Volume 13 Issue 3
Mar.  2023
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Zhigang Liang, Huanhuan Wang, Fangling Wu, Longfei Wang, Chenwei Li, Chuan-Fan Ding. Drug adulteration analysis based on complexation with cyclodextrin and metal ions using ion mobility spectrometry[J]. Journal of Pharmaceutical Analysis, 2023, 13(3): 287-295. doi: 10.1016/j.jpha.2022.11.002
Citation: Zhigang Liang, Huanhuan Wang, Fangling Wu, Longfei Wang, Chenwei Li, Chuan-Fan Ding. Drug adulteration analysis based on complexation with cyclodextrin and metal ions using ion mobility spectrometry[J]. Journal of Pharmaceutical Analysis, 2023, 13(3): 287-295. doi: 10.1016/j.jpha.2022.11.002

Drug adulteration analysis based on complexation with cyclodextrin and metal ions using ion mobility spectrometry

doi: 10.1016/j.jpha.2022.11.002
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This work was supported by the National Natural Science Foundation of China (Grant Nos.: 22004074 and 21927805), Zhejiang Natural Science Foundation (Grant No.: LY22B050006), and Foundation of Zhejiang Provincial Key Laboratory of Advanced Mass Spectrometry Technology and Molecular Detection (Grant No.: AMSMAKF2102).

  • Received Date: Jun. 17, 2022
  • Accepted Date: Nov. 02, 2022
  • Rev Recd Date: Nov. 02, 2022
  • Publish Date: Nov. 09, 2022
  • Drug adulteration and contamination are serious threats to human health therefore, their accurate monitoring is very important. Allopurinol (Alp) and theophylline (Thp) are commonly used drugs for the treatment of gout and bronchitis, while their isomers hypoxanthine (Hyt) and theobromine (Thm) have no effect and affect the efficacy of the drug. In this work, the drug isomers of Alp/Hyt and Thp/Thm are simply mixed with α-, β-, γ-cyclodextrin (CD) and metal ions and separated using trapped ion mobility spectrometry-mass spectrometry (TIMS-MS). TIMS-MS results showed that Alp/Hyt and Thp/Thm isomers could interact with CD and metal ions and form corresponding binary or ternary complexes to achieve their TIMS separation. Different metal ions and CDs showed different separation effect for the isomers, among which Alp and Hyt could be successfully distinguished from the complexes of [Alp/Hyt+γ-CD + Cu–H]+ with separation resolution (RP–P) of 1.51; whereas Thp and Thm could be baseline separated by [Thp/Thm+γ-CD + Ca–H]+ with RP–P of 1.96. Besides, chemical calculations revealed that the complexes were in the inclusion forms, and microscopic interactions were somewhat different, making their mobility separation. Moreover, relative and absolute quantification was investigated with an internal standard to determine the precise isomers content, and good linearity (R2 > 0.99) was obtained. Finally, the method was applied for the adulteration detection where different drugs and urine were analyzed. In addition, due to the advantages of fast speed, simple operation, high sensitivity, and no chromatographic separation required, the proposed method provides an effective strategy for the drug adulteration detection of isomers.
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  • P. Posadzki, L. Watson, E. Ernst, Contamination and adulteration of herbal medicinal products (HMPs): an overview of systematic reviews, Eur. J. Pharmacol. 69 (2013) 295-307.
    S. Nithaniyal, S.L. Vassou, S. Poovitha, et al., Identification of species adulteration in traded medicinal plant raw drugs using DNA barcoding, GENOME 60 (2017) 139-146.
    Y. Jiang, S. Cong, G. Song, et al., Defective cuprous oxide as a selective surface-enhanced Raman scattering sensor of dye adulteration in Chinese herbal medicines, J. Raman Spectrosc. 52 (2021) 1265-1274.
    J.-W. Hao, Y. Chen, N.-D. Chen, et al., Rapid Detection of Adulteration in Dendrobium huoshanense Using NIR Spectroscopy Coupled with Chemometric Methods, J. Aoac. Int. 104 (2021) 854-859.
