ChemicalBook > CAS DataBase List > CHROMOMYCIN A3

CHROMOMYCIN A3

Product Name: CHROMOMYCIN A3
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
Formula Weight: 1183.25
MOL File: 7059-24-7.mol

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CHROMOMYCIN A3 Property

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

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Safety

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).

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: C2659
Product name: Chromomycin A3 from Streptomyces griseus
Purity: ≥95% (HPLC)
Packaging: 5mg
Price: $321
Updated: 2025/07/31

Sigma-Aldrich

Product number: C2659
Product name: Chromomycin A3 from Streptomyces griseus
Purity: ≥95% (HPLC)
Packaging: 10mg
Price: $513
Updated: 2025/07/31

Cayman Chemical

Product number: 11315
Product name: Chromomycin A3
Purity: ≥98%
Packaging: 1mg
Price: $50
Updated: 2024/03/01

Cayman Chemical

Product number: 11315
Product name: Chromomycin A3
Purity: ≥98%
Packaging: 5mg
Price: $138
Updated: 2024/03/01

TRC

Product number: C433030
Product name: ChromomycinA3
Packaging: 1mg
Price: $205
Updated: 2021/12/16

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CHROMOMYCIN A3 Chemical Properties,Usage,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.

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

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

[1] Chromomycin, Mithramycin and olivomycin binding sites on heterogeneous deoxyribonucleic acid. Footprinting with methidiumpropyl-EDTA)iron(II)
[2] H A CRISSMAN R A T. Specific staining of DNA with the fluorescent antibiotics, mithramycin, chromomycin, and olivomycin.[J]. Methods in cell biology, 1990, 33: 97-103. DOI:10.1016/s0091-679x(08)60515-4
[3] SUKALYAN CHATTERJEE PHD, PHD. 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[J]. Annals of Neurology, 2001, 49 3: 345-354. DOI:10.1002/ana.71
[4] SUSANNE C. MILLER. Identification of known drugs that act as inhibitors of NF-κB signaling and their mechanism of action[J]. Biochemical pharmacology, 2010, 79 9: Pages 1272-1280. DOI:10.1016/j.bcp.2009.12.021
[5] SULAGNA DUTTA Ashok A Ralf Henkel. Comparative analysis of tests used to assess sperm chromatin integrity and DNA fragmentation[J]. Andrologia, 2020, 53 2. DOI:10.1111/and.13718

CHROMOMYCIN A3 Preparation Products And Raw materials

Raw materials

Preparation Products

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CHROMOMYCIN A3 Suppliers

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View Lastest Price from CHROMOMYCIN A3 manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd

Product: chromomycin A3 7059-24-7
Price: US $150.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20ton
Release date: 2024-04-24

Dideu Industries Group Limited

Product: CHROMOMYCIN A3 7059-24-7
Price: US $1.10/g
Min. Order: 1g
Purity: 99.9%
Supply Ability: 100 Tons Min
Release date: 2021-07-01

Longyan Tianhua Biological Technology Co., Ltd

Product: CHROMOMYCIN A3 7059-24-7
Price: US $12.00/Kg/Bag
Min. Order: 25Kg/Bag
Purity: 99%
Supply Ability: 20 Tons
Release date: 2020-11-17

7059-24-7, CHROMOMYCIN A3Related Search:

AburaMycin A, NSC 131187 6-Methoxy-2-naphthaldehyde 5-Hydroxy-4-octanone 2,3,6-TRIMETHYLNAPHTHALENE 6'-Methoxy-2'-propiononaphthone ISOVALEROPHENONE Naphthalen-2-ethanol 6-Methoxy-2-heptanonaphthone CHROMOMYCIN A3 2,6-DIMETHYLNAPHTHALENE 5,6,7,8-TETRAHYDRO-1-NAPHTHOL 2-Acetyl-6-methoxynaphthalene 2,6-HEPTANEDIONE 1,6-Dihydroxynaphthalene 2,3-DIMETHYLNAPHTHALENE 6-Hydroxy-2-naphthaldehyde 2,7-DIMETHYLNAPHTHALENE (R)-(-)-4-PHENYL-2-BUTANOL

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

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

antibiotic69895a

antibioticb599

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

Chromomycin A3, fluorescent DNA stain

Chromomycin A3 from Streptomyces griseus

Chromomycin A3

7059-24-7

C57H82O26

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