Fumagillin - CAS 23110-15-8
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Not Intended for Therapeutic Use. For research use only.
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Fumagillin is a compound isolated from the fungus Aspergillus fumigatus. Fumagillin is an antimicrobial agent used in the treatment of microsporidiosis. Fumagillin shows promise as both an an anti-infective and antiangiogenic agent.
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Amebacilin; NSC9168
1.Spiroepoxytriazoles Are Fumagillin-like Irreversible Inhibitors of MetAP2 with Potent Cellular Activity.
Morgen M1, Jöst C2, Malz M1, Janowski R3, Niessing D3,4, Klein CD2, Gunkel N1, Miller AK1. ACS Chem Biol. 2016 Apr 15;11(4):1001-11. doi: 10.1021/acschembio.5b00755. Epub 2016 Jan 19.
Methionine aminopeptidases (MetAPs) are responsible for the cotranslational cleavage of initiator methionines from nascent proteins. The MetAP2 subtype is up-regulated in many cancers, and selective inhibition of MetAP2 suppresses both vascularization and growth of tumors in animal models. The natural product fumagillin is a selective and potent irreversible inhibitor of MetAP2, and semisynthetic derivatives of fumagillin have shown promise in clinical studies for the treatment of cancer, and, more recently, for obesity. Further development of fumagillin derivatives has been complicated, however, by their generally poor pharmacokinetics. In an attempt to overcome these limitations, we developed an easily diversifiable synthesis of a novel class of MetAP2 inhibitors that were designed to mimic fumagillin's molecular scaffold but have improved pharmacological profiles. These substances were found to be potent and selective inhibitors of MetAP2, as demonstrated in biochemical enzymatic assays against three MetAP isoforms.
2.Fumagillin, a potent angiogenesis inhibitor, induces Kaposi sarcoma-associated herpesvirus replication in primary effusion lymphoma cells.
Kanno T1, Uehara T2, Osawa M2, Fukumoto H1, Mine S1, Ueda K3, Hasegawa H1, Katano H4. Biochem Biophys Res Commun. 2015 Aug 7;463(4):1267-72. doi: 10.1016/j.bbrc.2015.06.100. Epub 2015 Jun 18.
Kaposi sarcoma and primary effusion lymphoma cells are infected with Kaposi sarcoma-associated herpesvirus (KSHV), predominantly in the latent form, and KSHV replication is observed rarely. Angiogenesis plays a crucial role in the pathogenesis of both Kaposi sarcoma and primary effusion lymphoma. In this study, we found that fumagillin, a potent angiogenesis inhibitor, induced replication of KSHV in primary effusion lymphoma cell lines. The transcript and protein product of replication transcriptional activator (RTA) were induced by 1-10 μM fumagillin at 24 and 48 h, respectively. Western blot analysis demonstrated that 10 μM fumagillin induced not only RTA expression but also other KSHV-encoded lytic proteins. A real-time PCR array detecting KSHV gene expression demonstrated that the expression profiles of KSHV induced by fumagillin were similar to those induced by 12-O-tetradecanoylphorbol-13-acetate (TPA), but the amounts of each transcript were lower than those induced by TPA.
3.Dual-therapy with αvβ3-targeted Sn2 lipase-labile fumagillin-prodrug nanoparticles and zoledronic acid in the Vx2 rabbit tumor model.
Esser AK1, Schmieder AH2, Ross MH1, Xiang J1, Su X1, Cui G2, Zhang H2, Yang X2, Allen JS2, Williams T2, Wickline SA2, Pan D3, Lanza GM4, Weilbaecher KN5. Nanomedicine. 2016 Jan;12(1):201-11. doi: 10.1016/j.nano.2015.10.003. Epub 2015 Oct 27.
Fumagillin, an unstable anti-angiogenesis mycotoxin, was synthesized into a stable lipase-labile prodrug and incorporated into integrin-targeted lipid-encapsulated nanoparticles (αvβ3-Fum-PD NP). Dual anti-angiogenic therapy combining αvβ3-Fum-PD NP with zoledronic acid (ZA), a long-acting osteoclast inhibitor with proposed anti-angiogenic effects, was evaluated. In vitro, αvβ3-Fum-PD NP reduced (P<0.05) endothelial cell viability without impacting macrophage viability. ZA suppressed (P<0.05) macrophage viability at high dosages but not endothelial cell proliferation. 3D MR neovascular imaging of rabbit Vx2 tumors showed no effect with ZA, whereas αvβ3-Fum-PD NP alone and with ZA decreased angiogenesis (P<0.05). Immunohistochemistry revealed decreased (P<0.05) microvascularity with αvβ3-Fum-PD NP and ZA and further microvascular reduction (P<0.05) with dual-therapy. In vivo, ZA did not decrease tumor macrophage numbers nor cancer cell proliferation, whereas αvβ3-Fum-PD-NPs reduced both measures.
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CAS 23110-15-8 Fumagillin

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