    L. Childs, C. Dow, Allopurinol-induced hepatomegaly, BMJ case reports 2012 (2012).
    C.W. Wang, R.L. Dao, W.H. Chung, Immunopathogenesis and risk factors for allopurinol severe cutaneous adverse reactions, Curr. Opin. Allergy Cl. 16 (2016) 339-345.
    Z.Q. Feng, C.G. Sun, Z.J. Zheng, et al., Optimization of Spray-Drying Conditions and Pharmacodynamics Study of Theophylline/Chitosan/beta-Cyclodextrin Microspheres, Dry. Technol. 33 (2015) 55-65.
    J. Timson, Theobromine and theophylline, Mutat. Res-Gen Tox. En. 32 (1975) 169-177.
    C. Wu, F. Zhang, Y. Guo, Identification and distinction of acrolein-deoxyguanosine adduct isomers by high-performance liquid chromatography/ion mobility spectrometry/quadrupole time-of-flight mass spectrometry combined with in-source collision-induced dissociation, Rapid Commun. Mass Sp. 34 (2020), e8677.
    H. Tada, A. Fujisaki, K. Itoh, et al., Facile and rapid high-performance liquid chromatography method for simultaneous determination of allopurinol and oxypurinol in human serum, J. Clin. Pharm. Ther. 28(2003) 229-234.
    M.K. Reinders, L.C. Nijdam, E. N. van Roon, et al., A simple method for quantification of allopurinol and oxipurinol in human serum by high-performance liquid chromatography with UV-detection, J. Pharmaceut. Biomed. 45(2007) 312-317.
    G. Camurri, A. Zaramella, High-throughput liquid chromatography/mass spectrometry method for the determination of the chromatographic hydrophobicity index, Anal. Chem.73(2001) 3716-3722.
    K. Safranow, Z. Machoy, K. Ciechanowski, Analysis of purines in urinary calculi by high-performance liquid chromatography, Anal. Biochem. 286(2000) 224-230.
    K. Masuda, Y. Murano, Simultaneous analysis of various triacylglycerol isomers by supercritical fluid chromatography, J. Am. Oil Chem. Soc. 97 (2020) 20-20.
    H. Deng, Y. Wang, J. Wang, et al., Separation of N '-nitrosonornicotine isomers and enantiomers by supercritical fluid chromatography tandem mass spectrometry, J. Chromatogr. A 1641 (2021) 461971.
    M. Shah, N. Patel, N. Tripathi, et al., Capillary electrophoresis methods for impurity profiling of drugs: A review of the past decade, J. Pharm. Anal. 12 (2021) 15-28.
    T.L. Amorim, L.M. Duarte, H.F. Dos Santos, et al., Screening method for simultaneous detection of elaidic and vaccenic trans fatty acid isomers by capillary zone electrophoresis, Anal. Chim. Acta 1048 (2019) 212-220.
    H. Lu, H. Zhang, H.W. Chen, et al., Ambient mass spectrometry for food science and industry, TrAC Trend Anal. Chem. 107 (2018) 99-115.
    D.-Q. Han, Z.-P. Yao, Chiral mass spectrometry: An overview, TrAC Trend Anal. Chem. 123 (2020) 115763.
    Y. Huang, T. Wang, M. Fillet, et al., Simultaneous determination of amino acids in different teas using supercritical fluid chromatography coupled with single quadrupole mass spectrometry, J. Pharm. Anal. 9(2019) 254-258.
    J. Wu, R.M. Crist, S.E. McNeil, et al., Ion quantification in liposomal drug products using high performance liquid chromatography, J. Pharmaceut. Biomed. 165 (2019) 41-46.
    K.A. Morrison, B.H. Clowers, Contemporary glycomic approaches using ion mobility-mass spectrometry, Curr. Opin. Chem. Biol. 42 (2018) 119-129.
    L. Liu, R. Hua, H.-Wen. Chen (2014). Research Progress of Ionization Technologies for Ion Mobility Spectrometry. J. Chinese Mass Spectrom. Soc. 35(2014) 97.
