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Characterization of the Oxidation Degradation Products in Tigecycline by Column-Switching and Online Demineralization Technique for Dual Gradient Liquid Chromatography Combined With Q Orbitrap Mass Spectrometry

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Abstract

The oxidation degradation products in tigecycline were separated and identified by column-switching and online demineralization technique for dual gradient high-performance liquid chromatography (DGLC) combined with Q Orbitrap mass spectrometry for the further improvement of official monographs in pharmacopoeias. Each peak eluted from the non-volatile system was trapped by a switching valve and sent to an LC–MS system using a volatile mobile phase. Thermo Ultimate 3000 DGLC combined with Q Orbitrap MS equipped with electrospray ionization was scanning in positive and negative ion modes at the same time. The one-dimensional analytical column was Welch Ultimate XB-C18 (250 mm × 4.6 mm, 5 μm) with non-volatile salt mobile phase at the flow rate of 1.5 mL min−1 (left pump), and the two-dimensional analytical column was Thermo Acclaim™ 120 C18 (250 mm × 4.6 mm, 5 μm) with a volatile salt mobile phase at the flow rate of 0.3 mL min−1 (right pump). The column temperature was at 30 °C. The detection wavelength was 248 nm. The column-switching and online demineralization technique made it possible to characterize tigecycline in the condition of official standard. The complete fragmentation patterns of impurities were studied and used to obtain information about the structures of these impurities. Mass Frontier software version 7.0 from Thermo Finnigan was used to simulate and study the fragmentation behavior of the described compounds. The structures of six oxidation degradation products in tigecycline were deduced based on the high-resolution MSn data, in which five impurities were novel impurities. The forming mechanisms of oxidation degradation products in tigecycline were also studied. The method solved the problem of incompatibility between non-volatile salt mobile phase and mass spectrometry. It is worthy of widespread use and application, with the advantages of stability and repeatability.

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Authors and Affiliations

  1. College of Pharmacy, Zhejiang University of Technology, Hangzhou, People’s Republic of China

    Fang Gao, Hong Wang & Weike Su

  2. Zhejiang Institute for Food and Drug Control, Hangzhou, People’s Republic of China

    Jian Wang

Authors
  1. Jian Wang
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  2. Fang Gao
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  3. Hong Wang
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  4. Weike Su
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Correspondence to Weike Su.

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Wang, J., Gao, F., Wang, H. et al. Characterization of the Oxidation Degradation Products in Tigecycline by Column-Switching and Online Demineralization Technique for Dual Gradient Liquid Chromatography Combined With Q Orbitrap Mass Spectrometry. Chromatographia 79, 537–545 (2016). https://doi.org/10.1007/s10337-016-3070-8

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