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

• ChemBase编号: 134221
• 分子式: C26H52N6O11S
• 平均质量: 656.78968
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide; methanesulfonic acid
• IUPAC传统名: deferoxamine; methanesulfonic acid
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 7.915494
• 质子受体: 9
• 质子供体: 6
• LogD (pH = 5.5): -4.9015827
• LogD (pH = 7.4): -3.638875
• Log P: -3.365162
• 摩尔折射率: 144.9508 cm^3
• 极化性: 56.376564 Å^3
• 极化表面积: 205.84 Å^2
• 可自由旋转的化学键: 23
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: H2O: soluble50 mg/mL
• 外观: white to off-white powder

安全信息

• RTECS编号: UG5310000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥92.5% (TLC)

详细说明

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

参考文献

• 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)