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D9533 Sigma-Aldrich

Deferoxamine mesylate salt

powder, ≥92.5% (TLC)

Synonym: DFOM, Deferoxamine methanesulfonate salt, Desferrioxamine mesylate salt

  • CAS Number 138-14-7

  • Empirical Formula (Hill Notation) C25H48N6O8 · CH4O3S

  • Molecular Weight 656.79

  •  EC Number 205-314-3

  •  MDL number MFCD00058605

  •  PubChem Substance ID 24894304

  •  NACRES NA.32

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Properties

Related Categories Aerobic Glycolysis (the Warburg Effect), Antioxidants and Cytoprotectants, Cancer Metabolism, Cancer Research, Cell Biology,
assay   ≥92.5% (TLC)
form   powder
color   white to off-white
solubility   H2O: 50 mg/mL
storage temp.   −20°C
SMILES string   CS(O)(=O)=O.CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
InChI   1S/C25H48N6O8.CH4O3S/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26;1-5(2,3)4/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34);1H3,(H,2,3,4)
InChI key   IDDIJAWJANBQLJ-UHFFFAOYSA-N

Description

Biochem/physiol Actions

An iron chelator used often in the studies of cell proliferation and apoptosis. Has been shown to have anti-proliferative effects on vascular smooth muscle cells in vitro and in vivo and to arrest cells in the G1 phase. Also reported to induce p53. Induces apoptosis in HL-60 cells by chelating iron. After 48 hrs treatment with 1μM deferoxamine, DNA fragmentation was apparent. Cells treated with 0.1 μM deferoxamine for as little as 24 hours were committed to apoptosis; by 48 hrs nuclear collapse was observed. In some studies it has been shown to have antioxidant properties and to protect cells against H2O2-induced damage.

Deferoxamine is used as a hypoxia-mimetic agent to stabilize Hypoxia Inducible Factor 1 (HIF-1). Deferoxamine stabilizes HIF-1 through the inhibition of Prolyl Hydroxylases (PHDs) which target HIF-1 through degradation. The mechanism of deferoxamine inhibition is likely through the chelation of Fe2+ bound to the active site of PHD which is required for enzymatic activity.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
UG5310000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Oncogenes and Tumor Suppressors Reprogram Metabolism

Proliferating cells require the biosynthesis of structural components for biomass production and for genomic replication. This requires a reprogramming of the metabolic pathways to ensure nutrients s...
BioFiles v7 n4
Keywords: Aerobic, Antitumor agents, Apoptosis, Cancer, Citric Acid Cycle, Degradations, Environmental, Gene expression, Glycolysis, Growth factors, Metabolic Pathways, Metabolism, Metabolites, Nucleotide Synthesis, Pentose phosphate pathway, Phosphorylations

Viable but Nonculturable Bacteria

The expression “viable but nonculturable” (VNC) bacteria, describes cells that cannot normally be cultured. However this makes little sense, when one considers that the demonstration of culturability...
Jvo Siegrist
Microbiology Focus Edition 1.4
Keywords: Environmental, Gene expression, Metabolic Pathways

Peer-Reviewed Papers
15

References

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