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5.30310

Mithramycin A

Name: Mithramycin A
Brand: MM

Synonym(s):

Mithramycin A, Plicamycin, Mithramycin

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About This Item

Empirical Formula (Hill Notation):

C₅₂H₇₆O₂₄

CAS Number:

18378-89-7

Molecular Weight:

1085.15

UNSPSC Code:

12352200

MDL number:

MFCD00135618

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Properties

assay

≥98% (HPLC)

Quality Segment

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

Preparation Note

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

Disclaimer

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Pictograms

GHS07

Signal Word

Warning

Hazard Codes

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°C)

Not applicable

Flash Point (°F)