Nocardamine
(Synonyms: Desferrioxamine E, Proferrioxamine E) 目录号 : GC47787A ferrioxamine siderophore
Cas No.:26605-16-3
Sample solution is provided at 25 µL, 10mM.
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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
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. 80H647J. 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 speciesBiol. 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 activityMicrobiol. Res.166(8)654-661(2011) 4.Matsubara, K., Sakuda, S., Tanaka, M., et al.Morphological changes in insect BM-N4 cells induced by nocardamineBiosci. Biotechnol. Biochem.62(10)2049-2051(1998)
Cas No. | 26605-16-3 | SDF | |
别名 | Desferrioxamine E, Proferrioxamine E | ||
Canonical SMILES | O=C(CCC(N(O)CCCCCNC(CCC1=O)=O)=O)NCCCCCN(O)C(CCC(NCCCCCN1O)=O)=O | ||
分子式 | C27H48N6O9 | 分子量 | 600.7 |
溶解度 | Dichloromethane: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.6647 mL | 8.3236 mL | 16.6472 mL |
5 mM | 0.3329 mL | 1.6647 mL | 3.3294 mL |
10 mM | 0.1665 mL | 0.8324 mL | 1.6647 mL |
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Nocardamine-Dependent Iron Uptake in Pseudomonas aeruginosa: Exclusive Involvement of the FoxA Outer Membrane Transporter
ACS Chem Biol 2020 Oct 16;15(10):2741-2751.PMID:32902248DOI:10.1021/acschembio.0c00535.
Iron is a key nutrient for almost all living organisms. Paradoxically, it is poorly soluble and consequently poorly bioavailable. Bacteria have thus developed multiple strategies to access this metal. One of the most common consists of the use of siderophores, small compounds that chelate ferric iron with very high affinity. Many bacteria are able to produce their own siderophores or use those produced by other microorganisms (exosiderophores) in a piracy strategy. Pseudomonas aeruginosa produces two siderophores, pyoverdine and pyochelin, and is also able to use a large panel of exosiderophores. We investigated the ability of P. aeruginosa to use Nocardamine (NOCA) and ferrioxamine B (DFOB) as exosiderophores under iron-limited planktonic growth conditions. Proteomic and RT-qPCR approaches showed induction of the transcription and expression of the outer membrane transporter FoxA in the presence of NOCA or DFOB in the bacterial environment. Expression of the proteins of the heme- or pyoverdine- and pyochelin-dependent iron uptake pathways was not affected by the presence of these two tris-hydroxamate siderophores. 55Fe uptake assays using foxA mutants showed ferri-NOCA to be exclusively transported by FoxA, whereas ferri-DFOB was transported by FoxA and at least one other unidentified transporter. The crystal structure of FoxA complexed with NOCA-Fe revealed very similar siderophore binding sites between NOCA-Fe and DFOB-Fe. We discuss iron uptake by hydroxamate exosiderophores in P. aeruginosa cells in light of these results.
Bioactivities and Mode of Actions of Dibutyl Phthalates and Nocardamine from Streptomyces sp. H11809
Molecules 2022 Mar 31;27(7):2292.PMID:35408690DOI:10.3390/molecules27072292.
