7059-24-7 Usage
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
Check Digit Verification of cas no
The CAS Registry Mumber 7059-24-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,0,5 and 9 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 7059-24:
(6*7)+(5*0)+(4*5)+(3*9)+(2*2)+(1*4)=97
97 % 10 = 7
So 7059-24-7 is a valid CAS Registry Number.
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
