CAS 18378-89-7

Mithramycin

Description:

Mithramycin, also known as mithramycin A, is a polyketide antibiotic produced by the bacterium Streptomyces argillaceus. It is characterized by its complex structure, which includes a tetracyclic core and multiple sugar moieties, contributing to its biological activity. Mithramycin exhibits antitumor properties, primarily by binding to DNA and inhibiting transcription, which disrupts the synthesis of proteins necessary for cancer cell proliferation. It is particularly effective against certain types of tumors, including testicular cancer and various sarcomas. The compound has a low solubility in water, which can affect its bioavailability and therapeutic application. Mithramycin's mechanism of action involves the chelation of metal ions, which further enhances its ability to interfere with cellular processes. Due to its potent effects and potential side effects, its use is typically reserved for specific clinical situations, and ongoing research continues to explore its efficacy and safety in cancer treatment.

Formula: C₅₂H₇₆O₂₄

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

InChI key: InChIKey=CFCUWKMKBJTWLW-BKHRDMLASA-N

SMILES: O=C1C=2C(C[C@@]([C@@H](C([C@H]([C@@H](C)O)O)=O)OC)([C@@H]1O[C@H]3C[C@@H](O[C@H]4C[C@@H](O[C@H]5C[C@](C)(O)[C@H](O)[C@@H](C)O5)[C@@H](O)[C@@H](C)O4)[C@H](O)[C@@H](C)O3)[H])=CC=6C(C2O)=C(O)C(C)=C(O[C@H]7C[C@@H](O[C@H]8C[C@@H](O)[C@H](O)[C@@H](C)O8)[C@H](O)[C@@H](C)O7)C6

Synonyms:

• <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)-
• A 2371
• Antibiotic LA 7017
• Aureolic acid
• Mithracin
• Mithramycin
• Mithramycin A
• Mitramycin
• Nsc 24559
• Pa 144
• Plicamycin
• Plicatomycin
• [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

Plicamycin

CAS: 18378-89-7

Formula: C₅₂H₇₆O₂₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 1085.1454

Ref: IN-DA00I1FJ

Mithramycin A

CAS: 18378-89-7

Formula: C₅₂H₇₆O₂₄

Purity: ≥ 98.0%

Color and Shape: Yellow powder

Molecular weight: 1085.15

Ref: 7W-GA1050

Mithramycin A from Streptomyces argillaceus

CAS: 18378-89-7

Mithramycin A from Streptomyces argillaceus

Formula: C₅₂H₇₆O₂₄

Purity: By hplc: 98.0% (Typical Value in Batch COA)

Color and Shape: yellow powder

Molecular weight: 1,085.15g/mol

Ref: 54-BIM1003

Mithramycin A

CAS: 18378-89-7

Mithramycin A (Plicamycin), a DNA-binding antitumor antibiotic, is a selective specificity protein 1 (Sp1) inhibitor, which inhibits the growth of various

Formula: C₅₂H₇₆O₂₄

Purity: 99.28% - 99.92%

Color and Shape: Yellow Powder

Molecular weight: 1085.15

Ref: TM-T5530

Mithramycin A

CAS: 18378-89-7

Antineoplastic antibiotic; RNA synthesis inhibitor

Formula: C₅₂H₇₆O₂₄

Purity: Min. 95%

Color and Shape: Yellow Powder

Molecular weight: 1,085.15 g/mol

Ref: 3D-AM34906

Mithramycin A

Controlled Product

CAS: 18378-89-7

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),

Formula: C₅₂H₇₆O₂₄

Color and Shape: Yellow Crystalline Powder

Molecular weight: 1085.15

Ref: TR-M369500