TY  - JOUR
AU  - Dimitrijević, Milena S.
AU  - Bogdanović-Pristov, Jelena
AU  - Žižić, Milan
AU  - Stanković, Dalibor M.
AU  - Bajuk-Bogdanović, Danica V.
AU  - Stanić, Marina
AU  - Spasić, Snežana D.
AU  - Hagen, Wilfred
AU  - Spasojević, Ivan
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3066
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8200
AB  - Biliverdin (BV), a product of heme catabolism, is known to interact with transition metals, but the details of such interactions under physiological conditions are scarce. Herein, we examined coordinate/redox interactions of BV with Cu2+ in phosphate buffer at pH 7.4, using spectrophotometry, HESI-MS, Raman spectroscopy, 1 H NMR, EPR, fluorimetry, and electrochemical methods. BV formed a stable coordination complex with copper in 1 : 1 stoichiometry. The structure of BV was more planar and energetically stable in the complex. The complex showed strong paramagnetic effects that were attributed to an unpaired delocalized e−. The delocalized electron may come from BV or Cu2+, so the complex is formally composed either of BV radical cation and Cu1+ or of BV radical anion and Cu3+. The complex underwent oxidation only in the presence of both O2 and an excess of Cu2+, or a strong oxidizing agent, and it was resistant to reducing agents. The biological effects of the stable BV metallocomplex containing a delocalized unpaired electron should be further examined, and may provide an answer to the long-standing question of high energy investment in the catabolism of BV, which represents a relatively harmless molecule per se.
T2  - Dalton Transactions
T1  - Biliverdin-copper complex at physiological pH
VL  - 48
IS  - 18
SP  - 6061
EP  - 6070
DO  - 10.1039/c8dt04724c
ER  - 

@article{
author = "Dimitrijević, Milena S. and Bogdanović-Pristov, Jelena and Žižić, Milan and Stanković, Dalibor M. and Bajuk-Bogdanović, Danica V. and Stanić, Marina and Spasić, Snežana D. and Hagen, Wilfred and Spasojević, Ivan",
year = "2019",
abstract = "Biliverdin (BV), a product of heme catabolism, is known to interact with transition metals, but the details of such interactions under physiological conditions are scarce. Herein, we examined coordinate/redox interactions of BV with Cu2+ in phosphate buffer at pH 7.4, using spectrophotometry, HESI-MS, Raman spectroscopy, 1 H NMR, EPR, fluorimetry, and electrochemical methods. BV formed a stable coordination complex with copper in 1 : 1 stoichiometry. The structure of BV was more planar and energetically stable in the complex. The complex showed strong paramagnetic effects that were attributed to an unpaired delocalized e−. The delocalized electron may come from BV or Cu2+, so the complex is formally composed either of BV radical cation and Cu1+ or of BV radical anion and Cu3+. The complex underwent oxidation only in the presence of both O2 and an excess of Cu2+, or a strong oxidizing agent, and it was resistant to reducing agents. The biological effects of the stable BV metallocomplex containing a delocalized unpaired electron should be further examined, and may provide an answer to the long-standing question of high energy investment in the catabolism of BV, which represents a relatively harmless molecule per se.",
journal = "Dalton Transactions",
title = "Biliverdin-copper complex at physiological pH",
volume = "48",
number = "18",
pages = "6061-6070",
doi = "10.1039/c8dt04724c"
}

Dimitrijević, M. S., Bogdanović-Pristov, J., Žižić, M., Stanković, D. M., Bajuk-Bogdanović, D. V., Stanić, M., Spasić, S. D., Hagen, W.,& Spasojević, I.. (2019). Biliverdin-copper complex at physiological pH. in Dalton Transactions, 48(18), 6061-6070.
https://doi.org/10.1039/c8dt04724c

Dimitrijević MS, Bogdanović-Pristov J, Žižić M, Stanković DM, Bajuk-Bogdanović DV, Stanić M, Spasić SD, Hagen W, Spasojević I. Biliverdin-copper complex at physiological pH. in Dalton Transactions. 2019;48(18):6061-6070.
doi:10.1039/c8dt04724c .

Dimitrijević, Milena S., Bogdanović-Pristov, Jelena, Žižić, Milan, Stanković, Dalibor M., Bajuk-Bogdanović, Danica V., Stanić, Marina, Spasić, Snežana D., Hagen, Wilfred, Spasojević, Ivan, "Biliverdin-copper complex at physiological pH" in Dalton Transactions, 48, no. 18 (2019):6061-6070,
https://doi.org/10.1039/c8dt04724c . .

