| Identification | Back Directory | [Name]
N-desferriferrichrome | [CAS]
34787-28-5 | [Synonyms]
deferrichrome
DesferrichroMe
Deferriferrichrome
Ferrichrome Iron-free
N-desferriferrichrome
Cyclo(glycylglycylglycyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl) | [Molecular Formula]
C27H45N9O12 | [MDL Number]
MFCD28899080 | [MOL File]
34787-28-5.mol | [Molecular Weight]
687.7 |
| Chemical Properties | Back Directory | [Melting point ]
197-203°C | [storage temp. ]
2-8°C | [solubility ]
DMSO, Methanol | [form ]
Solid | [color ]
White to Off-White | [InChIKey]
ZFDAUYPBCXMSBF-ACRUOGEOSA-N | [SMILES]
C\C(CC(O)=O)=C/C1=[O][Fe]2345ON1CCCC6NC(=O)CNC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CCCN(O2)C(\C=C(\C)CC(O)=O)=[O]3)NC(=O)C(CCCN(O4)C(\C=C(/C)CC(O)=O)=[O]5)NC6=O |
| Hazard Information | Back Directory | [Description]
Ferrichrome is a hydroxamate siderophore produced by various fungi, including U. sphaerogena, that facilitates iron chelation and uptake by these organisms. It can be utilized as a heterologous siderophore by bacteria, including P. aeruginosa and V. parahaemolyticus. Ferrichrome (0.8 μM) inhibits proliferation of murine spleen mononuclear cells induced by concanavalin A and reduces the number of concanavalin A-stimulated CD4+ T cells expressing the IL-2 receptor. It also inhibits heme-catalyzed oxidation of LDL by hydrogen peroxide in a concentration-dependent manner. | [Uses]
Growth-promoting iron chelator. Ferrichrome iron-free from Ustilago sphaerogena. | [Definition]
ChEBI: A homodetic cyclic peptide composed from two units of three glycyl and three N5-acetyl-N5-hydroxy-L-ornithyl residues. | [Biochem/physiol Actions]
Growth-promoting iron chelator | [References]
[1] EMERY T. Role of ferrichrome as a ferric ionophore in Ustilago sphaerogena[J]. Biochemistry Biochemistry, 1971, 10 8: 1483-1488. DOI: 10.1021/bi00784a033
[2] I AUTENRIETH J H K Hantke. Immunosuppression of the host and delivery of iron to the pathogen: a possible dual role of siderophores in the pathogenesis of microbial infections?[J]. Medical Microbiology and Immunology, 1991, 180 3: 135-141. DOI: 10.1007/bf00206117
[3] ISTVáN PóCSI. Fungal siderophores function as protective agents of LDL oxidation and are promising anti-atherosclerotic metabolites in functional food[J]. Molecular Nutrition & Food Research, 2008, 52 12: 1434-1447. DOI: 10.1002/mnfr.200700467
[4] MéLISSA HANNAUER. The ferrichrome uptake pathway in Pseudomonas aeruginosa involves an iron release mechanism with acylation of the siderophore and recycling of the modified desferrichrome.[J]. Journal of Bacteriology, 2010: 1212-1220. DOI: 10.1128/jb.01539-09
[5] TATSUYA FUNAHASHI. Identification and characterization of genes required for utilization of desferri-ferrichrome and aerobactin in Vibrio parahaemolyticus.[J]. Biological & pharmaceutical bulletin, 2009, 32 3: 359-365. DOI: 10.1248/bpb.32.359 |
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