N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide; methanesulfonic acid

• ChemBase ID: 134221
• Molecular Formular: C26H52N6O11S
• Molecular Mass: 656.78968
• Monoisotopic Mass: 656.34147751
• SMILES: CC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCN)O)O)O.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.NCCCCCN(C(=O)CCC(=O)NCCCCCN(C(=O)CCC(=O)NCCCCCN(C(=O)C)O)O)O
• InChI: 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)
• InChIKey: IDDIJAWJANBQLJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide; methanesulfonic acid
• IUPAC Traditional name: deferoxamine; methanesulfonic acid
• Synonyms: DFOM; Deferoxamine methanesulfonate salt; Desferrioxamine mesylate salt; Deferoxamine mesylate salt; N1-(5-aminopentyl)-N1-hydroxy-N4-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]butanediamide Methanesulfonate; N-[5-[3-[(5-aminopentyl)hydroxycarbamoyl]propionamido]pentyl]-3-[[5-(N-hydroxyacetamido)pentyl]carbamoyl]propionohydroxamic Acid Methanesulfonate; Ba 33112; DFX mesylate; Deferoxamine B mesylate; Deferoxamine methanesulfonate; Deferrioxamine B methanesulfonate; Desferal mesylate; Desferrioxamine B mesylate; Desferrioxamine methanesulfonate; NSC 644468; Deferoxamine Mesylate

Database IDs

• CAS Number: 138-14-7
• EC Number: 205-314-3
• MDL Number: MFCD00058605
• PubChem SID: 24894304; 162228498
• PubChem CID: 62881

CALCULATED PROPERTIES

• Acid pKa: 7.915494
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.9015827
• LogD (pH = 7.4): -3.638875
• Log P: -3.365162
• Molar Refractivity: 144.9508 cm^3
• Polarizability: 56.376564 Å^3
• Polar Surface Area: 205.84 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white to off-white powder

Safety Information

• RTECS: UG5310000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥92.5% (TLC)

DETAILS

Sigma Aldrich - D9533

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.

Toronto Research Chemicals - D228980

An iron chelating agent used in therapy for patients with sickle cell diseases and iron overload. Studies suggest that it can exert potential antioxidant neuroprotective effects in stroke patients

REFERENCES

• Inati, A. et al.: Am. J. Hematol., 85, 782 (2010)
• Selim, M.: Translat. Stroke Res., 1, 35 (2010)
• Cappellini, M.D. et al.: Hemoblobin, 33, 258 (2010)