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Coordination and redox interactions of β-lactam antibiotics with Cu2+ in physiological settings and the impact on antibacterial activity

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2018
7626a21c743f3af5e6c4af7b1edf0499.pdf (859.3Kb)
Authors
Božić, Bojana
Korać, Jelena
Stanković, Dalibor
Stanić, Marina
Romanović, Mima
Bogdanović Pristov, Jelena
Spasić, Snežana
Popović-Bjelić, Ana
Spasojević, Ivan
Bajčetić, Milica
Article (Accepted Version)
,
Elsevier
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Abstract
An increase in the copper pool in body fluids has been related to a number of pathological conditions, including infections. Copper ions may affect antibiotics via the formation of coordination bonds and/or redox reactions. Herein, we analyzed the interactions of Cu2+ with eight β-lactam antibiotics using UV–Vis spectrophotometry, EPR spectroscopy, and electrochemical methods. Penicillin G did not show any detectable interactions with Cu2+. Ampicillin, amoxicillin and cephalexin formed stable colored complexes with octahedral coordination environment of Cu2+ with tetragonal distortion, and primary amine group as the site of coordinate bond formation. These β-lactams increased the solubility of Cu2+ in the phosphate buffer. Ceftazidime and Cu2+ formed a complex with a similar geometry and gave rise to an organic radical. Ceftriaxone-Cu2+ complex appears to exhibit different geometry. All complexes showed 1:1 stoichiometry. Cefaclor reduced Cu2+ to Cu1+ that further reacted with molecula...r oxygen to produce hydrogen peroxide. Finally, meropenem underwent degradation in the presence of copper. The analysis of activity against Escherichia coli and Staphylococcus aureus showed that the effects of meropenem, amoxicillin, ampicillin, and ceftriaxone were significantly hindered in the presence of copper ions. The interactions with copper ions should be taken into account regarding the problem of antibiotic resistance and in the selection of the most efficient antimicrobial therapy for patients with altered copper homeostasis.

Keywords:
Antibiotic / Complex / Copper / EPR spectroscopy / Free radicals
Source:
Free Radical Biology and Medicine, 2018, 129, 279-285
Publisher:
  • Elsevier
Funding / projects:
  • Molecular mechanisms of redox signalling in homeostasis: adaptation and pathology (RS-173014)
  • 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:
  • This is the peer-reviewed version of the following article: Božić, B.; Korać, J.; Stanković, D. M.; Stanić, M.; Romanović, M.; Pristov, J. B.; Spasić, S.; Popović-Bijelić, A.; Spasojević, I.; Bajčetić, M. Coordination and Redox Interactions of β-Lactam Antibiotics with Cu2+ in Physiological Settings and the Impact on Antibacterial Activity. Free Radical Biology and Medicine 2018, 129, 279–285. https://doi.org/10.1016/j.freeradbiomed.2018.09.038
  • The published version: https://cer.ihtm.bg.ac.rs/handle/123456789/3936
  • Supporting information: https://cer.ihtm.bg.ac.rs/handle/123456789/4489
Related info:
  • Version of
    https://doi.org/10.1016/j.freeradbiomed.2018.09.038
  • Version of
    https://cer.ihtm.bg.ac.rs/handle/123456789/3936
  • Referenced by
    https://cer.ihtm.bg.ac.rs/handle/123456789/4489

