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Mass Spectrometric Determination of Association Constants of Bovine Serum Albumin (BSA) with para-Sulphonato-Calix[n]arene Derivatives

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Abstract

Electrospray Ionization Mass Spectrometry (ESI/MS) has been used to determine the association constants (K As) and binding stoichiometries for parent para-Sulphonato-calix[n]arenes and their derivatives with bovine serum albumin (BSA). K A values were determined by titration experiments using a constant concentration of protein. K A measurements were carried out in a methanol–formic acid solution. 5,11,17,23–tetra-Sulphonato-calix[4]arene (1a) and 25-mono-(2-aminoethoxy)-5,11,17,23-tetra-Sulphonato-calix[4]arene (1d) interact strongly with BSA showing 3 non-equivalent binding sites with K A1 = 7.69 × 105 M−1, K A2 = 3.85 × 105 M−1, K A3 = 0.33 × 105 M−1 and K A1 = 1.69 × 105 M−1, K A2 = 2.94 × 105 M−1, K A3 = 0.60 × 105 M−1, respectively. The strength of the interactions between the calixarene and BSA is inversely proportional to the size of macrocyclic ring: n = 4 > n=6>>n=8.

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References

  1. J.W. Cornforth P. D'Arcy Hart G.A. Nicholls R.J.W. Rees J.A. Stock (1955) Br. J. Pharmacol 10 73 Occurrence Handle1:CAS:528:DyaG28XisVSjsA%3D%3D

    CAS  Google Scholar 

  2. (a) S. Shinkai, K. Araki, K. Tsubaki, A. Takayuki, and M.O. Takashi: J. Chem. Soc. Perkin Trans. 1, 11, 2297 (1987); (b) S. Shinkai, S. Mori, K. Tsubaki, T. Sone, and M.O. Takashi: Tetrahedron Lett. 25, 5315 (1984)

  3. J.L. Atwood, R.J. Bridges, R.K. Juneja, and A.K. Singh: US Patent 5,489,612 (1996)

  4. (a) K.M. Hwang, Y.M. Qi, S.Y. Liu, T.C. Lee, W. Choy, and J. Chen: US Patent 5,409,959 (1995), (b) S.J. Harris: PCT Int. Appl. (1995)[], (c) E. Aubert-Foucher, A.W. Coleman, and D.J.S. Hulmes: French patent FR 2782007 (1998)

  5. A. Moussa, A.W. Coleman, P. Shahgaldian, E. Da Silva, and A. Martin: French Patent 02/16383 (2002)

  6. Q. Lin A.D. Hamilton (2002) Comptes Rendus Chimie 5 441 Occurrence Handle10.1016/S1631-0748(02)01408-X Occurrence Handle1:CAS:528:DC%2BD38XotlWis7w%3D

    Article  CAS  Google Scholar 

  7. Q. Lin H.S. Park Y. Hamuro C.S. Lee A.D. Hamilton (1998) Biopolym 47 285 Occurrence Handle1:CAS:528:DyaK1MXjslGmtw%3D%3D Occurrence Handle10.1002/(SICI)1097-0282(1998)47:4<285::AID-BIP4>3.0.CO;2-C

    Article  CAS  Google Scholar 

  8. (a) N. Douteau-Guével, A.W. Coleman, J.-P. Morel, and N. Morel-Desrosiers: J. Phys. Org. Chem. 11, 693 (1998); (b) G. Arena, A. Contino, F.G. Gulino, A. Magri, F. Sansone, D. Sciotto, and R. Ungaro: Tetrahedron Lett. 40, 1597 (1999); (c) F. Sansone, F. Barboso, A. Casnati, D. Sciotto, and R. Ungaro: Tetrahedron. Lett. 40, 4741 (1999); (d) N. Douteau-Guével, A.W. Coleman, J.-P. Morel, and N. Morel-Desrosiers: J. Chem. Soc., Perkin Trans. 2, 629 (1999); (e) O.I. Kalchenko, F. Perret, and A.W. Coleman: J. Chem. Soc. Perkin Trans. 2, 258 (2001); (f) O.I. Kalchenko, E. Da Silva, and A.W. Coleman: J. Incl. Phenom. Macrocycl. Recogn. Chem. 43, 305 (2002)

    Google Scholar 

  9. N. Douteau-Guével F. Perret A.W. Coleman J.-P. Morel N. Morel-Desrosiers (2002) J. Chem. Soc. Perkin Trans 2 524

    Google Scholar 

  10. T. Peters SuffixJr. (Eds) (1996) All About Albumin Academic Press, Inc London, UK

    Google Scholar 

  11. (a) Y. Wang, M. Schubert, A. Ingendoh, and J. Franzen: Rapid Commun. Mass Spectrom. 14, 12 (2000); (b) J. Roboz, L. Deng, L. Ma, and J.F. Holland: Rapid Commun. Mass Spectrom. 12, 1319 (1998)

