Petković, Miloš

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  • Petković, Miloš (7)

Author's Bibliography

Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives

Jovanović, Predrag; Jovanović, Miloš; Petković, Miloš; Simić, Milena; Tasić, Gordana; Rodić, Marko; Rakić, Srđan; Vlahović, Filip; Savić, Vladimir

(John Wiley and Sons Inc, 2024)

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Jovanović, Miloš
AU  - Petković, Miloš
AU  - Simić, Milena
AU  - Tasić, Gordana
AU  - Rodić, Marko
AU  - Rakić, Srđan
AU  - Vlahović, Filip
AU  - Savić, Vladimir
PY  - 2024
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7800
AB  - Combining chemical reactivities of allenes and oximes created a methodology for the preparation of heterocyclic triquinane-type skeletons via a cascade process constructing four bonds in a single step. The initial reaction of allene moiety promoted by Pd-catalysis, affording π-allyl Pd-species, was followed by two additional transformations - nucleophilic displacement and dipolar cycloaddition - to furnish the product highly stereoselectively in moderate to good yields. For the process to be efficient, it was necessary to use a dipolarophilic component as a solvent. Intriguingly, while the reaction with cyclopentanone derived oxime progressed through the whole cascade, with cyclohexanone analogue it stopped at the nitrone stage, requiring an additional step to yield similar type of products. Some aspects of the studied cascade were examined by DFT.
PB  - John Wiley and Sons Inc
T2  - Advanced Synthesis and Catalysis
T1  - Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives
DO  - 10.1002/adsc.202400253
ER  - 
@article{
author = "Jovanović, Predrag and Jovanović, Miloš and Petković, Miloš and Simić, Milena and Tasić, Gordana and Rodić, Marko and Rakić, Srđan and Vlahović, Filip and Savić, Vladimir",
year = "2024",
abstract = "Combining chemical reactivities of allenes and oximes created a methodology for the preparation of heterocyclic triquinane-type skeletons via a cascade process constructing four bonds in a single step. The initial reaction of allene moiety promoted by Pd-catalysis, affording π-allyl Pd-species, was followed by two additional transformations - nucleophilic displacement and dipolar cycloaddition - to furnish the product highly stereoselectively in moderate to good yields. For the process to be efficient, it was necessary to use a dipolarophilic component as a solvent. Intriguingly, while the reaction with cyclopentanone derived oxime progressed through the whole cascade, with cyclohexanone analogue it stopped at the nitrone stage, requiring an additional step to yield similar type of products. Some aspects of the studied cascade were examined by DFT.",
publisher = "John Wiley and Sons Inc",
journal = "Advanced Synthesis and Catalysis",
title = "Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives",
doi = "10.1002/adsc.202400253"
}
Jovanović, P., Jovanović, M., Petković, M., Simić, M., Tasić, G., Rodić, M., Rakić, S., Vlahović, F.,& Savić, V.. (2024). Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives. in Advanced Synthesis and Catalysis
John Wiley and Sons Inc..
https://doi.org/10.1002/adsc.202400253
Jovanović P, Jovanović M, Petković M, Simić M, Tasić G, Rodić M, Rakić S, Vlahović F, Savić V. Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives. in Advanced Synthesis and Catalysis. 2024;.
doi:10.1002/adsc.202400253 .
Jovanović, Predrag, Jovanović, Miloš, Petković, Miloš, Simić, Milena, Tasić, Gordana, Rodić, Marko, Rakić, Srđan, Vlahović, Filip, Savić, Vladimir, "Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives" in Advanced Synthesis and Catalysis (2024),
https://doi.org/10.1002/adsc.202400253 . .
11

Regio‐ and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis

Jovanović, Miloš; Jovanović, Predrag; Tasić, Gordana; Simić, Milena R.; Maslak, Veselin; Rakić, Srđan; Rodić, Marko; Vlahović, Filip; Petković, Miloš; Savić, Vladimir

(John Wiley and Sons Inc, 2023)

