Coordination and redox interactions of β-lactam antibiotics with Cu2+ in physiological settings and the impact on antibacterial activity
Autori
Božić, BojanaKorać, Jelena
Stanković, Dalibor
Stanić, Marina
Romanović, Mima
Bogdanović Pristov, Jelena
Spasić, Snežana
Popović-Bjelić, Ana
Spasojević, Ivan
Bajčetić, Milica
Članak u časopisu (Recenzirana verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Antibiotic / Complex / Copper / EPR spectroscopy / Free radicalsIzvor:
Free Radical Biology and Medicine, 2018, 129, 279-285Izdavač:
- Elsevier
Finansiranje / projekti:
- Molekularni mehanizmi redoks signalinga u homeostazi, adaptaciji i patologiji (RS-MESTD-Basic Research (BR or ON)-173014)
- Ispitivanja odnosa struktura-funkcija u ćelijskom zidu biljaka i izmene strukture zida enzimskim inženjeringom (RS-MESTD-Basic Research (BR or ON)-173017)
- Strengthening of the MagBioVin Research and Innovation Team for Development of Novel Approaches for Tumour Therapy based on Nanostructured Materials (EU-FP7-621375)
Napomena:
- 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
Povezane informacije:
- Druga verzija
https://doi.org/10.1016/j.freeradbiomed.2018.09.038 - Druga verzija
https://cer.ihtm.bg.ac.rs/handle/123456789/3936 - Povezani sadržaj
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
Institucija/grupa
IHTMTY - 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 . .