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D9533

Deferoxamine mesylate salt

Name: Deferoxamine mesylate salt
Brand: SIGMA

≥92.5% (TLC), powder

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Synonym(s):

DFX mesylate, DFOM, Deferoxamine methanesulfonate salt, Desferrioxamine mesylate salt

Empirical Formula (Hill Notation):

C₂₅H₄₈N₆O₈ · CH₄O₃S

CAS Number:

138-14-7

Molecular Weight:

656.79

EC Number:

205-314-3

MDL number:

MFCD00058605

PubChem Substance ID:

24894304

NACRES:

NA.32

Quality Level

200

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Antiproliferative effect of desferrioxamine on vascular smooth muscle cells in vitro and in vivo.

E Porreca et al.

Arteriosclerosis and thrombosis : a journal of vascular biology, 14(2), 299-304 (1994-02-01)

Vascular smooth muscle cell (VSMC) growth is a primary component of accelerated and spontaneous atherosclerosis. Previous studies have shown that iron may be involved in the control of enzymatic activities that modulate DNA synthesis in human cells. In this study

Biodegradable hypoxia biomimicry microspheres for bone tissue regeneration.

Lina Hadidi et al.

Journal of biomaterials applications, 34(7), 1028-1037 (2019-10-28)

Regulation of ferritin-mediated cytoplasmic iron storage by the ferric uptake regulator homolog (Fur) of Helicobacter pylori.

S Bereswill et al.

Journal of bacteriology, 182(21), 5948-5953 (2000-10-13)

Homologs of the ferric uptake regulator Fur and the iron storage protein ferritin play a central role in maintaining iron homeostasis in bacteria. The gastric pathogen Helicobacter pylori contains an iron-induced prokaryotic ferritin (Pfr) which has been shown to be

Stabilization of wild-type p53 by hypoxia-inducible factor 1alpha.

W G An et al.

Nature, 392(6674), 405-408 (1998-04-16)

Although hypoxia (lack of oxygen in body tissues) is perhaps the most physiological inducer of the wild-type p53 gene, the mechanism of this induction is unknown. Cells may detect low oxygen levels through a haem-containing sensor protein. The hypoxic state

Ferroportin downregulation promotes cell proliferation by modulating the Nrf2-miR-17-5p axis in multiple myeloma.

Yuanyuan Kong et al.

Cell death & disease, 10(9), 624-624 (2019-08-20)

Recent findings demonstrate that aberrant downregulation of the iron-exporter protein, ferroportin (FPN1), is associated with poor prognosis and osteoclast differentiation in multiple myeloma (MM). Here, we show that FPN1 was downregulated in MM and that clustered regularly interspaced short palindromic

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