Fumagillin (Amebacilin; NSC9168)

Alias: NSC9168; NSC 9168; NSC-9168; Fumidil B; trade names: Fumagilina; Fugillin; Fumidil.
Cat No.:V1870 Purity: ≥98%
Fumagillin(NSC9168) is an antimicrobial compound first isolated in 1949 from the fungus Aspergillus fumigatu.
Fumagillin (Amebacilin; NSC9168) Chemical Structure CAS No.: 23110-15-8
Product category: Parasite
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Fumagillin (formerly known as NSC9168) is a novel, potent, selective and irreversible/covalent inhibitor of Methionine aminopeptidase 2 (MetAP2), it is primarily used as an antibiotic / antimicrobial to treat microsporidiosis. Fumagillin is a complex natural product antibiotic isolated in 1949 from the microbial organism Aspergillus fumigatus. It covalently binds a key histidine residue of methionine aminopeptidase type II (MetAP-2), inhibiting endothelial cell proliferation and angiogenesis. Fumagillin selectively inhibits the growth of a Δmap1 strain but not a wild-type or a Δmap2 S. cerevisiae strain missing MetAP-2.

Biological Activity I Assay Protocols (From Reference)
Targets
HIV-1;Amebae
ln Vitro
Fumagillin selectively inhibits the growth of a Δmap1 strain but not a wild-type or a Δmap2 S. cerevisiae strain missing MetAP-2. In budding yeast cells, as a potent inhibitor of angiogenesis, Fumagillin not only reverses the growth inhibitory activity of Vpr, but also inhibits Vpr-dependent viral gene expression upon the infection of human macrophages. Though the toxicity of fumagillin has limited its use for human applications, the analogues using structure-activity relationships relating to its angiogenesis properties may be further explored in the treatment of angiogenesis-dependent diseases.
ln Vivo
In DEN-treated rats, fumagillin (30 mg/kg, i.p.) inhibits both progression of HCC in the liver itself and systemic metastasis.
Animal Protocol
30 mg/kg, i.p.
Rats
References

[1]. Proc Natl Acad Sci U S A.1997 Jun 10;94(12):6099-103.

[2]. World J Gastroenterol.2005 Feb 14;11(6):771-7.

[3]. Expert Rev Anti Infect Ther, 2007. 5(4): p. 573-9.

[4]. FEBS Lett. 2006 May 15;580(11):2598-602.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H34O7
Molecular Weight
458.54
Exact Mass
458.23
Elemental Analysis
C, 68.10; H, 7.47; O, 24.42
CAS #
23110-15-8
Related CAS #
23110-15-8
Appearance
Solid powder
SMILES
O=C(O)/C=C/C=C/C=C/C=C/C(O[C@H](CC1)[C@@H](OC)[C@H]([C@@]2(C)OC2C/C=C(C)\C)[C@]31CO3)=O
InChi Key
NGGMYCMLYOUNGM-IJIYPQOHSA-N
InChi Code
InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+/t19-,20?,23-,24-,25+,26+/m1/s1
Chemical Name
(2E,4E,6E,8E)-10-(((3R,4S,5S,6R)-5-methoxy-4-((2R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl)oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
Synonyms
NSC9168; NSC 9168; NSC-9168; Fumidil B; trade names: Fumagilina; Fugillin; Fumidil.
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : 92~ 250 mg/mL ( 200.63~545.21 mM )
H2O :< 0.1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.45 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (5.45 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (4.54 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly..


Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (5.45 mM)

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1808 mL 10.9042 mL 21.8083 mL
5 mM 0.4362 mL 2.1808 mL 4.3617 mL
10 mM 0.2181 mL 1.0904 mL 2.1808 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Structure of fumagillin, the fumagillin analog in phase III clinical trials (TNP-470), and the fumagillin-based reagent used for affinity chromatography.[1]. Proc Natl Acad Sci U S A.1997 Jun 10;94(12):6099-103.
  • In vivo binding of biotinylated fumagillin to a 67-kDa protein in human endothelial cells. [1]. Proc Natl Acad Sci U S A.1997 Jun 10;94(12):6099-103.
  • Purification of a fumagillol-biotin binding protein from bovine brain. [1]. Proc Natl Acad Sci U S A.1997 Jun 10;94(12):6099-103.
  • In vivo inhibition of MAP2 activity. [1]. Proc Natl Acad Sci U S A.1997 Jun 10;94(12):6099-103.
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