Fumagillin

  • CAT Number: A000104
  • CAS Number: 23110-15-8
  • Molecular Formula: C₂₆H₃₄O₇
  • Molecular Weight: 458.54
  • Purity: ≥95%
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Fumagillin is a complex biomolecule and used as an antimicrobial agent. It was isolated in 1949 from the microbial organism Aspergillus fumigatus. Fumagillin has been used in the treatment of microsporidiosis. It is also an amebicide. Fumagillin can block blood vessel formation by binding to an enzyme methionine aminopeptidase and for this reason, the compound, together with semisynthetic derivatives, are investigated as an angiogenesis inhibitor in the treatment of cancer.

Catalog Number A000104
CAS Number 23110-15-8
Molecular Formula

C₂₆H₃₄O₇

Purity 95%
Target Aminopeptidase
Solubility Soluble to 3 mM in ethanol
Storage Store at -20°C
InChI 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
InChIKey NGGMYCMLYOUNGM-CSDLUJIJSA-N
SMILES CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)C=CC=CC=CC=CC(=O)O)OC)C
Reference

1: Mendoza Y, Diaz-Cetti S, Ramallo G, Santos E, Porrini M, Invernizzi C. Nosema
ceranae Winter Control: Study of the Effectiveness of Different Fumagillin
Treatments and Consequences on the Strength of Honey Bee (Hymenoptera: Apidae)
Colonies. J Econ Entomol. 2017 Feb 1;110(1):1-5. doi: 10.1093/jee/tow228. PubMed
PMID: 28025388.

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2: Boileau M, Ferreira J, Ahmad I, Lavallée C, Qvarnstrom Y, Dufresne SF.
Successful Treatment of Disseminated Anncaliia algerae Microsporidial Infection
With Combination Fumagillin and Albendazole. Open Forum Infect Dis. 2016 Jul
29;3(3):ofw158. eCollection 2016 Sep. PubMed PMID: 27704013; PubMed Central
PMCID: PMC5047403.
<br>

3: Giacobino A, Rivero R, Molineri AI, Cagnolo NB, Merke J, Orellano E, Salto C,
Signorini M. Fumagillin control of Nosema ceranae (Microsporidia:Nosematidae)
infection in honey bee (Hymenoptera:Apidae) colonies in Argentina. Vet Ital. 2016
Jun 30;52(2):145-51. doi: 10.12834/VetIt.120.337.6. PubMed PMID: 27393876.
<br>

4: Morgen M, J&#246;st C, Malz M, Janowski R, Niessing D, Klein CD, Gunkel N, Miller
AK. Spiroepoxytriazoles Are Fumagillin-like Irreversible Inhibitors of MetAP2
with Potent Cellular Activity. ACS Chem Biol. 2016 Apr 15;11(4):1001-11. doi:
10.1021/acschembio.5b00755. Epub 2016 Jan 19. PubMed PMID: 26686773.
<br>

5: Esser AK, Schmieder AH, Ross MH, Xiang J, Su X, Cui G, Zhang H, Yang X, Allen
JS, Williams T, Wickline SA, Pan D, Lanza GM, Weilbaecher KN. Dual-therapy with
αvβ3-targeted Sn2 lipase-labile fumagillin-prodrug nanoparticles and zoledronic
acid in the Vx2 rabbit tumor model. Nanomedicine. 2016 Jan;12(1):201-11. doi:
10.1016/j.nano.2015.10.003. Epub 2015 Oct 27. PubMed PMID: 26515754; PubMed
Central PMCID: PMC4727985.
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6: Kanno T, Uehara T, Osawa M, Fukumoto H, Mine S, Ueda K, Hasegawa H, Katano H.
Fumagillin, a potent angiogenesis inhibitor, induces Kaposi sarcoma-associated
herpesvirus replication in primary effusion lymphoma cells. Biochem Biophys Res
Commun. 2015 Aug 7;463(4):1267-72. doi: 10.1016/j.bbrc.2015.06.100. Epub 2015 Jun
18. PubMed PMID: 26093300.
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7: van den Heever JP, Thompson TS, Curtis JM, Pernal SF. Stability of
dicyclohexylamine and fumagillin in honey. Food Chem. 2015 Jul 15;179:152-8. doi:
10.1016/j.foodchem.2015.01.111. Epub 2015 Jan 31. PubMed PMID: 25722149.
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8: Zhang R, Pan D, Cai X, Yang X, Senpan A, Allen JS, Lanza GM, Wang LV.
alphaVbeta3-targeted copper nanoparticles incorporating an Sn 2 lipase-labile
fumagillin prodrug for photoacoustic neovascular imaging and treatment.
Theranostics. 2015 Jan 1;5(2):124-33. doi: 10.7150/thno.10014. eCollection 2015.
PubMed PMID: 25553103; PubMed Central PMCID: PMC4278999.
<br>

9: Zhou HF, Yan H, Hu Y, Springer LE, Yang X, Wickline SA, Pan D, Lanza GM, Pham
CT. Fumagillin prodrug nanotherapy suppresses macrophage inflammatory response
via endothelial nitric oxide. ACS Nano. 2014 Jul 22;8(7):7305-17. doi:
10.1021/nn502372n. Epub 2014 Jun 24. PubMed PMID: 24941020; PubMed Central PMCID:
PMC4108210.
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10: Blanchet E, Vansteelandt M, Le Bot R, Egorov M, Guitton Y, Pouchus YF, Grovel
O. Synthesis and antiproliferative activity of ligerin and new fumagillin analogs
against osteosarcoma. Eur J Med Chem. 2014 May 22;79:244-50. doi:
10.1016/j.ejmech.2014.04.012. Epub 2014 Apr 5. PubMed PMID: 24742383.

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