  12. L. Memmi A. Lazar A. Brioude V. Ball A.W. Coleman (2001) Chem. Commun 23 2474

    Google Scholar 

  13. (a) B. Salih, and R. Zenobi: Anal. Chem. 70, 1536 (1998); (b) S.D. Friess, J.M. Daniel, R. Hartmann, and R. Zenobi: Int. J. Mass Spectrom. 219, 269 (2002); (c) S.S. Ray, K. Singh, and P. Balaram: J. Am. Soc. Mass Spectrom. 12, 428 (2001); (d) S.D. Friess and R. Zenobi: J. Am. Soc. Mass Spectrom. 12, 810 (2001); (e) T.D. Veenstra: Biophys. Chem. 79, 63 (1999); (f) J.A. Loo: Mass Spectrom. Rev. 16, 1 (1997)

  14. (a) K. Wang and G.W. Gokel: J. Org. Chem. 61, 4693 (1996); (b) C.A. Schalley: Mass Spectrom. Rev. 20, 253 2001, (c) M. Przybylski, and M. O. Glocker, Chem. Int. Angew. Ed. Engl. 35, 806 (1996); (d) M.M. Stone, A.H. Franz, and C.B. Lebrilla: J. Am. Soc. Mass Spectrom. 13, 964 (2002)

  15. J.M. Daniel S.D. Friess S. Rajagopalan S. Wendt R. Zenobi (2002) Int. J. Mass. Spectrom 216 1 Occurrence Handle1:CAS:528:DC%2BD38Xis1enur4%3D

    CAS  Google Scholar 

  16. (a) X. Cheng, Q. Gao, R.D. Smith, K-.E. Jung, and C. Switzer: Chem. Commun. 747 (1996); (b) S.A. Hofstadler and R.H. Griffey: Chem. Rev. 101, 377 (2001)

  17. H.-K. Lim Y.L. Hsieh B. Ganem J. Henion (1995) J. Mass Spectrom 30 708 Occurrence Handle10.1002/jms.1190300509 Occurrence Handle1:CAS:528:DyaK2MXlvFams7s%3D

    Article  CAS  Google Scholar 

  18. E. Da Silva A.W. Coleman (2003) Tetrahedron 59 IssueID37 7357 Occurrence Handle10.1016/S0040-4020(03)01137-2 Occurrence Handle1:CAS:528:DC%2BD3sXmvFSjsr8%3D

    Article  CAS  Google Scholar 

  19. K. E. Van Holde (1985) Physical Biochemistry EditionNumber2 Prentrice-hall, Englewood cliffs NJ

    Google Scholar 

  20. (a) J. Rebek, Jr.: Acc. Chem. Res. 17, 258 (1984); (b) M.J. Greig, H. Gaus, L.L. Cummins, H. Sasmor, and R.H. Griffey: J. Am. Chem. Soc. 117, 10765 (1995); (c) K.A. Sannes-Lowery, R.H. Griffey, and S.A. Hofstadler: Anal. Biochem. 280, 264 (2000); (d) N. Carte, F. Legendre, E. Leize, E. Potier, F. Reeder, J.-C. Chottard, and A. van Dorsselear: Anal. Biochem. 284, 77 (2000); (e) R.M. Whittal, H.L. Ball, F.E. Cohen, A.L. Burlingame, S.B. Prusiner, and M.A. Baldwin: Protein Sci. 9, 332 (2000); (f) T.J.D Jorgensen and P. Roepstorff: Anal. Chem. 70, 4427 (1998)

  21. (a) S. Curry, H. Mandelkow, P. Brick, and N. Franks: Nat. Struct. Biol. 5, 827 (1998); (b) S. Sugio, A. Kashima, S. Mochizuki, M. Noda, and K. Kobayashi: Protein Eng. 12, 439 (1999)

  22. J.L. Atwood L.J. Barbour M.J. Hardie C.L. Raston (2001) Coord. Chem. Rev 222 3 Occurrence Handle10.1016/S0010-8545(01)00345-9 Occurrence Handle1:CAS:528:DC%2BD3MXnt1arurg%3D

    Article  CAS  Google Scholar 

  23. T. Peters SuffixJr. (1996) All About Albumin. Biochemistry, Genetics and Medical Applications Academic Press New York

    Google Scholar 

  24. R.G. Reed (1986) J. Biol. Chem 261 15619 Occurrence Handle1:CAS:528:DyaL28XmtVCqur8%3D

    CAS  Google Scholar 

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Authors and Affiliations

  1. Institut de Biologie et Chimie des Protéines, CNRS UMR 5086, 7 passage du Vercors, F69367, Lyon, France

    Eric Da Silva, Cécile F. Rousseau, Isabelle Zanella-Cléon, Michel Becchi & Anthony W. Coleman

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  1. Eric Da Silva
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  2. Cécile F. Rousseau
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  3. Isabelle Zanella-Cléon
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  4. Michel Becchi
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  5. Anthony W. Coleman
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Correspondence to Anthony W. Coleman.

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Silva, E.D., Rousseau, C.F., Zanella-Cléon, I. et al. Mass Spectrometric Determination of Association Constants of Bovine Serum Albumin (BSA) with para-Sulphonato-Calix[n]arene Derivatives. J Incl Phenom Macrocycl Chem 54, 53–59 (2006). https://doi.org/10.1007/s10847-005-3995-2

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  • DOI: https://doi.org/10.1007/s10847-005-3995-2

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