26605-16-3 Usage
Description
Nocardamine, a ferrioxamine siderophore, is a cyclic hydroxamic acid siderophore produced by various bacterial species, particularly Streptomyces. It exhibits diverse biological activities, including antitumor properties, and is known for its ability to chelate iron. Nocardamine has demonstrated the capacity to inhibit biofilm formation in certain bacteria and has shown cytotoxic effects on various cancer cell lines, as well as inducing morphological changes in insect cells.
Uses
Used in Anticancer Applications:
Nocardamine is used as an anticancer agent, specifically for its cytotoxic effects on cancer cells such as T47D, SK-MEL-5, SK-MEL-28, and RPMI-7951. It has the potential to be a promising pharmaceutical candidate in the fight against cancer due to its ability to target and inhibit the growth of cancer cells.
Used in Antibiofilm Applications:
In the field of microbiology, Nocardamine is used as an antibiofilm agent to inhibit biofilm formation in bacteria like M. smegmatis and M. bovis. Its effectiveness in disrupting biofilms can be reversed by the presence of iron, highlighting its role as a siderophore in targeting bacterial communities.
Used in Iron Chelation:
Nocardamine is utilized as an iron chelator in various assays, such as the chrome azurol S assay, where it has demonstrated its ability to bind and sequester iron with an IC50 of 9.9 μM. This property makes it a valuable tool in studying iron metabolism and its role in various biological processes.
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
Check Digit Verification of cas no
The CAS Registry Mumber 26605-16-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,6,0 and 5 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 26605-16:
(7*2)+(6*6)+(5*6)+(4*0)+(3*5)+(2*1)+(1*6)=103
103 % 10 = 3
So 26605-16-3 is a valid CAS Registry Number.
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)
26605-16-3Relevant articles and documents
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Keller-Schierlein,Prelog
, p. 1981 (1961)
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THE TOTAL SYNTHESIS OF DESFERRIOXAMINES E AND G
Bergeron, R. J.,McManis, J. S.
, p. 5881 - 5888 (2007/10/02)
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
