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Volumn 90, Issue 4, 2006, Pages 1350-1361

1H and 13C-NMR and molecular dynamics studies of cyclosporin A interacting with magnesium(II) or cerium(III) in acetonitrile. Conformational changes and cis-trans conversion of peptide bonds

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CARBONYL DERIVATIVE; CERIUM; CYCLOSPORIN A; MAGNESIUM ION; METAL ION; OXYGEN DERIVATIVE; PEPTIDE DERIVATIVE; PROTON; ACETONITRILE DERIVATIVE; CALCIUM; CYCLOSPORIN; MAGNESIUM;

EID: 33645774454     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1529/biophysj.105.074245     Document Type: Article
Times cited : (31)

References (44)
  • 1
    • 0017072249 scopus 로고
    • Cyclosporin A, a peptide metabolite from Trichoderma polysporum Rifai, with a remarkable immunosuppressive activity
    • Ruegger, A., M. Kuhn, H. Lichti, H. R. Loosli, R. Huguenin, C. Quiquerez, and A. von Wartburg. 1976. Cyclosporin A, a peptide metabolite from Trichoderma polysporum Rifai, with a remarkable immunosuppressive activity. Helv. Chim. Acta. 59:1075-1092.
    • (1976) Helv. Chim. Acta , vol.59 , pp. 1075-1092
    • Ruegger, A.1    Kuhn, M.2    Lichti, H.3    Loosli, H.R.4    Huguenin, R.5    Quiquerez, C.6    Von Wartburg, A.7
  • 2
    • 0021912607 scopus 로고
    • Synthesis of cyclosporine and analogues: Structural requirements for immunosuppressive activity
    • Wenger, R. M. 1985. Synthesis of cyclosporine and analogues: structural requirements for immunosuppressive activity. Angew. Chem. 24:77-85.
    • (1985) Angew. Chem. , vol.24 , pp. 77-85
    • Wenger, R.M.1
  • 3
    • 1542268918 scopus 로고    scopus 로고
    • Modular and stereoselective formal synthesis of MeBmt, an unusual amino acid constituent of cyclosporin A
    • Raghavan, S., and M. A. Rasheed. 2004. Modular and stereoselective formal synthesis of MeBmt, an unusual amino acid constituent of cyclosporin A. Tetrahedron. 60:3059-3065.
    • (2004) Tetrahedron , vol.60 , pp. 3059-3065
    • Raghavan, S.1    Rasheed, M.A.2
  • 4
    • 0141905842 scopus 로고    scopus 로고
    • Two new cyclosporin folds observed in the structures of the immunosuppressant cyclosporin G and the formyl peptide receptor antagonist cyclosporin H at ultra-high resolution
    • Potter, B., R. A. Palmer, R. Withnall, T. C. Jenkins, and B. Z. Chowdhry. 2003. Two new cyclosporin folds observed in the structures of the immunosuppressant cyclosporin G and the formyl peptide receptor antagonist cyclosporin H at ultra-high resolution. Org. Biomol. Chem. 1:1466-1474.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 1466-1474
    • Potter, B.1    Palmer, R.A.2    Withnall, R.3    Jenkins, T.C.4    Chowdhry, B.Z.5
  • 5
    • 0025312673 scopus 로고
    • Structural elements pertinent to the interaction of cyclosporin A with its specific receptor protein, cyclophilin
    • Hsu, W., S. L. Heald, M. W. Harding, R. E. Handschumacher, and I. M. Armitage. 1990. Structural elements pertinent to the interaction of cyclosporin A with its specific receptor protein, cyclophilin. Biochem. Pharmacol. 40:131-140.
    • (1990) Biochem. Pharmacol. , vol.40 , pp. 131-140
    • Hsu, W.1    Heald, S.L.2    Harding, M.W.3    Handschumacher, R.E.4    Armitage, I.M.5
  • 6
    • 0021923153 scopus 로고
    • Peptide conformations. Part 31. The conformation of cyclosporin A in the crystal and in solution
    • Loosli, H., H. Kessler, H. Oschkinat, H.-P. Weber, T. J. Petcher, and A. Widmer. 1985. Peptide conformations. Part 31. The conformation of cyclosporin A in the crystal and in solution. Helv. Chim. Acta. 68:682-703.
