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Research Paper

Resolution of co-eluting isomers of anti-inflammatory drugs conjugated to carbonic anhydrase inhibitors from plasma in liquid chromatography by energy-resolved tandem mass spectrometry

, , , , , , , & ORCID Icon show all
Pages 671-679 | Received 15 Jan 2018, Accepted 23 Feb 2018, Published online: 14 Mar 2018

References

  • Myasoedova E, Crowson CS, Kremers HM, et al. Is the incidence of rheumatoid arthritis rising? Results from Olmsted County, Minnesota, 1955–2007. Arthritis Rheum 2010;62:1576–82.
  • (a) Margheri F, Ceruso M, Carta F, et al. Overexpression of the transmembrane carbonic anhydrase isoforms IX and XII in the inflamed synovium. J Enzyme Inhib Med Chem 2016;31:60−3. (b) Supuran CT. Carbonic anhydrase inhibitors: an editorial. Expert Opin Ther Pat 2013;23:677–9. (c) Di Cesare Mannelli L, Micheli L, Carta F, et al. Carbonic anhydrase inhibition for the management of cerebral ischemia: in vivo evaluation of sulfonamide and coumarin inhibitors. J Enzyme Inhib Med Chem 2016;31:894–9.
  • Chang X, Han J, Zhao Y, et al. Increased expression of carbonic anhydrase I in the synovium of patients with ankylosing spondylitis. BMC Musculoskeletal Disord 2010;11:279–90.
  • Zheng Y, Wang L, Zhang W, et al. Transgenic mice over-expressing carbonic anhydrase I showed aggravated joint inflammation and tissue destruction. BMC Musculoskeletal Disord 2012;13:256–65.
  • Deutsch O, Krief G, Konttinen YT, et al. Identification of Sjo¨gren’s syndrome oral fluid biomarker candidates following high-abundance protein depletion. Rheumatology 2015;54:884–90.
  • Liu C, Wei Y, Wang J, et al. Carbonic anhydrases III and IV autoantibodies in rheumatoid arthritis, systemic lupus erythematosus, diabetes, hypertensive renal disease, and heart failure. Clin Dev Immunol 2012;2012:354594.
  • Crofford LJ. Use of NSAIDs in treating patients with arthritis. Arthritis Res Ther 2013;15:S2.
  • (a) Maresca A, Temperini C, Vu H, et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057–62. (b) Alterio V, Di FA, D’Ambrosio K, et al. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev 2012;112:4421–68.
  • (a) Maresca A, Temperini C, Pochet L, et al. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem 2010;53:335–44. (b) Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32.
  • Ferraroni M, Carta F, Scozzafava A, Supuran CT. Thioxocoumarins show an alternative carbonic anhydrase inhibition mechanism compared to coumarins. J Med Chem 2016;59:462–73.
  • (a) Touisni N, Maresca A, McDonald PC, et al. Glycosylcumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors. J Med Chem 2011;54:8271–7. (b) Scozzafava A, Supuran CT, Carta F. Antiobesity carbonic anhydrase inhibitors: a literature and patent review. Expert Opin Ther Pat 2013;23:725–35. (c) Pacchiano F, Aggarwal M, Avvaru BS, et al. Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency. Chem Commun (Camb) 2010;46:8371–3.
  • (a) Bonneau A, Maresca A, Winum JY, Supuran CT. Metronidazole-coumarin conjugates and 3-cyano-7-hydroxy-coumarin act as isoform-selective carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2013;28:397–401. (b) Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nature Rev Drug Discov 2008;7:168–81. (c) Supuran CT. Carbon- versus sulphur-based zinc binding groups for carbonic anhydrase inhibitors? J Enzyme Inhib Med Chem 2018;33:485–95.
  • (a) Sharma A, Tiwari M, Supuran CT. Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX. J Enzyme Inhib Med Chem 2014;29:292–6. (b) Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759–72. (c) Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60. (d) Carta F, Supuran CT. Diuretics with carbonic anhydrase inhibitory action: a patent and literature review (2005–2013). Expert Opin Ther Pat 2013;23:681–91.
  • Bua S, Di Cesare Mannelli L, Vullo D, et al. Design and synthesis of novel nonsteroidal anti-inflammatory drugs and carbonic anhydrase inhibitors hybrids (NSAIDs-CAIs) for the treatment of rheumatoid arthritis. J Med Chem 2017;60:1159–70.
  • Borth S, Hansel W, Rosner P, Junge T. Regioisomeric differentiation of 2,3- and 3,4-methylenedioxy ring-substituted phenylalkylamines by gas chromatography/tandem mass spectrometry. J Mass Spectrom 2000;35:705–10.
