Fumagillin dicyclohexylamine
Please note: As of 1 July 2025, the New Zealand Institute for Public Health and Forensic Science (PHF Science) is the new name for the Institute of Environmental Science and Research (ESR). Research and reports published prior to this date may reference the organisation’s former name.
Abstract
Fumagillin is a mycotoxin originally produced by the fungus Aspergillus fumigatus and currently used in a synthesized form. Fumagillin is registered as a veterinary drug in several Member States. It is used as an antimicrobial compound for the treatment of microsporidian infections in various fish species and in honeybees. Fumagillin has been used in human medicine for certain infectious diseases (Maillard et al., 2021; Molina et al., 2002; Guruceaga et al., 2019), and to treat various cancers, by inhibiting the formation of new blood vessels around growing tumours (angiogenesis), thereby limiting their blood supply (Ingber et al., 1990). Fumagillin is poorly soluble in water and undergoes rapid ultraviolet and thermal degradation. Therefore, to increase its stability and water solubility, commercial formulations used in veterinary medicine contain fumagillin as the dicyclohexylamine (DCH) salt in a 1:1 stoichiometric ratio. The mode of action of fumagillin is based on inhibition of type-2 methionine aminopeptidase (MetAP-2) activity via formation of a covalent bond with the histidine moiety (His231) of the enzyme. MetAP-2 is a cytosolic enzyme which removes the initial methionine from the amino terminus of newly synthesized proteins, for subsequent post-translational modifications, which affects the function of many proteins (Arico-Muendel et al., 2009; Guruceaga et al., 2019).
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