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CHROMOMYCIN A3

CHROMOMYCIN A3 Structure
CAS No.
7059-24-7
Chemical Name:
CHROMOMYCIN A3
Synonyms
TOYOMYCIN;nsc-58514;Chromomycin;aburamycinb;Olivomycin D;CHROMOMYCIN A3;Chromoycin A3;antibioticb599;ABURAMYCIN BETA;nosyl)-7-methyl-
CBNumber:
CB8356277
Molecular Formula:
C57H82O26
Molecular Weight:
1183.25
MOL File:
7059-24-7.mol
MSDS File:
SDS
Modify Date:
2024/5/10 17:26:08

CHROMOMYCIN A3 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.

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H300
Precautionary statements  P264-P270-P301+P310-P405-P501
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
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).
NFPA 704
0
4 0

CHROMOMYCIN A3 price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) C2659 Chromomycin A3 from Streptomyces griseus ≥95% (HPLC) 7059-24-7 5MG ₹32702.33 2022-06-14 Buy
Sigma-Aldrich(India) C2659 Chromomycin A3 from Streptomyces griseus ≥95% (HPLC) 7059-24-7 10MG ₹50379.55 2022-06-14 Buy
Product number Packaging Price Buy
C2659 5MG ₹32702.33 Buy
C2659 10MG ₹50379.55 Buy

CHROMOMYCIN A3 Chemical Properties,Uses,Production

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.

General Description

Chemical structure: aureolic acid

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.]

CHROMOMYCIN A3 Preparation Products And Raw materials

Raw materials

Preparation Products

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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 ABURAMYCIN BETA CHROMOMYCIN A3 CHROMOMYCIN A3 STREPTOMYCES GRISEUS 3D-O-(4-O-acetyl-2,6-dideoxy-3-C-methyl-alpha-L-arabino-hexopyranosyl)-7-methylolivomycin D CHROMOMYCIN A(3), FOR FLUORESCENCE CHROMOMYCIN A3 FROM STREPTOMYCESGRISEUS APPROX. 96 Chromomycin 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 chromomycin a3from streptomyces griseus 3'''-O-(4-O-Acetyl-3-C-methyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-7-methylolivomycin D Chromoycin A3 Olivomycin D AburaMycin, ToyoMycin, NSC 58514, B 599-III, SR1768E aburamycinb antibiotic69895a antibioticb599 Chromomycin A - CAS 7059-24-7 - Calbiochem [(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 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... CHROMOMYCIN A3 USP/EP/BP 7059-24-7 C57H82O26 Antibiotics Antibiotics A to Z Antibiotics A-F BioChemical antibiotic