    X. Garcia, M.d.M. Sabate, J. Aubets, et al., Ion Mobility-Mass Spectrometry for Bioanalysis, Separations 8(3) (2021) 33.
    J.C. May, J.A. McLean, Ion Mobility-Mass Spectrometry: Time-Dispersive Instrumentation, Anal. Chem. 87(3) (2015) 1422-1436.
    V. Domalain, M. Hubert-Roux, C.M. Lange, et al., Use of transition metals to improve the diastereomers differentiation by ion mobility and mass spectrometry, J. Mass Spectrom. 49(5) (2014) 423-427.
    X. Yu, Z.-P. Yao, Chiral differentiation of amino acids through binuclear copper bound tetramers by ion mobility mass spectrometry, Anal. Chim. Aata 981 (2017) 62-70.
    J. Hofmann, H.S. Hahm, P.H. Seeberger, et al., Identification of carbohydrate anomers using ion mobility-mass spectrometry, Nature 526 (2015) 241-244.
    A. Troc, M. Zimnicka, W. Danikiewicz, Separation of catechin epimers by complexation using ion mobility mass spectrometry, J. Mass Spectrom. 50 (2015) 542-548.
    J.D. Zhang, K.M.M. Kabir, W.A. Donald, Metal-ion free chiral analysis of amino acids as small as proline using high-definition differential ion mobility mass spectrometry, Anal. Chim. Aata 1036 (2018) 172-178.
    J.D. Zhang, K.M.M. Kabir, H.E. Lee, et al., Chiral recognition of amino acid enantiomers using high-definition differential ion mobility mass spectrometry, Int. J. Mass Spectrom. 428 (2018) 1-7.
    Y. Huang, E.D. Dodds, Ion Mobility Studies of Carbohydrates as Group I Adducts: Isomer Specific Collisional Cross Section Dependence on Metal Ion Radius, Anal. Chem. 85(20) (2013) 9728-9735.
    C. Xie, L. Gu, Q. Wu, et al., Effective Chiral Discrimination of Amino Acids through Oligosaccharide Incorporation by Trapped Ion Mobility Spectrometry, Anal. Chem. 93(2) (2021) 859-867.
    H. Wang, F. Wu, F. Xu, et al., Identification of Bi-2-naphthol and Its Phosphate Derivatives Complexed with Cyclodextrin and Metal Ions Using Trapped Ion Mobility Spectrometry, Anal. Chem. 93(45) (2021) 15096-15104.
    S. Yang, L. Gu, F. Wu, et al., The chirality determination of amino acids by forming complexes with cyclodextrins and metal ions using ion mobility spectrometry, and a DFT calculation, Talanta 243 (2022) 123363-123363.
    F. Wu, X. Wu, F. Xu, et al., Recognition of Cis-Trans and Chiral Proline and Its Derivatives by Ion Mobility Measurement of Their Complexes with Natamycin and Metal Ion, Anal. Chem. 94(8) (2022) 3553-3564.
    S. Yang, F. Wu, F. Yu, et al., Distinction of chiral penicillamine using metal-ion coupled cyclodextrin complex as chiral selector by trapped ion mobility-mass spectrometry and a structure investigation of the complexes, Anal. Chim. Aata 1184 (2021) 339017-339017.
    F. Fernandez-Lima, D.A. Kaplan, J. Suetering, M.A. Park, Gas-phase separation using a trapped ion mobility spectrometer, Int. J Ion Mobil. Spectrometry: official publication of the International Society for Ion Mobility Spec. 14(2011) 93-98.
    C.D. Chouinard, G. Nagy, I.K. Webb, S.V.B. Garimella, et al., Rapid Ion Mobility Separations of Bile Acid Isomers Using Cyclodextrin Adducts and Structures for Lossless Ion Manipulations, Aanl. Chem. 90(18) (2018) 11086-11091.
    M.E. Ridgeway, M. Lubeck, J. Jordens, et al., Trapped ion mobility spectrometry: A short review, International J. Mass Spectrom. 425(2018) 22-35.
    S. A. Ewing, M. T. Donor, J. W. Wilson, et al., Collidoscope: an improved tool for computing collisional cross-sections with the trajectory method. J Mass Spectrom. 28(2017) 587-596.
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