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Biliverdin-copper complex at physiological pH

Authorized Users Only
2019
Authors
Dimitrijević, Milena S.
Bogdanović Pristov, Jelena
Žižić, Milan
Stanković, Dalibor
Bajuk-Bogdanović, Danica
Stanić, Marina
Spasić, Snežana
Hagen, Wilfred
Spasojević, Ivan
Article (Published version)
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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.

Source:
Dalton Transactions, 2019, 48, 18, 6061-6070
Publisher:
  • Royal Society of Chemistry
Funding / projects:
  • Modulation of antioxidative metabolism in plants for improvement of plant abiotic stress tolerance and identification of new biomarkers for application in remediation and monitoring of degraded biotopes (RS-43010)
  • 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/123456789/3069
  • Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/3068

DOI: 10.1039/c8dt04724c

ISSN: 1477-9226

WoS: 000472449300020

Scopus: 2-s2.0-85065545631
[ Google Scholar ]
7
6
URI
https://cherry.chem.bg.ac.rs/handle/123456789/3066
Collections
  • Publikacije
Institution/Community
Inovacioni centar
TY  - JOUR
AU  - Dimitrijević, Milena S.
AU  - Bogdanović Pristov, Jelena
AU  - Žižić, Milan
AU  - Stanković, Dalibor
AU  - Bajuk-Bogdanović, Danica
AU  - Stanić, Marina
AU  - Spasić, Snežana
AU  - Hagen, Wilfred
AU  - Spasojević, Ivan
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3066
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 and Bajuk-Bogdanović, Danica and Stanić, Marina and Spasić, Snežana 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., Bajuk-Bogdanović, D., Stanić, M., Spasić, S., 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 D, Bajuk-Bogdanović D, Stanić M, Spasić S, 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, Bajuk-Bogdanović, Danica, Stanić, Marina, Spasić, Snežana, 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 . .

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