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Chemical Compound Review

Ferricrocin     N-[3-[5,8-bis[3-(ethanoyl- oxido...

Synonyms: AR-1J2530, AR-1J2531, AC1L4MR8, 23086-46-6
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Disease relevance of N-[3-[5,8-bis[3-(acetyl-oxido-amino)propyl]-14-methylol-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxido-acetamide

  • In an E. coli strain in which both proteins were expressed from the chromosome, a high molecular mass complex was detected when the ferrichrome homologue ferricrocin was added immediately prior to addition of cross-linker [1].
  • Polymer-bound ferricrocin protected cells against colicin M and phage T5 by competition for the common tonA-coded outer membrane receptor protein [2].

High impact information on N-[3-[5,8-bis[3-(acetyl-oxido-amino)propyl]-14-methylol-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxido-acetamide

  • FhuD T181C was reacted with two thiol-specific fluorescent probes; addition of the siderophore ferricrocin quenched fluorescence emissions of these conjugates [3].
  • Together these experiments establish that FhuA.TonB interactions are more intricate than originally predicted, that the TonB.FhuA stoichiometry is 2:1, and that ferricrocin modulates binding of FhuA to TonB at regions outside the C-terminal domain of TonB [4].
  • These results indicate that, in vivo, the binding of ferricrocin to FhuA enhances complex formation between the receptor and TonB [1].
  • Ferricrocin-deficiency caused an increased intracellular labile iron pool, upregulation of antioxidative enzymes and elevated sensitivity to the redox cycler paraquat [5].
  • TAF and ferricrocin both removed Tf-bound iron with second-order rate constants that were comparable to those of the siderophores of several bacterial pathogens, indicating they may play a role in iron uptake in vivo and thereby contribute to the virulence of A. fumigatus [6].

Chemical compound and disease context of N-[3-[5,8-bis[3-(acetyl-oxido-amino)propyl]-14-methylol-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxido-acetamide


Biological context of N-[3-[5,8-bis[3-(acetyl-oxido-amino)propyl]-14-methylol-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxido-acetamide


Anatomical context of N-[3-[5,8-bis[3-(acetyl-oxido-amino)propyl]-14-methylol-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxido-acetamide


Associations of N-[3-[5,8-bis[3-(acetyl-oxido-amino)propyl]-14-methylol-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxido-acetamide with other chemical compounds


Gene context of N-[3-[5,8-bis[3-(acetyl-oxido-amino)propyl]-14-methylol-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxido-acetamide

  • Cells disrupted for the TUP1 or SSN6 genes were constitutively derepressed for the uptake of ferrichrome, ferricrocin or ferrioxamine B, but not for the uptake of triacetylfusarinine C [9].
  • The principal hydroxamate siderophore produced, was identified as ferricrocin as confirmed by analytical HPLC, FAB-mass spectrometry and 1H- and 13C-NMR spectra [13].

Analytical, diagnostic and therapeutic context of N-[3-[5,8-bis[3-(acetyl-oxido-amino)propyl]-14-methylol-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxido-acetamide


  1. Cell envelope signaling in Escherichia coli. Ligand binding to the ferrichrome-iron receptor fhua promotes interaction with the energy-transducing protein TonB. Moeck, G.S., Coulton, J.W., Postle, K. J. Biol. Chem. (1997) [Pubmed]
  2. Iron supply of Escherichia coli with polymer-bound ferricrocin. Coulton, J.W., Naegeli, H.U., Braun, V. Eur. J. Biochem. (1979) [Pubmed]
  3. Interactions between TonB from Escherichia coli and the Periplasmic Protein FhuD. Carter, D.M., Miousse, I.R., Gagnon, J.N., Martinez, E., Clements, A., Lee, J., Hancock, M.A., Gagnon, H., Pawelek, P.D., Coulton, J.W. J. Biol. Chem. (2006) [Pubmed]
  4. Enhanced binding of TonB to a ligand-loaded outer membrane receptor: role of the oligomeric state of TonB in formation of a functional FhuA.TonB complex. Khursigara, C.M., De Crescenzo, G., Pawelek, P.D., Coulton, J.W. J. Biol. Chem. (2004) [Pubmed]
  5. The siderophore system is essential for viability of Aspergillus nidulans: functional analysis of two genes encoding l-ornithine N 5-monooxygenase (sidA) and a non-ribosomal peptide synthetase (sidC). Eisendle, M., Oberegger, H., Zadra, I., Haas, H. Mol. Microbiol. (2003) [Pubmed]
  6. Site-specific rate constants for iron acquisition from transferrin by the Aspergillus fumigatus siderophores N',N'',N'''-triacetylfusarinine C and ferricrocin. Hissen, A.H., Moore, M.M. J. Biol. Inorg. Chem. (2005) [Pubmed]
  7. The Intracellular Siderophore Ferricrocin Is Involved in Iron Storage, Oxidative-Stress Resistance, Germination, and Sexual Development in Aspergillus nidulans. Eisendle, M., Schrettl, M., Kragl, C., M??ller, D., Illmer, P., Haas, H. Eukaryotic Cell (2006) [Pubmed]
  8. Iron uptake studies on erythroid cells. Barnekow, A., Winkelmann, G. Biochim. Biophys. Acta (1978) [Pubmed]
  9. Siderophore uptake and use by the yeast Saccharomyces cerevisiae. Lesuisse, E., Blaiseau, P.L., Dancis, A., Camadro, J.M. Microbiology (Reading, Engl.) (2001) [Pubmed]
  10. Quantification of hydroxamate siderophores in soil solutions of podzolic soil profiles in Sweden. Essén, S.A., Bylund, D., Holmström, S.J., Moberg, M., Lundström, U.S. Biometals (2006) [Pubmed]
  11. Fusarinines and dimerum acid, mono- and dihydroxamate siderophores from Penicillium chrysogenum, improve iron utilization by strategy I and strategy II plants. Hördt, W., Römheld, V., Winkelmann, G. Biometals (2000) [Pubmed]
  12. Oxalate and ferricrocin exudation by the extramatrical mycelium of an ectomycorrhizal fungus in symbiosis with Pinus sylvestris. van Hees, P.A., Rosling, A., Essén, S., Godbold, D.L., Jones, D.L., Finlay, R.D. New Phytol. (2006) [Pubmed]
  13. Ferricrocin--an ectomycorrhizal siderophore of Cenococcum geophilum. Haselwandter, K., Winkelmann, G. Biometals (2002) [Pubmed]
  14. Iron uptake and intracellular metal transfer in mycobacteria mediated by xenosiderophores. Matzanke, B.F., Böhnke, R., Möllmann, U., Reissbrodt, R., Schünemann, V., Trautwein, A.X. Biometals (1997) [Pubmed]
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