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Jovanović, Predrag
AU  - Tasić, Gordana
AU  - Simić, Milena R.
AU  - Maslak, Veselin
AU  - Rakić, Srđan
AU  - Rodić, Marko
AU  - Vlahović, Filip
AU  - Petković, Miloš
AU  - Savić, Vladimir
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7166
AB  - Enallenylamideshave been utilizedforthe synthesisof heterobicycle[4.2.0]octanederiva-tives via Ir/hν promoted[2+2] cycloadditionreaction.The reactionspecificallytargets the distaldoublebond of the allene moiety, and resultsin theexclusiveformationof thetransproduct.Theprocessis conductedat room temperatureand underan inert atmosphere.An extensivestudy on thesubstituentpropensitiesduringthe cycloadditionstep revealedvariableeffects.Electron-withdrawinggroupsconjugatedwith the doublebond participat-ing in the cycloadditioneither hinderedthe processor reducedits yield. Conversely, electron-donatingsubstituentsenhancedthe efficiency, resultinginproductyields rangingfrom 60% to 88%. Our studyalso demonstratedthe influenceof protectinggroupson the reactionpathway.
PB  - John Wiley and Sons Inc
T2  - Advanced Synthesis and Catalysis
T1  - Regio‐ and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis
VL  - 365
IS  - 15
SP  - 2516
EP  - 2523
DO  - 10.1002/adsc.202300301
ER  - 
@article{
author = "Jovanović, Miloš and Jovanović, Predrag and Tasić, Gordana and Simić, Milena R. and Maslak, Veselin and Rakić, Srđan and Rodić, Marko and Vlahović, Filip and Petković, Miloš and Savić, Vladimir",
year = "2023",
abstract = "Enallenylamideshave been utilizedforthe synthesisof heterobicycle[4.2.0]octanederiva-tives via Ir/hν promoted[2+2] cycloadditionreaction.The reactionspecificallytargets the distaldoublebond of the allene moiety, and resultsin theexclusiveformationof thetransproduct.Theprocessis conductedat room temperatureand underan inert atmosphere.An extensivestudy on thesubstituentpropensitiesduringthe cycloadditionstep revealedvariableeffects.Electron-withdrawinggroupsconjugatedwith the doublebond participat-ing in the cycloadditioneither hinderedthe processor reducedits yield. Conversely, electron-donatingsubstituentsenhancedthe efficiency, resultinginproductyields rangingfrom 60% to 88%. Our studyalso demonstratedthe influenceof protectinggroupson the reactionpathway.",
publisher = "John Wiley and Sons Inc",
journal = "Advanced Synthesis and Catalysis",
title = "Regio‐ and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis",
volume = "365",
number = "15",
pages = "2516-2523",
doi = "10.1002/adsc.202300301"
}
Jovanović, M., Jovanović, P., Tasić, G., Simić, M. R., Maslak, V., Rakić, S., Rodić, M., Vlahović, F., Petković, M.,& Savić, V.. (2023). Regio‐ and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis
John Wiley and Sons Inc., 365(15), 2516-2523.
https://doi.org/10.1002/adsc.202300301
Jovanović M, Jovanović P, Tasić G, Simić MR, Maslak V, Rakić S, Rodić M, Vlahović F, Petković M, Savić V. Regio‐ and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis. 2023;365(15):2516-2523.
doi:10.1002/adsc.202300301 .
Jovanović, Miloš, Jovanović, Predrag, Tasić, Gordana, Simić, Milena R., Maslak, Veselin, Rakić, Srđan, Rodić, Marko, Vlahović, Filip, Petković, Miloš, Savić, Vladimir, "Regio‐ and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis" in Advanced Synthesis and Catalysis, 365, no. 15 (2023):2516-2523,
https://doi.org/10.1002/adsc.202300301 . .
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High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances

Mitrović, Jelena; Divović-Matović, Branka; Knutson, Daniel E.; Petković, Miloš; Đorović, Đordje; Randjelović, Danijela; Dobričić, Vladimir D.; Đoković, Jelena B.; Lunter, Dominique J.; Cook, James M.; Savić, Miroslav M.; Savić, Snežana D.

