Chromatographia

, Volume 52, Issue 5–6, pp 319–324 | Cite as

Development of a disulfiram-modified human serum albumin-based HPLC column

  • C. Bertucci
  • V. Andrisano
  • R. Gotti
  • V. Cavrini
Originals Column Liquid Chromatography

Summary

A human serum albumin (HSA)-based HPLC column has been modified in situ by disulfiram, an alcohol-deterrent drug reported to bind cys34, the only free cysteine in HSA, under physiological conditions.

The reversible and covalent binding of disulfiram was found to change the binding properties of the protein, giving rise to a new selector which performed differently from the native albumin-based stationary phase. When low concentrations of disulfiram were used as mobile phase modifier, reversible binding resulted in a cooperative allosteric effect with improved selector performance. Covalent modification resulted in markedly reduced affinity for binding of the drugs to sites I or II, while still maintaining enantioselectivity.

This study has enabled the monitoring of interactions of disulfiram with potentially coadministered drugs, and the preparation of a chiral selector with different drug affinity and enantioselectivity.

Key Words

Column liquid chromatography Human serum albumin column Disulfiram-modified phase Chiral selection 

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References

  1. [1]
    Domenici, E.; Bertucci, C.; Salvadori, P. Felix, G.; Cahagne, I.; Motellier, S.; Wainer, I. W.Chromatographia 2000,29, 170–176.CrossRefGoogle Scholar
  2. [2]
    Noctor, T.A.G.; Felix, G.; Wainer, I.W.Chromatographia 1991,31, 55–59.CrossRefGoogle Scholar
  3. [3]
    Chosson, E.; Uzan, S.; Gimenez, F.; Wainer, I.W.; Farinotti, R.Chirality 1993,5, 71–77.CrossRefGoogle Scholar
  4. [4]
    Loun, B.; Hage, D.S.Anal. Chem. 1994,66, 3814–3822.CrossRefGoogle Scholar
  5. [5]
    Hayball, P.J.; Holman, J.W.; Nation, R.L.J. Chromatogr. B Biomed. Appl.1994,662, 128–133.CrossRefGoogle Scholar
  6. [6]
    Andrisano, V.; Booth, T.D.; Cavrini, V.; Wainer, I.W.Chirality 1997,9, 178–183.CrossRefGoogle Scholar
  7. [7]
    Oravcová, J.; Böhs, B.; Lindner, W.J. Chromatogr. B Biomed Appl. 1996,677, 1–28.CrossRefGoogle Scholar
  8. [8]
    Yang, J.; Hage, D.S.J. Chromatogr. 1993,645, 241–250.CrossRefGoogle Scholar
  9. [9]
    Noctor, T.A.G.; Wainer, I.W.J. Liquid Chromatogr. 1993,16, 783–800.Google Scholar
  10. [10]
    Noctor, T.A.G.; Wainer, I.W.; Hage, D.S.J. Chromatogr. 1992,577, 305–315.Google Scholar
  11. [11]
    Hage, D.S.; Noctor, T.A.G.; Wainer, I.W.J. Chromatogr. A 1995,693, 23–32.CrossRefGoogle Scholar
  12. [12]
    Domenici, E.; Bertucci, C.; Salvadori, P.; Wainer, I.W.J. Pharm. Sci. 1991,80, 164–166.Google Scholar
  13. [13]
    Fitos, I.; Visy, J.; Simonyi, M.; Hermansson, J.Chirality 1999,11, 115–120.CrossRefGoogle Scholar
  14. [14]
    Ascoli, G.; Bertucci, C.; Salvadori, P.Biomed. Chromatogr. 1998,12, 248–254.CrossRefGoogle Scholar
  15. [15]
    Bertucci, C.; Canepa, A.; Ascoli, G.; Lopes Guimaraes, L.F.; Felix, G.Chirality,1999,11, 675–679.CrossRefGoogle Scholar
  16. [16]
