(2S,3S)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-2-{[(2S,4R,5R,6R)-4-{[(2S,4R,5R,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}-6-{[(2S,4R,5S,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-1,2,3,4-tetrahydroanthracen-1-one

• ChemBase ID: 131915
• Molecular Formular: C52H76O24
• Molecular Mass: 1085.14544
• Monoisotopic Mass: 1084.47265331
• SMILES: Cc1c(cc2cc3c(c(c2c1O)O)C(=O)[C@H]([C@@H](C3)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC)O[C@H]1C[C@H]([C@@H]([C@H](O1)C)O)O[C@H]1C[C@H]([C@@H]([C@H](O1)C)O)O[C@H]1C[C@]([C@@H]([C@H](O1)C)O)(C)O)O[C@H]1C[C@H]([C@H]([C@H](O1)C)O)O[C@H]1C[C@H]([C@@H]([C@H](O1)C)O)O
• Canonical SMILES: CO[C@@H]([C@@H]1Cc2cc3cc(O[C@@H]4O[C@H](C)[C@@H]([C@@H](C4)O[C@H]4C[C@@H](O)[C@@H]([C@H](O4)C)O)O)c(c(c3c(c2C(=O)[C@H]1O[C@@H]1O[C@H](C)[C@H]([C@@H](C1)O[C@@H]1O[C@H](C)[C@H]([C@@H](C1)O[C@@H]1O[C@H](C)[C@H]([C@@](C1)(C)O)O)O)O)O)O)C)C(=O)[C@H]([C@H](O)C)O
• 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
• InChIKey: CFCUWKMKBJTWLW-BGLFSJPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-2-{[(2S,4R,5R,6R)-4-{[(2S,4R,5R,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}-6-{[(2S,4R,5S,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-1,2,3,4-tetrahydroanthracen-1-one
• IUPAC Traditional name: (2S,3S)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-2-{[(2S,4R,5R,6R)-4-{[(2S,4R,5R,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}-6-{[(2S,4R,5S,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
• Synonyms: Mithramycin A from Streptomyces plicatus; Aureolic acid; Plicamycin; [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; Mithramycin; A 2371; Antibiotic LA 7017; Mithracin; Mitramycin; NSC 24559; PA 144; Plicatomycin; Mithramycin A; 普卡霉素; 金霉酸; 光辉霉素 A 来源于褶皱链霉菌

Database IDs

• CAS Number: 18378-89-7
• MDL Number: MFCD00135618
• Beilstein Number: 5236667
• PubChem SID: 24885983; 162226192
• PubChem CID: 457831

CALCULATED PROPERTIES

• Acid pKa: 8.491704
• H Acceptors: 24
• H Donor: 11
• LogD (pH = 5.5): 2.0724516
• LogD (pH = 7.4): 2.0391889
• Log P: 2.072891
• Molar Refractivity: 257.0091 cm^3
• Polarizability: 105.68714 Å^3
• Polar Surface Area: 358.2 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 440 nm; λem 523 nm in 5 mM Tris; DNA

Safety Information

• RTECS: PZ2800000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~80% (HPLC); 90-95%
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C52H76O24

DETAILS

Sigma Aldrich - 69823

Application
suitable for detection of DNA
Other Notes
Fluorescent stain for DNA in flow cytometry1,2
Biochem/physiol Actions
Anticancer antibiotic. Inhibits transcription and protein synthesis. Binds to DNA in native chromatin. Substrate of Pgp in MDR phenotypes.

Sigma Aldrich - M7393

Other Notes
Contains ~2.5% mithramycin A; balance is ~95% mannitol with a trace (1-3%) of sodium phosphate.
包装
Package size based on weight of mithramycin A
Biochem/physiol Actions
抗癌抗生素。抑制转录和蛋白质合成。与天然染色质中的 DNA 结合。MDR 表型的 Pgp 底物。

Sigma Aldrich - 289930

Biochem/physiol Actions
Anticancer antibiotic. Inhibits transcription and protein synthesis. Binds to DNA in native chromatin. Substrate of Pgp in MDR phenotypes.

Toronto Research Chemicals - M369500

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

REFERENCES

• Miller, et al.: Am. J. Med. Sci., 294, 388 (1987)
• Demicheli, et al.: Biochem. Biophys. Res. Commun., 177 511 (1987)
• Max, H., et al.: Cancer Res., 63, 7436 (1987)
• Lockman, J., et al.: J. Med. Chem., 53, 8734 (1987)