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Merck
CN

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

Key Documents

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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.

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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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
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
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)
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
A gene cluster encoding rhizoxin biosynthesis in "Burkholderia rhizoxina", the bacterial endosymbiont of the fungus Rhizopus microsporus.
Laila P Partida-Martinez et al.
Chembiochem : a European journal of chemical biology, 8(1), 41-45 (2006-12-13)
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