DOI: 10.1016/j.freeradbiomed.2018.09.038

ISSN: 0891-5849

PubMed: 30267756

WoS: 000450298400026

Scopus: 2-s2.0-85054184646
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4281
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Božić, Bojana
AU  - Korać, Jelena
AU  - Stanković, Dalibor
AU  - Stanić, Marina
AU  - Romanović, Mima
AU  - Bogdanović Pristov, Jelena
AU  - Spasić, Snežana
AU  - Popović-Bjelić, Ana
AU  - Spasojević, Ivan
AU  - Bajčetić, Milica
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4281
AB  - An increase in the copper pool in body fluids has been related to a number of pathological conditions, including infections. Copper ions may affect antibiotics via the formation of coordination bonds and/or redox reactions. Herein, we analyzed the interactions of Cu2+ with eight β-lactam antibiotics using UV–Vis spectrophotometry, EPR spectroscopy, and electrochemical methods. Penicillin G did not show any detectable interactions with Cu2+. Ampicillin, amoxicillin and cephalexin formed stable colored complexes with octahedral coordination environment of Cu2+ with tetragonal distortion, and primary amine group as the site of coordinate bond formation. These β-lactams increased the solubility of Cu2+ in the phosphate buffer. Ceftazidime and Cu2+ formed a complex with a similar geometry and gave rise to an organic radical. Ceftriaxone-Cu2+ complex appears to exhibit different geometry. All complexes showed 1:1 stoichiometry. Cefaclor reduced Cu2+ to Cu1+ that further reacted with molecular oxygen to produce hydrogen peroxide. Finally, meropenem underwent degradation in the presence of copper. The analysis of activity against Escherichia coli and Staphylococcus aureus showed that the effects of meropenem, amoxicillin, ampicillin, and ceftriaxone were significantly hindered in the presence of copper ions. The interactions with copper ions should be taken into account regarding the problem of antibiotic resistance and in the selection of the most efficient antimicrobial therapy for patients with altered copper homeostasis.
PB  - Elsevier
T2  - Free Radical Biology and Medicine
T1  - Coordination and redox interactions of β-lactam antibiotics with Cu2+ in physiological settings and the impact on antibacterial activity
VL  - 129
SP  - 279
EP  - 285
DO  - 10.1016/j.freeradbiomed.2018.09.038
ER  - 
@article{
author = "Božić, Bojana and Korać, Jelena and Stanković, Dalibor and Stanić, Marina and Romanović, Mima and Bogdanović Pristov, Jelena and Spasić, Snežana and Popović-Bjelić, Ana and Spasojević, Ivan and Bajčetić, Milica",
year = "2018",
abstract = "An increase in the copper pool in body fluids has been related to a number of pathological conditions, including infections. Copper ions may affect antibiotics via the formation of coordination bonds and/or redox reactions. Herein, we analyzed the interactions of Cu2+ with eight β-lactam antibiotics using UV–Vis spectrophotometry, EPR spectroscopy, and electrochemical methods. Penicillin G did not show any detectable interactions with Cu2+. Ampicillin, amoxicillin and cephalexin formed stable colored complexes with octahedral coordination environment of Cu2+ with tetragonal distortion, and primary amine group as the site of coordinate bond formation. These β-lactams increased the solubility of Cu2+ in the phosphate buffer. Ceftazidime and Cu2+ formed a complex with a similar geometry and gave rise to an organic radical. Ceftriaxone-Cu2+ complex appears to exhibit different geometry. All complexes showed 1:1 stoichiometry. Cefaclor reduced Cu2+ to Cu1+ that further reacted with molecular oxygen to produce hydrogen peroxide. Finally, meropenem underwent degradation in the presence of copper. The analysis of activity against Escherichia coli and Staphylococcus aureus showed that the effects of meropenem, amoxicillin, ampicillin, and ceftriaxone were significantly hindered in the presence of copper ions. The interactions with copper ions should be taken into account regarding the problem of antibiotic resistance and in the selection of the most efficient antimicrobial therapy for patients with altered copper homeostasis.",
publisher = "Elsevier",
journal = "Free Radical Biology and Medicine",
title = "Coordination and redox interactions of β-lactam antibiotics with Cu2+ in physiological settings and the impact on antibacterial activity",
volume = "129",
pages = "279-285",
doi = "10.1016/j.freeradbiomed.2018.09.038"
}
Božić, B., Korać, J., Stanković, D., Stanić, M., Romanović, M., Bogdanović Pristov, J., Spasić, S., Popović-Bjelić, A., Spasojević, I.,& Bajčetić, M.. (2018). Coordination and redox interactions of β-lactam antibiotics with Cu2+ in physiological settings and the impact on antibacterial activity. in Free Radical Biology and Medicine
Elsevier., 129, 279-285.
https://doi.org/10.1016/j.freeradbiomed.2018.09.038
Božić B, Korać J, Stanković D, Stanić M, Romanović M, Bogdanović Pristov J, Spasić S, Popović-Bjelić A, Spasojević I, Bajčetić M. Coordination and redox interactions of β-lactam antibiotics with Cu2+ in physiological settings and the impact on antibacterial activity. in Free Radical Biology and Medicine. 2018;129:279-285.
doi:10.1016/j.freeradbiomed.2018.09.038 .
Božić, Bojana, Korać, Jelena, Stanković, Dalibor, Stanić, Marina, Romanović, Mima, Bogdanović Pristov, Jelena, Spasić, Snežana, Popović-Bjelić, Ana, Spasojević, Ivan, Bajčetić, Milica, "Coordination and redox interactions of β-lactam antibiotics with Cu2+ in physiological settings and the impact on antibacterial activity" in Free Radical Biology and Medicine, 129 (2018):279-285,
https://doi.org/10.1016/j.freeradbiomed.2018.09.038 . .

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