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Chemical Compound Review

AC1L1D6V     N-[3-[5,8-bis[3-(ethanoyl- oxido...

Synonyms: AC1LD8UX, 11047-12-4, 15630-64-5, 21872-77-5, 162602-16-6, ...
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Disease relevance of N-[3-[5,8-bis[3-(acetyl-oxido-amino)propyl]-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxido-acetamide


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


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

  • The binding site of ferrichrome, an aromatic pocket near the cell surface, undergoes minor changes upon association with the ligand [1].
  • FhuA, the receptor for ferrichrome-iron in Escherichia coli, is a member of a family of integral outer membrane proteins, which, together with the energy-transducing protein TonB, mediate the active transport of ferric siderophores across the outer membrane of Gram-negative bacteria [6].
  • Upon binding of ferrichrome-iron, conformational changes are transduced to the periplasmic pocket of FhuA, signaling the ligand-loaded status of the receptor [6].
  • A receptor domain controls the intracellular sorting of the ferrichrome transporter, ARN1 [7].
  • Mutations within this domain lead to loss of ferrichrome binding and uptake activities and missorting of Arn1p, including a failure to relocalize to the plasma membrane in the presence of ferrichrome [7].

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


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


  1. Transmembrane signaling across the ligand-gated FhuA receptor: crystal structures of free and ferrichrome-bound states reveal allosteric changes. Locher, K.P., Rees, B., Koebnik, R., Mitschler, A., Moulinier, L., Rosenbusch, J.P., Moras, D. Cell (1998) [Pubmed]
  2. 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]
  3. The TonB-dependent ferrichrome receptor FcuA of Yersinia enterocolitica: evidence against a strict co-evolution of receptor structure and substrate specificity. Koebnik, R., Hantke, K., Braun, V. Mol. Microbiol. (1993) [Pubmed]
  4. fhuA of Actinobacillus pleuropneumoniae encodes a ferrichrome receptor but is not regulated by iron. Mikael, L.G., Srikumar, R., Coulton, J.W., Jacques, M. Infect. Immun. (2003) [Pubmed]
  5. Fingerprinting metal-containing biomolecules after reductive displacement of iron by gallium and subsequent column-switched LC-ICPMS analysis applied on siderophores. Moberg, M., Nilsson, E.M., Holmström, S.J., Lundström, U.S., Pettersson, J., Markides, K.E. Anal. Chem. (2004) [Pubmed]
  6. Siderophore-mediated iron transport: crystal structure of FhuA with bound lipopolysaccharide. Ferguson, A.D., Hofmann, E., Coulton, J.W., Diederichs, K., Welte, W. Science (1998) [Pubmed]
  7. A receptor domain controls the intracellular sorting of the ferrichrome transporter, ARN1. Kim, Y., Lampert, S.M., Philpott, C.C. EMBO J. (2005) [Pubmed]
  8. Permeability properties of a large gated channel within the ferric enterobactin receptor, FepA. Liu, J., Rutz, J.M., Feix, J.B., Klebba, P.E. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  9. The beta-barrel domain of FhuADelta5-160 is sufficient for TonB-dependent FhuA activities of Escherichia coli. Braun, M., Killmann, H., Braun, V. Mol. Microbiol. (1999) [Pubmed]
  10. Identification and Characterization of a Novel ABC Iron Transport System, fit, in Escherichia coli. Ouyang, Z., Isaacson, R. Infect. Immun. (2006) [Pubmed]
  11. Vibrio cholerae iron transport systems: roles of heme and siderophore iron transport in virulence and identification of a gene associated with multiple iron transport systems. Henderson, D.P., Payne, S.M. Infect. Immun. (1994) [Pubmed]
  12. Genomic subtractive hybridization and selective capture of transcribed sequences identify a novel Salmonella typhimurium fimbrial operon and putative transcriptional regulator that are absent from the Salmonella typhi genome. Morrow, B.J., Graham, J.E., Curtiss, R. Infect. Immun. (1999) [Pubmed]
