Mithramycin A

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Cat.No. 1489 - Mithramycin A | C52H76O24 | CAS No. 18378-89-7
Description: Inhibitor of DNA and RNA polymerase
Chemical Name: (1S)-5-Deoxy-1-C-[(2S,3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1.fwdarw.3)-O-2,6-dideoxy-β-D-lyxo-hexopyranosyl-(1.fwdarw.3)-2,6-dideoxy-β-D-arabino-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-D-threo-2-pentulose
Purity: ≥95% (HPLC)
Datasheet
Citations (6)
Reviews
Literature

Biological Activity

Anticancer antibiotic that selectively binds to G-C-rich DNA in the presence of Mg2+ or Zn2+, inhibiting RNA and DNA polymerase action. Inhibits c-myc expression and induces myeloid differentiation of HL-60 promyelocytic leukemia cells.

Technical Data

M. Wt 1085.16
Formula C52H76O24
Storage Desiccate at -20°C
Purity ≥95% (HPLC)
CAS Number 18378-89-7
PubChem ID 90479798
InChI Key CFCUWKMKBJTWLW-YZCDWGPJSA-N
Smiles OC1=C2C(C=C3C(C([C@@H](OC5OC(C)C(O)C(OC6OC(C)C(O)C(OC7OC(C)C(O)C(O)(C)C7)C6)C5)[C@@]([C@H](OC)C([C@@H](O)[C@H](O)C)=O)([H])C3)=O)=C2O)=CC(O[C@@H]4OC(C)C(O)C(OC8OC(C)C(O)C(O)C8)C4)=C1C

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 54.26 50

Preparing Stock Solutions

The following data is based on the product molecular weight 1085.16. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.5 mM 1.84 mL 9.22 mL 18.43 mL
2.5 mM 0.37 mL 1.84 mL 3.69 mL
5 mM 0.18 mL 0.92 mL 1.84 mL
25 mM 0.04 mL 0.18 mL 0.37 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Demicheli and Garnier-Suillerot (1991) Mithramycin cannot bind to left-handed poly(dG-m5dC) in the presence of Mg2+ ion. Biochem.Biophys.Res.Commun. 177 511 PMID: 1828342

Miller et al (1987) Mithramycin selectively inhibits transcription of G-C containing DNA. Am.J.Med.Sci. 294 388 PMID: 2962490

Ray et al (1990) Mithramycin selectively inhibits the transcriptional activity of a transfected human c-myc gene. Am.J.Med.Sci. 300 203 PMID: 2147360


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⚠ WARNING: This product can expose you to chemicals including Plicamycin, which is known to the State of California to cause reproductive toxicity with developmental effects. For more information, go to www.P65Warnings.ca.gov

6 Citations for Mithramycin A

Citations are publications that use Tocris products. Selected citations for Mithramycin A include:

Huang et al (2012) Prostaglandin E2 increases fibroblast gene-specific and global DNA methylation via increased DNA methyltransferase expression. FASEB J 26 3703 PMID: 22645246

Duverger et al (2004) The anticancer drug mithramycin A sensitises tumour cells to apoptosis induced by tumour necrosis factor (TNF). Cell Death Dis 90 2025 PMID: 15138489

Huang et al (2016) Hepatocellular carcinoma redirects to ketolysis for progression under nutrition deprivation stress. Cell Res 26 1112 PMID: 27644987

Siddesha et al (2014) Acetylsalicylic acid inhibits IL-18-induced cardiac fibroblast migration through the induction of RECK. J Cell Physiol 229 845 PMID: 24265116

Corsini et al (2007) Role of SP-1 in SDS-induced adipose differentiation related protein synthesis in human keratinocytes. Gene Regul Syst Bio 1 207 PMID: 19936089

Oh et al (2015) Arachidonic acid promotes skin wound healing through induction of human MSC migration by MT3-MMP-mediated fibronectin degradation. J Neurosci 6 e1750 PMID: 25950480


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