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. 1998 May;42(5):1151-9.
doi: 10.1128/AAC.42.5.1151.

Defluorinated sparfloxacin as a new photoproduct identified by liquid chromatography coupled with UV detection and tandem mass spectrometry

M Engler  1 , G Rüsing, F Sörgel, U Holzgrabe
Affiliations

Defluorinated sparfloxacin as a new photoproduct identified by liquid chromatography coupled with UV detection and tandem mass spectrometry

M Engler et al. Antimicrob Agents Chemother. 1998 May.

Abstract

Photodegradation of sparfloxacin was observed by means of high-pressure liquid chromatography with UV detection and liquid chromatography coupled with UV detection and tandem mass spectrometry (LC-MS/MS). Three products were detected. Comparison with an independently synthesized derivative of sparfloxacin revealed the structure of one product which is believed to be 8-desfluorosparfloxacin. The second product is likely to be formed by the splitting off of a fluorine and a cyclopropyl ring. Thus, photodefluorination of quinolone antibacterial agents is found and proved for the first time by LC-MS/MS.

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Figures

FIG. 1
FIG. 1
Synthesis of the reference compound, compound 10. Et, ethyl.
FIG. 2
FIG. 2
Photoproducts of sparfloxacin.
FIG. 3
FIG. 3
Product ion spectrum of sparfloxacin.
FIG. 4
FIG. 4
Fragmentation pathway of sparfloxacin under MS/MS conditions. Numbers in brackets are m/z’s.
FIG. 5
FIG. 5
Product ion spectrum of the photoproduct [M+H]+ with a mass of 375 Da.
FIG. 6
FIG. 6
Product ion spectrum of the photoproduct [M+H]+ with a mass of 335 Da.
FIG. 7
FIG. 7
Product ion spectrum of the photoproduct [M+H]+ with a mass of 405 Da.
FIG. 8
FIG. 8
Product ion spectrum of the reference compound, compound 10.
FIG. 9
FIG. 9
Fragmentation pathway of the reference compound, compound 10, under MS/MS conditions. Numbers in brackets are m/z’s.
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