Ferrichrome
 Ferrichrome (sticks) bound to an iron atom (orange)
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| IUPAC name
N-[3-[4,16-bis[3-[acetyl(oxido)amino]propyl]-2,5,8,11,14,17-hexaoxo-3,6,9,12,15,18-hexazacyclooctadec-1-yl]propyl]-N-oxidoacetamide; iron(3+)
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| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.036.081 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C27H42FeN9O12 | |
| Molar mass | 740.52 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ferrichrome is a cyclic hexa-peptide that forms a complex with iron atoms. It is a siderophore composed of three glycine and three modified ornithine residues with hydroxamate groups [-N(OH)C(=O)C-]. The 6 oxygen atoms from the three hydroxamate groups bind Fe(III) in near perfect octahedral coordination.
Ferrichrome was first isolated in 1952, has been found to be produced by fungi of the genera Aspergillus, Ustilago, and Penicillium.[1]
Biological Function of Ferrichrome
Ferrichrome is a Siderophore, which are metal chelating agents that have a low molecular mass and are produced by microorganisms and plants growing under low iron conditions. The main function of siderophores is to chelate ferric iron (Fe3+) from insoluble minerals from the environment and make it available for microbial and plant cells. Iron is important in biological functions as it acts as a catalyst in enzymatic processes, as well as for electron transfer, DNA and RNA synthesis, and oxygen metabolism.[2] Although iron is the fourth most abundant element in the earth’s crust,[3] bioavailability of iron in aerobic environments is low due to formation of insoluble ferric hydroxides. Under iron limitation, bacteria scavenge for ferric iron (Fe3+) by up-regulating the secretion siderophores in order to meet their nutritional requirements.[4] Recent studies have shown that ferrichrome has been used as a tumor- suppressive molecule produced by L. casei. The study from the Department of Medicine and Asahikawa Medical University, suggests that ferrichrome has a greater tumor-suppressive effect than other drugs currently used to fight colon cancer, including Cisplatin and 5-fluoro-uracil. Ferrichrome also had less of an effect on non-cancerous intestinal cells than the two previously mentioned cancer fighting drugs. It was determined that ferrichrome activated the C-Jun N-terminal kinases, which induced Apoptosis. The induction of apoptosis by ferrichrome is reduced by the inhibition of the c-jun N-terminal kinase signaling pathway.[5]
See also
References
- ^ Ferrichrome, Virtual Museum of Minerals and Molecules, University of Wisconsin
- ^ Ahmed, E (2014). "Siderophores in environmental research: roles and applications"". Microbial Biotechnology: 196.
- ^ Loper, Joyce (September 1990). "Siderophores in Microbial Interactions on Plant Surfaces". Molecular Plant-Microbe Interactions. 4: 5–13.
- ^ Chatterjee, Anushila (February 2018). "Rapid evolution of a bacterial acquisition system". Molecular Microbiology. 108: 90–100.
- ^ Konishi, Hiroaki (August 2016). "Probiotic-derived ferrichrome inhibits colon cancer progression via JNK-mediated apoptosis". Nature Communications.
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