  • Vouros P, Muller DR, Richter WJ. Low-energy collision-induced dissociation of B1-type sugar ions formed from peracetylated methyl pentosides and methyl 6-deoxyhexosides. J Mass Spectrom 1999;34:346–53.
  • Sheeley DM, Reinhold VN. Structural characterization of carbohydrate sequence, linkage, and branching in a quadrupole ion trap mass spectrometer, neutral oligosaccharides and Nlinked glycans. Anal Chem 1998;70:3053–9.
  • Zimmermann R, Rohwer ER, Heger H. In-line catalytic derivatization method for selective detection of chlorinated aromatics with a hyphenated gas chromatography/laser mass spectrometry technique, a concept for comprehensive detection of isomeric ensembles. Anal Chem 1999;71:4148–53.
  • Seymour JL, Turechek F. Distinction and quantitation of leucine–isoleucine isomers and lysine–glutamine isobars by electrospray ionization tandem mass spectrometry (MSn, n D 2,3) of copper(II)-diimine complexes. J Mass Spectrom 2000;35:566–71.
  • Wu L, Lemr K, Aggerholm T, Cooks RG. Recognition and quantification of binary and ternary mixtures of isomeric peptides by kinetic method, metal ion and ligand effects on the dissociation of metal-bound complexes. J Am Soc Mass Spectrom 2003;14:152–60.
  • Desaire H, Leary JA. Multicomponent quantification of diastereomeric hexosamine monosaccharides using ion trap tandem mass spectrometry. Anal Chem 1999;71:4142–247.
  • Kushnir MM, Rockwood AL, Nelson GJ. Simultaneous quantitative analysis of isobars by tandem mass spectrometry from unresolved chromatographic peaks. J Mass Spectrom 2004;39:532–40.
  • Memboeuf A, Jullien L, Lartia R, et al. Tandem mass spectrometric analysis of a mixture of isobars using the survival yield technique. J Am Soc Mass Spectrom 2011;22:1744–52.
  • Josse T, De Winter J, Dubois P, et al. A tandem mass spectrometry-based method to assess the architectural purity of synthetic polymers, a case of a cyclic polylactide obtained by click chemistry. Polym Chem 2015;6:64–9.
  • Dit Fouque DJ, Maroto A, Memboeuf A. Purification and quantification of an isomeric compound in a mixture by collisional excitation in multistage mass spectrometry experiments. Anal Chem 2016;88:10821–5.
  • Menicatti M, Guandalini L, Dei S, et al. The power of energy-resolved tandem mass spectrometry experiments for resolution of isomers: the case of drug plasma stability investigation of multidrug resistance inhibitors. Rapid Commun. Mass Spectrom 2016;30:423–32.
  • Menicatti M, Guandalini L, Dei S, et al. Energy resolved tandem mass spectrometry experiments for resolution of isobaric compounds: a case of cis/trans isomerism. Eur J Mass Spectrom 2016;22:235–43.
  • Di L, Kerns EH, Hong Y, Chen H. Development and application of high throughput plasma stability assay for drug discovery. Int J Pharm 2005;297:110–9.
  • Matuszewski BK, Constanzer ML, Chavez-Eng CM. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal Chem 2003;75:3019–30.
  • ICH Q2B, Validation of Analytical Procedure: Methodology, International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use, 1996. Available from: http://www.ich.org/products/guidelines/quality/article/quality-guidelines.html
  • Guandalini L, Soldani G, Rosi L, Calamai L, et al. A methodological approach to the selection of liquid reagents for chemical ionization ion trap-gas chromatography mass spectrometry: a case study of GBL and 1,4-BD. Int J Mass Spectrom 2015;388:34–9.
  • Martino MV, Guandalini L, Di Cesare Mannelli L, et al. Piperazines as nootropic agents: new derivatives of the potent cognition-enhancer DM235 carrying hydrophilic substituents. Bioorg Med Chem 2017;25:1795–803.
  • Teodori E, Dei S, Coronnello M, et al. N-alkanol-N-cyclohexanol amine aryl esters: multidrug resistance (MDR) reversing agents with high potency and efficacy. Eur J Med Chem 2017;127:586–98.
  • Jia L, Liu X. The conduct of drug metabolism studies considered good practice (II): in vitro experiments. Curr Drug Metab 2007;8:822–9.
  • Lapthorn C, Pullen F, Chowdhry BZ. Ion mobility spectrometry-mass spectrometry (IMS-MS) of small molecules: separating and assigning structures to ions. Mass Spectrom Rev 2013;32:43–71.
  • Kabir KMM, Donald WA. Microscale differential ion mobility spectrometry for field deployable chemical analysis. Trends Anal Chem 2017;97:399–427.