Chromomycin A3

• CAT Number: R000159
• CAS Number: 7059-24-7
• Molecular Formula: C57H82O26
• Molecular Weight: 1183.30
• Purity: 98%
• Target: Apoptosis
• Appearance: Yellow powder
• Storage: -20°C
• Analysis method: HPLC
• IUPAC Name: [(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
• InChI: InChI=1S/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
• InChIKey: ZYVSOIYQKUDENJ-WKSBCEQHSA-N
• SMILES: C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@H]2[C@@H](CC3=C(C2=O)C(=C4C(=C3)C=C(C(=C4O)C)O[C@H]5C[C@H]([C@H]([C@H](O5)C)OC(=O)C)O[C@@H]6C[C@H]([C@H]([C@H](O6)C)OC)O)O)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC)O[C@H]7C[C@H]([C@@H]([C@H](O7)C)O)O[C@H]8C[C@]([C@H]([C@@H](O8)C)OC(=O)C)(C)O)O

Chromomycin A3（Cat No.:R000159）is an antitumor antibiotic and DNA-binding compound derived from Streptomyces griseus, known for its ability to inhibit DNA-dependent RNA synthesis. By binding to guanine-cytosine-rich regions in DNA, it disrupts transcription and DNA replication, making it valuable in cancer research and cytogenetic studies. Chromomycin A3 is often used in fluorescent staining to visualize chromosomes, aiding in karyotyping and detecting chromosomal abnormalities. Its unique mechanism highlights its potential in targeting cancer cells, particularly in specific cancers like osteosarcoma, though its clinical use is limited due to toxicity concerns.

Reference

Studies on streptomycetes. On a new antibiotic, chromomycin. Shibata M. et al. J. Antibiotics Ser. B, 1960, 13, 1. 

Aureolic acid group of anti-tumor antibiotics. Berlin Y. A. Nature 1968, 218, 193. 

Transcriptional regulation of differentiation, selective toxicity and ATGCAAAT binding of bisbenzimidazole derivatives in human melanoma cells. Wong S. et al. Biochem. Pharmacol. 1994, 47, 827. 

Specific staining of DNA with the fluorescent antibiotics, mithramycin, chromomycin, and olivomycin. Crissman H. A. & Tobey R. . Methods. Cell Biol. 1990, 33, 97.