14836-73-8

Basic information

• Product Name: ferrioxamine B
• Synonyms: ferrioxamine B
• CAS NO: 14836-73-8
• Molecular Formula: C₂₅H₄₅FeN₆O₈
• Molecular Weight: 613.51
• Mol File: 14836-73-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: ferrioxamine B(CAS DataBase Reference)
• NIST Chemistry Reference: ferrioxamine B(14836-73-8)
• EPA Substance Registry System: ferrioxamine B(14836-73-8)

Safety Data

• Hazardous Substances Data: 14836-73-8(Hazardous Substances Data)

Usage

General Description

Ferrioxamine B is a natural iron-chelating agent produced by certain types of bacteria and fungi. It is characterized by a cyclic structure and contains three hydroxamate binding sites that can chelate ferric iron. This chemical is commonly used in clinical medicine for the treatment of iron overload, as it effectively binds excess iron in the body and aids in its excretion. Ferrioxamine B also shows potential as an antifungal and antibacterial agent, and has been studied for its ability to inhibit the growth of certain microorganisms. Additionally, it has been investigated as a potential treatment for certain types of cancer due to its ability to modulate iron metabolism in tumor cells. Overall, Ferrioxamine B is a versatile chemical with diverse potential applications in medicine and research.

InChI:InChI=1/C25H48N6O8.Fe/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;/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34);/q;+3

Upstream product

• 15377-81-8 hexaaquairon(III) 
• 138-14-7 deferoxamine mesylate 
• 18601-34-8 (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)] 
• 70-51-9 deferoxamine 

Relevant articles and documents

Multifunctional Pt(iv) prodrug candidates featuring the carboplatin core and deferoxamine

The synergistic combination of the anticancer drug carboplatin and the iron chelator deferoxamine (DFO) served as a foundation for the development of novel multifunctional prodrugs. Hence, five platinum(iv) complexes, featuring the equatorial coordination sphere of carboplatin, and one or two DFO units incorporated at axial positions, were synthesized and characterized using ESI-HRMS, multinuclear (1H,13C,15N,195Pt) NMR spectroscopy and elemental analysis. Analytical studies demonstrated that the chelating properties of the DFO moiety were not compromised after coupling to the platinum(iv) core. The cytotoxic activity of the compounds was evaluated in monolayer (2D) and spheroid (3D) cancer cell models, derived from ovarian teratocarcinoma (CH1/PA-1), colon carcinoma (SW480) and non-small cell lung cancer (A549). The platinum(iv)-DFO prodrugs demonstrated moderatein vitrocytotoxicity (a consequence of their slow activation kinetics) but with less pronounced differences between intrinsically chemoresistant and chemosensitive cell lines as well as between 2D and 3D models than the clinically used platinum(ii) drug carboplatin.

ThIV-Desferrioxamine: Characterization of a fluorescent bacterial probe

Diversifying our ability to guard against emerging pathogenic threats is essential for keeping pace with global health challenges, including those presented by drug-resistant bacteria. Some modern diagnostic and therapeutic innovations to address this challenge focus on targeting methods that exploit bacterial nutrient sequestration pathways, such as the desferrioxamine (DFO) siderophore used by Staphylococcus aureus (S. aureus) to sequester FeIII. Building on recent studies that have shown DFO to be a versatile vehicle for chemical delivery, we show proof-of-principle that the FeIII sequestration pathway can be used to deliver a potential radiotherapeutic. Our approach replaces the FeIII nutrient sequestered by H4DFO+ with ThIV and made use of a common fluorophore, FITC, which we covalently bonded to DFO to provide a combinatorial probe for simultaneous chelation paired with imaging and spectroscopy, H3DFO_FITC. Combining insight provided from FITC-based imaging with characterization by NMR spectroscopy, we demonstrated that the fluorescent DFO_FITC conjugate retained the ThIV chelation properties of native H4DFO+. Fluorescence microscopy with both [Th(DFO_FITC)] and [Fe(DFO_FITC)] complexes showed similar uptake by S. aureus and increased intercellular accumulation as compared to the FITC and unchelated H3DFO_FITC controls. Collectively, these results demonstrate the potential for the newly developed H3DFO_FITC conjugate to be used as a targeting vector and bacterial imaging probe for S. aureus. The results presented within provide a framework to expand H4DFO+ and H3DFO_FITC to relevant radiotherapeutics (like 227Th).

Effect of pressure on the complex formation and aquation kinetics of iron (III) with hydroxamic acids

The activation and reaction volumes for the formation and aquation of (acethydroxamato)iron(III) complexes, as well as the activation volumes for the formation of the (desferrioxamine B)iron(III) complex, have been obtained by high-pressure stopped-flow and UV-vis spectral measurements. The data indicate a gradual mechanistic changeover from Ia to Id for the stepwise proton-catalyzed hydrolysis of the tris(acethydroxamato)iron(III) complex and vice versa for the corresponding formation reactions. The activation volumes for the complexation of Fe(H2O)63+ and Fe(H2O)5(OH)2+ with both acethydroxamic acid (HA) and desferrioxamine B in its fully protonated form (H4dfb+) exhibit opposite signs, indicating associative and dissociative modes of activation, respectively. The obtained results suggest that the substitution behavior of the Fe(III) complexes is controlled by the presence of OH- or A- in the coordination sphere.