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Determination of photostability and photodegradation products of moxifloxacin in the presence of metal ions in solutions and solid phase. Kinetics and identification of photoproducts

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Abstract

Photostability of moxifloxacin (MOXI) after UVA irradiation in solutions and solid phase, with and without participation of Cu(ii), Zn(ii), Al(iii), and Fe(iii) was tested. The studies were carried out by the TLC-densitometric method and LC-MS/MS method. Elaborated and validated chromatography-densitometric method was used for assaying. It was shown that the number and type of photoproducts depend on the environment and type of the metal ion. The studied ions enhanced the degradation of MOXI in solutions, and the influence of Cu(ii) and Fe(iii) ions was higher than that of Zn(ii) and Al(iii) ions. In solid phase, in contrast to solutions, all metal ions decreased the photodegradation, however the influence of ions, Al(iii) and Zn(ii), was weaker than that of Cu(ii) and Fe(iii) ions. Identification of the degradation products performed with LC-MS/MS and 1H NMR identified them as: 1-cyclopropyl-6-fluoro-7-amino-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(2-oxo-octahydro-6H-pyrrolo[3,4-b]pyridine-6-yl)-1,4-dihydroquinoline-3-carboxylic acid, 7-[3-hydroxyamino-4-(2-carboxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid.

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Authors and Affiliations

  1. Department of Inorganic and Analytical Chemistry, Jagiellonian University, Medical College, Pharmaceutical Faculty, Medyczna 9, 30-688, Krakow, Poland

    Urszula Hubicka, Jan Krzek, Barbara Żuromska & Daniel Pawlowski

  2. Department of Pharmacokinetics and Physical Pharmacy, Jagiellonian University, Medical College, Pharmaceutical Faculty, Krakow, Poland

    Maria Walczak

  3. Department of Organic Chemistry, Jagiellonian University, Medical College, Pharmaceutical Faculty, Krakow, Poland

    Marek Żylewski

Authors
  1. Urszula Hubicka
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  2. Jan Krzek
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  3. Barbara Żuromska
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  4. Maria Walczak
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  5. Marek Żylewski
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Correspondence to Jan Krzek.

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Electronic supplementary information (ESI) available: See DOI: 10.1039/c1pp05259d

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Hubicka, U., Krzek, J., Żuromska, B. et al. Determination of photostability and photodegradation products of moxifloxacin in the presence of metal ions in solutions and solid phase. Kinetics and identification of photoproducts. Photochem Photobiol Sci 11, 351–357 (2012). https://doi.org/10.1039/c1pp05259d

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  • DOI: https://doi.org/10.1039/c1pp05259d

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