LKT Labs

Biochemicals for Life Science Research

Mithramycin

Product ID M3476
Cas No. 18378-89-7
Purity ≥95%
Product Unit SizeCostQuantityStock
1 mg $70.40 In stock
5 mg $281.30 In stock
10 mg $515.70 In stock
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Description

Mithramycin is an aureolic acid-type polyketide antibiotic initially produced by species of Streptomyces. Mithramycin exhibits neuroprotective and anticancer chemotherapeutic activities. In animal models of Huntington’s disease, mithramycin prevented increases in H3 histone methylation, delaying disease pathology, improving motor performance, and increasing survival rates. Mithramycin is a reversible inhibitor of RNA synthesis, binding CG and GC sequences and inhibiting transcription initiation. Mithramycin also inhibits CpG methylation of tumor-suppressor genes through direct inhibition of DNA methyltransferase 1 (DNMT1) activity in lung cancer cells. In cellular and animal models of prostate cancer, mithramycin increases levels of tBid and decreases levels of mTOR and Mcl-1, inducing apoptosis and inhibiting tumor growth.

Product Info

Cas No.

18378-89-7
Purity

≥95%
Formula

C52H76O25

Formula Wt.

1084.47
IUPAC Name

(2S,3S)-2-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4-[(2S,4S,5R,6R)-4, 5-dihydroxy-4, 6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6- methyloxan-2-yl]oxy-3-[(1S,3S,4R)-3, 4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4, 5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8, 9-dihydroxy-7-methyl-3,4-dihydro-2H-anthracen-1-one InChI: 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
Synonym

Plicamycin, Mithramycin A
Melting Point

175-180°C
Solubility

DMSO (20 mg/ml), Methanol, Ethanol (10 mg/ml)
Appearance

Yellow Powder

Shipping and Storage

Store Temp

4°C
Ship Temp

Ambient

Downloads

MSDS

M3476 MSDS PDF
Info Sheet

M3476 Info Sheet PDF
Brochures

Epigenetic Modifiers Booklet

References

Choi ES, Chung T, Kim JS, et al. Mithramycin A induces apoptosis by regulating the mTOR/Mcl-1/tBid pathway in androgen-independent prostate cancer cells. J Clin Biochem Nutr. 2013 Sep;53(2):89-93. PMID: 24062605.

Choi ES, Jung JY, Lee JS, et al. Myeloid cell leukemia-1 is a key molecular target for mithramycin A-induced apoptosis in androgen-independent prostate cancer cells and a tumor xenograft animal model. Cancer Lett. 2013 Jan 1;328(1):65-72. PMID: 23000424.

Lin RK, Hsu CH, Wang YC. Mithramycin A inhibits DNA methyltransferase and metastasis potential of lung cancer cells. Anticancer Drugs. 2007 Nov;18(10):1157-64. PMID: 17893516.

Ferrante RJ, Ryu H, Kubilus JK, et al. Chemotherapy for the brain: the antitumor antibiotic mithramycin prolongs survival in a mouse model of Huntington's disease. J Neurosci. 2004 Nov 17;24(46):10335-42. PMID: 15548647.

Miller DM, Polansky DA, Thomas SD, et al. Mithramycin selectively inhibits transcription of G-C containing DNA. Am J Med Sci. 1987 Nov;294(5):388-94. PMID: 2962490.

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