An antibacterial and anticancer aureolic acid
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Chromomycin A2

Item No. 26954

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-2,6-dideoxy-3-C-methyl-4-O-(2-methyl-1-oxopropyl)-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
6992-70-7
Synonyms
  • Aburamycin A
  • CMA2
  • NSC 131187
Molecular Formula
C59H86O26
Formula Weight
1211.3
Purity
≥98%
Formulation (Request formulation change)
A powder
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
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(C)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/C59H86O26/c1-22(2)58(70)85-57-29(9)78-43(21-59(57,11)71)82-37-18-40(74-25(5)49(37)66)81-36-19-42(75-26(6)48(36)65)84-56-33(55(73-13)52(69)47(64)24(4)60)15-31-14-32-16-35(23(3)46(63)44(32)50(67)45(31)51(56)68)80-41-20-38(54(28(8)77-41)79-30(10)61)83-39-17-34(62)53(72-12)27(7)76-39/h14,16,22,24-29,33-34,36-43,47-49,53-57,60,62-67,71H,15,17-21H2,1-13H3/t24-,25-,26-,27-,28-,29+,33+,34-,36-,37-,38-,39-,40+,41+,42+,43+,47+,48-,49-,53+,54+,55+,56+,57+,59+/m1/s1
InChi Key
WPLCTUHONLQGIX-TWTCTLMISA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Chromomycin A2 is an aureolic acid that has been found in several marine actinomycetes and has antibacterial and anticancer activities.1,2 Chromomycin A2 inhibits the growth of B. subtilis in an agar diffusion assay.1 It also inhibits the growth of human SGC7901 gastric cancer, HepG2 hepatocellular carcinoma, A549 lung epithelial adenocarcinoma, HCT116 colon cancer, and COC1 ovarian cancer cells, as well as human umbilical vein endothelial cells (HUVECs; IC50s = 4, 0.5, 3, 5, 5, and 8 nM, respectively).2 Chromomycin A2 (30 nM) halts the cell cycle in the G0/G1 phase and increases the protein levels of LC3A and LC3B in MALME-3M melanoma cells, indicating that it induces autophagy.3 It also increases the levels and promoter activity of the autophagic proteins ATG7 and ATG10 and reduces cell viability to 50% in human SCC-11 squamous cell carcinoma cells when used at a concentration of 30 nM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yoshimoto, A., Oki, T., and Inui, T. Differential antimicrobial activities of anthracycline antibiotics on rec-Bacillus subtilis. J. Antibiot. (Tokyo) 31(1), 92-94 (1978).

    2. Lu, J., Ma, Y., Liang, J., et al. Aureolic acids from a marine-derived Streptomyces sp. WBF16. Microbiol. Res. 167(10), 590-595 (2012).

    3. Guimarães, L.A., Jimenez, P.C., da Silva Sousa, T., et al. Chromomycin A2 induces autophagy in melanoma cells. Mar. Drugs 12(12), 5839-5855 (2014).

    4. Ratovitski, E.A. Tumor protein (TP)-p53 members as regulators of autophagy in tumor cells upon marine drug exposure. Mar. Drugs 14(8), E154 (2016).