Chromomycin A3 from Streptomyces griseus

Base Information

• Chemical Name: Chromomycin A3 from Streptomyces griseus
• CAS No.: 7059-24-7
• Molecular Formula: C57H82 O26
• Molecular Weight: 1183.39
• Hs Code.: 29419090
• European Community (EC) Number: 230-348-0
• Metabolomics Workbench ID: 55005
• NCI Thesaurus Code: C895
• Wikidata: Q105386461
• Wikipedia: Chromomycin_A3
• Mol file: 7059-24-7.mol

Synonyms:Chromomycin A3;Toyomicin;Toyomycin

Chemical Property of Chromomycin A3 from Streptomyces griseus

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 185℃
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 1147.6°C at 760 mmHg
• PKA: 4.54±0.60(Predicted)
• Flash Point: 311.1°C
• PSA: 359.34000
• Density: 1.43g/cm³
• LogP: 1.54640
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ethanol, DMSO, and ethyl acetate (10 mg/ml).
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 26
• Rotatable Bond Count: 20
• Exact Mass: 1182.50943272
• Heavy Atom Count: 83
• Complexity: 2190

Purity/Quality:

98%,99%, ^*data from raw suppliers

Chromomycin A3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,T
• Hazard Codes: T+,T
• Statements: 61-28
• Safety Statements: 53-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2C(CC3=C(C2=O)C(=C4C(=C3)C=C(C(=C4O)C)OC5CC(C(C(O5)C)OC(=O)C)OC6CC(C(C(O6)C)OC)O)O)C(C(=O)C(C(C)O)O)OC)OC7CC(C(C(O7)C)O)OC8CC(C(C(O8)C)OC(=O)C)(C)O)O
• Isomeric SMILES: C[C@@H]1[C@H]([C@@H](CC(O1)O[C@H]2[C@@H](CC3=C(C2=O)C(=C4C(=C3)C=C(C(=C4O)C)OC5C[C@@H]([C@@H]([C@@H](O5)C)OC(=O)C)OC6C[C@@H]([C@@H]([C@@H](O6)C)OC)O)O)[C@H](C(=O)[C@H]([C@H](C)O)O)OC)OC7C[C@@H]([C@H]([C@@H](O7)C)O)OC8C[C@]([C@H]([C@@H](O8)C)OC(=O)C)(C)O)O
• Description: Chromomycin A3 is an anthraquinone antibiotic and antitumor agent isolated from S. griseus that is used as a fluorescent probe for DNA with excitation/emission spectra of 445/575 nm. Its DNA binding is specific to two or more contiguous GC base pairs, which makes it suitable for characterizing heterochromatin in plants with species-specific AT:GC ratios. Chromomycin A3 is cytotoxic against non-small cell lung cancer and cervical cancer in vitro (IC50s = 1, 42, 60, and 40 nM for HCC44, A549, ME180, and HeLa cells, respectively). It also inhibits oxidative stress- and DNA damage-induced neuronal injury by enhancing Sp1 and Sp3 transcription factor binding.
• Uses: Chromomycin A3 is the major component of the chromomycin complex of the aureolic acid class, isolated from several Streptomyces species, and first reported in 1960. Chromomycin A3 exhibits a broad biological profile as an antibacterial, antifungal and antitumour agent. It binds reversibly to GC-specific DNA ligand in the minor groove which inhibits transcription, DNA gyrase and topoisomerase II activity. The intense UV spectrum and strong fluorescence makes chromomycin a useful stain for DNA. Fluorescent DNA stain in flow cytometry and karyotype analysis of chromosomes. Chromomycin A3, is used as a G-C specific DNA ligand which inhibits transcription and acts as a DNA binding dye. Chromomycin A3 antagonizes enhanced DNA binding of the transcription factors Sp1 and Sp3 to their cognate "G-C" box, induced by oxidative stress or DNA damage. Furthermore, by inhibiting transcription, Chromomycin A3 and its structural analogs can inhibit protein biosynthesis.