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Applications of NMR in Drug:Cyclodextrin Complexes

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Supramolecules in Drug Discovery and Drug Delivery

Part of the book series: Methods in Molecular Biology ((MIMB,volume 2207))

Abstract

NMR spectroscopy is an effective technique, applicable for studying bioactive materials or drug delivery systems in order to obtain comprehensive details related to structural and dynamic characteristics at atomic resolution. The applications of NMR spectroscopy have been increased considerably as a result of the combination of advancement in technological NMR instrumentation and scientific knowledge. This chapter is dedicated to highlight the applications of NMR spectroscopy in drug:cyclodextrin complexes using both liquid- and solid-state NMR spectroscopy.

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References

  1. Pellecchia M, Bertini I, Cowburn D et al (2008) Perspectives on NMR in drug discovery: a technique comes of age. Nat Rev Drug Discov 7(9):738–745

    Article  CAS  Google Scholar 

  2. Ntountaniotis D (2018) Rational drug design: methods and protocols. Reactions in NMR tubes as key weapon in rational drug design. Methods Mol Biol 1824:417–430. (Springer Science)

    Article  CAS  Google Scholar 

  3. Fello IC, Pierattelli R (eds) (2014) Advances in experimental medicine and biology. Intrinsically disordered proteins studies by NMR spectroscopy. Springer International Publishing, Switzerland

    Google Scholar 

  4. Hu H, Katyayan KK, Czeskis BA et al (2017) Comparison between radioanalysis and 19F Nuclear Magnetic Resonance spectroscopy in the determination of mass balance, metabolism, and distribution of pefloxacin. Drug Metab Dispos 45:399–408

    Article  CAS  Google Scholar 

  5. Bradley SA, Smitka TA, Russell DJ et al (2015) Quantitative NMR analysis of complex mixtures using CRAFT (complete reduction to amplitude frequency table) method. Curr Metabolomics 3:21–31

    Article  CAS  Google Scholar 

  6. Barding GA Jr, Salditos R, Larive CK (2012) Quantitative NMR for bioanalysis and metabolomics. Anal Bioanal Chem 404:1165–1179

    Article  CAS  Google Scholar 

  7. Holzgrabe U, Deubner R, Schollmayer C et al (2005) Quantitative NMR spectroscopy—applications in drug analysis. J Pharm Biomed Anal 38:806–812

    Article  CAS  Google Scholar 

  8. Do NM, Olivier MA, Salisbury JJ et al (2011) Application of quantitative 19F and 1H NMR for reaction monitoring and in situ yield determinations for an early stage pharmaceutical candidate. Anal Chem 83:8766–8771

    Article  CAS  Google Scholar 

  9. Pauli GF, Gödecke T, Jaki BU et al (2012) Quantitative 1H NMR: development and potential of an analytical method: an update. J Nat Prod 75:834–851

    Article  CAS  Google Scholar 

  10. Schneider H-J, Hacket F, Volker R (1988) NMR studies of cyclodextrins and cyclodextrin complexes. Chem Rev 98:1755–1785

    Article  Google Scholar 

  11. Dugoni GC, Pietro M, Ferro M et al (2019) Effect of water on DES/β-cyclodextrin systems. ACS Sustain Chem Eng 7:7277–7285

    Article  CAS  Google Scholar 

  12. Inoue Y, Shinohara I, Murata I et al (2019) Study on the molecular stability, solubility, and diffusibility of guaiazulene included in β- and γ-cyclodextrin. J Mol Struct 1186:50–59

    Article  CAS  Google Scholar 

  13. Leyva E, Moctezuma E, Strouse J et al (2001) Spectrometric and 2D NMR studies on the complexation of chlorophenols with cyclodextrins. J Incl Phenom 39:41–46

    Article  CAS  Google Scholar 

  14. Bendeby B, Kenne L, Sandström C (2004) 1H-NMR studies of the inclusion complexes between α-cyclodextrin and adamantane derivatives using both exchangeable hydroxy protons and non-exchangeable aliphatic protons. J Incl Phenom Macrocycl Chem 50:173–181

    Article  CAS  Google Scholar 

  15. Hakkarainen B, Fujita K, Immel S et al (2005) 1H-NMR studies on the hydrogen-bonding network in mono-altro-β-cyclodextrin and its complex with adamantane-1-carboxylic acid. Carbohydr Res 340(8):1539–1545

    Article  CAS  Google Scholar 

  16. Wójcik J, Ejchart A, Nowakowski M (2019) Shape adaptation of quinine in cyclodextrin cavities: NMR studies. Phys Chem Chem Phys 21:6925–6934

    Article  Google Scholar 

  17. Fielding L (2000) Determination of association constants (Ka) from solution NMR data. Tetrahedron 56:6151–6170

    Article  CAS  Google Scholar 

  18. Monticelli C, Fantin G, Carmine G et al (2019) Inclusion of 5-mercapto-1-phenyl-tetrazole into β-cyclodextrin for entrapment in silane coatings: an improvement in bronze corrosion protection. Coatings 9(8):508

    Article  CAS  Google Scholar 

  19. Fernandes A, Ivanova G, Bras NF et al (2014) Structural characterization of inclusion complexes between cyanidin-3-O-glucoside and β-cyclodextrin. Carbohydr Polym 102(1):269–277

    Article  CAS  Google Scholar 

  20. Greatbanks D, Pickford R (1987) Cyclodextrins as chiral complexing agents in water, and their application to optical purity measurements. Magn Reson Chem 25:208–215

    Article  CAS  Google Scholar 

  21. Armstrong DW, Ward DJ, Armstrong RD et al (1986) Separation of drug stereoisomers by the formation of β-cyclodextrin complexes. Science 232(4754):1132–1135

