A fungal metabolite with diverse biological activities
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Fumagillin

Item No. 11332

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2E,4E,6E,8E-decatetraenedioic acid, 1-[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester
CAS Number
23110-15-8
Synonyms
  • Amebacilin
  • NSC 9168
Molecular Formula
C26H34O7
Formula Weight
458.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 0.25 mg/ml
λmax
334, 348 nm
SMILES
O=C(O[C@H]1[C@@H](OC)[C@]([H])([C@@]2(C)O[C@@H]2C/C=C(C)/C)[C@@]3(CO3)CC1)/C=C/C=C/C=C/C=C/C(O)=O
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
InChi Key
NGGMYCMLYOUNGM-CSDLUJIJSA-N
Origin
Fungus/Aspergillus fumigatus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Fumagillin is a fungal metabolite that has been found in A. fumigatus and has diverse biological activities.1,2,3,4,5 It inhibits methionyl aminopeptidase 2 (METAP2; IC50 = 10 nM).1 Fumagillin (10 ng/ml) inhibits tube formation in a rat blood vessel organ culture assay.2 It inhibits E. cuniculi replication in isolated rabbit kidney cells and canine embryo cells when used at a concentration of 5 µg/ml.3 In vivo, fumagillin (30 mg/kg per day) decreases tumor growth and the number of metastases in a mouse model of diethylnitrosamine-induced hepatocellular carcinoma.4 It also reduces subcutaneous and gonadal fat mass in a mouse model of high-fat diet-induced obesity.5 Formulations containing fumagillin have been used to treat conjunctival and intestinal microsporidial infections in immunocompromised patients.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Griffith, E.C., Su, Z., Niwayama, S., et al. Molecular recognition of angiogenesis inhibitors fumagillin and ovalicin by methionine aminopeptidase 2. Proc. Natl. Acad. Sci. USA 95(26), 15183-15188 (1998).

    2. Kusaka, M., Sudo, K., Fujita, T., et al. Potent anti-angiogenic action of AGM-1470: Comparison to the fumagillin parent. Biochem. Biophys. Res. Commun. 174(3), 1070-1076 (1991).

    3. Shadduck, J.A. Effect of fumagillin on in vitro multiplication of Encephalitozoon cuniculi. J. Protozool. 27(2), 202-208 (1980).

    4. Sheen, I.S., Jeng, K.S., Jeng, W.J., et al. Fumagillin treatment of hepatocellular carcinoma in rats: An in vivo study of antiangiogenesis. World J. Gastroenterol. 11(6), 771-777 (2005).

    5. Lijnen, H.R., Frederix, L., and Van Hoef, B. Fumagillin reduces adipose tissue formation in murine models of nutritionally induced obesity. Obesity 18(2), 2241-2246 (2010).