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Complexation of the barium cation with cyclosporin A: an experimental and theoretical study

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Abstract

On the basis of extraction experiments in the two-phase water–nitrobenzene system and γ-activity measurements, we determined the stability constant of the cyclosporin A–Ba2+ cationic complex dissolved in nitrobenzene saturated with water as 109.1 ± 0.2. Using quantum mechanical calculations, the most probable structure of this complex species was derived. In the resulting complex, the “central” cation Ba2+ is bound by six bonds to the respective six carbonyl oxygen atoms of the parent cyclosporin A ligand. The interaction energy of this proven cationic complex was found to be −769.5 kJ mol−1, confirming also the formation of the mentioned complex species.

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References

  1. Cantrell DA, Smith KA (1984) Science 224:1312

    Article  CAS  Google Scholar 

  2. Swarstad H, Bugge HC, Dhillion SS (2000) Biodivers Conserv 9:1521

    Article  Google Scholar 

  3. Borel JF (2002) Wien Klin Wochenschr 114:433

    CAS  Google Scholar 

  4. Dittmann J, Wenger RM, Kleinkauf H, Lawen A (1994) J Biol Chem 269:2841

    CAS  Google Scholar 

  5. Hoppert M, Gentzsch C, Schörgendorfer K (2001) Arch Microbiol 176:285

    Article  CAS  Google Scholar 

  6. Handschumacher RE, Harding MW, Rice J, Drugge RJ, Speicher DW (1984) Science 226:544

    Article  CAS  Google Scholar 

  7. Takahashi N, Hayano T, Suzuki M (1989) Nature 337:473

    Article  CAS  Google Scholar 

  8. Fischer G, Wittmann-Liebold B, Lang K, Kiefhaber T, Schmid FX (1989) Nature 337:476

    Article  CAS  Google Scholar 

  9. Loosli HR, Kessler H, Oschkinat H, Weber HP, Petcher TJ, Widmer A (1985) Helv Chim Acta 68:682

    Article  CAS  Google Scholar 

  10. Weber C, Wider G, von Freyberg B, Traber R, Braun W, Widmer H, Wüthrich K (1991) Biochemistry 30:6563

    Article  CAS  Google Scholar 

  11. Fesik SW, Gampe RT Jr, Eaton HL, Gemmecker G, Olejniczak ET, Neri P, Holzmann TF, Egan DA, Edalji R, Simmer R, Helfrich R, Hochlowski J, Jackson M (1991) Biochemistry 30:6574

    Article  CAS  Google Scholar 

  12. Wüthrich K, Spitzfaden C, Memmert K, Widmer H, Wider G (1991) FEBS Lett 285:237

    Article  Google Scholar 

  13. Kallen J, Spitzfaden C, Zurini MGM, Wider G, Widmer H, Wüthrich K, Walkinshaw MD (1991) Nature 353:276

    Article  CAS  Google Scholar 

  14. Neri P, Meadows R, Gemmecker G, Olejniczak E, Nettesheim D, Logan T, Simmer R, Helfrich R, Holzman T, Severin J, Fesik S (1991) FEBS Lett 294:81

    Article  CAS  Google Scholar 

  15. Ke HM, Zydowsky LD, Liu J, Walsh CT (1991) Proc Natl Acad Sci USA 88:9483

    Article  CAS  Google Scholar 

  16. Fesik SW, Neri P, Meadows R, Olejniczak ET, Gemmecker G (1992) J Am Chem Soc 114:3165

    Article  CAS  Google Scholar 

  17. Schreiber SL (1991) Science 251:283

    Article  CAS  Google Scholar 

  18. Liu J, Farmer JD Jr, Lane WS, Friedman J, Weissman I, Schreiber SL (1991) Cell 66:807

    Article  CAS  Google Scholar 

  19. Makrlík E, Vaňura P (1985) Talanta 32:423

    Article  Google Scholar 

  20. Makrlík E, Božek F (1998) Polish J Chem 72:949

    Google Scholar 

  21. Makrlík E, Vaňura P (2010) J Radioanal Nucl Chem 285:683

    Article  Google Scholar 

  22. Makrlík E, Vaňura P, Daňková M (1999) J Radioanal Nucl Chem 240:579

    Article  Google Scholar 

  23. Makrlík E, Vaňura P (2006) Monatsh Chem 137:157

    Article  Google Scholar 

  24. Makrlík E, Böhm S, Vaňura P (2015) J Mol Struct 1100:184

    Article  Google Scholar 

  25. Makrlík E, Toman P, Vaňura P (2013) J Radioanal Nucl Chem 295:1887

    Article  Google Scholar 

  26. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  27. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  28. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision C.01. Gaussian Inc, Wallingford

    Google Scholar 

  29. Kříž J, Toman P, Makrlík E, Budka J, Shukla R, Rathore R (2010) J Phys Chem A 114:5327

    Google Scholar 

  30. Kříž J, Dybal J, Makrlík E, Vaňura P, Moyer BA (2011) J Phys Chem B 115:7578

    Article  Google Scholar 

  31. Toman P, Makrlík E, Vaňura P (2012) Monatsh Chem 143:985

    Article  CAS  Google Scholar 

  32. Makrlík E, Toman P, Vaňura P (2013) Monatsh Chem 144:919

    Article  Google Scholar 

  33. Makrlík E, Vaňura P (1997) Polish J Chem 71:1494

    Google Scholar 

  34. Hawthorne MF, Young DC, Andrews TD, Howe DV, Pilling RL, Pitts AD, Reintjes M, Warren LF, Wegner PA (1968) J Am Chem Soc 90:879

    Article  CAS  Google Scholar 

  35. Makrlík E (1992) Collect Czech Chem Commun 57:289

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by the Grant Agency of the Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Project No. 42900/1312/3114, entitled “Environmental Aspects of Sustainable Development of Society”, and by the Czech Ministry of Education, Youth, and Sports (Project MSMT No.: 20/2015).

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Authors and Affiliations

  1. Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Czech Republic

    Emanuel Makrlík

  2. University of Chemistry and Technology, Prague, Czech Republic

    Stanislav Böhm & Petr Vaňura

Authors
  1. Emanuel Makrlík
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  2. Stanislav Böhm
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  3. Petr Vaňura
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Correspondence to Emanuel Makrlík.

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Makrlík, E., Böhm, S. & Vaňura, P. Complexation of the barium cation with cyclosporin A: an experimental and theoretical study. Monatsh Chem 147, 1475–1479 (2016). https://doi.org/10.1007/s00706-016-1769-8

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