    Article  CAS  Google Scholar 

  22. Fronza G, Mele A, Redenti E et al (1996) 1H NMR and molecular modeling study on the inclusion complex β-cyclodextrin-indomethacin. J Org Chem 61(3):909–914

    Article  CAS  Google Scholar 

  23. Gardner KH, Zhang X, Gehring K et al (1998) NMR studies of a 42 KDa Escherichia coli maltose binding protein/β-Cyclodextrin complex: chemical shift assignments and analysis. J Am Chem Soc 120:11738–11748

    Article  CAS  Google Scholar 

  24. Murray DT, Das N, Cross TA (2013) Solid state NMR strategy for characterizing native membrane protein structures. Acc Chem Res 46(9):2172–2181

    Article  CAS  Google Scholar 

  25. Priotti J, Ferreira MJ, Lamas MC et al (2015) First solid-state NMR spectroscopy evaluation of complexes of benznidazole with cyclodextrin derivatives. Carbohydr Polym 131:90–97

    Article  CAS  Google Scholar 

  26. Nevzorov AA, Opella SJ (2007) Selective averaging for high-resolution solid-state NMR spectroscopy of aligned samples. J Magn Reson 185:59–70

    Article  CAS  Google Scholar 

  27. Dvinskikh SV, Yamamoto K, Ramamoorthy A (2006) Heteronuclear isotopic mixing separated local field NMR spectroscopy. J Chem Phys 125:034507

    Article  Google Scholar 

  28. Berliner L (ed) (2015) Biological magnetic resonance. Protein NMR: modern techniques and biomedical applications. Springer Science Business Media LLC, New York

    Google Scholar 

  29. Molugu TR, Lee S, Brown FB (2017) Concepts and methods of solid-state NMR spectroscopy applied to biomembranes. Chem Rev 117(19):12087–12132

    Article  CAS  Google Scholar 

  30. Vogt F, Strohmeier M (2012) 2D Solid-state NMR analysis of inclusion in drug-cyclodextrin complexes. Mol Pharm 9(11):3357–3374

    Article  CAS  Google Scholar 

  31. Tulumello DV, Deber CM (2009) SDS micelles as a membrane-mimetic environment for transmembrane segments. Biochemistry 48:12096–12103

    Article  CAS  Google Scholar 

  32. http://chem.ch.huji.ac.il/nmr/preparation/preparation.html

  33. Liossi AS, Ntountaniotis D, Kellici TF et al (2017) Exploring the interactions of irbesartan and irbesartan-2-HP-β-cyclodextrin complex with model membranes. Biochim Biophys Acta Biomembr 1859(6):1089–1098

    Article  CAS  Google Scholar 

  34. Chattah AK, Mroue KH, Pfund LY, Ramamoorthy A, Longhi MR, Garnero C (2013) Insights into Novel Supramolecular Complexes of Two Solid Forms of Norfloxacin and β-Cyclodextrin. J Pharm Sci 102(10):3717–3724

    Google Scholar 

  35. Fukami T, Ishii T, Io T, Suzuki N, Suzuki T, Yamamoto K, Xu J, Ramamoorthy A, Tomono K (2009) Nanoparticle Processing in the Solid State Dramatically Increases the Cell Membrane Permeation of a Cholesterol-Lowering Drug, Probucol. Mol Pharm 6(3):1029–1035

    Google Scholar 

  36. Io T, Fukami T, Yamamoto K, Suzuki T, Xu J, Tomono K, Ramamoorthy A (2009) Homogeneous Nanoparticles To Enhance the Efficiency of a Hydrophobic Drug, Antihyperlipidemic Probucol, Characterized by Solid-State NMR. Mol Pharm 7(1):299–305

    Google Scholar 

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Acknowledgments

This work has been co-financed by the European Union and Greek national funds through the program “Support for Researchers with Emphasis on Young Researchers” (call code: EDBM34, ΚΕ 14995) and under the research title “Preparation and study of innovative forms of administration of pharmaceutical molecules targeting at improved pharmacological properties.”

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Authors and Affiliations

  1. Chemistry Department, Laboratory of Organic Chemistry, National Kapodistrian University of Athens, Athens, Greece

    Dimitrios Ntountaniotis, Georgios Leonis, Eirini Christodoulou & Thomas Mavromoustakos

Authors
  1. Dimitrios Ntountaniotis
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  2. Georgios Leonis
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  3. Eirini Christodoulou
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  4. Thomas Mavromoustakos
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Editor information

Editors and Affiliations

  1. Department of Chemistry, National and Kapodistrian University of Athens, Zografou, Greece

    Thomas Mavromoustakos

  2. Department of Chemistry Section of Organic Chemistry and Biochemistry, University of Ioannina, Ioannina, Greece

    Andreas G. Tzakos

  3. Computational Biology and Molecular Simulations Laboratory Department of Biophysics, School of Medicine, Bahcesehir University, Istanbul, Turkey

    Serdar Durdagi

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Ntountaniotis, D., Leonis, G., Christodoulou, E., Mavromoustakos, T. (2021). Applications of NMR in Drug:Cyclodextrin Complexes. In: Mavromoustakos, T., Tzakos, A.G., Durdagi, S. (eds) Supramolecules in Drug Discovery and Drug Delivery. Methods in Molecular Biology, vol 2207. Humana, New York, NY. https://doi.org/10.1007/978-1-0716-0920-0_22

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  • DOI: https://doi.org/10.1007/978-1-0716-0920-0_22

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  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-0716-0919-4

  • Online ISBN: 978-1-0716-0920-0

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