Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate

References

• Frias Gomes, C. Gastrointestinal diseases during pregnancy: What does the gastroenterologist need to know? Ann. Gastroenterol. 2018, 31, 1–11.
   PubMed Web of Science ®Google Scholar
• KuKanich, K.; KuKanich, B.; Guess, S.; Heinrich, E. Effect of sucralfate on the relative bioavailability of enrofloxacin and ciprofloxacin in healthy fed dogs. J. Vet. Intern. Med. 2016, 30, 108–115. DOI: 10.1111/jvim.13796.
   PubMed Web of Science ®Google Scholar
• KuKanich, K.; KuKanich, B.; Harris, A.; Heinrich, E. Effect of sucralfate on oral minocycline absorption in healthy dogs. J. Vet. Pharmacol. Ther. 2014, 37, 451–456. DOI: 10.1111/jvp.12116.
   PubMed Web of Science ®Google Scholar
• Van Slooten, A. D.; Nix, D. E.; Wilton, J. H.; Love, J. H.; Spivey, J. M.; Goldstein, H. R. Combined use of ciprofloxacin and sucralfate. DICP 1991, 25, 578–582.
   PubMedGoogle Scholar
• Capila, I.; Linhardt, R. J. Heparin-protein interactions. Angew. Chemie Int. Ed. 2002, 41, 390–412. DOI: 10.1002/1521-3773.
   Web of Science ®Google Scholar
• Mulloy, B.; Linhardt, R. J. Order out of complexity-protein structures that interact with heparin. Curr. Opin. Struct. Biol. 2001, 11, 623–628.
   PubMed Web of Science ®Google Scholar
• Baker, R. J. Mass spectrometry of basic aluminum sucrose octasulfate using fast atom bombardment with a saturated tetramethylammonium ion sample matrix. Org. Mass Spectrom. 1989, 24, 895–897. DOI: 10.1002/oms.1210241008.
   Google Scholar
• Ifa, D. R.; Wu, C.; Ouyang, Z.; Cooks, R. G. Desorption electrospray ionization and other ambient ionization methods: Current progress and preview. Analyst 2010, 135, 669. DOI: 10.1039/b925257f.
   PubMed Web of Science ®Google Scholar
• Gunay, N. S.; Tadano-Aritomi, K.; Toida, T.; Ishizuka, I.; Linhardt, R. J. Evaluation of counterions for electrospray ionization mass spectral analysis of a highly sulfated carbohydrate, sucrose octasulfate. Anal. Chem. 2003, 75, 3226–3231. DOI: 10.1021/ac034053l.
   PubMed Web of Science ®Google Scholar
• Ke, Y.; Li, S. L.; Chang, L. D.; Kapanadze, T. A novel ultra performance liquid chromatography–tandem mass spectrometry method for the determination of sucrose octasulfate in dog plasma. J. Chromatogr. B 2015, 978–979, 151–156. DOI: 10.1016/j.jchromb.2014.11.031.
   PubMed Web of Science ®Google Scholar
• Laremore, T. N.; Linhardt, R. J. Improved matrix-assisted laser desorption/ionization mass spectrometric detection of glycosaminoglycan disaccharides as cesium salts. Rapid Commun. Mass Spectrom. 2007, 21, 1315–1320. DOI: 10.1002/rcm.2964.
   PubMed Web of Science ®Google Scholar
• Laremore, T. N.; Murugesan, S.; Park, T.-J.; Avci, F. Y.; Zagorevski, D. V.; Linhardt, R. J. Matrix-assisted laser desorption/ionization mass spectrometric analysis of uncomplexed highly sulfated oligosaccharides using ionic liquid matrices. Anal. Chem. 2006, 78, 1774–1779. DOI: 10.1021/ac051121q.
   PubMed Web of Science ®Google Scholar
• Wolff, J. J.; Laremore, T. N.; Leach, F. E.; Linhardt, R. J.; Amster, I. J. Electron capture dissociation, electron detachment dissociation and infrared multiphoton dissociation of sucrose octasulfate. Eur. J. Mass Spectrom. (Chichester) 2009, 15, 275–281. DOI: 10.1255/ejms.951.
   PubMed Web of Science ®Google Scholar
• Guerrini, M.; Beccati, D.; Shriver, Z.; Naggi, A.; Viswanathan, K.; Bisio, A.; Capila, I.; Lansing, J. C.; Guglieri, S.; Fraser, B.; et al. Oversulfated chondroitin sulfate is a contaminant in heparin associated with adverse clinical events. Nat. Biotechnol. 2008, 26, 669–675. DOI: 10.1038/nbt1407.
