LAPSE:2023.2486
Published Article

LAPSE:2023.2486
Study of Oxidation of Ciprofloxacin and Pefloxacin by ACVA: Identification of Degradation Products by Mass Spectrometry and Bioautographic Evaluation of Antibacterial Activity
February 21, 2023
Abstract
The new RP-HPLC-DAD method for the determination of ciprofloxacin and pefloxacin, next to their degradation products after the oxidation reaction with 4,4′-azobis(4-cyanopentanoic acid) (ACVA) was developed. The method was validated according to the guidelines of the International Council for Harmonization of Technical Requirements for Pharmaceuticals for Human Use (ICH) and meets the acceptance criteria. The experimental data indicate that the course of the oxidation process depends on the type of fluoroquinolone (FQ), the incubation time and temperature. The performed kinetic evaluation allowed us to state that the oxidation of FQs proceeds according to the second-order kinetics. The degradation products of the FQs were identified using the UHPLC-MS/MS method and their structures were proposed. The results obtained by the TLC-direct bioautography technique allowed us to state that the main ciprofloxacin and pefloxacin oxidation products probably retained antibacterial activity against Escherichia coli.
The new RP-HPLC-DAD method for the determination of ciprofloxacin and pefloxacin, next to their degradation products after the oxidation reaction with 4,4′-azobis(4-cyanopentanoic acid) (ACVA) was developed. The method was validated according to the guidelines of the International Council for Harmonization of Technical Requirements for Pharmaceuticals for Human Use (ICH) and meets the acceptance criteria. The experimental data indicate that the course of the oxidation process depends on the type of fluoroquinolone (FQ), the incubation time and temperature. The performed kinetic evaluation allowed us to state that the oxidation of FQs proceeds according to the second-order kinetics. The degradation products of the FQs were identified using the UHPLC-MS/MS method and their structures were proposed. The results obtained by the TLC-direct bioautography technique allowed us to state that the main ciprofloxacin and pefloxacin oxidation products probably retained antibacterial activity against Escherichia coli.
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Keywords
ACVA, ciprofloxacin, degradation products, direct bioautography, mass spectrometry, oxidation studies, pefloxacin, RP-HPLC-DAD method
Subject
Suggested Citation
Żuromska-Witek B, Żmudzki P, Szlósarczyk M, Abram M, Maślanka A, Hubicka U. Study of Oxidation of Ciprofloxacin and Pefloxacin by ACVA: Identification of Degradation Products by Mass Spectrometry and Bioautographic Evaluation of Antibacterial Activity. (2023). LAPSE:2023.2486
Author Affiliations
Żuromska-Witek B: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland [ORCID]
Żmudzki P: Department of Medicinal Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland [ORCID]
Szlósarczyk M: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland [ORCID]
Abram M: Department of Medicinal Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland
Maślanka A: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland [ORCID]
Hubicka U: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland [ORCID]
Żmudzki P: Department of Medicinal Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland [ORCID]
Szlósarczyk M: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland [ORCID]
Abram M: Department of Medicinal Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland
Maślanka A: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland [ORCID]
Hubicka U: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Kraków, Poland [ORCID]
Journal Name
Processes
Volume
10
Issue
5
First Page
1022
Year
2022
Publication Date
2022-05-20
ISSN
2227-9717
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Original Submission
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PII: pr10051022, Publication Type: Journal Article
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LAPSE:2023.2486
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https://doi.org/10.3390/pr10051022
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Feb 21, 2023
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