Valilactone
(Synonyms: 缬基内酯,(-)-Valilactone) 目录号 : GC41409
An esterase inhibitor
Cas No.:113276-96-3
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
Valilactone is an esterase inhibitor produced by a cultured strain of soil actinomycetes. It is reported to inhibit hog liver esterase and hog pancreas lipase with IC50 values of 29 and 0.14 ng/ml, respectively. Valilactone can also inhibit fatty acid synthase with an IC50 value of 0.30 µM and demonstrates selective toxicity towards MDA-MB-231 breast cancer cells with an IC50 value of 10.5 µM.
| Cas No. | 113276-96-3 | SDF | |
| 别名 | 缬基内酯,(-)-Valilactone | ||
| Canonical SMILES | CCCCC[C@H](OC([C@@H](NC([H])=O)C(C)C)=O)C[C@H]1[C@H](CCCCCC)C(O1)=O | ||
| 分子式 | C22H39NO5 | 分子量 | 397.6 |
| 溶解度 | DMF: 25 mg/ml,DMSO: 25 mg/ml,DMSO:PBS(pH 7.2) (1:2): 0.3 mg/ml,Ethanol: 10 mg/ml | 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 | 2.5151 mL | 12.5755 mL | 25.1509 mL |
| 5 mM | 0.503 mL | 2.5151 mL | 5.0302 mL |
| 10 mM | 0.2515 mL | 1.2575 mL | 2.5151 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。
Total synthesis and comparative analysis of orlistat, Valilactone, and a transposed orlistat derivative: Inhibitors of fatty acid synthase
Org Lett 2006 Sep 28;8(20):4497-500.PMID:16986934DOI:10.1021/ol061651o.
Concise syntheses of orlistat (Xenical), a two-carbon transposed orlistat derivative, and Valilactone are described that employ the tandem Mukaiyama aldol-lactonization (TMAL) process as a key step. This process allows facile modification of the alpha-side chain. Versatile strategies for modifying the delta-side chain are described, involving cuprate addition and olefin metathesis. Comparative antagonistic activity of these derivatives toward a recombinant form of the thioesterase domain of fatty acid synthase is reported along with comparative activity-based profiling.
An expeditious enantioselective total synthesis of Valilactone
J Org Chem 2006 Jul 21;71(15):5748-51.PMID:16839158DOI:10.1021/jo060844m.
The title compound was synthesized through an expeditious route using Crimmins aldolization to establish the two key stereogenic centers and a hydroxyl group activation (HGA) protocol to construct the anti alpha,beta-disubstituted beta-lactone from the corresponding syn aldol.
Synthesis of novel beta-lactone inhibitors of fatty acid synthase
J Med Chem 2008 Sep 11;51(17):5285-96.PMID:18710210DOI:10.1021/jm800321h.
Fatty acid synthase (FAS) is necessary for growth and survival of tumor cells and is a promising drug target for oncology. Here, we report on the syntheses and activity of novel inhibitors of the thioesterase domain of FAS. Using the structure of orlistat as a starting point, which contains a beta-lactone as the central pharmacophore, 28 novel congeners were synthesized and examined. Structural features such as the length of the alpha- and beta-alkyl chains, their chemical composition, and amino ester substitutions were altered and the resulting compounds explored for inhibitory activity toward the thioesterase domain of FAS. Nineteen congeners show improved potency for FAS in biochemical assays relative to orlistat. Three of that subset, including the natural product Valilactone, also display an increased potency in inducing tumor cell death and improved solubility compared to orlistat. These findings support the idea that an orlistat congener can be optimized for use in a preclinical drug design and for clinical drug development.
Panclicins, novel pancreatic lipase inhibitors. II. Structural elucidation
J Antibiot (Tokyo) 1994 Dec;47(12):1376-84.PMID:7844032DOI:10.7164/antibiotics.47.1376.
Panclicins A-E are novel and potent pancreatic lipase inhibitors produced by Streptomyces sp. NR 0619. Their structures have been elucidated based on NMR and FAB-MS experiments. The relative configurations have also been determined by NMR experiments. The absolute stereochemistry has been determined by the chiral HPLC analysis of the hydrolysates of panclicins A and B and by modified Mosher's method on a derivative of panclicin A. They are structurally related to beta-lactone esterase inhibitors of microbial origin, lipstatin, Valilactone, ebelactones and esterastin. Panclicins also contain a beta-lactone structure with two alkyl chains, one of which has an N-formylalanyloxy or N-formylglycyloxy substituent.