    Bertucci, C.; Wainer, I.W.Chirality 1997,9, 335–340.CrossRefGoogle Scholar
  17. [17]
    Bertucci, C.; Canepa, A.; Altemura, P.Annali di Chimica 1997,87, 45–52.Google Scholar
  18. [18]
    Chattopadhyay, A.; Tian, T; Kortum, L.; Hage, D.S.J. Chromatogr. B Biomed. Appl. 1998,715, 183–190.CrossRefGoogle Scholar
  19. [19]
    Noctor, T.A.G.; Wainer, I.W.Pharm. Res. 1992,9, 480–484.CrossRefGoogle Scholar
  20. [20]
    Kragh-Hansen, U.Dan. Med. Bull. 1990,37, 54–84.Google Scholar
  21. [21]
    Day, J.F.; Thorpe, S.R.; Baynes, J.W.J. Biol. Chem. 1979,254, 595–597.Google Scholar
  22. [22]
    Dolhofer, R.; Wieland, O.H.FEBS Lett. 1979,103, 282–286.CrossRefGoogle Scholar
  23. [23]
    Baynes, J.W.; Thorpe, S.R.; Murtiashaw, M.H.Methods Enzymol. 1984,106, 88–98.CrossRefGoogle Scholar
  24. [24]
    Harding, J.J.Adv. Protein Chem. 1985,37, 247–334.CrossRefGoogle Scholar
  25. [25]
    Okabe, N.; Hashizume, N.Biol. Pharm. Bull. 1994,17, 16–21.Google Scholar
  26. [26]
    Koizumi, K.; Iweda, C.; Ito, M.; Suzuki, I.; Kinoshita, T.; Yasukawa, K.; Hanai, T.,Biomed. Chromatogr. 1998,12, 203–210.CrossRefGoogle Scholar
  27. [27]
    Yvon, M.; Wal, J.M.FEBS Lett. 1988,239, 237–240.CrossRefGoogle Scholar
  28. [28]
    Yvon, M.; Anglade, P.; Wal, J.M.FEBS Lett. 1990,263, 237–240.CrossRefGoogle Scholar
  29. [29]
    Lapresle, C.; Lafaye, P.Ann. Inst. Pasteurl Immunol. 1985,136C, 375–382.Google Scholar
  30. [30]
    Lafaye, P.; Lapresle, C.FEBS Lett. 1987,220, 206–208.CrossRefGoogle Scholar
  31. [31]
    Yvon, M.; Anglade, P.; Wal, J.M.FEBS Lett. 1989,247, 273–278.CrossRefGoogle Scholar
  32. [32]
    Pinckard, R.N.; Hawkins, D.; Farr, R.S.Nature 1969,219, 68–69.CrossRefGoogle Scholar
  33. [33]
    Farr, R.S.J. Allergy 1970,45, 321–328.CrossRefGoogle Scholar
  34. [34]
    Walker, J.E.FEBS Lett. 1976,66, 173–175.CrossRefGoogle Scholar
  35. [35]
    Bertucci, C.; Viegi, A.; Ascoli, G.; Salvadori, P.Chirality 1995,7, 57–61.CrossRefGoogle Scholar
  36. [36]
    Bertucci, C.; Nanni, B.; Salvadori, P.Chirality 1999,11, 33–38.CrossRefGoogle Scholar
  37. [37]
    Takamura, N.; Haruta, A.; Kodama, H.; Tsuruoka, M.; Yamasaki, K.; Suenaga, A.; Otagiri, M.Pharm. Res. 1996,13, 1015–1019.CrossRefGoogle Scholar
  38. [38]
    Sellers, E.M.; Koch-Weser, JClin. Pharmacol. Ther. 1970 11, 524–529.Google Scholar
  39. [39]
    Agarwal, R.P.; Phillips, M.; McPherson, R.A.; Hensley, P.Biochem. Pharmacol. 1986,35, 3341–3347.CrossRefGoogle Scholar
  40. [40]
    Mahieu, J.P.; Gosselet, N.M.; Sebille, B.; Garel, M.C.; Beuzard, Y.Int. J. Biol. Macromol. 1993,15, 233–240.CrossRefGoogle Scholar
  41. [41]
    Bell, S.C.; McCaully, R.J.; Gochman, C.; Childress, S.J.; Gluckman, M.I.J. Med. Chem. 1968,11, 457–461.CrossRefGoogle Scholar

Copyright information

© Frieder. Vieweg & Sohn Verlagsgesellschaft mbH 2000

Authors and Affiliations

  • C. Bertucci
    • 1
  • V. Andrisano
    • 1
  • R. Gotti
    • 1
  • V. Cavrini
    • 1
  1. 1.Dipartimento di Scienze FarmaceuticheUniversità di BolognaBolognaItaly

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