NOCARDAMINE Chemical Properties

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.

NOCARDAMINE Usage And Synthesis

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

[1] VINCENT NORMANT. Nocardamine-Dependent Iron Uptake in Pseudomonas aeruginosa: Exclusive Involvement of the FoxA Outer Membrane Transporter[J]. ACS Chemical Biology, 2020, 15 10: 2741-2751. DOI:10.1021/acschembio.0c00535
[2] UEKI M, SUZUKI R, TAKAMATSU S, et al. Nocardamin Production by Streptomyces avermitilis[C]//285 1. 2009: 0. DOI:10.3209/saj.saj230203
[3] HONG-FA YAN. Ferroptosis: mechanisms and links with diseases.[J]. Signal Transduction and Targeted Therapy, 2021, 6 1: 49. DOI:10.1038/s41392-020-00428-9
[4] NATALIYA I. KALINOVSKAYA . Marine isolate Citricoccus sp. KMM 3890 as a source of a cyclic siderophore nocardamine with antitumor activity[J]. Microbiological research, 2011, 166 8: Pages 654-661. DOI:10.1016/j.micres.2011.01.004
[5] F. MAHMUD. Bioactivities and Mode of Actions of Dibutyl Phthalates and Nocardamine from Streptomyces sp. H11809[J]. Molecules, 2022. DOI:10.3390/molecules27072292

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