Nocardamine
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| Category | Antibiotics |
| Catalog number | BBF-02606 |
| CAS | 26605-16-3 |
| Molecular Weight | 600.70 |
| Molecular Formula | C27H48N6O9 |
| Purity | ≥95% |
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Description
Nocardamine, derived from Nocardia sp., has anti-mycobacterium activity.
Specification
| Synonyms | Nocardamin; Deferrioxamine E; 1,12,23-tris(oxidanyl)-1,6,12,17,23,28-hexazacyclotritriacontane-2,5,13,16,24,27-hexone |
| Storage | Store at -20°C |
| IUPAC Name | 1,12,23-trihydroxy-1,6,12,17,23,28-hexazacyclotritriacontane-2,5,13,16,24,27-hexone |
| Canonical SMILES | C1CCNC(=O)CCC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCNC(=O)CCC(=O)N(CC1)O)O)O |
| InChI | InChI=1S/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) |
| InChI Key | NHKCCADZVLTPPO-UHFFFAOYSA-N |
Properties
| Appearance | Needle Crystal |
| Antibiotic Activity Spectrum | mycobacteria |
| Melting Point | 183-184°C |
| Density | 1.16 g/cm3 |
| Solubility | Soluble in water, DMSO, and hot methanol. Insoluble in chloroform, ethyl acetate, and hexane. |
Reference Reading
1. Nocardamine-Dependent Iron Uptake in Pseudomonas aeruginosa: Exclusive Involvement of the FoxA Outer Membrane Transporter
Vincent Normant, Inokentijs Josts, Lauriane Kuhn, Quentin Perraud, Sarah Fritsch, Philippe Hammann, Gaëtan L A Mislin, Henning Tidow, Isabelle J Schalk ACS Chem Biol. 2020 Oct 16;15(10):2741-2751. doi: 10.1021/acschembio.0c00535. Epub 2020 Sep 24.
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.
2. Aromatic Polyketides and Hydroxamate Siderophores from a Marine-Algae-Derived Streptomyces Species
Kunyu Xia, Hui Luo, Rui Ma, Rongxin Zhang, Weiming Zhu, Peng Fu J Nat Prod. 2021 May 28;84(5):1550-1555. doi: 10.1021/acs.jnatprod.1c00061. Epub 2021 May 13.
Four new aromatic polyketides, wailupemycins M-P (1-4), and two new hydroxamate siderophores, streptamides A (5) and B (6), together with the previously reported nocardamine (7), were isolated from the marine-algae-derived Streptomyces sp. OUCMDZ-3434. Wailupemycins M-P (1-4), possessing an α-pyrone moiety, were isolated from the extract of a liquid fermentation, and the siderophores (5-7) were isolated from the extract of a solid fermentation. Their structures were assigned based on detailed spectroscopic analysis and quantum chemical calculations. Compounds 5-7 were capable of binding Fe(III). Compound 5 can form a tighter Fe(III) complex than that of deferoxamine B mesylate (DFB).
3. Bioactivities and Mode of Actions of Dibutyl Phthalates and Nocardamine from Streptomyces sp. H11809
Fauze Mahmud, Ngit Shin Lai, Siew Eng How, Jualang Azlan Gansau, Khairul Mohd Fadzli Mustaffa, Chiuan Herng Leow, Hasnah Osman, Hasidah Mohd Sidek, Noor Embi, Ping-Chin Lee Molecules. 2022 Mar 31;27(7):2292. doi: 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.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
