A microbial metabolite with anticancer activity
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N,N'-bis(2,3-Dihydroxybenzoyl)-O-L-seryl-L-serine

Item No. 31778

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2,3-dihydroxybenzoyl)-O-[N-(2,3-dihydroxybenzoyl)-L-seryl]-L-serine
CAS Number
30414-15-4
Molecular Formula
C20H20N2O11
Formula Weight
464.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Slightly soluble: 0.1-1 mg/ml
SMILES
O=C(C1=C(C(O)=CC=C1)O)N[C@H](C(O)=O)COC([C@H](CO)NC(C2=C(C(O)=CC=C2)O)=O)=O
InChi Code
InChI=1S/C20H20N2O11/c23-7-11(21-17(28)9-3-1-5-13(24)15(9)26)20(32)33-8-12(19(30)31)22-18(29)10-4-2-6-14(25)16(10)27/h1-6,11-12,23-27H,7-8H2,(H,21,28)(H,22,29)(H,30,31)/t11-,12-/m0/s1
InChi Key
KLXJDVFEFZPIMN-RYUDHWBXSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

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    Product Description

    N,N'-bis(2,3-Dihydroxybenzoyl)-O-L-seryl-L-serine is a microbial metabolite and degradation product of the bacterial siderophore enterobactin that has been found in Streptomyces and has anticancer activity.1,2,3 It inhibits invasion of 26-L5 murine colon cancer cells in a Matrigel™ assay with an IC50 value of 2.7 µM.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Igarashi, Y., Iida, T., Fukuda, T., et al. Catechoserine, a new catecholate-type inhibitor of tumor cell invasion from Streptomyces sp. J. Antibiot. (Tokyo) 65(4), 207-209 (2012).

    2. O'Brien, I.G., Cox, G.B., and Gibson, F. Enterochelin hydrolysis and iron metabolism in Escherichia coli. Biochim. Biophys. Acta 237(3), 537-549 (1971).

    3. Raines, D.J., Moroz, O.V., Blagova, E.V., et al. Bacteria in an intense competition for iron: Key component of the Campylobacter jejuni iron uptake system scavenges enterobactin hydrolysis product. Proc. Natl. Acad. Sci. USA 113(21), 5850-5855 (2016).