TY  - JOUR
AU  - Dimitrijević, Milena S.
AU  - Bogdanović-Pristov, Jelena
AU  - Žižić, Milan
AU  - Stanković, Dalibor M.
AU  - Bajuk-Bogdanović, Danica V.
AU  - Stanić, Marina
AU  - Spasić, Snežana D.
AU  - Hagen, Wilfred
AU  - Spasojević, Ivan
PY  - 2019
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8258
AB  - Biliverdin (BV), a product of heme catabolism, is known to interact with transition metals, but the details of such interactions under physiological conditions are scarce. Herein, we examined coordinate/redox interactions of BV with Cu2+ in phosphate buffer at pH 7.4, using spectrophotometry, HESI-MS, Raman spectroscopy, 1 H NMR, EPR, fluorimetry, and electrochemical methods. BV formed a stable coordination complex with copper in 1 : 1 stoichiometry. The structure of BV was more planar and energetically stable in the complex. The complex showed strong paramagnetic effects that were attributed to an unpaired delocalized e−. The delocalized electron may come from BV or Cu2+, so the complex is formally composed either of BV radical cation and Cu1+ or of BV radical anion and Cu3+. The complex underwent oxidation only in the presence of both O2 and an excess of Cu2+, or a strong oxidizing agent, and it was resistant to reducing agents. The biological effects of the stable BV metallocomplex containing a delocalized unpaired electron should be further examined, and may provide an answer to the long-standing question of high energy investment in the catabolism of BV, which represents a relatively harmless molecule per se.
T2  - Dalton Transactions
T1  - Biliverdin-copper complex at physiological pH
VL  - 48
IS  - 18
SP  - 6061
EP  - 6070
DO  - 10.1039/c8dt04724c
ER  - 

@article{
author = "Dimitrijević, Milena S. and Bogdanović-Pristov, Jelena and Žižić, Milan and Stanković, Dalibor M. and Bajuk-Bogdanović, Danica V. and Stanić, Marina and Spasić, Snežana D. and Hagen, Wilfred and Spasojević, Ivan",
year = "2019",
abstract = "Biliverdin (BV), a product of heme catabolism, is known to interact with transition metals, but the details of such interactions under physiological conditions are scarce. Herein, we examined coordinate/redox interactions of BV with Cu2+ in phosphate buffer at pH 7.4, using spectrophotometry, HESI-MS, Raman spectroscopy, 1 H NMR, EPR, fluorimetry, and electrochemical methods. BV formed a stable coordination complex with copper in 1 : 1 stoichiometry. The structure of BV was more planar and energetically stable in the complex. The complex showed strong paramagnetic effects that were attributed to an unpaired delocalized e−. The delocalized electron may come from BV or Cu2+, so the complex is formally composed either of BV radical cation and Cu1+ or of BV radical anion and Cu3+. The complex underwent oxidation only in the presence of both O2 and an excess of Cu2+, or a strong oxidizing agent, and it was resistant to reducing agents. The biological effects of the stable BV metallocomplex containing a delocalized unpaired electron should be further examined, and may provide an answer to the long-standing question of high energy investment in the catabolism of BV, which represents a relatively harmless molecule per se.",
journal = "Dalton Transactions",
title = "Biliverdin-copper complex at physiological pH",
volume = "48",
number = "18",
pages = "6061-6070",
doi = "10.1039/c8dt04724c"
}

Dimitrijević, M. S., Bogdanović-Pristov, J., Žižić, M., Stanković, D. M., Bajuk-Bogdanović, D. V., Stanić, M., Spasić, S. D., Hagen, W.,& Spasojević, I.. (2019). Biliverdin-copper complex at physiological pH. in Dalton Transactions, 48(18), 6061-6070.
https://doi.org/10.1039/c8dt04724c

Dimitrijević MS, Bogdanović-Pristov J, Žižić M, Stanković DM, Bajuk-Bogdanović DV, Stanić M, Spasić SD, Hagen W, Spasojević I. Biliverdin-copper complex at physiological pH. in Dalton Transactions. 2019;48(18):6061-6070.
doi:10.1039/c8dt04724c .

Dimitrijević, Milena S., Bogdanović-Pristov, Jelena, Žižić, Milan, Stanković, Dalibor M., Bajuk-Bogdanović, Danica V., Stanić, Marina, Spasić, Snežana D., Hagen, Wilfred, Spasojević, Ivan, "Biliverdin-copper complex at physiological pH" in Dalton Transactions, 48, no. 18 (2019):6061-6070,
https://doi.org/10.1039/c8dt04724c . .