   PubMed Web of Science ®Google Scholar
• Qian, Y.; Pan, J.; Zhou, X.; Hourcade, D. E.; Liszewski, M. K.; Atkinson, J. P.; Lu, H.; Zhang, L. Oversulfated heparin by-products induce thrombin generation in human plasmas through contact system activation. Clin. App. Thromb./Hem. 2010, 16, 244–250.
   PubMed Web of Science ®Google Scholar
• Mans, D. J.; Ye, H.; Dunn, J. D.; Kolinski, R. E.; Long, D. S.; Phatak, N. L.; Ghasriani, H.; Buhse, L. F.; Kauffman, J. F.; Keire, D. A. Synthesis and detection of N-sulfonated oversulfated chondroitin sulfate in marketplace heparin. Anal. Biochem. 2015, 490, 52–54.
   PubMed Web of Science ®Google Scholar
• Harvey, D. J. Matrix-assisted laser desorption/ionisation mass spectrometry of oligosaccharides and glycoconjugates. J. Chromatogr. A 1996, 720, 429–446. DOI: 10.1016/0021-9673(95)00307-X.
   PubMed Web of Science ®Google Scholar
• Cheng, S.; Chan, T.-W. D. Use of ammonium halides as co-matrices for matrix-assisted laser desorption/ionization studies of oligonucleotides. Rapid Commun. Mass Spectrom. 1996, 10, 907–910. DOI: 10.1002/(SICI)1097-0231.
   PubMedGoogle Scholar
• Zabet-Moghaddam, M.; Heinzle, E.; Tholey, A. Qualitative and quantitative analysis of low molecular weight compounds by ultraviolet matrix-assisted laser desorption/ionization mass spectrometry using ionic liquid matrices. Rapid Commun. Mass Spectrom. 2004, 18, 141–148. DOI: 10.1002/rcm.1293.
   PubMed Web of Science ®Google Scholar
• Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian 09, Revision C.01. Gaussian, Inc.: Wallingford, CT, USA, 2009.
   Google Scholar
• Dunning, T. H. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen. J. Chem. Phys. 1989, 90, 1007–1023. DOI: 10.1063/1.456153.
   Web of Science ®Google Scholar
• Becke, A. D. Density-functional exchange-energy approximation with correct asymptotic behaviour. Phys. Rev. A 1988, 38, 3098–3100. DOI: 10.1103/PhysRevA.38.3098.
   PubMed Web of Science ®Google Scholar
• Brizuela, A. B.; Bichara, L. C.; Romano, E.; Yurquina, A.; Locatelli, S.; Brandán, S. A. A complete characterization of the vibrational spectra of sucrose. Carbohydr. Res. 2012, 361, 212–218. DOI: 10.1016/j.carres.2012.07.009.
   PubMed Web of Science ®Google Scholar
• Márquez, M. J.; Brizuela, A. B.; Davies, L.; Brandán, S. A. Spectroscopic and structural studies on lactose species in aqueous solution combining the HATR and Raman spectra with SCRF calculations. Carbohydr. Res. 2015, 407, 34–41. DOI: 10.1016/j.carres.2015.01.019.
   PubMed Web of Science ®Google Scholar
• Wu, F.-Z.; Zhang, P. 2,3,6,3′,4′-Penta-O-acetyl-4,1′,6′-trichloro-4,1′,6′-trideoxysucrose. Acta Crystallogr. E Struct. Rep. Online 2011, 67, o2323–o2323. DOI: 10.1107/S1600536811032120.
   Google Scholar
• French, D. Unit-cell data for maltose hydrate and some acyl saccharide derivatives. Acta Cryst. 1954, 7, 136–137. DOI: 10.1107/S0365110X54000357.
   Google Scholar
• Foster, J. P.; Weinhold, F. Natural hybrid orbitals. J. Am. Chem. Soc. 1980, 102, 7211–7218. DOI: 10.1021/ja00544a007.
   Web of Science ®Google Scholar
• Lemmnitzer, K.; Griesinger, H.; Süß, R.; Matheis, K.; Schulz, M.; Schiller, J. Analysis of glycosaminoglycan oligosaccharides by combined HPTLC/MALDI-TOF MS: Reduced silica gel thickness leads to improved spectral qualities and reduced side reactions. Chromatographia 2015, 78, 1409–1413. DOI: 10.1007/s10337-015-2971-2.
