A fluorescent probe and antitumor agent
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Chromomycin A3

Item No. 11315

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S)-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]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-5-deoxy-1-O-methyl-D-threo-2-pentulose
CAS Number
7059-24-7
Synonyms
  • Aburamycin B
  • CMA3
  • NSC 58514
Molecular Formula
C57H82O26
Formula Weight
1183.3
Purity
≥95%
Emission
575 nm
Excitation
445 nm
Formulation (Request formulation change)
A powder
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleEthyl Acetate: 10 mg/ml
λmax
229, 279, 414 nm
SMILES
C[C@H]1O[C@@](O[C@@H]2C[C@H](OC3=CC(C=C(C[C@]([C@H](OC)C([C@@H](O)[C@H](O)C)=O)([H])[C@H](O[C@]4([H])O[C@H](C)[C@@H](O)[C@H](O[C@]5([H])O[C@H](C)[C@@H](O)[C@H](O[C@@]6([H])C[C@@](O)(C)[C@@H](OC(C)=O)[C@H](C)O6)C5)C4)C7=O)C7=C8O)=C8C(O)=C3C)O[C@H](C)[C@@H]2OC(C)=O)([H])C[C@@H](O)[C@H]1OC
InChi Code
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
InChi Key
ZYVSOIYQKUDENJ-WKSBCEQHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product 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.1,2 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.2,3 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).4,5 It also inhibits oxidative stress- and DNA damage-induced neuronal injury by enhancing Sp1 and Sp3 transcription factor binding.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Crissman, H.A., and Tobey, R.A. Methods in cell biology. 33, (1990).

    2. Van Dyke, M.W., and Dercan, P.B. Chromomycin, mithramycin, and olivomycin binding sites on heterogeneous deoxyribonucleic acid. Footprinting with (methidiumpropyl-EDTA)iron(II). Biochemistry 22(10), 2373-2377 (1983).

    3. Schwarzacher, T. Methods in molecular biology. 1370, (2016).

    4. Miller, S.C., Huang, R., Sakamuru, S., et al. Identification of known drugs that act as inhibitors of NF-κB signaling and their mechanism of action. Biochem. Pharmacol. 79(9), 1272-1280 (2016).

    5. Chatterjee, S., Zaman, K., Ryu, H., et al. 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. Ann. Neurol. 49(3), 345-354 (2001).