(Elsevier B.V., 2023)

TY  - JOUR
AU  - Mitrović, Jelena
AU  - Divović-Matović, Branka
AU  - Knutson, Daniel E.
AU  - Petković, Miloš
AU  - Đorović, Đordje
AU  - Randjelović, Danijela
AU  - Dobričić, Vladimir D.
AU  - Đoković, Jelena B.
AU  - Lunter, Dominique J.
AU  - Cook, James M.
AU  - Savić, Miroslav M.
AU  - Savić, Snežana D.
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5665
AB  - Preclinical development of deuterated pyrazoloquinolinone ligands, promising drug candidates for various neuropsychiatric disorders, was hindered by unusually low solubility in water and oils. DK-I-60-3 (7-methoxy-d3-2-(4-methoxy-d3-phenyl)-2,5-dihydro-3Hpyrazolo[4,3-c]quinolin-3-one) is one of such pyrazoloquinolinones, and we recently reported about increased oral bioavailability of its nanocrystal formulation (NC). Lipid nanoparticles (LNP) with a high concentration of lecithin, which enhances loading capacity of the lipid matrix, may give rise to further improvement. After preformulation studies by differential scanning calorimetry and polarized light microscopy, LNP were prepared by the hot high pressure homogenization, and characterized in terms of particle size, morphology, and encapsulation efficacy. The layered structure visible on atomic force micrographs was confirmed by nuclear magnetic resonance. Obtained formulations were desirably stable, with small particle size (<100 nm), and high encapsulation efficacy (>99 %). Lecithin was partially fluid and most probably located in the outer shell of the particle, together with DK-I-60-3. While the hydrophobic part of polysorbate 80 was completely immobilized, its hydrophilic part was free in the aqueous phase. In oral neuropharmacokinetic study in rats, an around 1.5-fold increase of area under the curve with LNP compared to NC was noticed both in brain and plasma. In bioavailability study, F value of LNP (34.7 ± 12.4 %) was 1.4-fold higher than of NC (24.5 ± 7.8 %); however, this difference did not reach statistical significance. Therefore, employment of LNP platform in preclinical formulation of DK-I-60-3 imparted an incremental improvement of its physicochemical as well as pharmacokinetic behavior.
PB  - Elsevier B.V.
T2  - International Journal of Pharmaceutics
T1  - High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances
VL  - 633
SP  - 122613
DO  - 10.1016/j.ijpharm.2023.122613
ER  - 
@article{
author = "Mitrović, Jelena and Divović-Matović, Branka and Knutson, Daniel E. and Petković, Miloš and Đorović, Đordje and Randjelović, Danijela and Dobričić, Vladimir D. and Đoković, Jelena B. and Lunter, Dominique J. and Cook, James M. and Savić, Miroslav M. and Savić, Snežana D.",
year = "2023",
abstract = "Preclinical development of deuterated pyrazoloquinolinone ligands, promising drug candidates for various neuropsychiatric disorders, was hindered by unusually low solubility in water and oils. DK-I-60-3 (7-methoxy-d3-2-(4-methoxy-d3-phenyl)-2,5-dihydro-3Hpyrazolo[4,3-c]quinolin-3-one) is one of such pyrazoloquinolinones, and we recently reported about increased oral bioavailability of its nanocrystal formulation (NC). Lipid nanoparticles (LNP) with a high concentration of lecithin, which enhances loading capacity of the lipid matrix, may give rise to further improvement. After preformulation studies by differential scanning calorimetry and polarized light microscopy, LNP were prepared by the hot high pressure homogenization, and characterized in terms of particle size, morphology, and encapsulation efficacy. The layered structure visible on atomic force micrographs was confirmed by nuclear magnetic resonance. Obtained formulations were desirably stable, with small particle size (<100 nm), and high encapsulation efficacy (>99 %). Lecithin was partially fluid and most probably located in the outer shell of the particle, together with DK-I-60-3. While the hydrophobic part of polysorbate 80 was completely immobilized, its hydrophilic part was free in the aqueous phase. In oral neuropharmacokinetic study in rats, an around 1.5-fold increase of area under the curve with LNP compared to NC was noticed both in brain and plasma. In bioavailability study, F value of LNP (34.7 ± 12.4 %) was 1.4-fold higher than of NC (24.5 ± 7.8 %); however, this difference did not reach statistical significance. Therefore, employment of LNP platform in preclinical formulation of DK-I-60-3 imparted an incremental improvement of its physicochemical as well as pharmacokinetic behavior.",
publisher = "Elsevier B.V.",
journal = "International Journal of Pharmaceutics",
title = "High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances",
volume = "633",
pages = "122613",
doi = "10.1016/j.ijpharm.2023.122613"
}
Mitrović, J., Divović-Matović, B., Knutson, D. E., Petković, M., Đorović, Đ., Randjelović, D., Dobričić, V. D., Đoković, J. B., Lunter, D. J., Cook, J. M., Savić, M. M.,& Savić, S. D.. (2023). High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances. in International Journal of Pharmaceutics
Elsevier B.V.., 633, 122613.
https://doi.org/10.1016/j.ijpharm.2023.122613
Mitrović J, Divović-Matović B, Knutson DE, Petković M, Đorović Đ, Randjelović D, Dobričić VD, Đoković JB, Lunter DJ, Cook JM, Savić MM, Savić SD. High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances. in International Journal of Pharmaceutics. 2023;633:122613.
doi:10.1016/j.ijpharm.2023.122613 .
Mitrović, Jelena, Divović-Matović, Branka, Knutson, Daniel E., Petković, Miloš, Đorović, Đordje, Randjelović, Danijela, Dobričić, Vladimir D., Đoković, Jelena B., Lunter, Dominique J., Cook, James M., Savić, Miroslav M., Savić, Snežana D., "High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances" in International Journal of Pharmaceutics, 633 (2023):122613,
https://doi.org/10.1016/j.ijpharm.2023.122613 . .
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Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3

