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AdipoGen Life Sciences
Fumagillin
60
CHF
CHF 60.00
In stock
AG-CN2-0529-M0011 mgCHF 60.00
AG-CN2-0529-M0055 mgCHF 180.00
AG-CN2-0529-M02525 mgCHF 450.00
Replaces BVT-0424
| Product Details | |
|---|---|
| Synonyms | Amebacilin; Fugilin; Fumidil; Fumadil B; NSC9168; U5762 |
| Product Type | Chemical |
| Properties | |
| Formula |
C26H34O7 |
| MW | 458.6 |
| Merck Index | 14: 4286 |
| CAS | 23110-15-8 |
| RTECS | HE1750000 |
| Source/Host Chemicals | Isolated from Aspergillus fumigatus. |
| Purity Chemicals | ≥98% (1H-NMR) |
| Appearance | Off-white solid. |
| Solubility | Soluble in DMSO, acetone or chloroform. Slightly soluble in methanol (5mg/ml) or ethanol. Insoluble in water. |
| InChi Key | NGGMYCMLYOUNGM-IWMBURASSA-N |
| Smiles | [H][C@@]1([C@H](OC)[C@@H](CC[C@]11CO1)OC(=O)\C=C\C=C\C=C\C=C\C(O)=O)[C@@]1(C)O[C@@H]1CC=C(C)C |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice | Protect from light. |
| Use/Stability |
Stable for at least 2 years after receipt when stored at -20°C. Store solutions at -20°C in the dark. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Meroterpenoid antibiotic.
- Anticancer, antimicrobial, antimalarial and amoebicidal compound. Potent, selective and covalent inhibitor of methionine aminopeptidase-2 (MetAP2).
- Anti-angiogenic by impairing the growth of endothelial cells and altering gene expression.
- Inhibits endothelial cell proliferation in vitro and tumor-induced angiogenesis in vivo.
- Suppresses the HIV-1 infection of human macrophages through the inhibition of HIV-1 viral protein R (Vpr) activity.
- Inhibits neovascularization and might be useful in non-tumor diseases such as diabetic retinopathy, arthritis and psoriasis, which involve neovascularisation processes.
- Reduces diet-induced adipose tissue formation in mice, independent of its effects on angiogenesis.
Product References
- Antibiotic substance produced by Aspergillus fumigatus: T.E. Eble, et al.; Antibiot. Chemother. 1, 54 (1951)
- Synthetic analogues of fumagillin that inhibit angiogenesis and suppress tumour growth: D. Ingber, et al.; Nature 348, 555 (1990)
- The anti-angiogenic agent fumagillin covalently binds and inhibits the methionine aminopeptidase, MetAP-2: N. Sin, et al.; PNAS 94, 6099 (1997)
- Inhibition of Angiogenesis In Vivo by ets-1 Antisense Oligonucleotides-Inhibition of Ets-1 Transcription Factor Expression by the Antibiotic Fumagillin: N. Wernert, et al.; Angew. Chem. Int. Ed. Engl. 38, 3228 (1999)
- Structure elucidation of fumagillin-related natural products: J. Halasz, et al.; Tetrahedron 56, 10081 (2000)
- A re-evaluation of fumagillin selectivity towards endothelial cells: S. Rodriguez-Nieto, et al.; Anticancer Res. 21, 3457 (2001)
- Fumagillin treatment of intestinal microsporidiosis: J. Molina, et al.; N. Engl. J. Med. 346, 1963 (2002)
- Early genetic mechanisms underlying the inhibitory effects of endostatin and fumagillin on human endothelial cells: C.M. Mazzanti, et al.; Genome Res. 14, 1585 (2004)
- Fumagillin suppresses HIV-1 infection of macrophages through the inhibition of Vpr activity: N. Watanabe, et al.; FEBS Lett. 580, 2598 (2006)
- Fumagillin: an anti-infective as a parent molecule for novel angiogenesis inhibitors: B. Lefkove, et al.; Expert Rev. Anti-Infect. Ther. 5, 573 (2007)
- Fumagillin and fumarranol interact with P. falciparum methionine aminopeptidase 2 and inhibit malaria parasite growth in vitro and in vivo: X. Chen, et al.; Chem. Biol. 16, 193 (2009)
- Fumagillin inhibits colorectal cancer growth and metastasis in mice: in vivo and in vitro study of anti-angiogenesis: L. Hou, et al.; Pathol. Int. 59, 448 (2009)
- Syntheses of fumagillin and ovalicin: J. Yamaguchi & Y. Hayashi; Chem. Eur. J. 16, 3884 (2010)
- Fumagillin reduces adipose tissue formation in murine models of nutritionally induced obesity: H.R. Lijnen, et al.; Obesity 18, 2241 (2010)
- Inhibition of neutrophil function following exposure to the Aspergillus fumigatus toxin fumagillin: J.P. Fallon, et al.; J. Med. Microbiol. 59, 625 (2010)
- Fumagillin and structurally related molecules as source of new drugs: D. Gamba-Sanches; Mini-Rev. Org. Chem. 9, 126 (2012)
- Stimulation of suicidal erythrocyte death by fumagillin: M. Zbidah, et al.; Basic Clin. Pharmacol. Toxicol. 112, 346 (2013)