    • (1985) Helv. Chim. Acta , vol.68 , pp. 682-703
    • Loosli, H.1    Kessler, H.2    Oschkinat, H.3    Weber, H.-P.4    Petcher, T.J.5    Widmer, A.6
  • 7
    • 0021911350 scopus 로고
    • 6 by a combination of homo- and heteronuclear two-dimensional techniques
    • 6 by a combination of homo- and heteronuclear two-dimensional techniques. Helv. Chim. Acta. 68:661-681.
    • (1985) Helv. Chim. Acta , vol.68 , pp. 661-681
    • Kessler, H.1    Loosli, H.R.2    Oschkinat, H.3
  • 9
    • 0027141121 scopus 로고
    • Solvent-dependent conformation and hydrogen-bonding capacity of cyclosporin A: Evidence from partition coefficients and molecular dynamics simulations
    • El Tayar, N., A. E. Mark, P. Vallat, R. M. Brunne, B. Testa, and W. F. van Gunsteren. 1993. Solvent-dependent conformation and hydrogen-bonding capacity of cyclosporin A: evidence from partition coefficients and molecular dynamics simulations. J. Med. Chem. 36:3757-3764.
    • (1993) J. Med. Chem. , vol.36 , pp. 3757-3764
    • El Tayar, N.1    Mark, A.E.2    Vallat, P.3    Brunne, R.M.4    Testa, B.5    Van Gunsteren, W.F.6
  • 15
    • 0001104552 scopus 로고
    • The cell cycle, signal transduction, and immunophilin-ligand complexes
    • Schreiber, S. L., M. W. Albers, and E. J. Brown. 1993. The cell cycle, signal transduction, and immunophilin-ligand complexes. Acc. Chem. Res. 26:412-420.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 412-420
    • Schreiber, S.L.1    Albers, M.W.2    Brown, E.J.3
  • 16
    • 0032577483 scopus 로고    scopus 로고
    • Regulation of the calmodulin-stimulated protein phospatase, calcineurin
    • Klee, C. B., H. Ren, and X. Wang. 1998. Regulation of the calmodulin-stimulated protein phospatase, calcineurin. J. Biol. Chem. 273:13367-13370.
    • (1998) J. Biol. Chem. , vol.273 , pp. 13367-13370
    • Klee, C.B.1    Ren, H.2    Wang, X.3
  • 17
    • 0024976004 scopus 로고
    • Cyclosporine
    • Kahan, B. D. 1989. Cyclosporine. N. Engl. J. Med. 321:1725-1738.
    • (1989) N. Engl. J. Med. , vol.321 , pp. 1725-1738
    • Kahan, B.D.1
  • 18
    • 0034045947 scopus 로고    scopus 로고
    • Mechanisms of action of cyclosporin
    • Matsuda, S., and S. Koyasu. 2000. Mechanisms of action of cyclosporin. Immunopharmacology. 47:119-125.
    • (2000) Immunopharmacology , vol.47 , pp. 119-125
    • Matsuda, S.1    Koyasu, S.2
  • 19
    • 84893435531 scopus 로고
    • Binding of the immunosuppressant peptide cyclosporin A to calcium, zinc and copper. Is cyclosporin A an Ionophore?
    • Dancer, R. J., A. Jones, and D. P. Fairlie. 1995. Binding of the immunosuppressant peptide cyclosporin A to calcium, zinc and copper. Is cyclosporin A an Ionophore? Aust. J. Chem. 48:1835-1841.
    • (1995) Aust. J. Chem. , vol.48 , pp. 1835-1841
    • Dancer, R.J.1    Jones, A.2    Fairlie, D.P.3
  • 21
    • 0141851299 scopus 로고    scopus 로고
    • Studies of the interaction of potassium(I), calcium(II), magnesium(II) and copper(II) with CsA
    • Cusack, R., L. Grondhal, D. Fairlie, G. Hanson, and L. Gahan. 2003. Studies of the interaction of potassium(I), calcium(II), magnesium(II) and copper(II) with CsA. J. Inorg. Biochem. 97:191-198.
