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Merck
CN

R8149

Sigma-Aldrich

Rhizoxin from Rhizopus sp.

>95% (HPLC)

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About This Item

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

Key Documents

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
095K4133
073K4055
081K4092

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T Sawada et al.
Biochemical pharmacology, 45(7), 1387-1394 (1993-04-06)
The rhizoxin (RZX)-binding site on porcine brain tubulin was investigated by photoaffinity labeling with the 5-azido-1-naphthalene sulfonyl (azidodansyl) derivative of RZX, nor-rhizoxin-22-al-5'-azidonaphthalene-1'-sulfonylhydrazo ne (azidodansylrhizoxin: Adan-RZX). Upon ultraviolet irradiation, Adan-RZX generates a highly reactive nitrene, which irreversibly binds to an amino
Impact of endofungal bacteria on infection biology, food safety, and drug development.
Gerald Lackner et al.
PLoS pathogens, 7(6), e1002096-e1002096 (2011-07-09)
T Tsuruo et al.
Cancer research, 46(1), 381-385 (1986-01-01)
Rhizoxin, isolated from a plant pathogenic fungus which causes rice seedling blight, inhibits the mitosis of the tumor cells in a manner similar to that of Vinca alkaloids as revealed by morphological study and flow cytometry analysis. This new 16-membered
S Ikubo et al.
Anticancer research, 19(5B), 3985-3988 (2000-01-11)
The improvement of treatment outcome of small-cell lung cancer (SCLC), and search for new effective drugs and to overcome drug-resistance are essential. We evaluated the cytotoxicity of antimicrotubule agents to seven human SCLC cell lines consisting of one cell line
Imke Schmitt et al.
The ISME journal, 2(6), 632-641 (2008-03-01)
The rice seedling blight fungus Rhizopus microsporus harbors endosymbiotic Burkholderia sp. for the production of the virulence factor, the antimitotic agent rhizoxin. Since the toxin highly efficiently blocks mitosis in most eukaryotes, it remained elusive how self-resistance emerged in the
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