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Synthesis and iron-binding properties of quinolobactin, a siderophore from a pyoverdine-deficient Pseudomonas fluorescens

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Abstract

Quinolobactin is a new siderophore produced by a pyoverdine deficient mutant of Pseudomonas fluorescens. A simple and efficient synthesis of quinolobactin is described, starting from xanthurenic acid. The protonation constants of quinolobactin were determined by potentiometric titrations as pKa2=5.50 ± 0.07, pKa1=10.30 ± 0.05. The equilibria of the metal complexes were studied by means of spectrophotometric and potentiometric titrations. The overall stability constants of the quinolobactin-FeIII complexes was found to be log β111=18.60 ± 0.10, log β121=32.60 ± 0.20, log β120=28.20 ± 0.25 resulting in a pFeIII value of 18.2 at pH 7.4. The UV-visible spectral parameters of the [FeL2] are in agreement with a complex containing two ligands coordinated to one Fe3+ cation through the oxygen and nitrogen quinoline atoms.

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References

  • Abdallah MA. 1991 Pyoverdins and Pseudobactins. In: Winkelman G, ed. Handbook of Microbial Iron Chelates.Boca Raton: CRC Press: 139–153.

    Google Scholar 

  • Albrecht-Gary AM., Crumbliss AL. 1998 Coordination Chem-istry of Siderophores: Thermodynamics and Kinetics of Iron Chelation and Release. In: Sigel A, Sigel H, eds. Metal ions in biological systems,Vol.35: Iron transport and storage in microorganisms, plants and animals. New-York: M. Dekker: 239–327.

    Google Scholar 

  • Bastian R, Weberling R, Palilla F. 1956 Determination of iron by ultraviolet spectrophotometry. Anal Chem 28, 459–462.

    Google Scholar 

  • Boukhalfa H, Thomas F, Serratrice G, Béguin C. 2002 Kin-etics of aqueous acid hydrolysis of iron(III) 5-substituted-8-hydroxyquinoline complexes: mechanistic implications. Inor-ganic Reaction Mechanisms 3, 153–172.

    Google Scholar 

  • Gans P, Sabatini A, Vacca A. 1996 Investigation of equilibria in solution. Determination of equilibrium constants with Hyper-quad suite of programs. Talanta 43, 1739–1753.

    Google Scholar 

  • Gans P, O'Sullivan B. 2000 Glee, A new computer program for glass electrode calibration. Talanta 51, 33–37

    Google Scholar 

  • Garrett TM, Miller PW, Raymond KN. 1989 2,3-dihydroxyterephthalamides: highly efficient iron(III) chelating agents. Inorg Chem 28, 128–133.

    Google Scholar 

  • Kotrly S, Sucha L. 1985, Handbook of Chemical Equilibria in Ana-lytical Chemistry, Ellis Horwood Series in Analytical Chemistry, Wiley and son's.

  • Martell AE, Motekaitis RJ. 1992 Determination and use of stability constants; Vol. 1; 2nd ed.; New-York VCH Publishers.

  • Mossialos D, Meyer J M, Budzikiewicz HP et al.2000 Quino-lobactin, a new siderophore of Pseudomonas fluorescens ATCC 17400, the production of which is repressed by the cognate pyoverdine. Appl Environ Microbiol 66, 487–492.

    Google Scholar 

  • Neilands JB. 1995 Siderophores: Structure and function of micro-bial iron transport compounds. J Biol Chem 270, 26723–26726.

    Google Scholar 

  • Neuenhaus W, Budzikiewicz H, Korth H, Pulverer G.1980 Bacterial components. Part IX. 8-Hydroxy-4-methoxymonothioquinaldic acid-a further thioacid from Pseudomonas. Z Naturforsch Sect B 35(12), 1569–1571.

    Google Scholar 

  • Pierre JL, Baret P, Serratrice G. 2003 Hydroxyquinolines as iron chelators. Current Med Chem 10, 1077–1084

    Google Scholar 

  • Sillen LG, Warnqvist B. 1969 Application of LETAGROP to spec-trophotometric data for testing models and adjusting equilibrium constants. Arkiv Kemi 31, 377–390.

    Google Scholar 

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du Moulinet d'Hardemare, A., Serratrice, G. & Pierre, JL. Synthesis and iron-binding properties of quinolobactin, a siderophore from a pyoverdine-deficient Pseudomonas fluorescens . Biometals 17, 691–697 (2004). https://doi.org/10.1007/s10534-004-1205-0

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  • DOI: https://doi.org/10.1007/s10534-004-1205-0

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