  13. Ferrichrome induces endosome to plasma membrane cycling of the ferrichrome transporter, Arn1p, in Saccharomyces cerevisiae. Kim, Y., Yun, C.W., Philpott, C.C. EMBO J. (2002) [Pubmed]
  14. The structure of Escherichia coli BtuF and binding to its cognate ATP binding cassette transporter. Borths, E.L., Locher, K.P., Lee, A.T., Rees, D.C. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  15. Ferrioxamine uptake in Yersinia enterocolitica: characterization of the receptor protein FoxA. Bäumler, A.J., Hantke, K. Mol. Microbiol. (1992) [Pubmed]
  16. The mechanism of ferrichrome transport through Arn1p and its metabolism in Saccharomyces cerevisiae. Moore, R.E., Kim, Y., Philpott, C.C. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  17. Ligand-induced conformational change in the ferrichrome-iron receptor of Escherichia coli K-12. Moeck, G.S., Tawa, P., Xiang, H., Ismail, A.A., Turnbull, J.L., Coulton, J.W. Mol. Microbiol. (1996) [Pubmed]
  18. tonB-independent ferrichrome-mediated iron transport in Escherichia coli spheroplasts. Weaver, C.A., Konisky, J. J. Bacteriol. (1980) [Pubmed]
  19. urbs1, a gene regulating siderophore biosynthesis in Ustilago maydis, encodes a protein similar to the erythroid transcription factor GATA-1. Voisard, C., Wang, J., McEvoy, J.L., Xu, P., Leong, S.A. Mol. Cell. Biol. (1993) [Pubmed]
  20. The role of the FRE family of plasma membrane reductases in the uptake of siderophore-iron in Saccharomyces cerevisiae. Yun, C.W., Bauler, M., Moore, R.E., Klebba, P.E., Philpott, C.C. J. Biol. Chem. (2001) [Pubmed]
  21. Peptide hydrogen bonding. Conformation dependence of the carbonyl carbon-13 nuclear magnetic resonance chemical shifts in ferrichrome. A study by 13C-[15N] Fourier double resonance spectroscopy1a. Llinás, M., Wilson, D.M., Klein, M.P. J. Am. Chem. Soc. (1977) [Pubmed]
  22. Three cell wall mannoproteins facilitate the uptake of iron in Saccharomyces cerevisiae. Protchenko, O., Ferea, T., Rashford, J., Tiedeman, J., Brown, P.O., Botstein, D., Philpott, C.C. J. Biol. Chem. (2001) [Pubmed]
  23. The siderophore iron transporter of Candida albicans (Sit1p/Arn1p) mediates uptake of ferrichrome-type siderophores and is required for epithelial invasion. Heymann, P., Gerads, M., Schaller, M., Dromer, F., Winkelmann, G., Ernst, J.F. Infect. Immun. (2002) [Pubmed]
  24. Insertion mutagenesis of the gene encoding the ferrichrome-iron receptor of Escherichia coli K-12. Carmel, G., Hellstern, D., Henning, D., Coulton, J.W. J. Bacteriol. (1990) [Pubmed]
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  26. Involvement of ExbB and TonB in transport across the outer membrane of Escherichia coli: phenotypic complementation of exb mutants by overexpressed tonB and physical stabilization of TonB by ExbB. Fischer, E., Günter, K., Braun, V. J. Bacteriol. (1989) [Pubmed]
  27. Extracellular siderophores from Aspergillus ochraceous. Jalal, M.A., Mocharla, R., Barnes, C.L., Hossain, M.B., Powell, D.R., Eng-Wilmot, D.L., Grayson, S.L., Benson, B.A., van der Helm, D. J. Bacteriol. (1984) [Pubmed]
  28. Molecular cloning of the ferrichrome-iron receptor of Escherichia coli K-12. Coulton, J.W., Mason, P., DuBow, M.S. J. Bacteriol. (1983) [Pubmed]
  29. Bioassay for siderophore utilization by Candida albicans. Minnick, A.A., Eizember, L.E., McKee, J.A., Dolence, E.K., Miller, M.J. Anal. Biochem. (1991) [Pubmed]
  30. Determination of ferrichrome binding to the FhuA outer membrane transport protein, periplasmic accumulation of ferrichrome, or transport of ferrichrome into cells using a three-layer oil technique. Killmann, H., Gestwa, G. Anal. Biochem. (2002) [Pubmed]
  31. Siderophore uptake and use by the yeast Saccharomyces cerevisiae. Lesuisse, E., Blaiseau, P.L., Dancis, A., Camadro, J.M. Microbiology (Reading, Engl.) (2001) [Pubmed]
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