InChI
1S/C35H47NO9/c1-19(13-25-18-41-23(5)36-25)9-8-10-21(3)32(40-7)22(4)27-17-29(37)35(6)30(45-35)12-11-20(2)26-14-24(16-31(38)42-26)15-28-33(43-28)34(39)44-27/h8-13,18,20,22,24,26-30,32-33,37H,14-17H2,1-7H3/b9-8+,12-11+,19-13+,21-10+/t20-,22+,24+,26-,27+,28+,29+,30-,32+,33-,35+/m1/s1
SMILES string
[H][C@@]12C[C@@H]3O[C@H]3C(=O)O[C@@]([H])(C[C@H](O)[C@]4(C)O[C@]4([H])\C=C\[C@@H](C)[C@@]([H])(C1)OC(=O)C2)[C@H](C)[C@@H](OC)\C(C)=C\C=C\C(C)=C\c5coc(C)n5
InChI key
OWPCHSCAPHNHAV-LMONGJCWSA-N
assay
>95% (HPLC)
antibiotic activity spectrum
neoplastics
mode of action
cell wall synthesis | interferes
storage temp.
−20°C
Biochem/physiol Actions
An antitumor agent, rhizoxin is a 16-member ring lactone having an oxazole ring in its structure. This macrolide inhibits microtubule assembly and also depolymerizes pre-formed microtubles.
Rhizoxin binds to β-tubulin in most eucaryotic cells including animals, plants and fungi. It completely prevents formation of an intrachain cross-link in β-tubulin by N,N′-ethylenebis(iodoacetamide). Due to its antimitotic activity it is used as an antitumor agent e.g., in human small cell lung cancer cell lines.
Rhizoxin binds to β-tubulin in most eucaryotic cells including animals, plants and fungi. It completely prevents formation of an intrachain cross-link in β-tubulin by N,N′-ethylenebis(iodoacetamide). Due to its antimitotic activity it is used as an antitumor agent e.g., in human small cell lung cancer cell lines.
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
法规信息
新产品
此项目有
Amogh A Sahasrabuddhe et al.
Journal of cell science, 122(Pt 10), 1691-1699 (2009-04-30)
In general, coronins play an important role in actin-based processes, and are expressed in a variety of eukaryotic cells, including Leishmania. Here, we show that Leishmania coronin preferentially distributes to the distal tip during cytokinesis, and interacts with microtubules through
Ashraf S Ibrahim et al.
The Journal of infectious diseases, 198(7), 1083-1090 (2008-08-13)
Environmental isolates of the fungus Rhizopus have been shown to harbor a bacterial endosymbiont (Burkholderia) that produces rhixozin, a plant mycotoxin. We sought to define the role of rhizoxin production by endosymbionts in the pathogenesis of mucormycosis. Endosymbiotic bacteria were
Björn Kusebauch et al.
Angewandte Chemie (International ed. in English), 48(27), 5001-5004 (2009-03-07)
A new "branch" for polyketide synthases was discovered in the biosynthesis of the antimitotic rhizoxin complex in the endofungal bacterium Burkholderia rhizoxinica. Genetic engineering and the structural elucidation of pathway intermediates revealed that a complex polyketide chain is branched at
Functionally distinct modules operate two consecutive alpha,beta-->beta,gamma double-bond shifts in the rhizoxin polyketide assembly line.
Björn Kusebauch et al.
Angewandte Chemie (International ed. in English), 49(8), 1460-1464 (2009-12-25)
Antiproliferative effects of ester- and amide-functionalized rhizoxin derivatives.
Björn Kusebauch et al.
ChemMedChem, 6(11), 1998-2001 (2011-10-13)
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