A ferrioxamine siderophore
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Nocardamine

Item No. 28745

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,12,23-trihydroxy-1,6,12,17,23,28-hexaazacyclotritriacontane-2,5,13,16,24,27-hexone
CAS Number
26605-16-3
Synonyms
  • Desferrioxamine E
  • Proferrioxamine E
Molecular Formula
C27H48N6O9
Formula Weight
600.7
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C(CCC(N(O)CCCCCNC(CCC1=O)=O)=O)NCCCCCN(O)C(CCC(NCCCCCN1O)=O)=O
InChi Code
InChI=1S/C27H48N6O9/c34-22-10-14-26(38)32(41)20-8-3-6-18-30-24(36)12-15-27(39)33(42)21-9-2-5-17-29-23(35)11-13-25(37)31(40)19-7-1-4-16-28-22/h40-42H,1-21H2,(H,28,34)(H,29,35)(H,30,36)
InChi Key
NHKCCADZVLTPPO-UHFFFAOYSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $120

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    Product Description

    Nocardamine is a ferrioxamine siderophore that has been found in Streptomyces and has diverse biological activities.1,2,3,4 It chelates iron in a chrome azurol S assay (IC50 = 9.9 µM).1 Nocardamine inhibits M. smegmatis and M. bovis biofilm formation (MIC = 10 µM for both), an effect that can be reversed by iron.2 It is cytotoxic to T47D, SK-MEL-5, SK-MEL-28, and RPMI-7951 cancer cells (IC50s = 6, 18, 12, and 14 µM, respectively).3 Nocardamine also induces morphological changes in BM-N4 insect cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lopez, J.A.V., Nogawa, T., Futamura, Y., et al. Nocardamin glucuronide, a new member of the ferrioxamine siderophores isolated from the ascamycin-producing strain Streptomyces sp. 80H647. J. Antibiot. (Tokyo) 72(12), 991-995 (2019).

    2. Ishida, S., Arai, M., Niikawa, H., et al. Inhibitory effect of cyclic trihydroxamate siderophore, desferrioxamine E, on the biofilm formation of Mycobacterium species. Biol. Pharm. Bull. 34(6), 917-920 (2011).

    3. Kalinovskaya, N.I., Romaneko, L.A., Irisawa, T., et al. Marine isolate Citricoccus sp. KMM 3890 as a source of a cyclic siderophore nocardamine with antitumor activity. Microbiol. Res. 166(8), 654-661 (2011).

    4. Matsubara, K., Sakuda, S., Tanaka, M., et al. Morphological changes in insect BM-N4 cells induced by nocardamine. Biosci. Biotechnol. Biochem. 62(10), 2049-2051 (1998).