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cancer research reagents

Fumagillin

MSDS Sample CoA
 
Source: Aspergillus fumigatus
SynonymsFumidil 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:

fumagillin pure research grade for sale

 

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 point190°C-192°C
Solubility 
Storage+4°c. Protect from light. Store in tightly sealed vial.
ApplicationsA 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

WarningsHarmful if swallowed
Classificationfatty 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

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


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ddrug discovery, novel analogs, Pure fumagillin for sale at Fermentek biochemicals. Fumagillin research grade not intended for veterinary use.