Mitrović, Jelena; Petković, Miloš; Randjelović, Danijela; Đoković, Jelena; Knutson, Daniel; Cook, James; Savić, Vladimir; Savić, Miroslav; Savić, Snežana

(2022)

TY  - CONF
AU  - Mitrović, Jelena
AU  - Petković, Miloš
AU  - Randjelović, Danijela
AU  - Đoković, Jelena
AU  - Knutson, Daniel
AU  - Cook, James
AU  - Savić, Vladimir
AU  - Savić, Miroslav
AU  - Savić, Snežana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5259
AB  - Poster presented at 13th World meeting on pharmaceutics, biopharmaceutics and pharmaceutical technology, 28-31 March 2022, Rotterdam, Netherlands
T1  - Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3
UR  - https://hdl.handle.net/21.15107/rcub_cer_5259
ER  - 
@conference{
author = "Mitrović, Jelena and Petković, Miloš and Randjelović, Danijela and Đoković, Jelena and Knutson, Daniel and Cook, James and Savić, Vladimir and Savić, Miroslav and Savić, Snežana",
year = "2022",
abstract = "Poster presented at 13th World meeting on pharmaceutics, biopharmaceutics and pharmaceutical technology, 28-31 March 2022, Rotterdam, Netherlands",
title = "Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3",
url = "https://hdl.handle.net/21.15107/rcub_cer_5259"
}
Mitrović, J., Petković, M., Randjelović, D., Đoković, J., Knutson, D., Cook, J., Savić, V., Savić, M.,& Savić, S.. (2022). Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3. .
https://hdl.handle.net/21.15107/rcub_cer_5259
Mitrović J, Petković M, Randjelović D, Đoković J, Knutson D, Cook J, Savić V, Savić M, Savić S. Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3. 2022;.
https://hdl.handle.net/21.15107/rcub_cer_5259 .
Mitrović, Jelena, Petković, Miloš, Randjelović, Danijela, Đoković, Jelena, Knutson, Daniel, Cook, James, Savić, Vladimir, Savić, Miroslav, Savić, Snežana, "Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3" (2022),
https://hdl.handle.net/21.15107/rcub_cer_5259 .

Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes

Husinec, Suren; Petković, Miloš; Savić, Vladimir; Simić, Milena

(Stuttgart : Georg Thieme Verlag Kg, 2012)

TY  - JOUR
AU  - Husinec, Suren
AU  - Petković, Miloš
AU  - Savić, Vladimir
AU  - Simić, Milena
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4173
AB  - pi-Allylpalladium intermediates are known to participate efficiently in transformations involving nucleophilic species. Exploring these processes, we have developed a method for the preparation of allyl acetates via palladium-catalysed functionalisation of allenes and 1,3-dienes. Reactions of aryl iodides with either of these two classes of compounds and excess sodium acetate in the presence of Pd(OAc) (2) and Ph3P as the catalytic system afforded the respective allyl acetates in moderate to good yields. The scope of this process has been investigated. The described method is an addition to the synthetic repertoire for the preparation of allyl acetates, and may be useful, in particular, for the synthesis of structurally complex compounds of this type.
PB  - Stuttgart : Georg Thieme Verlag Kg
T2  - Synthesis
T1  - Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes
VL  - 44
IS  - 3
SP  - 399
EP  - 408
DO  - 10.1055/s-0031-1289658
ER  - 
@article{
author = "Husinec, Suren and Petković, Miloš and Savić, Vladimir and Simić, Milena",
year = "2012",
abstract = "pi-Allylpalladium intermediates are known to participate efficiently in transformations involving nucleophilic species. Exploring these processes, we have developed a method for the preparation of allyl acetates via palladium-catalysed functionalisation of allenes and 1,3-dienes. Reactions of aryl iodides with either of these two classes of compounds and excess sodium acetate in the presence of Pd(OAc) (2) and Ph3P as the catalytic system afforded the respective allyl acetates in moderate to good yields. The scope of this process has been investigated. The described method is an addition to the synthetic repertoire for the preparation of allyl acetates, and may be useful, in particular, for the synthesis of structurally complex compounds of this type.",
publisher = "Stuttgart : Georg Thieme Verlag Kg",
journal = "Synthesis",
title = "Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes",
volume = "44",
number = "3",
pages = "399-408",
doi = "10.1055/s-0031-1289658"
}
Husinec, S., Petković, M., Savić, V.,& Simić, M.. (2012). Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes. in Synthesis
Stuttgart : Georg Thieme Verlag Kg., 44(3), 399-408.
https://doi.org/10.1055/s-0031-1289658
Husinec S, Petković M, Savić V, Simić M. Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes. in Synthesis. 2012;44(3):399-408.
doi:10.1055/s-0031-1289658 .
Husinec, Suren, Petković, Miloš, Savić, Vladimir, Simić, Milena, "Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes" in Synthesis, 44, no. 3 (2012):399-408,
https://doi.org/10.1055/s-0031-1289658 . .
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Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties

Stankovic, Nada; Radulovic, Vanja; Petković, Miloš; Vučković, Ivan; Jadranin, Milka; Vasiljevic, Branka; Nikodinović-Runić, Jasmina

(Springer, New York, 2012)

