5.30310

Mithramycin A

• Synonym(s): Mithramycin A, Plicamycin, Mithramycin
• Empirical Formula (Hill Notation): C₅₂H₇₆O₂₄
• CAS Number: 18378-89-7
• Molecular Weight: 1085.15
• MDL number: MFCD00135618
• UNSPSC Code: 12352200

Properties

• assay: ≥98% (HPLC)
• Quality Level: 100
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: yellow
• solubility: DMSO: 50 mg/mL
• storage temp.: 2-8°C
• InChI: 1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27+,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43-,44-,45-,49+,50+,51-,52+/m1/s1
• InChI key: CFCUWKMKBJTWLW-WZIVUMCRSA-N

Description

General description

An aureolic acid type tricyclic pentaglycoside antibiotics with anti-tumor properties. Binds to G-C rich DNA and displaces Sp1 transcription factor from its sites in the promoters of selected oncogenes, such as c-Myc and c-Src. Mithramycin A-induced inhibition of Sp1 activity has been linked to greater DNA damage and cell death in cells that are homozygous for SNP309. Specifically reduces the levels of MDM2 in human ductal breast epithelial tumor cell line, T47D (5-fold reduction at 200 nM), but does not affect cells that are wild-type for SNP309. Shown to induce myeloid differentiation of leukemic blasts that leads to reduction in the level of expression of c-Myc and c-Abl proto oncogenes that harbor G-C rich promoters. Inhibits Mcl-1 activity and mTOR phosphorylation (Ser2448) in prostate cancer cells without affecting normal human prostate epithelial cells. Shown to reduce expression of endogenous transient receptor potential vanilpod receptor (TRPV1)-like protein in dorsal root ganglionic neurons.

Biochem/physiol Actions

Primary Target
Sp1 transcription factor

Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Zavala, K., et al. 2014. Neurosci Lett.562,in press.
Choi, E. S., et al. 2013. J. Clin. Biochem. Nutr.53, 89.

Sleiman S. F., et al. 2011. J. Neurosci.31, 6858.
Bond, G, et al. 2004. Cell.119, 591.
Blume, S, et al. 1991. J. Clin. Invest.88, 1613.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_c: Not applicable