A DNA-binding antitumor antibiotic
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Mithramycin A

Item No. 11434

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal 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→3)-O-2,6-dideoxy-β-D-lyxo-hexopyranosyl-(1→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
CAS Number
18378-89-7
Synonyms
  • A 2371
  • Antibiotic LA 7017
  • Aureolic Acid
  • NSC 24559
  • PA 144
  • Plicamycin
Molecular Formula
C52H76O24
Formula Weight
1085.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
229, 279, 318, 331, 414 nm
SMILES
O=C1C2=C(O)C3=C(O)C(C)=C(O[C@@H]4O[C@H](C)[C@@H](O)[C@H](O[C@@H]5O[C@H](C)[C@@H](O)[C@H](O)C5)C4)C=C3C=C2C[C@]([C@H](OC)C([C@@H](O)[C@H](O)C)=O)([H])[C@@H]1O[C@@H]6O[C@H](C)[C@@H](O)[C@H](O[C@@H]7O[C@H](C)[C@H](O)[C@H](O[C@@H]8O[C@H](C)[C@@H](O)[C@@](C)(O)C8)C7)C6
InChi Code
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-BKHRDMLASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Mithramycin A is a DNA-binding, anti-tumor and neuroprotective antibiotic originally isolated from S. grieseus that has long been used as a chemotherapeutic agent. It mediates its protective function, in part, by regulating acetylation of histones or transcription factors and, thereby, chromatin accessibility to transcriptional machinery. As a selective Sp1 inhibitor, mithramycin A binds to GC rich DNA sequences, displacing Sp1 transcription factor binding to oncogene promoters, which inhibits their expression.1,2 Mithramycin A (at 10-200 nM) can sensitize tumor cells to TRAIL-induced apoptosis and has been used to selectively target tumor cells in many different cancer models.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sleiman, S.F., Berlin, J., Basso, M., et al. Histone deacetylase inhibitors and mithramycin A impact a similar neuroprotective pathway at a crossroad between cancer and neurodegeneration. Pharmaceuticals 4, 1183-1195 (2011).

    2. Sleiman, S.F., Langley, B.C., Basso, M., et al. Mithramycin is a gene-selective Sp1 inhibitor that identifies a biological intersection between cancer and neurodegeneration. J. Neurosci. 31(18), 6858-6870 (2011).

    3. Lee, T.J., Jung, E.M., Lee, J.T., et al. Mithramycin A sensitizes cancer cells to TRAIL-mediated apoptosis by down-regulation of XIAP gene promoter through Sp1 sites. Mol. Cancer Ther. 5, 2737-2746 (2006).

    4. Jia, Z., Gao, Y., Wang, L., et al. Combined treatment of pancreatic cancer with mithramycin A and tolfenamic acid promotes Sp1 degradation and synergistic antitumor activity. Cancer Res. 70, 1111-1119 (2010).

    5. Duverger, V., Murphy, A.M., Sheehan, D., et al. The anticancer drug mithramycin A sensitises tumour cells to apoptosis induced by tumour necrosis factor (TNF). Br. J. Cancer 90, 2025-2031 (2004).