| Identification | Back Directory | [Name]
CHROMOMYCIN A3 | [CAS]
7059-24-7 | [Synonyms]
nsc-58514
TOYOMYCIN
Chromomycin
aburamycinb
Olivomycin D
Chromoycin A3
antibioticb599
CHROMOMYCIN A3
ABURAMYCIN BETA
antibiotic69895a
nosyl)-7-methyl-
chromomycina(sub3)
CHROMOMYCIN A3 USP/EP/BP
CHROMOMYCIN A(3), FOR FLUORESCENCE
CHROMOMYCIN A3 STREPTOMYCES GRISEUS
chromomycin a3from streptomyces griseus
Chromomycin A - CAS 7059-24-7 - Calbiochem
CHROMOMYCIN A3 FROM STREPTOMYCESGRISEUS APPROX. 96
AburaMycin, ToyoMycin, NSC 58514, B 599-III, SR1768E
olivomycind,3b-o-(4-o-acetyl-2,6-dideoxy-3-c-methyl-alpha-l-arabinohexopyra
3B-O-(4-O-ACETYL-2,6-DIDEXY-3-C-METHYL-ALPHA-L-ARABINO-HEXOPYRANOSYL)-7-METHYLOLIVOMYCIN
3'''-O-(4-O-Acetyl-3-C-methyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-7-methylolivomycin D
3D-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
3BETA-O-(4-O-ACETYL-2.6-DIDEOXY-3-C-METHYL-ALPHA-L-ARABINO HEXOPYRANOSYL)-7-METHYLOLIVOMYCIN D
D-threo-2-Pentulose, 1-C-(2S,3S)-7-4-O-acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-.alpha.-D-lyxo-hexopyranosyl)-.beta.-D-lyxo-hexopyranosyloxy-3-O-4-O-acetyl-2,6-dideoxy-3-C-methyl-.alpha.-L-arabino-hexopyranosyl-(1?3)-O-2,6-dideoxy-.beta.-D-arabino-h
D-threo-2-Pentulose, 1-C-[(2S,3S)-7-[[4-O-acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy]-3-[[O-4-O-acetyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy...
[(2R,3S,4R,6S)-6-[[(6S,7S)-6-[(2S,4R,5R,6R)-4-[(2S,4R,5R,6R)-4-[(2S,4S,5S,6S)-5-acetyloxy-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-7-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-4,10-dihydroxy-3-methyl-5-oxo-7,8-dihydro-6H-anthracen-2-yl]oxy]-4-[(2R,4R,5R,6R)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy-2-methyloxan-3-yl] acetate | [EINECS(EC#)]
230-348-0 | [Molecular Formula]
C57H82O26 | [MDL Number]
MFCD00043151 | [MOL File]
7059-24-7.mol | [Molecular Weight]
1183.25 |
| Chemical Properties | Back Directory | [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. | [InChIKey]
ZYVSOIYQKUDENJ-ZKWPLOTFNA-N |
| Safety Data | Back Directory | [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). |
| Hazard Information | Back Directory | [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]
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. | [Uses]
Fluorescent DNA stain in flow cytometry and karyotype analysis of chromosomes. | [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 |
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