Idification and structural characterisation of a catecholate-type siderophore produced by K279a Free

Abstract

Siderophores are produced by several bacteria that utilise iron in various environments. Elucidating the structure of a specific siderophore may have valuable applications in drug development. , a Gram-negative bacterium that inhabits a wide range of environments and can cause pneumonia, produces siderophores. However, the structure was unknown, and therefore, in this study, we aimed to elucidate it. We purified siderophores from cultures of K279a using preparative reversed-phase HPLC. The structure was analysed through LC-MS and H and C NMR. The results demonstrated that K279a produces 2,3-dihydroxybenzoylserine (DHBS), a monomer unit of enterobactin. We suggested the uptake of Iron(III) by the DHBS complex. DHBS production by K279a could be attributed to an incomplete enterobactin pathway. Drugs targeting DHBS synthesis could prevent infection.

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2021-07-19
2024-03-28
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References

  1. Berg G, Roskot N, Smalla K. Genotypic and phenotypic relationships between clinical and environmental isolates of Stenotrophomonas maltophilia. J Clin Microbiol 1999; 37:3594–3600 [View Article] [PubMed]
    [Google Scholar]
  2. Senol E. Stenotrophomonas maltophilia: the significance and role as a nosocomial pathogen. J Hosp Infect 2004; 57:1–7 [View Article] [PubMed]
    [Google Scholar]
  3. Kalidasan V, Joseph N, Kumar S, Awang Hamat R, Neela VK. Iron and virulence in Stenotrophomonas maltophilia: all we know so far, Front. Front Cell Infect Microbiol 2018; 8:401 [View Article]
    [Google Scholar]
  4. Ratledge C, Dover LG. Iron metabolism in pathogenic bacteria. Annu Rev Microbiol 2000; 54:881–941 [View Article]
    [Google Scholar]
  5. Miethke M, Marahiel MA. Siderophore-based iron acquisition and pathogen control. Microbiol Mol Biol Rev 2007; 71:413–451 [View Article] [PubMed]
    [Google Scholar]
  6. Ali SS, Vidhale NN. Bacterial siderophore and their application: a review. Int J Curr Microbiol App Sci 2013; 2:303–312
    [Google Scholar]
  7. García CA, Passerini De Rossi B, Alcaraz E, Vay C, Franco M. Siderophores of Stenotrophomonas maltophilia: detection and determination of their chemical nature. Rev Argent Microbiol 2012; 44:150–154 [PubMed]
    [Google Scholar]
  8. Ryan RP, Monchy S, Cardinale M, Taghavi S, Crossman L et al. The versatility and adaptation of bacteria from the genus Stenotrophomonas. Nat Rev Microbiol 2009; 7:514–525 [View Article] [PubMed]
    [Google Scholar]
  9. Nas MY, Cianciotto NP. Stenotrophomonas maltophilia produces an EntC-dependent catecholate siderophore that is distinct from enterobactin. Microbiology (Reading) 2017; 163:1590–1603 [View Article] [PubMed]
    [Google Scholar]
  10. Schwyn B, Neilands JB. Universal chemical assay for the detection and determination of siderophores. Anal Biochem 1987; 160:47–56 [View Article] [PubMed]
    [Google Scholar]
  11. Arnow LE. Colorimetric determination of the components of 3,4-dihydroxyphenylalanine tyrosine mixtures. Anal Chim Acta 1937; 118:531–537
    [Google Scholar]
  12. Berner I, Greiner M, Metzger J, Jung G, Winkelmann G. Identification of enterobactin and linear dihydroxybenzoylserine compounds by HPLC and ion spray mass spectrometry (LC/MS and MS/MS. Biol Met 1991; 4:113–118 [View Article] [PubMed]
    [Google Scholar]
  13. Wensing A, Braun SD, Büttner P, Expert D, Völksch B et al. Impact of siderophore production by Pseudomonas syringae pv. syringae 22d/93 on epiphytic fitness and biocontrol activity against Pseudomonas syringae pv. glycinea 1a/96. Appl Environ Microbiol 2010; 76:2704–2711 [View Article] [PubMed]
    [Google Scholar]
  14. McEldowney S. The impact of surface attachment on cadmium accumulation by Pseudomonas fluorescens H2, FEMS Microbiol. . Ecol 2000; 33:121–128
    [Google Scholar]
  15. Bergstrom CP, Lu MC, Bell CL. NMR studies of dimeric 2,3-dihydroxy-N-benzoyl serine. J Nat Prod 1991; 54:1003–1008 [View Article]
    [Google Scholar]
  16. Hantke K. Dihydroxybenzolyserine–a siderophore for E. coli. FEMS Microbiol Lett 1990; 55:5–8 [View Article] [PubMed]
    [Google Scholar]
  17. Nikaido H, Rosenberg EY. Cir and Fiu proteins in the outer membrane of Escherichia coli catalyze transport of monomeric catechols: study with β-lactam antibiotics containing catechol and analogous groups. J Bacteriol 1990; 172:1361–1367 [View Article] [PubMed]
    [Google Scholar]
  18. Armstrong SK, Francis CL, McIntosh MA. Molecular analysis of the Escherichia coli ferric enterobactin receptor FepA. J Biol Chem 1990; 265:14536–14543 [PubMed]
    [Google Scholar]
  19. Pierce JR, Pickett CL, Earhart CF. Two fep genes are required for ferrienterochelin uptake in Escherichia coli K-12. J Bacteriol 1983; 155:330–336 [View Article] [PubMed]
    [Google Scholar]
  20. García CA, Alcaraz ES, Franco MA, Passerini de Rossi BN. Iron is a signal for Stenotrophomonas maltophilia biofilm formation, oxidative stress response, OMPs expression, and virulence. Front Microbiol 2015; 6:926 [View Article] [PubMed]
    [Google Scholar]
  21. Raymond KN, Dertz EA, Kim SS. Enterobactin: an archetype for microbial iron transport. Proc Natl Acad Sci U S A 2003; 100:3584–3588
    [Google Scholar]
  22. Chu BCH, Otten R, Krewulak KD, Mulder FAA, Vogel HJ. The solution structure, binding properties, and dynamics of the bacterial siderophore-binding protein FepB. J Biol Chem 2014; 289:29219–29234 [View Article] [PubMed]
    [Google Scholar]
  23. Palacios M, Broberg CA, Walker KA, Miller VL. A serendipitous mutation reveals the severe virulence defect of a Klebsiella pneumoniae fepB Mutant. mSphere 2017; 2:e00341–17 [View Article]
    [Google Scholar]
  24. Gehring AM, Mori I, Walsh CT. Reconstitution and characterization of the Escherichia coli enterobactin synthetase from EntB, EntE, and EntF. Biochemistry 1998; 37:2648–2659 [View Article] [PubMed]
    [Google Scholar]
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