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Complexation of ephedrine withβ-cyclodextrin: An NMR spectroscopy study

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Abstract

This study focuses on the inclusion complex of ephedrine with β-CD. The association of β-CD and ephedrine has been examined using1H NMR and circular dichroism. The systematic shifts of the proton resonances of the phenyl moiety of ephedrine and that of the protons located inside the β-CD cavity, provide evidence of intracavity inclusion. Two-dimensional ROESY show preferential localization of ephedrine in close proximity with protons located inside the β-CD cavity. The systematic variation of circular dichroism spectra with increasing concentration of β-CD is used to estimate the apparent formation constant.

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References

  1. M. Those, J. Norwig, W. Mehnert, and K.H. Frömming:Proceedings of the 4th International Symposium on Cyclodextrins: (O. Huber and J. Szejtli, Eds.), p. 355, Reidel: Dordrecht (1988).

    Google Scholar 

  2. D.W. Armstrong:Anal. Chem. 59, 84A-91A (1987).

    Google Scholar 

  3. I. Tabushi:Pure Appl. Chem. 58, 1529–1534 (1986).

    Google Scholar 

  4. I. Tabushi:Acc. Chem. Res. 15, 66–72 (1982).

    Google Scholar 

  5. S.P. Jones, D.J.W. Grant, J. Hadgraft, and G.D. Parr:Acta. Pharm. Technol. 30, 213 (1984).

    Google Scholar 

  6. G.D. Reddy, B. Jayasree, and V. Ramamurthy:J. Org. Chem. 52, 3107–3113 (1987).

    Google Scholar 

  7. W.L. Hinze:Sep. Purif. Methods 10, 159–237 (1981).

    Google Scholar 

  8. F.T. Noggle, Jr., J. DeRuiter, and C.R. Clark:Anal. Chem. 58, 1643–1648 (1986).

    Google Scholar 

  9. J. Gal:J. Chromatogr. 307, 220–223 (1984).

    Google Scholar 

  10. A.H. Beckett and B. Testa:J. Chromatogr. 69, 285–289 (1972).

    Google Scholar 

  11. I.W. Waiver, T.D. Doyle, Z. Hamidzadeh, and M. Aldridge:J. Chromatogr. 261, 123–126 (1983).

    Google Scholar 

  12. E.A. Mularz, L.J. Cline Love, and M. Petersheim:Anal. Chem. 60, 2751–2755 (1988).

    Google Scholar 

  13. Y. Inoue, F.-H. Kuan, and R. Chûjô:Bull. Chem. Soc. Jpn. 60, 2539–2545 (1987).

    Google Scholar 

  14. Y. Inoue, T. Okuda, Y. Miyata, and R. Chûjô:Carbohydr. Res. 125, 65–76 (1984).

    Google Scholar 

  15. H.-J. Schneider and J. Pîhlman:Bioorg. Chem. 15, 183–193 (1987).

    Google Scholar 

  16. H.-J. Schneider, R. Kramer, S. Simova, and U. Schneider:J. Am. Chem. Soc. 110, 6442–6448 (1988).

    Google Scholar 

  17. R.I. Gelb, L.M. Schwartz, J.E. Markinac, and D.A. Laufer:J. Am. Chem. Soc. 101, 1864–1868 (1979).

    Google Scholar 

  18. Y. Inoue, M. Kitagawa, H. Hoshi, M. Sakurai, and R. Chûjô:J. Incl. Phenom. 5, 55–58 (1987).

    Google Scholar 

  19. C.R. Sanders, II., and J.H. Prestegard:J. Am. Chem. Soc. 113, 1987–1996 (1991).

    Google Scholar 

  20. J.H. Noggle and R.E. Schirmer:The Nuclear Overhauser Effect. Chemical Applications, Academic Press: New York (1971).

    Google Scholar 

  21. A. Kumar, R.R. Ernst, and K. Wüthrich:Biochem. Biophys. Res. Commun. 95, 1–6 (1980).

    Google Scholar 

  22. L.D. Hall, G.A. Morris, and S. Sukumar:J. Am. Chem. Soc. 102, 1745–1747 (1980).

    Google Scholar 

  23. G. Wider, S. Macura, A. Kumar, and K. Wüthrich:J. Magn. Reson. 56, 207–234 (1984).

    Google Scholar 

  24. A.A. Bothner-By, R.L. Stephens, J. Lee, C.D. Warren, and R.W. Jeanloz:J. Am. Chem. Soc. 106, 811–813 (1984).

    Google Scholar 

  25. A. Bax and D.G. Davis:J. Magn. Reson. 63, 207–213 (1985).

    Google Scholar 

  26. C. Griesinger and R.R. Ernst:J. Magn. Reson. 75, 261–271 (1987).

