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Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH

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2018
2095.pdf (6.107Mb)
Authors
Korać, Jelena
Stanković, Dalibor
Stanić, Marina
Bajuk-Bogdanović, Danica
Žižić, Milan
Pristov-Bogdanović, Jelena
Grgurić-Šipka, Sanja
Popović-Bijelić, Ana
Spasojević, Ivan
Article (Published version)
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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 pl...ausible 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.

Source:
Scientific Reports, 2018, 8
Publisher:
  • Nature Publishing Group, London
Funding / projects:
  • Study of structure-function relationships in the plant cell wall and modifications of the wall structure by enzyme engineering (RS-173017)
  • Strengthening of the MagBioVin Research and Innovation Team for Development of Novel Approaches for Tumour Therapy based on Nanostructured Materials (EU-621375)
Note:
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3040

DOI: 10.1038/s41598-018-21940-7

ISSN: 2045-2322

PubMed: 29476145

WoS: 000425934200018

Scopus: 2-s2.0-85042549576
[ Google Scholar ]
6
7
URI
https://cherry.chem.bg.ac.rs/handle/123456789/2097
Collections
  • Publikacije
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Korać, Jelena
AU  - Stanković, Dalibor
AU  - Stanić, Marina
AU  - Bajuk-Bogdanović, Danica
AU  - Žižić, Milan
AU  - Pristov-Bogdanović, Jelena
AU  - Grgurić-Šipka, Sanja
AU  - Popović-Bijelić, Ana
AU  - Spasojević, Ivan
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2097
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.
PB  - Nature Publishing Group, London
T2  - Scientific Reports
T1  - Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH
VL  - 8
DO  - 10.1038/s41598-018-21940-7
UR  - Kon_3428
ER  - 
@article{
author = "Korać, Jelena and Stanković, Dalibor and Stanić, Marina and Bajuk-Bogdanović, Danica and Žižić, Milan and Pristov-Bogdanović, Jelena and Grgurić-Šipka, Sanja and Popović-Bijelić, Ana 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.",
publisher = "Nature Publishing Group, London",
journal = "Scientific Reports",
title = "Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH",
volume = "8",
doi = "10.1038/s41598-018-21940-7",
url = "Kon_3428"
}
Korać, J., Stanković, D., Stanić, M., Bajuk-Bogdanović, D., Žižić, M., Pristov-Bogdanović, J., Grgurić-Šipka, S., Popović-Bijelić, A.,& Spasojević, I.. (2018). Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH. in Scientific Reports
Nature Publishing Group, London., 8.
https://doi.org/10.1038/s41598-018-21940-7
Kon_3428
Korać J, Stanković D, Stanić M, Bajuk-Bogdanović D, Žižić M, Pristov-Bogdanović J, Grgurić-Šipka S, Popović-Bijelić A, Spasojević I. Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH. in Scientific Reports. 2018;8.
doi:10.1038/s41598-018-21940-7
Kon_3428 .
Korać, Jelena, Stanković, Dalibor, Stanić, Marina, Bajuk-Bogdanović, Danica, Žižić, Milan, Pristov-Bogdanović, Jelena, Grgurić-Šipka, Sanja, Popović-Bijelić, Ana, Spasojević, Ivan, "Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH" in Scientific Reports, 8 (2018),
https://doi.org/10.1038/s41598-018-21940-7 .,
Kon_3428 .

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