R8149
Rhizoxin from Rhizopus sp.
>95% (HPLC)
方案
>95% (HPLC)
抗生素抗菌谱
neoplastics
作用机制
cell wall synthesis | interferes
储存温度
−20°C
SMILES字符串
[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
生化/生理作用
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.
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
Eyeshields, Gloves, type N95 (US)
法规信息
新产品
Ploubidou, A., et al.
Journal of Cell Science, 11, 4641-4641 (1999)
Nicole Brendel et al.
Organic & biomolecular chemistry, 5(14), 2211-2213 (2007-07-05)
Targeted gene inactivation and metabolic profiling revealed that the cryptic PKS-NRPS gene cluster in the genome of the plant commensal Pseudomonas fluorescens Pf-5 codes for the biosynthesis of antiproliferative and antifungal rhizoxin derivatives.
Kirstin Scherlach et al.
Organic & biomolecular chemistry, 10(30), 5756-5759 (2012-03-29)
Through metabolic profiling of mutants and wild type of the endofungal bacterium Burkholderia rhizoxinica two novel rhizoxin derivatives with unusual nitrile substitutions were discovered. The nitrile groups result from a photochemical oxidative cleavage of the oxazolyl moiety. In vitro studies
Joyce E Loper et al.
Applied and environmental microbiology, 74(10), 3085-3093 (2008-03-18)
The products synthesized from a hybrid polyketide synthase/nonribosomal peptide synthetase gene cluster in the genome of Pseudomonas fluorescens Pf-5 were identified using a genomics-guided strategy involving insertional mutagenesis and subsequent metabolite profiling. Five analogs of rhizoxin, a 16-member macrolide with
Symbiotic cooperation in the biosynthesis of a phytotoxin.
Kirstin Scherlach et al.
Angewandte Chemie (International ed. in English), 51(38), 9615-9618 (2012-08-24)
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