VL  - 48
DO  - 10.1016/S0959-8049(12)71674-X
ER  - 

@conference{
author = "Žižak, Željko S. and Opsenica, Dejan M. and Šolaja, Bogdan A. and Juranić, Z.",
year = "2012",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "European Journal of Cancer / EJC",
title = "Investigation of Some Small Heterocyclic Compounds as Potential Antitumor Agents",
volume = "48",
doi = "10.1016/S0959-8049(12)71674-X"
}

Žižak, Ž. S., Opsenica, D. M., Šolaja, B. A.,& Juranić, Z.. (2012). Investigation of Some Small Heterocyclic Compounds as Potential Antitumor Agents. in European Journal of Cancer / EJC
Elsevier Sci Ltd, Oxford., 48.
https://doi.org/10.1016/S0959-8049(12)71674-X

Žižak ŽS, Opsenica DM, Šolaja BA, Juranić Z. Investigation of Some Small Heterocyclic Compounds as Potential Antitumor Agents. in European Journal of Cancer / EJC. 2012;48.
doi:10.1016/S0959-8049(12)71674-X .

Žižak, Željko S., Opsenica, Dejan M., Šolaja, Bogdan A., Juranić, Z., "Investigation of Some Small Heterocyclic Compounds as Potential Antitumor Agents" in European Journal of Cancer / EJC, 48 (2012),
https://doi.org/10.1016/S0959-8049(12)71674-X . .