7059-24-7

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 NO: 7059-24-7
• Molecular Formula: C57H82O26
• Molecular Weight: 1183.25
• EINECS: 230-348-0
• Product Categories: antibiotic
• Mol File: 7059-24-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 185℃
• Boiling Point: 780.13°C (rough estimate)
• Flash Point: 311.1°C
• Appearance: /
• Density: 1.1451 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in ethanol, DMSO, and ethyl acetate (10 mg/ml).
• PKA: 4.54±0.60(Predicted)
• 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.
• Merck: 13,2258
• CAS DataBase Reference: CHROMOMYCIN A3(CAS DataBase Reference)
• NIST Chemistry Reference: CHROMOMYCIN A3(7059-24-7)
• EPA Substance Registry System: CHROMOMYCIN A3(7059-24-7)

Safety Data

• Hazard Codes: T+,T
• 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
• Hazardous Substances Data: 7059-24-7(Hazardous Substances Data)

Usage

Description

Chromomycin A3 is an anthraquinone antibiotic and antitumor agent isolated from S. griseus. It is characterized by its yellow powder form and 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, making it suitable for characterizing heterochromatin in plants with species-specific AT:GC ratios. Chromomycin A3 exhibits a broad biological profile as an antibacterial, antifungal, and antitumor 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 make chromomycin a useful stain for DNA.

Uses

Used in Anticancer Applications:
Chromomycin A3 is used as an antitumor agent, particularly against non-small cell lung cancer and cervical cancer in vitro. It demonstrates cytotoxic effects with IC50s of 1, 42, 60, and 40 nM for HCC44, A549, ME180, and HeLa cells, respectively. Additionally, it inhibits oxidative stressand DNA damage-induced neuronal injury by enhancing Sp1 and Sp3 transcription factor binding.
Used in Fluorescent DNA Staining:
Chromomycin A3 is used as a G-C specific DNA ligand which inhibits transcription and acts as a DNA binding dye. It is employed as a fluorescent DNA stain in flow cytometry and karyotype analysis of chromosomes, thanks to its strong fluorescence and specific DNA binding properties.
Used in DNA Binding Studies:
Chromomycin A3 is used to antagonize the enhanced DNA binding of transcription factors Sp1 and Sp3 to their cognate "G-C" box, induced by oxidative stress or DNA damage. By inhibiting transcription, Chromomycin A3 and its structural analogs can inhibit protein biosynthesis, making it a valuable tool for studying DNA-protein interactions and the effects of various stressors on gene expression.

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

InChI:InChI=1/C57H82O26/c1-21-34(79-40-19-37(53(26(6)75-40)77-28(8)59)82-38-16-33(61)52(70-11)25(5)74-38)15-31-13-30-14-32(54(71-12)51(68)46(63)22(2)58)55(50(67)44(30)49(66)43(31)45(21)62)83-41-18-35(47(64)24(4)73-41)80-39-17-36(48(65)23(3)72-39)81-42-20-57(10,69)56(27(7)76-42)78-29(9)60/h13,15,22-27,32-33,35-42,46-48,52-56,58,61-66,69H,14,16-20H2,1-12H3/t22-,23-,24-,25-,26-,27+,32+,33-,35-,36-,37-,38-,39+,40+,41+,42+,46+,47-,48-,52+,53+,54+,55+,56+,57+/m1/s1