Dibutyl phthalate (DBP) produced by Streptomyces sp. H11809 exerted inhibitory activity against human GSK-3β (Hs GSK-3β) and Plasmodiumfalciparum 3D7 (Pf 3D7) malaria parasites. The current study aimed to determine DBP's plausible mode of action against Hs GSK-3β and Pf 3D7. Molecular docking analysis indicated that DBP has a higher binding affinity to the substrate-binding site (pocket 2; -6.9 kcal/mol) than the ATP-binding site (pocket 1; -6.1 kcal/mol) of Hs GSK-3β. It was suggested that the esters of DBP play a pivotal role in the inhibition of Hs GSK-3β through the formation of hydrogen bonds with Arg96/Glu97 amino acid residues in pocket 2. Subsequently, an in vitro Hs GSK-3β enzymatic assay revealed that DBP inhibits the activity of Hs GSK-3β via mixed inhibition inhibitory mechanisms, with a moderate IC50 of 2.0 µM. Furthermore, the decrease in Km value with an increasing DBP concentration suggested that DBP favors binding on free Hs GSK-3β over its substrate-bound state. However, the antimalarial mode of action of DBP remains unknown since the generation of a Pf 3D7 DBP-resistant clone was not successful. Thus, the molecular target of DBP might be indispensable for Pf survival. We also identified Nocardamine as another active compound from Streptomyces sp. H11809 chloroform extract. It showed potent antimalarial activity with an IC50 of 1.5 μM, which is ~10-fold more potent than DBP, but with no effect on Hs GSK-3β. The addition of ≥12.5 µM ferric ions into the Pf culture reduced Nocardamine antimalarial activity by 90% under in vitro settings. Hence, the iron-chelating ability of Nocardamine was shown to starve the parasites from their iron source, eventually inhibiting their growth.
Cyclic peptides of the Nocardamine class from a marine-derived bacterium of the genus Streptomyces
J Nat Prod 2005 Apr;68(4):623-5.PMID:15844966DOI:10.1021/np040220g.
Two new cyclic peptides (2 and 3) along with the previously reported Nocardamine (1) were isolated from the culture broth of an actinomycete of the genus Streptomyces isolated from an unidentified marine sponge. On the basis of the results of combined spectral analyses, the structures of the new compounds were defined to be the dehydroxy and desmethylenyl derivatives of Nocardamine, respectively. The new compounds exhibited weak inhibition against the enzyme sortase B.
Genome Sequencing of Streptomyces atratus SCSIOZH16 and Activation Production of Nocardamine via Metabolic Engineering
Front Microbiol 2018 Jun 13;9:1269.PMID:29963027DOI:10.3389/fmicb.2018.01269.
The Actinomycetes are metabolically flexible microorganisms capable of producing a wide range of interesting compounds, including but by no means limited to, siderophores which have high affinity for ferric iron. In this study, we report the complete genome sequence of marine-derived Streptomyces atratus ZH16 and the activation of an embedded siderophore gene cluster via the application of metabolic engineering methods. The S. atratus ZH16 genome reveals that this strain has the potential to produce 26 categories of natural products (NPs) barring the ilamycins. Our activation studies revealed S. atratus SCSIO ZH16 to be a promising source of the production of nocardamine-type (desferrioxamine) compounds which are important in treating acute iron intoxication and performing ecological remediation. We conclude that metabolic engineering provides a highly effective strategy by which to discover drug-like compounds and new NPs in the genomic era.
nonG, a constituent of the nonactin biosynthetic gene cluster, regulates Nocardamine synthesis in Streptomyces albus J1074
Biochem Biophys Res Commun 2017 Aug 26;490(3):664-669.PMID:28634080DOI:10.1016/j.bbrc.2017.06.098.
Many factors regulate the expression of specialised secondary metabolite biosynthetic gene clusters, which have been recognised as important for the discovery of novel microbial natural products. A cosmid library based on genomic DNA of the marine-derived Streptomyces puniceus Act1085 was constructed and screened to identify a short gene cluster similar to the nonactin biosynthetic cluster. The ORFs of the gene cluster isolated had high amino acid sequence identity, from 82% to 96%, with corresponding ORFs of the nonactin biosynthetic gene cluster from S. griseus subsp. griseus ETH A7796. Despite the expectation that nonactin or its derivatives would be made from heterologous expression of the gene cluster found in S. albus J1074, Nocardamine was isolated. The heterologous expression data indicate that the production of Nocardamine in S. albus J1074 is due to an ortholog of nonG, a TetR family transcriptional regulator, from S. puniceus Act1085.