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R8149

Rhizoxin from Rhizopus sp.

>95% (HPLC)

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About This Item

CAS Number:
90996-54-6
UNSPSC Code:
12352200
PubChem Substance ID:
24899405
MDL number:
MFCD01939948
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assay

>95% (HPLC)

antibiotic activity spectrum

neoplastics

mode of action

cell wall synthesis | interferes

storage temp.

−20°C

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

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

InChI key

OWPCHSCAPHNHAV-LMONGJCWSA-N

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
095K4133
073K4055
081K4092

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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
Antiproliferative effects of ester- and amide-functionalized rhizoxin derivatives.
Björn Kusebauch et al.
ChemMedChem, 6(11), 1998-2001 (2011-10-13)
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
Björn Kusebauch et al.
Chembiochem : a European journal of chemical biology, 12(15), 2284-2288 (2012-10-30)
Chain armor against tumor cells: The oxazole side chain in the antimitotic agent rhizoxin S2 (1) was successfully replaced through mutasynthesis by using an engineered mutant impaired in heterocyclization. Incorporation of 12 non-natural surrogates into fully processed rhizoxin analogues revealed
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