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F6771

Sigma-Aldrich

Fumagillin

from Aspergillus sp. (Aspergillus fumigatus), ≥90% (HPLC), powder, MetAP2 inhibitor

Synonym(s):

Fugillin

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About This Item

Empirical Formula (Hill Notation):
C26H34O7
CAS Number:
23110-15-8
Molecular Weight:
458.54
EC Number:
245-433-8
MDL number:
MFCD03990453
UNSPSC Code:
12352200
PubChem Substance ID:
24894920
NACRES:
NA.77

product name

Fumagillin from Aspergillus fumigatus, ≥90%, powder

biological source

Aspergillus sp. (Aspergillus fumigatus)

Quality Level

200

assay

≥90%

form

powder

color

white

mp

197-198  °C

solubility

ethanol: 1 mg/mL

antibiotic activity spectrum

fungi

mode of action

DNA synthesis | interferes

storage temp.

−20°C

SMILES string

COC1C(CCC2(CO2)C1C3(C)OC3C\C=C(\C)C)OC(=O)\C=C\C=C\C=C\C=C\C(O)=O

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+

InChI key

NGGMYCMLYOUNGM-HCNIIHBUSA-N

General description

Fumagillin is a metabolic product of fungi. It is originally isolated from Aspergillus fumigatus.

Application

Fumagillin from Aspergillus fumigatus has been used:
  • in chick chorioallantoic membrane (CAM) assay to study the changes in protein expression in response to anti-angiogenic agent
  • to study its effects on the mortality of caged Nosema ceranae-infected honey bees- write in this way
  • as a positive control in in vitro and ex vivo studies

Biochem/physiol Actions

Fumagillin is known to be effective against microsporidian fungal infections.
Methionine aminopeptidase-2 (MetAP-2) inhibitor; inhibits endothelial cell proliferation and angiogenesis.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fumagillin: an overview of recent scientific advances and their significance for apiculture
van den Heever JP, et al.
Journal of Agricultural and Food Chemistry, 62(13), 2728-2737 (2014)
The effect of dicyclohexylamine and fumagillin on Nosema ceranae-infected honey bee (Apis mellifera) mortality in cage trial assays
Van den Heever JP, et al.
Apidologie, 47(5), 663-670 (2016)
A novel technique for quantifying changes in vascular density, endothelial cell proliferation and protein expression in response to modulators of angiogenesis using the chick chorioallantoic membrane (CAM) assay
Miller WJ, et al.
Journal of Translational Medicine, 2(1), 4-4 (2004)
Fred R Musser et al.
Journal of invertebrate pathology, 111(2), 101-105 (2012-07-24)
A consistent supply of healthy tarnished plant bug, Lygus lineolaris (Palisot de Beauvois) (Hemiptera: Miridae), is necessary for the development of novel management strategies targeting this pest. After being in culture for several years, a substantial portion of a tarnished
Hsiao-Ching Lin et al.
Journal of the American Chemical Society, 135(12), 4616-4619 (2013-03-16)
Fumagillin 1 is a meroterpenoid from Aspergillus fumigatus that is known for its anti-angiogenic activity by binding to human methionine aminopeptidase 2. The genetic and molecular basis for biosynthesis of 1 had been an enigma despite the availability of the
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