26605-16-3

Basic information

• Product Name: NOCARDAMINE
• Synonyms: NOCARDAMINE;PROFERRIOXAMIN E;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;Desferri-ferrioxamine E;Desferrioxamine E;Nocardamin
• CAS NO: 26605-16-3
• Molecular Formula: C27H48N6O9
• Molecular Weight: 600.7
• Mol File: 26605-16-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 192-195°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.162g/cm³
• Refractive Index: 1.495
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (5 mg/ml)
• PKA: 8?+-.0.20(Predicted)
• 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.
• CAS DataBase Reference: NOCARDAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: NOCARDAMINE(26605-16-3)
• EPA Substance Registry System: NOCARDAMINE(26605-16-3)

Safety Data

• Hazardous Substances Data: 26605-16-3(Hazardous Substances Data)

Usage

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.

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

InChI:InChI=1/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)

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 130946-44-0 1,12,23-tris(benzyloxy)-1,6,12,17,23,28-hexaazacyclotritriacontane-2,5,13,16,24,27-hexone 
• 130946-40-6 27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile 
• 130946-42-8 5,16,27-tris(benzyloxy)-31-cyano-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazahentriacontanoic acid 
• 130946-43-9 5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid 
• 130946-41-7 27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile 
• 129245-24-5 5,16-bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid 
• 129245-21-2 O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine 

Relevant articles and documents

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THE TOTAL SYNTHESIS OF DESFERRIOXAMINES E AND G

The total syntheses of the hexacoordinate amino acid, 32-amino-5,16,27-trihydroxy-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid (desferrioxamine G) and the corresponding macrocyclic lactam 1,12,23-trihydroxy-1,6,12,17,23,28-hexaazacycl