    • (2003) J. Inorg. Biochem. , vol.97 , pp. 191-198
    • Cusack, R.1    Grondhal, L.2    Fairlie, D.3    Hanson, G.4    Gahan, L.5
  • 22
    • 0026651050 scopus 로고
    • Lithium Chloride perturbation of cis-trans peptide bond equilibria: Effect on conformational equilibria in cyclosporin A and on time-dependent inhibition of cyclophilin
    • Kofron, J. L., P. Kuzmic, V. Kishore, G. Gemmecker, S. W. Fesik, and D. H. Rich. 1992. Lithium Chloride perturbation of cis-trans peptide bond equilibria: effect on conformational equilibria in cyclosporin A and on time-dependent inhibition of cyclophilin. J. Am. Chem. Soc. 114:2670-2675.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2670-2675
    • Kofron, J.L.1    Kuzmic, P.2    Kishore, V.3    Gemmecker, G.4    Fesik, S.W.5    Rich, D.H.6
  • 23
    • 0028284256 scopus 로고
    • Conformational changes in the cyclic undecapeptide cyclosporin induced by interaction with metal ions
    • Shaw, R., H. H. Mantsch, and B. Z. Chowdhry. 1994. Conformational changes in the cyclic undecapeptide cyclosporin induced by interaction with metal ions. Int. J. Biol. Macromol. 16:143-148.
    • (1994) Int. J. Biol. Macromol. , vol.16 , pp. 143-148
    • Shaw, R.1    Mantsch, H.H.2    Chowdhry, B.Z.3
  • 24
    • 0026637286 scopus 로고
    • Novel backbone conformation of CsA: The complex with lithium chloride
    • Kock, M., D. Seebach, H. Kessler, and A. Thaler. 1992. Novel backbone conformation of CsA: the complex with lithium chloride. J. Am. Chem. Soc. 114:2676-2686.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2676-2686
    • Kock, M.1    Seebach, D.2    Kessler, H.3    Thaler, A.4
  • 25
    • 84944648082 scopus 로고
    • Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides
    • Shannon, R. D. 1976. Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides. Acta Crystallogr. A. A32:751-767.
    • (1976) Acta Crystallogr. A , vol.A32 , pp. 751-767
    • Shannon, R.D.1
  • 26
    • 0342325307 scopus 로고
    • Lanthanide ion luminescence probes of the structure of biological macromolecules
    • Horrocks, W., and D. R. Sudnick. 1981. Lanthanide ion luminescence probes of the structure of biological macromolecules. Acc. Chem. Res. 14:384-392.
    • (1981) Acc. Chem. Res. , vol.14 , pp. 384-392
    • Horrocks, W.1    Sudnick, D.R.2
  • 27
    • 0037508832 scopus 로고    scopus 로고
    • The structure of the Ce(III)-Angiotensin II complex as obtained from NMR data and molecular dynamics calculations
    • D'Amelio, N., E. Gaggelli, N. Gaggelli, F. Mancini, E. Molteni, D. Valensin, and G. Valensin. 2003. The structure of the Ce(III)-Angiotensin II complex as obtained from NMR data and molecular dynamics calculations. J. Inorg. Biochem. 95:225-229.
    • (2003) J. Inorg. Biochem. , vol.95 , pp. 225-229
    • D'Amelio, N.1    Gaggelli, E.2    Gaggelli, N.3    Mancini, F.4    Molteni, E.5    Valensin, D.6    Valensin, G.7
  • 28
    • 0034798810 scopus 로고    scopus 로고
    • Magnetic susceptibility tensor anisotropies for a lanthanide ion series in a fixed protein matrix
    • Bertini, I., M. B. Janik, Y. M. Lee, C. Luchinat, and A. Rosato. 2001. Magnetic susceptibility tensor anisotropies for a lanthanide ion series in a fixed protein matrix. J. Am. Chem. Soc. 123:4181-4188.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4181-4188
    • Bertini, I.1    Janik, M.B.2    Lee, Y.M.3    Luchinat, C.4    Rosato, A.5
  • 29
    • 0029661901 scopus 로고    scopus 로고
    • 1H longitudinal relaxation times in the solution structure of paramagnetic proteins. application to [4Fe-4S] proteins
    • 1H longitudinal relaxation times in the solution structure of paramagnetic proteins. application to [4Fe-4S] proteins. Biochemistry. 35:12705-12711.
    • (1996) Biochemistry , vol.35 , pp. 12705-12711
    • Huber, J.G.1    Moulis, J.M.2    Gaillard, J.3
  • 30
    • 0031576336 scopus 로고    scopus 로고
    • Torsion angle dynamics for NMR structure calculation with the program DYANA
    • Güntert, P., C. Mumenthaler, and K. Wüthrich. 1997. Torsion angle dynamics for NMR structure calculation with the program DYANA. J. Mol. Biol. 273:283-298.
