Mithramycin A

CAS: 18378-89-7

Ref. TR-M369500

Product Information

• Name: Mithramycin A
• Synonyms: [1S(2S,3S)]-5-Deoxy-1-C-[7-[[2,6-dideoxy-3-O-(2,6-dideoxy-ß-D-arabino-hexopyranosyl)-ß-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-ß-D-ribo-hexopyranosyl-(1?3)-O-2,6-dideoxy-ß-D-arabino-hexopyranosyl-(1?3)-2,6-dideoxy-ß-D-lyxo-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-D-threo-2-pentulose, Mithramycin, A 2371, Antibiotic LA 7017, Aureolic Acid, Mithracin, Mitramycin, NSC 24559, PA 144, Plicamycin, Plicatomycin, <span class="text-smallcaps">D</smallcap>-threo-2-Pentulose, 5-deoxy-1-C-[(2S,3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-<smallcap>D</smallcap>-arabino-hexopyranosyl)-β-<smallcap>D</smallcap>-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-<smallcap>D</smallcap>-lyxo-hexopyranosyl-(1→3)-2,6-dideoxy-β-<smallcap>D</span>-arabino-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-, (1S)-, Aureolic acid, Nsc 24559, Pa 144, [1S(2S,3S)]-5-Deoxy-1-C-[7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-<span class="text-smallcaps">D</smallcap>-arabino-hexopyranosyl)-β-<smallcap>D</smallcap>-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-<smallcap>D</smallcap>-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-<smallcap>D</smallcap>-lyxo-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-<smallcap>D</span>-threo-2-pentulose, [1S(2S,3S)]-5-Deoxy-1-C-[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-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-lyxo-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-D-threo-2-pentulose

Description

Applications Mithramycin A is an anticancer antibiotic that selectively binds to G-C-rich DNA in the presence of Mg2+ or Zn2+, inhibiting RNA and DNA polymerase action. Mithramycin A inhibits c-myc expression and induces myeloid differentiation of HL-60 promyelocytic leukemia cells.
References Miller, et al.: Am. J. Med. Sci., 294, 388 (1987), Demicheli, et al.: Biochem. Biophys. Res. Commun., 177 511 (1991), Max, H., et al.: Cancer Res., 63, 7436 (2003), Lockman, J., et al.: J. Med. Chem., 53, 8734 (2010),

• Brand: TRC

Chemical properties

• Molecular weight: 1085.15
• Formula: C₅₂H₇₆O₂₄
• Color/Form: Yellow Crystalline Powder
• InChI: InChI=1S/C30H38N2O13/c1-15(33)31-12-11-19-14-32(29(38)45-30(5,6)7)22-10-9-20(13-21(19)22)43-28-26(42-18(4)36)24(41-17(3)35)23(40-16(2)34)25(44-28)27(37)39-8/h9-10,13-14,23-26,28H,11-12H2,1-8H3,(H,31,33)/t23-,24?,25?,26?,28-/m1/s1
• InChI key: InChIKey=RSLJLPFHYCLDBE-AYVREFAGSA-N
• SMILES: CO[C@H](C(=O)[C@@H](O)[C@@H](C)O)[C@@H]1Cc2cc3cc(O[C@H]4C[C@@H](O[C@H]5C[C@@H](O)[C@H](O)[C@@H](C)O5)[C@@H](O)[C@@H](C)O4)c(C)c(O)c3c(O)c2C(=O)[C@H]1O[C@@H]1C[C@H](O[C@@H]2C[C@H](O[C@@H]3C[C@@](C)(O)[C@@H](O)[C@H](C)O3)[C@@H](O)[C@H](C)O2)[C@@H](O)[C@H](C)O1