TY  - JOUR
AU  - Korać, Jelena
AU  - Stanković, Dalibor M.
AU  - Stanić, Marina
AU  - Bajuk-Bogdanović, Danica V.
AU  - Žižić, Milan
AU  - Bogdanović-Pristov, Jelena
AU  - Grgurić-Šipka, Sanja
AU  - Popović-Bijelić, Ana D.
AU  - Spasojević, Ivan
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7582
AB  - Coordinate and redox interactions of epinephrine (Epi) with iron at physiological pH are essential for understanding two very different phenomena - the detrimental effects of chronic stress on the cardiovascular system and the cross-linking of catecholamine-rich biopolymers and frameworks. Here we show that Epi and Fe3+ form stable high-spin complexes in the 1:1 or 3:1 stoichiometry, depending on the Epi/Fe3+ concentration ratio (low or high). Oxygen atoms on the catechol ring represent the sites of coordinate bond formation within physiologically relevant bidentate 1:1 complex. Redox properties of Epi are slightly impacted by Fe3+. On the other hand, Epi and Fe2+ form a complex that acts as a strong reducing agent, which leads to the production of hydrogen peroxide via O-2 reduction, and to a facilitated formation of the Epi-Fe3+ complexes. Epi is not oxidized in this process, i.e. Fe2+ is not an electron shuttle, but the electron donor. Epi-catalyzed oxidation of Fe2+ represents a plausible chemical basis of stress-related damage to heart cells. In addition, our results support the previous findings on the interactions of catecholamine moieties in polymers with iron and provide a novel strategy for improving the efficiency of cross-linking.
T2  - Scientific Reports
T1  - Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH
VL  - 8
SP  - 3530
DO  - 10.1038/s41598-018-21940-7
ER  - 

@article{
author = "Korać, Jelena and Stanković, Dalibor M. and Stanić, Marina and Bajuk-Bogdanović, Danica V. and Žižić, Milan and Bogdanović-Pristov, Jelena and Grgurić-Šipka, Sanja and Popović-Bijelić, Ana D. and Spasojević, Ivan",
year = "2018",
abstract = "Coordinate and redox interactions of epinephrine (Epi) with iron at physiological pH are essential for understanding two very different phenomena - the detrimental effects of chronic stress on the cardiovascular system and the cross-linking of catecholamine-rich biopolymers and frameworks. Here we show that Epi and Fe3+ form stable high-spin complexes in the 1:1 or 3:1 stoichiometry, depending on the Epi/Fe3+ concentration ratio (low or high). Oxygen atoms on the catechol ring represent the sites of coordinate bond formation within physiologically relevant bidentate 1:1 complex. Redox properties of Epi are slightly impacted by Fe3+. On the other hand, Epi and Fe2+ form a complex that acts as a strong reducing agent, which leads to the production of hydrogen peroxide via O-2 reduction, and to a facilitated formation of the Epi-Fe3+ complexes. Epi is not oxidized in this process, i.e. Fe2+ is not an electron shuttle, but the electron donor. Epi-catalyzed oxidation of Fe2+ represents a plausible chemical basis of stress-related damage to heart cells. In addition, our results support the previous findings on the interactions of catecholamine moieties in polymers with iron and provide a novel strategy for improving the efficiency of cross-linking.",
journal = "Scientific Reports",
title = "Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH",
volume = "8",
pages = "3530",
doi = "10.1038/s41598-018-21940-7"
}

Korać, J., Stanković, D. M., Stanić, M., Bajuk-Bogdanović, D. V., Žižić, M., Bogdanović-Pristov, J., Grgurić-Šipka, S., Popović-Bijelić, A. D.,& Spasojević, I.. (2018). Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH. in Scientific Reports, 8, 3530.
https://doi.org/10.1038/s41598-018-21940-7

Korać J, Stanković DM, Stanić M, Bajuk-Bogdanović DV, Žižić M, Bogdanović-Pristov J, Grgurić-Šipka S, Popović-Bijelić AD, Spasojević I. Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH. in Scientific Reports. 2018;8:3530.
doi:10.1038/s41598-018-21940-7 .

Korać, Jelena, Stanković, Dalibor M., Stanić, Marina, Bajuk-Bogdanović, Danica V., Žižić, Milan, Bogdanović-Pristov, Jelena, Grgurić-Šipka, Sanja, Popović-Bijelić, Ana D., Spasojević, Ivan, "Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH" in Scientific Reports, 8 (2018):3530,
https://doi.org/10.1038/s41598-018-21940-7 . .