Amicoumacin B
(Synonyms: Compound 5195A) 目录号 : GC46840
An amicoumacin with quorum-sensing inhibitory activity
Cas No.:82768-33-0
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Amicoumacin B is an amicoumacin that has been found in N. jinanensis and has quorum-sensing inhibitory activity.1 It is active against C. violaceum (MIC = 250 µg/ml) and reduces the expression of the C. violaceum operons vioA, vioB, vioD, and vioE, but increases the expression of vioC, indicating quorum sensing inhibitory activity.2 Amicoumacin B increases the expression of bone morphogenetic protein 2 (BMP2) in MG-63 cells.1,3
1.Sun, W., Zhang, Y.-Q., Huang, Y., et al.Nocardia jinanensis sp. nov., an amicoumacin B-producing actinomyceteInt. J. Syst. Evol. Microbiol.59(Pt 2)417-420(2009) 2.Shi, W.-P., Zeng, H., Wan, C.-X., et al.Amicoumacins from a desert bacterium: quorum sensing inhibitor against Chromobacterium violaceumNat. Prod. Res.(2020) 3.Zhao-Yong, Y., Zhi-Fei, Z., Xiao-Bo, H., et al.Study on the effect of amicoumacin B on up-regulating bmp-2 transcription and expression in MG63 cellsChin. J. Antibiot.33(4)203-205(2008)
| Cas No. | 82768-33-0 | SDF | |
| 别名 | Compound 5195A | ||
| Canonical SMILES | O=C(CC(C(C(C(NC(C1OC(C2=C(C1)C=CC=C2O)=O)CC(C)C)=O)O)O)N)O | ||
| 分子式 | C20H28N2O8 | 分子量 | 424.4 |
| 溶解度 | 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.3563 mL | 11.7813 mL | 23.5627 mL |
| 5 mM | 0.4713 mL | 2.3563 mL | 4.7125 mL |
| 10 mM | 0.2356 mL | 1.1781 mL | 2.3563 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。
Asymmetric Total Synthesis of Hetiamacins A-F
ACS Omega 2021 Mar 17;6(12):8239-8245.PMID:33817482DOI:10.1021/acsomega.0c06267.
Herein, we report a concise and stereoselective approach for the asymmetric total synthesis of hetiamacins A-F on the basis of the total synthesis of amicoumacin C, which could be synthesized from a known l-aspartic acid derivative. The synthesis of hetiamacin A was accomplished by an 11-step sequence that featured 1,3-oxazinane ring formation of Amicoumacin B followed by amidation in one pot. Hetiamacins B-F were synthesized from amicoumacin A in only one step.
Nocardia jinanensis sp. nov., an amicoumacin B-producing actinomycete
Int J Syst Evol Microbiol 2009 Feb;59(Pt 2):417-20.PMID:19196788DOI:10.1099/ijs.0.002899-0.
A novel actinomycete, strain 04-5195(T), that produces Amicoumacin B, which targets bone morphogenetic protein-2, was isolated from a soil sample collected in Jinan, Shandong Province, China. Strain 04-5195(T) had morphological, biochemical, physiological and chemotaxonomic properties that were consistent with its classification in the genus Nocardia and it formed a phyletic line in the Nocardia 16S rRNA gene tree. It was evident from the phylogenetic data that strain 04-5195(T) was most closely associated with Nocardia speluncae N2-11(T). However, the two organisms were distinguishable from one another using DNA-DNA relatedness and phenotypic data. The isolate was readily differentiated from other related Nocardia strains by a set of phenotypic properties and by its phylogenetic position. Therefore, it is proposed that the isolate represents a novel species in the genus Nocardia, Nocardia jinanensis sp. nov.; the type strain is 04-5195(T) (=CGMCC 4.3508(T) =DSM 45048(T)).
Amicoumacins from a desert bacterium: quorum sensing inhibitor against Chromobacterium violaceum
Nat Prod Res 2021 Dec;35(23):5508-5512.PMID:32640925DOI:10.1080/14786419.2020.1788554.
In our study, the anti-quorum sensing (QS) activity of fermentation broth from TRM B-02, a bacterium isolated from Taklimakan desert, was investigated using the biosensor bioassay on Chromobacterium violaceum ATCC12472. TRM B-02 was 100% similar to Bacillus subtilis subsp. Inaquosorum KCTC 13429(T) by genotypic and phenotypic analyses. Based on anti-QS activity tracking, six known amicoumacins, named as AI-77-H (1), AI-77-F (2), Amicoumacin B (3), amicoumacin C (4), AI-77-C (5) and bacilosarcins D (6), were isolated and identified. Among them, compounds 1-3 exhibited a better inhibitory effect on C. violaceum ATCC12472. Further research suggested that compounds 1-3 could significantly down-regulate the expressions of violacein operon A (vioA), vioB, vioD and vioE and up-regulate vioC. Docking experiments indicated that compounds 1-3 may act as an inhibitor of violacein biosynthetic pathway competitively inhibiting the binding of flavin adenine dinucleotide (FAD) with the vioD enzyme.[Figure: see text].
Original preparation of conjugates for antibody production against Amicoumacin-related anti-microbial agents
Bioorg Med Chem 2008 Oct 15;16(20):9383-91.PMID:18818086DOI:10.1016/j.bmc.2008.08.017.
Amicoumacins are natural products with potent anti-ulcerogenic and anti-bacterial activities, and have been isolated from different Bacillus genera. They belong to a family of 3,4-dihydroisocoumarin derivatives bearing hydroxylated amino acid side chains. The 3,4-dihydroisocoumarin moiety of Amicoumacins has been obtained in two steps from 2-methoxybenzoic acid by combining directed and benzylic metalation strategies. The use of s-BuLi in both steps gave satisfactory and reproducible yields. For the development of an immunoassay (ELISA) of Amicoumacin-related compounds in biological media, the deprotected 3,4-dihydroisocoumarin moiety has been coupled to the BSA carrier protein via a homobifunctional linker deriving from d-tartaric acid. This approach enabled to introduce the hydroxylated portion of Amicoumacin directly during the preparation of hapten-protein conjugates. The coupling ratio was evaluated by mass spectrometry. The hapten-protein conjugate showing the best coupling ratio was used to generate polyclonal immunosera in rabbits. After immunoserum titration, ELISA conditions were set up and specificity tests were performed on solutions of pure parent compounds, semi-purified Amicoumacin B as well as on culture supernatants of strains known for their Amicoumacin production. This immunoassay is suitable for a rapid and simple screening test for the production of Amicoumacins and its related compounds by bacterial strains.