    Google Scholar 

  27. H.J. Schneider, T. Blatter, and S. Simova:J. Am. Chem. Soc. 113, 1996–2000 (1991).

    Google Scholar 

  28. A. Muũnoz de la Peña, T.T. Ndou, J.B. Zung, and I.M. Warner:J. Phys. Chem. 95, 3330–3334 (1991).

    Google Scholar 

  29. A. Muñoz de la Peña, T.T. Ndou, V.C. Anigbogu, and I.M. Warner:Anal. Chem. 63, 1018–1023 (1991).

    Google Scholar 

  30. M. Barra, C. Bohne, and J.C. Scaiano:J. Am. Chem. Soc. 112, 8075–8079 (1990).

    Google Scholar 

  31. Y. Ishizuka, Y. Nagawa, H. Nakanishi, and A. Kuboyama:J. Incl. Phenom. 9, 219–225 (1990).

    Google Scholar 

  32. J.M. Bowen and N. Purdie:Anal. Chem. 53, 2239–2242 (1981).

    Google Scholar 

  33. S.M. Han, W.M. Atkinson, and N. Purdie:Anal. Chem. 56, 2827–2830 (1984).

    Google Scholar 

  34. H. Hirai, H. Toshima, and S. Uenoyam:Bull. Chem. Soc. Jpn. 58, 1156–1164 (1985).

    Google Scholar 

  35. A.L. Thakkar and P.V. Dermarco:Chem. Commun. 2–4 (1971).

  36. A.L. Thakkar and P.V. Dermarco:J. Pharm. Sci. 60, 652–653 (1971).

    Google Scholar 

  37. D.J. Wood, P.E. Hruska, and W.J. Säenger:J. Am. Chem. Soc. 99, 1735–1740 (1977).

    Google Scholar 

  38. V.K. Smith, T.T. Ndou, A. Muñoz de la Peña, and I.M. Warner:J. Incl. Phenom. 10, 471–484 (1991).

    Google Scholar 

  39. J.M. Schuette, T.T. Ndou, A. Muñoz de la Peña, K.L. Greene, and I.M. Warner:J. Phys. Chem. 95, 4897–4902 (1991).

    Google Scholar 

  40. Y. Yamamoto, Y. Kanda, Y. Inoue, R. Chûjô, and S. Kobayashi:Chem. Lett. 495–498 (1988).

  41. J. Lehmann, J. Kleinpeter, and J. Krechl:J. Incl. Phenom. 10, 233–239 (1991).

    Google Scholar 

  42. K. Wakamatsu, A. Okanda, T. Higashijima, and T. Miyaziwa:Biopolymers 25, s193-s200 (1986).

    Google Scholar 

  43. Y. Yamamoto, M. Onda, M. Kitagawa, Y. Inoue, and R. Chûjô:Carbohydr. Res. 167, c11-c16 (1987).

    Google Scholar 

  44. K. Wüthrich:NMR of Proteins and Nucleic Acids, Wiley: New York (1986).

    Google Scholar 

  45. R. Fornasier, P. Lucchini, and P. Scrimin:J. Incl. Phenom. 4, 291–294 (1986).

    Google Scholar 

  46. J. Tinoco, Jr.:Adv. Chem. Phys. 4, 113 (1962).

    Google Scholar 

  47. K. Harata and H. Uedaira:Bull. Chem. Soc. Jpn. 48, 375 (1975).

    Google Scholar 

  48. H. Shimizu, A. Kaito, and M. Hatano:J. Am. Chem. Soc. 104, 7059 (1982).

    Google Scholar 

  49. M. Kodaka and T. Fukuya:Bull. Chem. Soc. Jpn. 62, 1154–1157 (1989).

    Google Scholar 

  50. M. Kodaka:J. Phys. Chem. 95, 2110–2112 (1991).

    Google Scholar 

  51. H. Shimizu, A. Kaito, and M. Hatano:Bull. Chem. Soc. Jpn. 52, 2678–2684 (1979).

    Google Scholar 

  52. H. Yamaguchi and M. Higashi:J. Incl. Phenom. 5, 725–728 (1987).

    Google Scholar 

  53. N. Kobayashi and T. Osa:Chem. Lett. 421–424 (1986).

  54. K. Kano, M. Takai, and S. Hashimoto:J. Phys. Chem. 94, 2181–2187 (1990).

    Google Scholar 

  55. M. Ata, Y. Kubozoro, Y. Suzuki, M. Aoyagi, and Y. Gondo:Bull. Chem. Soc. Jpn. 62, 3706–3708 (1989).

    Google Scholar 

  56. M. Kobayashi and M. Opallo:J. Chem. Soc. Chem. Commun. 477–479 (1990).

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Emory University School of Medicine, Atlanta, GA 30322, U.S.A.

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Ndou, T.T., Mukundan, S. & Warner, I.M. Complexation of ephedrine withβ-cyclodextrin: An NMR spectroscopy study. Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 15, 9–25 (1993). https://doi.org/10.1007/BF00706470

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  • DOI: https://doi.org/10.1007/BF00706470

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