Oxidation of the Antiviral Drug Acyclovir and Its Biodegradation Product Carboxy-acyclovir with Ozone: Kinetics and Identification of Oxidation Products.
In: Environmental Science & Technology, Jg. 46 (2012-02-21), Heft 4, S. 2169-2178
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Zugriff:
The oxidation of the antiviral drug acyclovir (ACV) and its main biotransformation product carboxy-acyclovir (carboxy-ACV) by ozone was investigated. Both compounds have recently been detected in surface water, and carboxy-ACV has also been detected in drinking water. The experiments revealed a strong pH dependence of the oxidation of ACV and carboxy-ACV with reaction rate constants increasing by 4 orders of magnitude between the protonated, positively charged form (kox,PH+,~2.5 × 102 M-1 s-1) and the deprotonated, negatively charged form (kox,P-, 3.4 × 106 M-1 s-1). At pH 8 a single oxidation product was formed which was identified via LC-LTQ-Orbitrap MS and NMR as N-(4-carbamoyl-2-imino-5-oxoimidazolidin)formamido-N-methoxyacetic acid (COFA). Using Vibrio fischeri, an acute bacterial toxicity was found for COFA while carboxy-ACV revealed no toxic effects. Ozonation experiments with guanine and guanosine at pH 8 led to the formation of the respective 2-imino-5-oxoimidazolidines, confirming that guanine derivatives such as carboxy-ACV are undergoing the same reactions during ozonation. Furthermore, COFA was detected in finished drinking water of a German waterworks after ozonation and subsequent activated carbon treatment. [ABSTRACT FROM AUTHOR]
Titel: |
Oxidation of the Antiviral Drug Acyclovir and Its Biodegradation Product Carboxy-acyclovir with Ozone: Kinetics and Identification of Oxidation Products.
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Autor/in / Beteiligte Person: | Prasse, Carsten ; Wagner, Manfred ; Schulz, Ralf ; Ternes, Thomas A. |
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Zeitschrift: | Environmental Science & Technology, Jg. 46 (2012-02-21), Heft 4, S. 2169-2178 |
Veröffentlichung: | 2012 |
Medientyp: | academicJournal |
ISSN: | 0013-936X (print) |
DOI: | 10.1021/es203712z |
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