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Different iron-chelating properties of pyochelin diastereoisomers revealed by LC/MS

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Abstract

Pyochelin is a siderophore and virulence factor common to Burkholderia cepacia and several Pseudomonas strains. It is isolated from bacterial media as a mixture of two epimers, which readily equilibrate in most solvents. Experiments based on high-performance liquid chromatography/electrospray ionization mass spectrometry are reported here, allowing the investigation of the different Fe(III)-chelating properties of pyochelin diastereomers in solution without the need for labourious isolation. It is demonstrated in this study that only one of the two pyochelin diastereomers is able to chelate Fe(III); no Fe(III) complexes of the other diastereomer could be detected. The Fe(III)–pyochelin complex exhibited a 1:1 metal-to-siderophore ratio and no evidence for other stoichiometries was found.

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References

  1. Neilands JB (1995) J Bio Chem 270:26723–26726

    CAS  Google Scholar 

  2. Drechsel H, Jung G (1998) J Pept Sci 4:147–181

    Article  PubMed  CAS  Google Scholar 

  3. Boukhalfa H, Crumbliss AL (2002) BioMetals 15:325–339

    Article  PubMed  CAS  Google Scholar 

  4. Ratledge C, Dover LG (2000) Annu Rev Microbiol 54:881–941

    Article  PubMed  CAS  Google Scholar 

  5. Poole K, McKay GA (2003) Front Biosci 8:661–686

    Article  Google Scholar 

  6. Denton M, Wilcox MH (1997) J Antimicrob Chemother 40:468–474

    Article  PubMed  CAS  Google Scholar 

  7. Budzikiewicz H (2001) Curr Top Med Chem 1:1–6

    Article  PubMed  CAS  Google Scholar 

  8. Cox CD, Graham R (1979) J Bacteriol 137:357–364

    PubMed  CAS  Google Scholar 

  9. Rinehard KL, Staley AL, Wilson SR, Ankenbauer RG, Cox CD (1995) J Org Chem 60:2786–2791

    Article  Google Scholar 

  10. Schlegel K, Tarat K, Budzikiewicz H (2004) BioMetals 17:409–414]

    Article  PubMed  CAS  Google Scholar 

  11. Visca P, Colotti G, Serino L, Verzili D, Orsi N, Chiancone E (1992) Appl Environ Microbiol 58:2886–2893

    PubMed  CAS  Google Scholar 

  12. Galatin CL, Turecek F (1997) In: Cole RB (ed) Electrospray ionization mass spectrometry. Wiley, New York, pp 527–570

    Google Scholar 

  13. Rosenberg E (2003) J Chromatogr A 1000:841–889

    Article  PubMed  CAS  Google Scholar 

  14. Gledhill M (2001) Analyst 126:1359–1362

    Article  PubMed  CAS  Google Scholar 

  15. Spasojevi I, Boukhalfa H, Stevens RD, Crumbliss AL (2001) Inorg Chem 40:49–58

    Article  PubMed  CAS  Google Scholar 

  16. Neubert H, Hider RC, Cowan DA (2002) Rapid Commun Mass Spectrom 16:1556–1561

    Article  CAS  Google Scholar 

  17. Budimir N, Fournier F, Bailly T, Burgada, Tabet JC (2005) Rapid Commun Mass Spectrom 19:1822–1828

    Article  PubMed  CAS  Google Scholar 

  18. Cox CD, Rinehart KL, Moore ML, Cook JC (1981) Proc Natl Acad Sci USA 78:4256–4260

    Article  PubMed  CAS  Google Scholar 

  19. Collins RN (2004) J Chromatogr A 1059:1–12

    Article  PubMed  CAS  Google Scholar 

  20. Namiranian S, Richardson DJ, Russel DA, Sodeau JR (1997) Photochem Photobiol 65:777–782

    Article  PubMed  CAS  Google Scholar 

  21. Ankenbauer RG, Quan HN (1994) J Bacteriol 176:307–319

    PubMed  CAS  Google Scholar 

  22. Visca P, Colotti G, Serino L, Verzili D, Orsi N, Chiancone E (1992) Appl Environ Microbiol 58:2886–2893

    PubMed  CAS  Google Scholar 

  23. Klumpp C, Burger A, Mislin GL, Abdallah MA (2005) Bioinorg Med Chem Lett 15:1721–1724

    Article  CAS  Google Scholar 

  24. Meyer JM, Hohnadel D, Halle F (1989) J Gen Microbiol 135:1479–1487

    PubMed  CAS  Google Scholar 

  25. Cobessi D, Celia H, Pattus F (2005) J Mol Biol 352:893–904

    Article  PubMed  CAS  Google Scholar 

  26. Hayen H, Volmer DA (2005) Rapid Commun Mass Spectrom 19:711–720

    Article  PubMed  CAS  Google Scholar 

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Acknowledgements

The authors thank Stacey Owen for technical support, and Dr. Roger Ebanks for preparing the Ps. aeruginosa samples. HH acknowledges the Deutsche Forschungsgemeinschaft (DFG, Bonn, Germany) for a visiting fellowship. DAV would like to acknowledge research support to his group from the Natural Sciences and Engineering Research Council of Canada (NSERC, Discovery Grant “Experimental studies of biological coordination chemistry using advanced analytical mass spectrometry techniques”).

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Authors and Affiliations

  1. Institute for Analytical Sciences, Bunsen-Kirchhoff-Str. 11, 44139, Dortmund, Germany

    Heiko Hayen

  2. Institute for Marine Biosciences, National Research Council, 1411, Oxford Street, Halifax, Nova Scotia, B3H 3Z1, Canada

    Heiko Hayen & Dietrich A. Volmer

  3. Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3, Canada

    Dietrich A. Volmer

Authors
  1. Heiko Hayen
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  2. Dietrich A. Volmer
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Correspondence to Heiko Hayen or Dietrich A. Volmer.

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Hayen, H., Volmer, D.A. Different iron-chelating properties of pyochelin diastereoisomers revealed by LC/MS. Anal Bioanal Chem 385, 606–611 (2006). https://doi.org/10.1007/s00216-006-0443-0

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  • DOI: https://doi.org/10.1007/s00216-006-0443-0

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