    • (1997) J. Mol. Biol. , vol.273 , pp. 283-298
    • Güntert, P.1    Mumenthaler, C.2    Wüthrich, K.3
  • 31
    • 0029881007 scopus 로고    scopus 로고
    • MOLMOL: A program for display and analysis of macromolecular structures
    • Koradi, R., M. Billeter, and K. Wüthrich. 1996. MOLMOL: a program for display and analysis of macromolecular structures. J. Mol. Graph. 14:51-58.
    • (1996) J. Mol. Graph , vol.14 , pp. 51-58
    • Koradi, R.1    Billeter, M.2    Wüthrich, K.3
  • 32
    • 0035789518 scopus 로고    scopus 로고
    • GROMACS 3.0: A package for molecular simulation and trajectory analysis
    • Lindahl, E., B. Hess, and D. van der Spoel. 2001. GROMACS 3.0: a package for molecular simulation and trajectory analysis. J. Mol. Model. (Online). 7:306-317.
    • (2001) J. Mol. Model. (Online) , vol.7 , pp. 306-317
    • Lindahl, E.1    Hess, B.2    Van Der Spoel, D.3
  • 33
    • 0029633168 scopus 로고
    • GROMACS: A message-passing parallel molecular dynamics implementation
    • Berendsen, H., D. van der Spoel, and R. van Drunen. 1995. GROMACS: a message-passing parallel molecular dynamics implementation. Comput. Phys. Comm. 91:43-56.
    • (1995) Comput. Phys. Comm. , vol.91 , pp. 43-56
    • Berendsen, H.1    Van Der Spoel, D.2    Van Drunen, R.3
  • 35
    • 0347119205 scopus 로고    scopus 로고
    • Comparison of different three site interaction potentials for liquid acetonitrile
    • Guàrdia, E., R. Pinzón, J. Casulleras, M. Orozco, and F. J. Luque. 2001. Comparison of different three site interaction potentials for liquid acetonitrile. Mol. Simul. 26:287-306.
    • (2001) Mol. Simul. , vol.26 , pp. 287-306
    • Guàrdia, E.1    Pinzón, R.2    Casulleras, J.3    Orozco, M.4    Luque, F.J.5
  • 36
    • 0000437307 scopus 로고
    • Time-dependent distance restraints in molecular dynamics simulations
    • Torda, E. A., R. M. Scheek, and W. F. van Gunsteren. 1989. Time-dependent distance restraints in molecular dynamics simulations. Chem. Phys. Lett. 157:289-294.
    • (1989) Chem. Phys. Lett. , vol.157 , pp. 289-294
    • Torda, E.A.1    Scheek, R.M.2    Van Gunsteren, W.F.3
  • 38
    • 33646940952 scopus 로고
    • Numerical integration of the Cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes
    • Ryckaert, J., G. Ciccotti, and H. Berendsen. 1977. Numerical integration of the Cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes. J. Comput. Phys. 23:327-341.
    • (1977) J. Comput. Phys. , vol.23 , pp. 327-341
    • Ryckaert, J.1    Ciccotti, G.2    Berendsen, H.3
  • 39
    • 0002469944 scopus 로고
    • Treatment of long range forces in molecular dynamics
    • J. Hermans, editor. Polycrystal Book Service, Western Springs, IL
    • Berendsen, H. 1995. Treatment of long range forces in molecular dynamics. In Molecular Dynamics and Protein Structure. J. Hermans, editor. Polycrystal Book Service, Western Springs, IL. 18-22.
    • (1995) Molecular Dynamics and Protein Structure , pp. 18-22
    • Berendsen, H.1
  • 42
    • 0000808787 scopus 로고
    • Coordination of water to magnesium cations
    • Bock, C., J. Glusker, and A. Kaufman. 1994. Coordination of water to magnesium cations. Inorg. Chem. 33:419-427.
    • (1994) Inorg. Chem. , vol.33 , pp. 419-427
    • Bock, C.1    Glusker, J.2    Kaufman, A.3
  • 43
    • 0004226423 scopus 로고
    • The Chemical Society, London, Special Publication No. 25
    • Sillèn, L. G., and A. Martell. 1971. Stability constants. The Chemical Society, London, Special Publication No. 25.
    • (1971) Stability Constants
    • Sillèn, L.G.1    Martell, A.2
  • 44
    • 0002228715 scopus 로고    scopus 로고
    • NMR of paramagnetic substances
    • Bertini, I., and C. Luchinat. 1996. NMR of paramagnetic substances. Coord. Chem. Rev. 150:1-292.
    • (1996) Coord. Chem. Rev. , vol.150 , pp. 1-292
    • Bertini, I.1    Luchinat, C.2


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