TY  - JOUR
AU  - Stankovic, Nada
AU  - Radulovic, Vanja
AU  - Petković, Miloš
AU  - Vučković, Ivan
AU  - Jadranin, Milka
AU  - Vasiljevic, Branka
AU  - Nikodinović-Runić, Jasmina
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1125
AB  - A Gram-positive, red-pigment-producing bacterial strain, designated JS520 was isolated from the pristine sediment from the cave on mountain Miroc in Serbia. Strain was confirmed to belong to Streptomyces genus based on phenotypic and genetic analysis. Streptomyces sp. JS520 has the ability to produce exceptionally high amounts of deep red pigment into both solid and liquid media. Liquid chromatography and mass spectroscopy of the purified pigments revealed the major component to be undecylprodigiosin (93 %) with minor component being oxidatively cyclized derivative. The pigment production was affected by medium composition, temperature, pH, and the aeration rate. By medium optimization, yields of undecylprodigiosin of 138 mg l(-1) were achieved, what is the highest level of undecylprodigiosin production reported for the members of Gram-positive Streptomyces genus. Purified pigment had antimicrobial properties against bacterial Bacillus and Micrococcus species (50 mu g ml(-1)) and against Candida albicans species (100-200 mu g ml(-1) range). The ability to affect auto-oxidation of the linoleic acid was demonstrated for the purified undecylprodigiosin, suggesting antioxidative properties of this pigment. Multiple ecophysiological roles of the pigment were revealed by comparing cultures grown under pigment-producing and pigment-nonproducing conditions. Cells grown under undecylprodigiosin-producing conditions could tolerate presence of hydrogen peroxide exhibiting three times smaller zones of inhibition at 100 mM H2O2. Undecylprodigiosin-producing cells were also less susceptible to tetracycline, kanamycin, chloramphenicol, and 8-hydroxyquinoline. While the growth of the cells not producing pigment was completely inhibited by 15 min of exposure to ultraviolet light (254 nm), cells producing undecylprodigiosin and cells supplied with purified pigment in vitro showed survival rates at 22 and 8 %, respectively.
PB  - Springer, New York
T2  - Applied Microbiology and Biotechnology
T1  - Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties
VL  - 96
IS  - 5
SP  - 1217
EP  - 1231
DO  - 10.1007/s00253-012-4237-3
ER  - 
@article{
author = "Stankovic, Nada and Radulovic, Vanja and Petković, Miloš and Vučković, Ivan and Jadranin, Milka and Vasiljevic, Branka and Nikodinović-Runić, Jasmina",
year = "2012",
abstract = "A Gram-positive, red-pigment-producing bacterial strain, designated JS520 was isolated from the pristine sediment from the cave on mountain Miroc in Serbia. Strain was confirmed to belong to Streptomyces genus based on phenotypic and genetic analysis. Streptomyces sp. JS520 has the ability to produce exceptionally high amounts of deep red pigment into both solid and liquid media. Liquid chromatography and mass spectroscopy of the purified pigments revealed the major component to be undecylprodigiosin (93 %) with minor component being oxidatively cyclized derivative. The pigment production was affected by medium composition, temperature, pH, and the aeration rate. By medium optimization, yields of undecylprodigiosin of 138 mg l(-1) were achieved, what is the highest level of undecylprodigiosin production reported for the members of Gram-positive Streptomyces genus. Purified pigment had antimicrobial properties against bacterial Bacillus and Micrococcus species (50 mu g ml(-1)) and against Candida albicans species (100-200 mu g ml(-1) range). The ability to affect auto-oxidation of the linoleic acid was demonstrated for the purified undecylprodigiosin, suggesting antioxidative properties of this pigment. Multiple ecophysiological roles of the pigment were revealed by comparing cultures grown under pigment-producing and pigment-nonproducing conditions. Cells grown under undecylprodigiosin-producing conditions could tolerate presence of hydrogen peroxide exhibiting three times smaller zones of inhibition at 100 mM H2O2. Undecylprodigiosin-producing cells were also less susceptible to tetracycline, kanamycin, chloramphenicol, and 8-hydroxyquinoline. While the growth of the cells not producing pigment was completely inhibited by 15 min of exposure to ultraviolet light (254 nm), cells producing undecylprodigiosin and cells supplied with purified pigment in vitro showed survival rates at 22 and 8 %, respectively.",
publisher = "Springer, New York",
journal = "Applied Microbiology and Biotechnology",
title = "Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties",
volume = "96",
number = "5",
pages = "1217-1231",
doi = "10.1007/s00253-012-4237-3"
}
Stankovic, N., Radulovic, V., Petković, M., Vučković, I., Jadranin, M., Vasiljevic, B.,& Nikodinović-Runić, J.. (2012). Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties. in Applied Microbiology and Biotechnology
Springer, New York., 96(5), 1217-1231.
https://doi.org/10.1007/s00253-012-4237-3
Stankovic N, Radulovic V, Petković M, Vučković I, Jadranin M, Vasiljevic B, Nikodinović-Runić J. Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties. in Applied Microbiology and Biotechnology. 2012;96(5):1217-1231.
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Stankovic, Nada, Radulovic, Vanja, Petković, Miloš, Vučković, Ivan, Jadranin, Milka, Vasiljevic, Branka, Nikodinović-Runić, Jasmina, "Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties" in Applied Microbiology and Biotechnology, 96, no. 5 (2012):1217-1231,
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A Base Promoted Cyclization of N-Propargylaminopyridines. Synthesis of Imidazo[1,2-a]pyridine Derivatives

