| Source: | Aspergillus fumigatus |
| Synonyms | Fumidil B, Amebacilin,
EINECS 245-433-8 |
| Description: | Fumagillin : Antiamoebic. Inhibitor of angiogenesis. Attention: The Research grade (98% or better) Fumagillin is
not intended for veterinary use.
It is very different from the veterinary preparate "Fumadil B" which contains approximately
3% Fumagillin. |
| CAS number: | 23110-15-8 |
| Merck index: | 13, 4307 |
| Molecular weight: | 458.6 |
| Structure: | 
 |
| Molecular Formula: |
C26H34O7 |
| Canonical SMILES: |
CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)C=CC=CC=CC=CC(=O)O)OC)C |
Solubility
information: | DMSO, Methanol. alkaline aqueous solutions |
| Specifications |
|
| Appearance: | Off-white powder |
| Purity: | At least 98% by TLC, HPLC |
| λmax: | 334, 349 (in Ethanol) |
| Melting point | 190°C-192°C |
| Solubility | |
| Storage | +4°c. Protect from light. Store in tightly sealed vial. |
| Applications | A crude preparation of Fumagillin is marketed under the trade name "Fumidil B". It is an effective treatment for intestinal microsporidiosis caused by Enterocytozoon bieneusi. Used to treat () the Nosema disease in honey bees. Applied topically to the conjunctiva in the treatment of microsporidial keratoconjunctivitis. Once used to treat malaria.
Since Fumidil B only contains about 3% of Fumagillin, it
is not clear whether its therapeutic activity should be ascribed to
Fumagillin.
The Research grade Fumagillin is used in the angiogenesis research. In the connection to its anti angiogenetic capabilities, Fumagillin is mentioned as an potential anti-neoplastic antibiotic.
Fumagillin is a starting material for several
anticancer drug candidates, such as TNP-470. Fumagillin was also shown to be able to protect macrophages from the HIV infection |
| Warnings | Harmful if swallowed |
| Classification | fatty
acid antibiotic
antiprotozoal |
| Related products | |
| | For Research use only. Not for Human or Drug use
GMP/API grade available on request
fumagillin by Fermentek is not produced from or contains any ingredients from animal origin.
No genetically modified organisms are used.
The Research grade (98% or better) Fumagillin is not intended for veterinary use.
|
| Publications | |
| | Lefkove B, Govindarajan B, Arbiser JL.
Fumagillin Review: an anti-infective as a parent molecule for novel angiogenesis inhibitors.
Expert Rev Anti Infect Ther. 2007 Aug;5(4):573-9. . |
| | Lee HW, Cho CS, Kang SK, Yoo YS, Shin JS, Ahn SK.
Free Full Text Design, synthesis, and antiangiogenic effects of a series of potent novel fumagillin analogues.
Chem Pharm Bull (Tokyo). 2007 Jul;55(7):1024-9. |
| | Winter PM, Neubauer AM, Caruthers SD, Harris TD, Robertson JD, Williams TA, Schmieder AH, Hu G, Allen JS, Lacy EK, Zhang H, Wickline SA, Lanza GM.
Endothelial alpha(v)beta3 integrin-targeted fumagillin nanoparticles inhibit angiogenesis in atherosclerosis.
Arterioscler Thromb Vasc Biol. 2006 Sep;26(9):2103-9. |
| | Didier PJ, Phillips JN, Kuebler DJ, Nasr M, Brindley PJ, Stovall ME, Bowers LC, Didier ES.
Antimicrosporidial activities of fumagillin, TNP-470, ovalicin, and ovalicin derivatives in vitro and in vivo.
Antimicrob Agents Chemother. 2006 Jun;50(6):2146-55. |
| | Watanabe N, Nishihara Y, Yamaguchi T, Koito A, Miyoshi H, Kakeya H, Osada H.
Fumagillin suppresses HIV-1 infection of macrophages through the inhibition of Vpr activity.
FEBS Lett. 2006 May 15;580(11):2598-602. |
|
Fumagillin on Wikipedia
|
 |
Aspergillus fumigatus under scanning electron microscope |
|
Fumagillin class inhibitors of methionine aminopeptidase-2
Author(s): Department
of Preclinical Research PRAFCLS
BERNIER Sylvie G. ; WESTLIN William F. ; HANNIG Gerhard ;
Abstract
The growth of solid tumors and the formation of
metastases are critically dependent on neovascularization. This
dependence on neovascularization, however, is not limited to cancer but
is also a major contributing factor in the pathology of autoimmune
diseases such as rheumatoid arthritis. Hence, antiangiogenic therapy was
recognized as a potentially powerful therapeutic approach in the
treatment of these devastating diseases. The discovery of fumagillin and
its potent antiangiogenic and antiproliferative activities provided the
rationale for the development of fumagillin analogues as a novel class
of antiproliferative agents. Molecules of the fumagillin class inhibit
the enzymatic activity of methionine aminopeptidase-2 (MetAP-2), and
this inhibition is the first step required for the selective growth
inhibition of cell types that are dependent on MetAP-2 function for
growth. Mechanistically, this growth inhibition is characterized by
cytostasis and arrest in the late G1 phase of the cell cycle. TNP-470
was the first MetAP-2 inhibitor of the fumagillin class to enter phase I
clinical trials in cancer. Despite some encouraging results in several
solid tumors in early phase I/II studies, further clinical development
of this molecule was halted, primarily due to dose-limiting
neurotoxicities and a poor clinical pharmacokinetic profile. More
recently, fumagillin analogues specifically designed to improve upon the
clinical deficiencies of TNP-470, such as PPI-2458, have advanced into
phase I trials in cancer.
Drugs of the future
2005, vol. 30, no5, pp. 497-508 | |
