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| | CHROMOMYCIN A3 Basic information |
| Product Name: | CHROMOMYCIN A3 | | Synonyms: | chromomycina(sub3);nosyl)-7-methyl-;nsc-58514;olivomycind,3b-o-(4-o-acetyl-2,6-dideoxy-3-c-methyl-alpha-l-arabinohexopyra;TOYOMYCIN;3BETA-O-(4-O-ACETYL-2.6-DIDEOXY-3-C-METHYL-ALPHA-L-ARABINO HEXOPYRANOSYL)-7-METHYLOLIVOMYCIN D;3B-O-(4-O-ACETYL-2,6-DIDEOXY-3-C-METHYL-ALPHA-L-ARABINO-HEXOPYRANOSYL)-7-METHYLOLIVOMYCIN D;3B-O-(4-O-ACETYL-2,6-DIDEXY-3-C-METHYL-ALPHA-L-ARABINO-HEXOPYRANOSYL)-7-METHYLOLIVOMYCIN | | CAS: | 7059-24-7 | | MF: | C57H82O26 | | MW: | 1183.25 | | EINECS: | 230-348-0 | | Product Categories: | antibiotic | | Mol File: | 7059-24-7.mol |  |
| | CHROMOMYCIN A3 Chemical Properties |
| Melting point | 185℃ | | alpha | D23 -57° (ethanol) | | Boiling point | 780.13°C (rough estimate) | | density | 1.1451 (rough estimate) | | refractive index | 1.6500 (estimate) | | storage temp. | 2-8°C | | solubility | Soluble in ethanol, DMSO, and ethyl acetate (10 mg/ml). | | form | Yellow solid | | pka | 4.54±0.60(Predicted) | | color | Yellow | | Merck | 13,2258 | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. |
| Hazard Codes | T+,T | | Risk Statements | 61-28 | | Safety Statements | 53-28-36/37/39-45 | | RIDADR | UN 3462 6.1/PG 1 | | WGK Germany | 3 | | RTECS | GB7875000 | | F | 3-8-10 | | HazardClass | 6.1(a) | | PackingGroup | I | | HS Code | 29419090 | | Toxicity | Excitation max: ~445 nm. Emission max: ~575 nm. Sol in ethanol, ethyl acetate, DMSO, methanol. LD50 in mice (mg/kg): 1.85 i.v. (Slavik, Carter). |
| | CHROMOMYCIN A3 Usage And Synthesis |
| 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. | | Chemical Properties | Yellow powder | | Uses | Fluorescent DNA stain in flow cytometry and karyotype analysis of chromosomes. | | Uses | 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. | | 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. | | Definition | ChEBI: Chromomycin A3 is a chromomycin. | | General Description | Chemical structure: aureolic acid | | Biochem/physiol Actions | Chromomycin A3 from Streptomyces griseus is an antibiotic exhibiting anti-bacterial, anti-fungal and antitumor activities. It serves as a fluorescent DNA stain. It is useful for the detection of protamine deficiency in sperm chromatin. The compound blocks macromolecule synthesis by a specific, reversible interaction with DNA in the presence of bivalent metal ions. Binding to DNA minor groove mediates an efficient competitive inhibition of DNA gyrase and significantly affects topoisomerase II activity. | | Purification Methods | Dissolve the antibiotic (10g) in EtOAc and add to a column of Silica Gel (Merck 0.05-0.2microns, 4x70cm) in EtOAc containing 1% oxalic acid. Elute with EtOAc+1% oxalic acid and check fractions by TLC. Pool fractions, wash with H2O thoroughly, dry and evaporate. Recrystallise the residue from EtOAc. The heptaacetate has m 214o, [] D -20o (c 1, EtOH). [Miyamoto et al. Tetrahedron 23 421 1967, Harada et al. J Am Chem Soc 91 5896 1969, Beilstein 17/5 V 673.] | | References | Van Dyke et al. (1983), Chromomycin, Mithramycin and olivomycin binding sites on heterogeneous deoxyribonucleic acid. Footprinting with methidiumpropyl-EDTA)iron(II); ?Biochemistry, 22 2373
Crissman and Tobey (1990), Specific staining of DNA with the fluorescent antibiotic, mithramycin, chromomycin, and olivomycin; Methods Cell Biol., 33 97
Chatterjee et al. (2001), Sequence-selective DNA binding drugs mithramycin A and chromomycin A3 are potent inhibitors of neuronal apoptosis induced by oxidative stress and DNA damage in cortical neurons; Neurol., 49 345
Miller et al. (2010), Identification of known drugs that act as inhibitors of NF-kappaB signaling and their mechanism of action; Pharmacol., 79 1272
Dutta et al. (2020), Comparative analysis of tests used to assess sperm chromatin integrity and DNA fragmentation; Andrologia, 53?e13718 |
| | CHROMOMYCIN A3 Preparation Products And Raw materials |
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