Husinec, Suren; Marković, Rade; Petković, Miloš; Nasufović, Veselin; Savić, Vladimir

(American Chemical Society (ACS), 2011)

TY  - JOUR
AU  - Husinec, Suren
AU  - Marković, Rade
AU  - Petković, Miloš
AU  - Nasufović, Veselin
AU  - Savić, Vladimir
PY  - 2011
UR  - http://farfar.pharmacy.bg.ac.rs/handle/123456789/1527
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3506
AB  - A base promoted cyclization of the protected N-propargylaminopyridines was shown to be an efficient method for the preparation of imidazo[1,2-a] pyridine derivatives. The reactions were carried out with a small excess of base, at room temperature or slightly above producing the heterocyclic products in moderate to good yields. The stereoelectronic properties of substituents on the pyridine ring were shown to influence the cyclization process.
PB  - American Chemical Society (ACS)
T2  - Organic Letters
T1  - A Base Promoted Cyclization of N-Propargylaminopyridines. Synthesis of Imidazo[1,2-a]pyridine Derivatives
VL  - 13
IS  - 9
SP  - 2286
EP  - 2289
DO  - 10.1021/ol200508x
ER  - 
@article{
author = "Husinec, Suren and Marković, Rade and Petković, Miloš and Nasufović, Veselin and Savić, Vladimir",
year = "2011",
abstract = "A base promoted cyclization of the protected N-propargylaminopyridines was shown to be an efficient method for the preparation of imidazo[1,2-a] pyridine derivatives. The reactions were carried out with a small excess of base, at room temperature or slightly above producing the heterocyclic products in moderate to good yields. The stereoelectronic properties of substituents on the pyridine ring were shown to influence the cyclization process.",
publisher = "American Chemical Society (ACS)",
journal = "Organic Letters",
title = "A Base Promoted Cyclization of N-Propargylaminopyridines. Synthesis of Imidazo[1,2-a]pyridine Derivatives",
volume = "13",
number = "9",
pages = "2286-2289",
doi = "10.1021/ol200508x"
}
Husinec, S., Marković, R., Petković, M., Nasufović, V.,& Savić, V.. (2011). A Base Promoted Cyclization of N-Propargylaminopyridines. Synthesis of Imidazo[1,2-a]pyridine Derivatives. in Organic Letters
American Chemical Society (ACS)., 13(9), 2286-2289.
https://doi.org/10.1021/ol200508x
Husinec S, Marković R, Petković M, Nasufović V, Savić V. A Base Promoted Cyclization of N-Propargylaminopyridines. Synthesis of Imidazo[1,2-a]pyridine Derivatives. in Organic Letters. 2011;13(9):2286-2289.
doi:10.1021/ol200508x .
Husinec, Suren, Marković, Rade, Petković, Miloš, Nasufović, Veselin, Savić, Vladimir, "A Base Promoted Cyclization of N-Propargylaminopyridines. Synthesis of Imidazo[1,2-a]pyridine Derivatives" in Organic Letters, 13, no. 9 (2011):2286-2289,
https://doi.org/10.1021/ol200508x . .
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