Fusarisetin A
(Synonyms: (+)-Fusarisetin A) 目录号 : GC43719
An inhibitor of acinar morphogenesis
Cas No.:1300041-53-5
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
Fusarisetin A is a pentacyclic fungal metabolite first isolated from Fusarium species. At 3-30 µg/ml, it is reported to inhibit acinar morphogenesis, cell migration, and invasion in a 3D-matrigel assay system designed to study tumor cell motility.
| Cas No. | 1300041-53-5 | SDF | |
| 别名 | (+)-Fusarisetin A | ||
| Canonical SMILES | O=C1[C@]23[C@]([C@H](C)O[C@@]2(O)[C@H](CO)N(C)C3=O)([H])[C@]4([H])C=C[C@]5([H])C[C@H](C)CC[C@@]5([H])[C@@]41C | ||
| 分子式 | C22H31NO5 | 分子量 | 389.5 |
| 溶解度 | Soluble in DMSO | 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 | 2.5674 mL | 12.837 mL | 25.6739 mL |
| 5 mM | 0.5135 mL | 2.5674 mL | 5.1348 mL |
| 10 mM | 0.2567 mL | 1.2837 mL | 2.5674 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。
Fusarisetin A: Scalable Total Synthesis and Related Studies
Chem Sci 2012 Jan 1;3(12):3378-3386.PMID:23227303DOI:10.1039/C2SC21308G.
Fusarisetin A (1) is a recently isolated natural product that displays an unprecedented chemical motif and remarkable bioactivities as a potent cancer migration inhibitor. We describe here our studies leading to an efficient and scalable total synthesis of 1. Essential to the strategy was the development of a new route for the formation of a trans-decalin moiety of this compound and the application of an oxidative radical cyclization (ORC) reaction that produces Fusarisetin A (1) from equisetin (2) via a bio-inspired process. TEMPO-induced and metal/O(2)-promoted ORC reactions were evaluated. Biological screening in vitro confirms the reported potency of (+)-1. Importantly, ex vivo studies show that this compound is able to inhibit different types of cell migration. Moreover, the C(5) epimer of (+)-1 was also identified as a potent cancer migration inhibitor, while (-)-1 and 2 were found to be significantly less potent. The optimized synthesis is applicable on gram scale and provides a solid platform for analogue synthesis and methodical biological study.
Fusarisetin A, an acinar morphogenesis inhibitor from a soil fungus, Fusarium sp. FN080326
J Am Chem Soc 2011 May 11;133(18):6865-7.PMID:21500849DOI:10.1021/ja1110688.
An acinar morphogenesis inhibitor named Fusarisetin A (1) that possesses both an unprecedented carbon skeleton and a new pentacyclic ring system has been identified from an in-house fractionated fungal library using a three-dimensional matrigel-induced acinar morphogenesis assay system. The structure of 1 was determined in detail by NMR and circular dichroism spectroscopy, X-ray analysis, and chemical reaction experiments.
Asymmetric total synthesis of (+)-fusarisetin A via the intramolecular Pauson-Khand reaction
Org Lett 2013 Aug 2;15(15):4018-21.PMID:23869720DOI:10.1021/ol401831w.
An asymmetic total synthesis of (+)-fusarisetin A has been achieved. The essential to our strategy was the application of the intramolecular Pauson-Khand reaction for the stereoselective construction of the trans-decalin subunit of (+)-fusarisetin A with a unique C16 quarternary chiral center. The developed chemistry offers an alternative to the IMDA reaction that has been used for Fusarisetin A, and is applicable to analogue synthesis for biological evaluation.
Total synthesis and biological studies of cryptocin and derivatives of equisetin and Fusarisetin A
Org Biomol Chem 2014 Oct 14;12(38):7591-7.PMID:25139438DOI:10.1039/c4ob01149j.
Total synthesis of cryptocin, a fungus metabolite, was achieved based on the biosynthetic hypothesis. A variety of derivatives of cryptocin, equisetin and Fusarisetin A were prepared, wherein the racemization of C-3 and diastereoselectivity of C-5 were investigated. We further examined their inhibitory effects on breast cancer cell survival and metastasis, and summarized the structure-activity relationship.
Fusarisetins: Structure-function studies on a novel class of cell migration inhibitors
Org Chem Front 2014 Apr 1;1(2):135-139.PMID:24910777DOI:10.1039/C3QO00067B.
Herein, we report the effects of Fusarisetin A on cell morphology focusing in particular on actin and microtubules dynamics. We also report the synthesis and structure-function studies of a designed library of synthetic fusarisetins in cell-based assays.