S6076
Siomycin A
from Streptomyces sioyaensis, ≥98% (HPLC)
Synonym(s):
Antibiotic 6741-21, Mutabillicin, Mutabilycin, Sporangiomycin
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About This Item
Empirical Formula (Hill Notation):
C71H81N19O18S5
CAS Number:
Molecular Weight:
1648.84
UNSPSC Code:
12352200
NACRES:
NA.77
biological source
Streptomyces sioyaensis
Quality Level
Assay
≥98% (HPLC)
solubility
DMSO: complete 10 mg/ml, clear, colorless to faintly yellow
DMSO: soluble
storage temp.
−20°C
General description
Siomycin A is a member of the thiazole antibiotics family.
Application
Siomycin A from Streptomyces sioyaensis yields clear, colorless to faint yellow solution in DMSO at 10 mg/ml.
Siomycin A from Streptomyces sioyaensis may be used in cell signaling studies.
Siomycin A has been used as a forkhead box protein M1 (FOXM1) inhibitor to study the effect of pharmacological inhibition of FOXM1 on isocitrate dehydrogenases 1 (IDH1) protein levels.
Biochem/physiol Actions
Siomycin A is a macrocyclic antibiotic with potent and selective antibacterial activity against gram negative and gram positive bacteria, including Mcobacterium tuberculosis and other clinical resistant strains. Siomycin inhibits antibody production and also inhibits the oncogenic transcription factor forkhead box M1 (FoxM1). Siomycin A has been shown to reduce anchorage-independent growth of cells in soft agar. Moveover in vitro asays show that Siomycin A selectively induces apoptosis of transformed, but not normal cells.
Siomycin A is a macrocyclic antibiotic with potent and selective antibacterial activity.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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K Tokura et al.
The Journal of antibiotics, 34(7), 800-810 (1981-07-01)
The peptide antibiotic siomycin-A was transformed into half-esters with dicarboxylic acids with the intention of making siomycin-A soluble in water. Sodium salts of the half-esters were also prepared. Some of the salts showed antibacterial activities comparable to siomycin-A against Gram-positive
N J Clayden et al.
European journal of biochemistry, 123(1), 127-131 (1982-03-01)
A trial application of a recent two-dimensional nuclear magnetic resonance experiment to the polypeptide antibiotic siomycin A is described. Proton--carbon-13 chemical shift correlation measures the proton and carbon-13 chemical shift for each directly bonded CH group in a molecule, in
Thiazole antibiotics against breast cancer.
Marianna Halasi et al.
Cell cycle (Georgetown, Tex.), 9(6), 1214-1217 (2010-04-23)
Bulbul Pandit et al.
The Prostate, 70(8), 825-833 (2010-01-09)
We previously described the identification of a transcriptional inhibitor ARC and FoxM1 inhibitors, thiazole antibiotics, Siomycin A and thiostrepton that were able to induce potent p53-independent apoptosis in cancer cell lines of different origin. Here, we report the characterization of
Tomonori Mori et al.
Chemistry, an Asian journal, 3(6), 984-1012 (2008-05-09)
The five practical segments for the total synthesis of siomycin A, that is, the dehydropiperidine segment A (5), the pentapeptide segment B (3), the dihydroquinoline segment C (6), and the beta-phenylselenoalanine dipeptide segments D (7) and E (4), were synthesized.
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