   Web of Science ®Google Scholar
• Nimptsch, A.; Schiller, J. The selected matrix influences the matrix-assisted laser desorption/ionization time-of-flight mass spectral patterns of partially deuterated glycosaminoglycan disaccharides: Deuterium incorporation determined by MALDI-TOF MS. Rapid Commun. Mass Spectrom. 2016, 30, 2164–2170. DOI: 10.1002/rcm.7694.
   PubMed Web of Science ®Google Scholar
• Silvey, G. L. Two‐dimensional and deuterium‐induced, differential‐isotope‐shift nuclear magnetic resonance characterization of potassium sucrose octasulfate and sucralfate. J Pharm. Sci. 1992, 81, 471–474. DOI: 10.1002/jps.2600810517.
   PubMed Web of Science ®Google Scholar
• Hillenkamp, F., Peter-Katalinic, J., Eds. MALDI MS. Wiley-VCH Verlag GmbH & Co.: KGaA, Weinheim, Germany, 2007.
   Google Scholar
• Hoteling, A. J.; Nichols, W. F.; Giesen, D. J.; Lenhard, J. R.; Knochenmuss, R. Electron transfer reactions in laser desorption/ionization and matrix-assisted laser desorption/ionization: Factors influencing matrix and analyte ion intensities. Eur. J. Mass Spectrom. (Chichester) 2006, 12, 345–358. DOI: 10.1255/ejms.820.
   Web of Science ®Google Scholar
• D. Dimić, D.; Milenković, D.; Dimitrić Marković, J.; Marković, Z. Antiradical activity of catecholamines and metabolites of dopamine: Theoretical and experimental study. Phys. Chem. Chem. Phys. 2017, 19, 12970–12980. DOI: 10.1039/C7CP01716B.
   PubMed Web of Science ®Google Scholar
• Muthu, M.; S. Chun, S.; Wu, H.-F.; M.W. Duncan, M. W.; Gopal, J. The ongoing evolution of laser desorption/ionization mass spectrometry: Some observations on current trends and future directions. J. Mass Spectrom. 2018, 53, 525–540. DOI: 10.1002/jms.4083.
   PubMed Web of Science ®Google Scholar
• Niehaus, M.; Soltwisch, J. New insights into mechanisms of material ejection in MALDI mass spectrometry for a wide range of spot sizes. Sci. Rep. 2018, 8, 7755DOI: 10.1038/s41598-018-25946-z.
   PubMed Web of Science ®Google Scholar
• Soltwisch, J.; Jaskolla, T. W.; Hillenkamp, F.; Karas, M.; Dreisewerd, K. Ion yields in UV-MALDI mass spectrometry as a function of excitation laser wavelength and optical and physico-chemical properties of classical and halogen-substituted MALDI matrixes. Anal. Chem. 2012, 84, 6567–6576. DOI: 10.1021/ac3008434.
   PubMed Web of Science ®Google Scholar
• Armstrong, D. W.; Zhang, L.-K.; He, L.; Gross, M. L. Ionic liquids as matrixes for matrix-assisted laser desorption/ionization mass spectrometry. Anal. Chem. 2001, 73, 3679–3686. DOI: 10.1021/ac010259f.
   PubMed Web of Science ®Google Scholar
• Zhao, X.; Shen, S.; Wu, D.; Cai, P.; Pan, Y. Novel ionic liquid matrices for qualitative and quantitative detection of carbohydrates by matrix assisted laser desorption/ionization mass spectrometry. Anal. Chim. Acta 2017, 985, 114–120. DOI: 10.1016/j.aca.2017.07.027.
   PubMed Web of Science ®Google Scholar
• Nimptsch, K.; Süß, R.; Schnabelrauch, M.; Nimptsch, A.; Schiller, J. Positive ion MALDI-TOF mass spectra are more suitable than negative ion spectra to characterize sulphated glycosaminoglycan oligosaccharides. Int. J. Mas Spectrom. 2012, 310, 72–76. DOI: 10.1016/j.ijms.2011.11.003.
   Web of Science ®Google Scholar
• Alquraini, M.; Alshamsi, F.; Møller, M. H.; Belley-Cote, E.; Almenawer, S.; Jaeschke, R.; MacLaren, R.; Alhazzani, W. Sucralfate versus histamine 2 receptor antagonists for stress ulcer prophylaxis in adult critically ill patients: A meta-analysis and trial sequential analysis of randomized trials. J. Crit. Care 2017, 40, 21–30. DOI: 10.1016/j.jcrc.2017.03.005.
   PubMed Web of Science ®Google Scholar