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26605-16-3

26605-16-3 Structure

26605-16-3 Structure
IdentificationBack Directory
[Name]

NOCARDAMINE
[CAS]

26605-16-3
[Synonyms]

Nocardamin
NOCARDAMINE
PROFERRIOXAMIN E
deferrioxamine E
Desferrioxamine E
Desferri-ferrioxamine E
Nocardamine (Deferrioxamine E)
1,12,23-Trihydroxy-1,6,12,17,23,28-hexaazacyclotritriacontane-2,5,13,16,24,27-hexone
6,17,28-Trihydroxy-1,6,12,17,23,28-hexaazacyclotritriacontane-2,5,13,16,24,27-hexaone
1,6,12,17,23,28-Hexaazacyclotritriacontane-2,5,13,16,24,27-hexone, 1,12,23-trihydroxy-
[Molecular Formula]

C27H48N6O9
[MDL Number]

MFCD08457937
[MOL File]

26605-16-3.mol
[Molecular Weight]

600.7
Chemical PropertiesBack Directory
[Melting point ]

192-195°
[density ]

1.162±0.06 g/cm3(Predicted)
[storage temp. ]

-20°C
[solubility ]

Soluble in DMSO (5 mg/ml)
[form ]

solid
[pka]

8?+-.0.20(Predicted)
[color ]

Off-white
[Stability:]

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
Hazard InformationBack Directory
[Description]

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

Nocardamine is a cyclic siderophore.
[Definition]

ChEBI: A cyclic hydroxamic acid siderophore that is produced by several bacterial species and exhibits antitumour activity.
[storage]

+4°C
[References]

Normant et al. (2020), Nocardamine-Dependent Iron Uptake in Pseudomonas aeruginosa: Exclusive Involvement of the FoxA Outer Membrane Transporter; ACS Chem. Biol. 15 2741 Ueki et al. (2009), Nocardamin Production by Streptomyces avermitilis; Actinomycetologica 23 34 Yan et al. (2021), Ferroptosis: mechanisms and links with diseases; Signal Transduct. Target Ther. 6 49 Kalinovskaya et al. (2011), Marine isolate Citricoccus sp. KMM 3890 as a source of a cyclic siderophore nocardamine with antitumor activity; Res. 166 654 Mahmud et al. (2022), Bioactivities and Mode of Actions of Dibutyl Phthalates and Nocardamine from Streptomyces sp. H11809; Molecules 27 2292
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