Myxochelin A
(Synonyms: (S)-Myxochelin A) 目录号 : GC47716
A microbial metabolite with diverse biological activities
Cas No.:120243-02-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Myxochelin A is a microbial metabolite that has been found in A. disciformis and has diverse biological activities.1 It is active against Gram-positive bacteria, including B. cereus, S. aureus, and M. luteus, but not Gram-negative bacteria or fungi in an agar diffusion assay when used at a concentration of 80 µg/disc. Myxochelin A inhibits 5-lipoxygenase (5-LO) activity with an IC50 value of 1.9 µM for the recombinant human enzyme.2 It is cytotoxic to 26-L5 colon cancer cells when used at a concentration of 3 µg/ml.3
1.Kunze, B., Bedorf, N., Kohl, W., et al.Myxochelin A, a new iron-chelating compound from Angiococcus disciformis (Myxobacterales). Production, isolation, physico-chemical and biological propertiesJ. Antibiot. (Tokyo)42(1)14-17(1989) 2.Schieferdecker, S., KÖnig, S., Koeberle, A., et al.Myxochelins target human 5-lipoxygenaseJ. Nat. Prod.78(2)335-338(2015) 3.Miyanaga, S., Obata, T., Onaka, H., et al.Absolute configuration and antitumor activity of myxochelin A produced by Nonomuraea pusilla TP-A0861J. Antibiot. (Tokyo)59(11)698-703(2006)
| Cas No. | 120243-02-9 | SDF | |
| 别名 | (S)-Myxochelin A | ||
| Canonical SMILES | OC1=C(O)C(C(N[C@H](CO)CCCCNC(C2=CC=CC(O)=C2O)=O)=O)=CC=C1 | ||
| 分子式 | C20H24N2O7 | 分子量 | 404.4 |
| 溶解度 | DMSO: soluble,Ethanol: soluble,Methanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.4728 mL | 12.364 mL | 24.728 mL |
| 5 mM | 0.4946 mL | 2.4728 mL | 4.9456 mL |
| 10 mM | 0.2473 mL | 1.2364 mL | 2.4728 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Myxochelin- and Pseudochelin-Derived Lipoxygenase Inhibitors from a Genetically Engineered Myxococcus xanthus Strain
J Nat Prod 2019 Sep 27;82(9):2544-2549.PMID:31465225DOI:10.1021/acs.jnatprod.9b00403.
Precursor-directed biosynthesis was used to introduce selected aryl carboxylic acids into the pseudochelin pathway, which had recently been assembled in Myxococcus xanthus. Overall, 14 previously undescribed analogues of the natural products myxochelin B and pseudochelin A were generated and structurally characterized. A subset of 10 derivatives together with their parental molecules were evaluated for their activity toward human 5-lipoxygenase. This testing revealed pseudochelin A as the most potent 5-lipoxygenase inhibitor among the naturally occurring compounds, whereas Myxochelin A is the least active. Replacement of the catechol moieties in myxochelin B and pseudochelin A affected the bioactivity to different degrees.
Myxochelin A, a new iron-chelating compound from Angiococcus disciformis (Myxobacterales). Production, isolation, physico-chemical and biological properties
J Antibiot (Tokyo) 1989 Jan;42(1):14-7.PMID:2493439DOI:10.7164/antibiotics.42.14.
Myxochelin A, a new catechole siderophore, was isolated from the culture broth of the myxobacterium, Angiococcus disciformis strain An d30. As is the case with other iron-chelating compounds the production of Myxochelin A could be markedly increased up to 44 mg/liter by fermentation at low iron concentrations (10(-7) M FeCl3). The new substance showed weak activity against some bacteria.
Draft Genome Sequence of Nonomuraea sp. TP-A0861, a Producer of Myxochelin A
Genome Announc 2015 Dec 10;3(6):e01430-15.PMID:26659677DOI:10.1128/genomeA.01430-15.
Nonomuraea sp. TP-A0861 produces the nonribosomal peptide Myxochelin A, which is known as a microbial siderophore. Here, we report its draft genome sequence. The genome contains at least three nonribosomal peptide synthetase gene clusters, one of which is proposed to be responsible for the biosynthesis of Myxochelin A.
Myxochelin-Inspired 5-Lipoxygenase Inhibitors: Synthesis and Biological Evaluation
ChemMedChem 2017 Jan 5;12(1):23-27.PMID:27875023DOI:10.1002/cmdc.201600536.
A total of 48 analogues of the natural product Myxochelin A were prepared and evaluated for their inhibitory effects on human 5-lipoxygenase in both cell-free and cell-based assays. Structure-activity relationship analysis revealed that the secondary alcohol function and only chiral center of Myxochelin A is not required for biological activity. By expanding the diaminoalkane linker of the two aromatic residues it was possible to generate a myxochelin derivative with superior activity against 5-lipoxygenase in intact cells.
Myxochelin biosynthesis: direct evidence for two- and four-electron reduction of a carrier protein-bound thioester
J Am Chem Soc 2008 Jun 18;130(24):7554-5.PMID:18498160DOI:10.1021/ja8025278.
Microorganisms produce small molecules known as siderophores to scavenge iron from the environment. Insight into iron acquisition in myxobacteria has been provided recently by the sequencing of the gene cluster for the catecholate myxochelins A and B, from the myxobacterium Stigmatella aurantiaca Sg a15. The gene cluster contains enzymes (MxcCDEF) for assembly of 2,3-dihydroxybenzoic acid (DHBA), an amino transferase, MxcL, and a nonribosomal peptide synthetase (NRPS) subunit, MxcG. In the proposed pathway to the myxochelins, two molecules of DHBA are condensed with the two amino groups of lysine, which is itself tethered to the peptidyl carrier protein domain (PCP) of MxcG. The resulting thioester is then reduced by the NADPH-dependent reductase (Red) domain of MxcG to generate an aldehyde intermediate; subsequent Red-catalyzed reduction yields Myxochelin A, while transamination by MxcL produces myxochelin B. Although Myxochelin A has been obtained successfully in vitro, it has not been possible to date to reconstitute the transamination reaction to give myxochelin B nor to unequivocally establish the intermediacy of the aldehyde. We report here the successful biosynthesis of myxochelin B in vitro. Furthermore, we demonstrate for the first time the existence of an aldehyde intermediate in the four-electron reduction of a PCP-bound thioester. Finally, we show that the relative levels of Myxochelin A and B are likely to be controlled by the direct competition of MxcL and the MxcG Red domain for a free aldehyde intermediate.