Identifiers | |
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3D model (
JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
|
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| |
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Properties | |
C35H47NO9 | |
Molar mass | 625.749 g/mol |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Rhizoxin is an antimitotic agent with anti- tumor activity. [1] [2] It is isolated from the fungus Rhizopus microsporus which causes rice seedling blight.
Rhizoxin is biosynthesised by Paraburkholderia rhizoxinica, a bacterial endosymbiont of the fungus Rhizopus microsporus. [3] It is one of a large group of rhizoxin-like compounds produced by the bacteria. [4] The bacterial endosymbiont can be grown independently in culture. This may allow easy harvesting of rhizoxin and the related compounds avoiding total chemical synthesis, although total chemical synthesis is possible. [5]
Rhizoxin binds beta tubulin in eukaryotic cells disrupting microtubule formation. This, in turn, prevents formation of the mitotic spindle inhibiting cell division. Additionally rhizoxin can depolymerise assembled microtubules. [6] The function of rhizoxin is similar to Vinca alkaloids.
Rhizoxin has undergone clinical trials as an anti-cancer drug [7] although it did not reach later stages of clinical trials due to low activity in vivo. Related compounds to rhizoxin have improved biological activity (E.G Mertansine) . [4]
Rhizoxin is a 16-membered lactone ring connected to an oxazole ring by a long unsaturated chain. [8]
Identifiers | |
---|---|
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C35H47NO9 | |
Molar mass | 625.749 g/mol |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Rhizoxin is an antimitotic agent with anti- tumor activity. [1] [2] It is isolated from the fungus Rhizopus microsporus which causes rice seedling blight.
Rhizoxin is biosynthesised by Paraburkholderia rhizoxinica, a bacterial endosymbiont of the fungus Rhizopus microsporus. [3] It is one of a large group of rhizoxin-like compounds produced by the bacteria. [4] The bacterial endosymbiont can be grown independently in culture. This may allow easy harvesting of rhizoxin and the related compounds avoiding total chemical synthesis, although total chemical synthesis is possible. [5]
Rhizoxin binds beta tubulin in eukaryotic cells disrupting microtubule formation. This, in turn, prevents formation of the mitotic spindle inhibiting cell division. Additionally rhizoxin can depolymerise assembled microtubules. [6] The function of rhizoxin is similar to Vinca alkaloids.
Rhizoxin has undergone clinical trials as an anti-cancer drug [7] although it did not reach later stages of clinical trials due to low activity in vivo. Related compounds to rhizoxin have improved biological activity (E.G Mertansine) . [4]
Rhizoxin is a 16-membered lactone ring connected to an oxazole ring by a long unsaturated chain. [8]