Skip to main content
SpringerLink
Log in

Microbial growth promotion studies of exochelin MN and analogues thereof

  • Published:
Biometals Aims and scope Submit manuscript

Abstract

The ability of exochelin MN and three synthetic analogues to promote the growth of various strains of mycobacteria and Gram-negative bacteria was investigated. The results indicated that growth promotion ability of these compounds depends either on ligand exchange with mycobactin or on the exochelin permease. Despite stronger iron complexing capacity, the structural analogues showed weaker growth promotion ability than exochelin MN, which further supported our hypothesis of pH-dependent iron(III)-release of exochelin MN.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Braun V, Braun M. 2002 Active transport of iron and siderophore antibiotics. Curr Opin Microbiol 5, 194-201.

    Google Scholar 

  • Dong L, Miller MJ. 2002 Total synthesis of exochelin MN and analogues. J Org Chem 67, 4759-4770.

    Google Scholar 

  • Dhungana S, Miller MJ, Dong L, Ratledge C, Crumbliss AL. 2003 Fe(III) coordination properties of an extracellular siderophore exochelin MN. J Amer Chem Soc (in press).

  • Deutsches Arzneibuch, 9th Edition, 1986, 47-48 and 424-430, Deutscher Apotheker Verlag Stuttgart.

  • Hider RC. 1984 Siderophore mediated absorption of iron. Siderophores Microorg Plants 58, 26-87.

    Google Scholar 

  • Harris WR, Carrano CJ, Cooper SR, Sofen SR, Avdeef AE, McArdle JV, Raymond KN. 1979 Coordination chemistry of Microbial iron transport compounds. 19. Stability constants and electrochemical behavial of ferric enterobactin and model complexes. J Am Chem Soc 101, 6097-6104.

    Google Scholar 

  • Hancock DK, Coxon B, Wang SY, White EV, Reeder DJ. 1993 L-threo-beta-Hydroxyhistidine, an unprecedented iron(III) ionbinding amino-acid in a pyoverdine-type siderophore from Pseudomonas-fluorescens-244. J Chem Soc Chem Commun 5, 468-469.

    Google Scholar 

  • Hantke K. 1990 Dihydroxybenzoylserine, a Siderophore for E. coli. FEMS Microbiol Lett 67, 5-8.

    Google Scholar 

  • Matzanke BF, BÖhnke R, MÖllmann U, Reissbrodt R, SchÜnemann V, Trautwein AX. 1997 Iron uptake and intracellular metal transfer in mycobacteria mediated by xenosiderophores. BioMetals 10, 193-203.

    Google Scholar 

  • Miller MJ, Malouin F. 1993 Microbial iron chelators as drug delivery agents: The rational design and synthesis of siderophore-drug conjugates. Accts Chem Res 26, 241-249.

    Google Scholar 

  • Miller MJ. 1989 Syntheses and therapeutic potential of hydroxamic acid based siderophores and analogs. Chem Rev 89, 1563-1579.

    Google Scholar 

  • Neilands JB. 1993 Siderophores. Arch Biochem Biophys 30

  • 1 Curr Med Chem 7, 159-197.

  • Schumann G, MÖllmann U, Heinemann I. Mutants of Mycobacterium species and their use for screening of antibiotic vectors Patent application DE 19817021,9. (17.4.1998) GrÜnenthal GmbH.

  • Schumann G, MÖllmann U. 2001 A screening system for xenosiderophores as potential drug delivery agents in Mycobacteria. Antimicrob Agents Chemother 45, 1317-1322.

    Google Scholar 

  • Schwynn B, Neilands JB. 1987 Universal chemical assay for the detection and determination of siderophores. Anal Biochem 160, 47-56.

    Google Scholar 

  • Sharman GJ, Williams DH, Ewing DF, Ratledge C. 1995 Determination of the structure of exochelin MN, the extracellular siderophore from Mycobacterium neoaurum. Chem Biochem 2, 553-561.

    Google Scholar 

  • Snapper SB, Melton RE, Mustafa, Kieser ST, Jacobs WR Jr. 1990 Isolation and characterization of efficient plasmid transformation mutants of Mycobacterium smegmatis. Mol Microbiol 4, 1911-1919.

    Google Scholar 

  • Sugiura, Y 1980 Bleomycin-iron complexes. Electron spin resonance study, ligand effect, and implication for action mechanism. J Am Chem Soc 102, 5208-5215.

    Google Scholar 

  • Vergne AF, Walz AJ, Miller MJ. 2000 Iron chelators from mycobacteria (1954-1999) and potential therapeutic applications. Nat Prod Rep 17, 99-116.

    Google Scholar 

  • Winkelman G. 1991 Handbook of Microbial Iron Chelates CRC press.

  • Winkelmann G, Carrano CJ. 1997 Transition Metals in Microbial Metabolism. Harwood Academic Publishers.

  • Wooldridge KG, Williams PH. 1993 Siderophores: Iron uptake mechanisms of pathogenic bacteria. FEMS Microbiol Rev 12, 325-348.

    Google Scholar 

  • Zimmermann W. 1979. Penetration through the gram-negative cell wall: A co-determinant of the efficacy of beta-lactam antibiotics. J Clin Pharmacol Biopharm 17, 131-134.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN, 46556, USA

    Li Dong & Marvin J. Miller

  2. Hans-Knöll Institut für Naturstoff-Forschung, Jena, Germany

    Ute Möllmann

Authors
  1. Li Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marvin J. Miller
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ute Möllmann
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dong, L., Miller, M.J. & Möllmann, U. Microbial growth promotion studies of exochelin MN and analogues thereof. Biometals 17, 99–104 (2004). https://doi.org/10.1023/B:BIOM.0000018348.89904.60

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:BIOM.0000018348.89904.60

Search

Navigation