CAS 70-51-9|Deferoxamine

Introduction：Basic information about CAS 70-51-9|Deferoxamine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common NameDeferoxamine
CAS Number70-51-9Molecular Weight560.68400
Density1.212g/cm3Boiling Point627.9°C (rough estimate)
Molecular FormulaC25H48N6O8Melting Point139°C
MSDS/Flash Point/

Names

Namedesferrioxamine B
SynonymMore Synonyms

Deferoxamine BiologicalActivity

DescriptionDeferoxamine (Deferoxamine B) is an iron chelator (binds to Fe(III) and many other metal cations), is widely used to reduce iron accumulation and deposition in tissues. Deferoxamine upregulates HIF-1α levels with good antioxidant activity. Deferoxamine also shows anti-proliferative activity, can induce apoptosis and autophagy in cancer cells. Deferoxamine can be used in studies of diabetes, neurodegenerative diseases as well as anti-cancer and anti-COVID-19[1][2][3][4][5].
Related CatalogSignaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Autophagy >>AutophagySignaling Pathways >>PI3K/Akt/mTOR >>AktResearch Areas >>Inflammation/ImmunologySignaling Pathways >>Metabolic Enzyme/Protease >>HIF/HIF Prolyl-HydroxylaseResearch Areas >>Metabolic DiseaseResearch Areas >>Neurological Disease
In VitroDeferoxamine (1 mM; 16 h or 4 weeks) improves HIF-1α function under hypoxic and hyperglycemic conditions and decreases ROS in MEFs cells[1]. Deferoxamine (100 µM; 24 h) increases InsR expression and activity and also induces an increase in p-Akt/total Akt/PKB levels[2]. Deferoxamine (5, 10, 25, 50, 100 µM; 7 or 9 days) inhibits the proliferation of tumor-associated MSCs and bone marrow MSCs[3]. Deferoxamine (5, 10, 25, 50, 100 µM; 7 days) induces apoptosis of MSCs[3]. Deferoxamine (10 µM ; 3 days) influencs the expression of adhesion proteins on MSCs[3]. Deferoxamine (100 µM; 24 h) induces autophagy mediated by the level of HIF-1α in SH-SY5Y cells[4]. Western Blot Analysis[1] Cell Line: MEFs cells Concentration: 1 mM Incubation Time: 16 h (hypoxia condition); 4 weeks (hyperglycemic conditions) Result: Significantly attenuated the hyperglycemia-associated increase in ROS levels under hypoxic high glucose conditions. Notably increased normoxic HIF transactivation in MEFs under both high glucose and normal glucose conditions. Western Blot Analysis[2] Cell Line: HepG2 cells Concentration: 100 µM Incubation Time: 24 h Result: Showed a twofold increase of InsR mRNA levels in cells. Increased by twofold InsR binding activity at the half-maximal concentration of 1.1 nM. Cell Proliferation Assay[3] Cell Line: TAMSCs and BMMSCs (all isolated from Male C57BL/6J mice (8 week-old; EG-7 induced tumor model)) Concentration: 5, 10, 25, 50, 100 µM Incubation Time: 7 days (TAMSCs); 9 days (BMMSCs). Result: Inhibited the growth of TAMSCs and BMMSCs, and most cells are died at day 7 or 9 when exposed to 50 and 100 µM dose. Apoptosis Analysis[3] Cell Line: TAMSCs, BMMSCs Concentration: 5, 10, 25, 50, 100 µM Incubation Time: 7 days Result: Exhibited proapoptotic effect on TAMSCs and BMMSCs cells. Western Blot Analysis[3] Cell Line: TAMSCs, BMMSCs Concentration: 10 µM Incubation Time: 3 days Result: Remarkably decreased VCAM-1 expression in both TAMSCs and BMMSCs. Cell Autophagy Assay[4] Cell Line: SH-SY5Y cells Concentration: 100 µM Incubation Time: 24 h Result: Increased the ratio of LC3-II/I, an indicator of autophagy, which effects were blocked when autophagy-related gene Beclin 1 was suppressed by Beclin 1 siRNA transfection. Caused a time and dose-dependent increase of HIF-1a, accompanied by the induction of autophagy.
In VivoDeferoxamine (560.68 mg/per; drip-on; once daily for 21 days) enhances wound healing and increases neovascularization in aged or diabetic mice[1]. Deferoxamine (200 mg/kg; i.p.; daily for 2 weeks) results in HIF-1α stabilization and increases glucose uptake, hepatic InsR expression, and signaling in vivo[2]. Animal Model: Aged (21-month-old) and diabetic (12-week-old) C57BL/6J mice (excisional wound model)[1]. Dosage: 560.68 mg/per (10 uL of 1 mM) Administration: Drip-on; once daily for 21 days. Result: Displayed significantly accelerated healing and increased neovascularization in both aged and diabetic mice model. Animal Model: Male Sprague-Dawley rats (180-200 g)[2]. Dosage: 200 mg/kg Administration: Intraperitoneal injection; daily for 2 weeks. Result: Significantly increased hepatic HIF-1α protein levels, InsR protein levels, as well as Akt/PKB and activated Akt/PKB were significantly higher in the liver.
References

