Mithramycin A

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. 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.Formal Name: (1S)-5-deoxy-1-C-[(2S,3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-beta-D-arabino-hexopyranosyl)-beta-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-beta-D-ribo-hexopyranosyl-(1->3)-O-2,6-dideoxy-beta-D-lyxo-hexopyranosyl-(1->3)-2,6-dideoxy-beta-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: DMF: 20 mg/ml, DMSO: 20 mg/ml, Ethanol: 10 mg/ml, PBS (pH 7.2): 2 mg/ml. lambdamax: 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.