TY - JOUR

T1 - Characterization of photo-transformation products of the antibiotic drug Ciprofloxacin with liquid chromatography-tandem mass spectrometry in combination with accurate mass determination using an LTQ-Orbitrap

AU - Haddad, Tarek

AU - Kümmerer, Klaus

N1 - Copyright © 2014 Elsevier Ltd. All rights reserved.

PY - 2014/11

Y1 - 2014/11

N2 - The presence of pharmaceuticals, especially antibiotics, in the aquatic environment is of growing concern. Several studies have been carried out on the occurrence and environmental risk of these compounds. Ciprofloxacin (CIP), a broad-spectrum anti-microbial second-generation fluoroquinolone, is widely used in human and veterinary medicine. In this work, photo-degradation of CIP in aqueous solution using UV and xenon lamps was studied. The transformation products (TPs), created from CIP, were initially analyzed by an ion trap in the MS, MS/MS and MS(3) modes. These data were used to clarify the structures of the degradation products. Furthermore, the proposed products were confirmed by accurate mass measurement and empirical formula calculation for the molecular ions of TPs using LTQ-Orbitrap XL mass spectrometer. The degree of mineralization, the abundance of detected TPs and degradation pathways were determined. Eleven TPs were detected in the present study. TP1, which was never detected before, was structurally characterized in this work. All TPs still retained the core quinolone structure, which is responsible for the biological activity. As mineralization of CIP and its transformation products did not happen, the formation of stable TPs can be expected in waste water treatment and in surface water with further follow-up problems.

AB - The presence of pharmaceuticals, especially antibiotics, in the aquatic environment is of growing concern. Several studies have been carried out on the occurrence and environmental risk of these compounds. Ciprofloxacin (CIP), a broad-spectrum anti-microbial second-generation fluoroquinolone, is widely used in human and veterinary medicine. In this work, photo-degradation of CIP in aqueous solution using UV and xenon lamps was studied. The transformation products (TPs), created from CIP, were initially analyzed by an ion trap in the MS, MS/MS and MS(3) modes. These data were used to clarify the structures of the degradation products. Furthermore, the proposed products were confirmed by accurate mass measurement and empirical formula calculation for the molecular ions of TPs using LTQ-Orbitrap XL mass spectrometer. The degree of mineralization, the abundance of detected TPs and degradation pathways were determined. Eleven TPs were detected in the present study. TP1, which was never detected before, was structurally characterized in this work. All TPs still retained the core quinolone structure, which is responsible for the biological activity. As mineralization of CIP and its transformation products did not happen, the formation of stable TPs can be expected in waste water treatment and in surface water with further follow-up problems.

KW - Chemistry

KW - Accurate mass measurement

KW - Aquatic environment

KW - Ciprofoloxacin

KW - Structure elucidation

KW - Tandem Mass Spectrometry

KW - Transformation product

UR - http://www.scopus.com/inward/record.url?scp=84921680982&partnerID=8YFLogxK

U2 - 10.1016/j.chemosphere.2014.02.013

DO - 10.1016/j.chemosphere.2014.02.013

M3 - Journal articles

C2 - 24630245

VL - 115

SP - 40

EP - 46

JO - Chemosphere

JF - Chemosphere

SN - 0045-6535

IS - 1

ER -