A bacterial metabolite with diverse biological activities
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Collismycin A

Item No. 27622

Technical Information
Formal Name
[C(E)]-4-methoxy-5-(methylthio)-[2,2'-bipyridine]-6-carboxaldehyde oxime
CAS Number
158792-24-6
Synonyms
  • SF 2738A
Molecular Formula
C13H13N3O2S
Formula Weight
Purity
≥95%
A solid
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
COC1=C(SC)C(/C=N/O)=NC(C2=NC=CC=C2)=C1
InChi Code
InChI=1S/C13H13N3O2S/c1-18-12-7-10(9-5-3-4-6-14-9)16-11(8-15-17)13(12)19-2/h3-8,17H,1-2H3/b15-8+
InChi Key
NQGMIPUYCWIEAW-OVCLIPMQSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Collismycin A is a bacterial metabolite originally isolated from Streptomyces that has diverse biological activities, including antibacterial, antiproliferative, and neuroprotective properties.1 It is active against a variety of bacteria (MICs = 6.25 and 100 µg/ml) and fungi (MICs = 12.5-100 µg/ml). It inhibits proliferation of A549 lung, HCT116 colon, and HeLa cervical cancer cells (IC50s = 0.3, 0.6, and 0.3 µM, respectively) and NIH373 fibroblasts (IC50 = 56.6 µM) but not MDA-MD-231 breast cancer cells (IC50 = >100 µM).2,3 Collismycin A forms a complex with Fe(II) and Fe(III) at a 2:1 ratio, and the addition of iron ions inhibits the antiproliferative effect of collismycin A on HeLa cells, an effect that does not occur with the addition of zinc, manganese, copper, or magnesium ions.3 Collismycin A (1 µM) prevents apoptosis in the brain region of zebrafish larvae by 44% in a model of neuronal cell death induced by all-trans retinoic acid (Item No. 11017).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gomi, S., Amano, S., Sato, E., et alNovel antibiotics SF2738A, B and C, and their analogs produced by Streptomyces sp. J. Antibiot. (Tokyo) 47(12), 1385-1394 (1994).

    2. Garcia, I., Vior, N.M., González-Sabín, J., et alEngineering the biosynthesis of the polyketide-nonribosomal peptide collismycin A for generation of analogs with neuroprotective activity. Chem. Biol. 20(8), 1022-1032 (2013).

    3. Kawatani, M., Muroi, M., Wada, A., et alProteomic profiling reveals that collismycin A is an iron chelator. Sci. Rep. 6:38385, (2016).