[1]. Duscher D, et al. Comparison of the Hydroxylase Inhibitor Dimethyloxalylglycine and the Iron Chelator Deferoxamine in Diabetic and Aged Wound Healing. Plast Reconstr Surg. 2017 Mar;139(3):695e-706e.

[2]. Dongiovanni P, et al. Iron depletion by deferoxamine up-regulates glucose uptake and insulin signaling in hepatoma cells and in rat liver. Am J Pathol. 2008 Mar;172(3):738-47.

[3]. Wang G, et al. In vitro assessment of deferoxamine on mesenchymal stromal cells from tumor and bone marrow. Environ Toxicol Pharmacol. 2017 Jan;49:58-64.

[4]. Wu Y, et al. Neuroprotection of deferoxamine on rotenone-induced injury via accumulation of HIF-1 alpha and induction of autophagy in SH-SY5Y cells. Neurochem Int. 2010 Oct;57(3):198-205.

[5]. Bellotti D, et al. Deferoxamine B: A Natural, Excellent and Versatile Metal Chelator. Molecules. 2021 May 28;26(11):3255.

Chemical & Physical Properties

Density1.212g/cm3
Boiling Point627.9°C (rough estimate)
Melting Point139°C
Molecular FormulaC25H48N6O8
Molecular Weight560.68400
Exact Mass560.35300
PSA205.84000
LogP2.40420
Index of Refraction1.537
InChIKeyUBQYURCVBFRUQT-UHFFFAOYSA-N
SMILESCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
Storage condition-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UG5300000
CHEMICAL NAME :
Propionohydroxamic acid, N-(5-(3-((5-aminopentyl)hydroxycarbamoyl)propionamido )pentyl)- 3-((5-(N-hydroxyacetamido)pentyl)carbamoyl)-
CAS REGISTRY NUMBER :
70-51-9
LAST UPDATED :
199612
DATA ITEMS CITED :
18
MOLECULAR FORMULA :
C25-H48-N6-O8
MOLECULAR WEIGHT :
560.79
WISWESSER LINE NOTATION :
Z5NQV/2VM5NQV/ 21

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
12 gm/kg/17W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - optic nerve neuropathy Sense Organs and Special Senses (Ear) - change in acuity
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Human
DOSE/DURATION :
37 gm/kg/2Y-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - optic nerve neuropathy
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - visual field changes Sense Organs and Special Senses (Eye) - hemorrhage
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
86 mg/kg/1H-C
TOXIC EFFECTS :
Blood - thrombocytopenia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Multiple routes
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
440 mg/kg/6D-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
12240 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
329 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1340 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1680 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1450 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52 gm/kg/52W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - changes in lung weight Kidney, Ureter, Bladder - changes in bladder weight Endocrine - changes in adrenal weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg/9D-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - changes in calcium Nutritional and Gross Metabolic - changes in iron Nutritional and Gross Metabolic - changes in metals, not otherwise specified

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Cells - not otherwise specified
DOSE/DURATION :
11 mg/L
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 35,1209,1985 *** REVIEWS *** TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 1(1),93,1971

Safety Information

HS Code2924199090

Customs

HS Code2924199090
Summary2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Synonyms

desferrioxamine mesylate
Deferoxamin
EINECS 201-064-4
Desferal
Deferrioxamine B
Deferrioxamine
Desferin
DESFERRIOXAMINE
deferoxamine
MFCD00004679
Deferoxamine B
Desferrioxamine B
N-[5-[[4-[5-[acetyl(hydroxy)amino]pentylamino]-4-oxobutanoyl]-hydroxyamino]pentyl]-N'-(5-aminopentyl)-N'-hydroxybutanediamide
Deferoxaminum
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