Platensimycin
(Synonyms: 平板霉素) 目录号 : GC44660A selective inhibitor of fatty acid biosynthesis
Cas No.:835876-32-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Platensimycin (PTM) is an antibiotic produced by S. platensis that inhibits Gram-positve bacteria by selectively inhibiting cellular lipid biosynthesis (IC50 = 0.1 μM). It targets the β-ketoacyl-acyl-carrier-protein synthase I/II, FabF/B, an enzyme that participates in the biosynthesis of fatty acids (IC50s = 48 and 160 nM for S. aureus and E. coli enzymes, respectively). By specifically targeting fatty acid synthesis in bacteria, PTM is thought to be a promising agent for overcoming antibiotic resistance. PTM is also a selective inhibitor of the mammalian fatty acid synthase and has been shown to reduce liver triglyceride levels and to improve insulin sensitivity in a diabetic mouse model after an oral dose of 30 mg/kg.
| Cas No. | 835876-32-9 | SDF | |
| 别名 | 平板霉素 | ||
| Canonical SMILES | O=C(O)C1=C(O)C(NC(CC[C@@]2(C)[C@@]([C@](O3)([H])C[C@]([H])(C4)[C@]3(C)C5)([H])[C@]54C=CC2=O)=O)=C(O)C=C1 | ||
| 分子式 | C24H27NO7 | 分子量 | 441.5 |
| 溶解度 | DMF: Soluble,DMSO: Soluble,Ethanol: Soluble,Methanol: Soluble | 储存条件 | Store at -20°C, protect from light |
| 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 | 2.265 mL | 11.325 mL | 22.6501 mL |
| 5 mM | 0.453 mL | 2.265 mL | 4.53 mL |
| 10 mM | 0.2265 mL | 1.1325 mL | 2.265 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。
A Review on Platensimycin: A Selective FabF Inhibitor
Int J Med Chem 2016;2016:9706753.PMID:26942008DOI:10.1155/2016/9706753.
Emerging resistance to existing antibiotics is an inevitable matter of concern in the treatment of bacterial infection. Naturally occurring unique class of natural antibiotic, Platensimycin, a secondary metabolite from Streptomyces platensis, is an excellent breakthrough in recent antibiotic research with unique structural pattern and significant antibacterial activity. β-Ketoacyl-(acyl-carrier-protein (ACP)) synthase (FabF) whose Gram-positive bacteria need to biosynthesize cell membranes is the target of inhibition of Platensimycin. So, isolation, retrosynthetic analysis, synthesis of Platensimycin, and analogues of Platensimycin synthesized till today are the objectives of this review which may be helpful to further investigate and to reveal untouched area on this molecule and to obtain a potential antibacterial lead with enhanced significant antibacterial activity.
Platensimycin: a promising antimicrobial targeting fatty acid synthesis
Curr Med Chem 2008;15(7):705-10.PMID:18336284DOI:10.2174/092986708783885255.
Platensimycin was recently discovered by Merck Research Laboratories and has created considerable interest given its potent antibacterial activity and mode of action. The use of RNA gene-silencing techniques and screening libraries of natural products allowed Merck to find this antibiotic which may have otherwise been missed using conventional methods. Interestingly, Platensimycin has shown good activity against a panel of Gram positive organisms which included various resistant strains. Platensimycin works by inhibiting beta-ketoacyl synthases I/II (FabF/B) which are key enzymes in the production of fatty acids required for bacterial cell membranes. So far, a number of groups have explored synthetic strategies for Platensimycin and this work has subsequently lead to the synthesis of active analogues. Given its mode of action, it is intriguing as to why Merck themselves patented only a single compound and have not apparently sought to generate further libraries. This review will discuss the origins of Platensimycin, its mechanism of action, synthetic schemes and where the future may take us following this fascinating discovery.
Synthesis of Platensimycin
Angew Chem Int Ed Engl 2008;47(14):2548-55.PMID:18327757DOI:10.1002/anie.200705303.
In modern drug discovery, antibodies or libraries of simple synthetic organic compounds, mostly of heterocyclic origin, are favored. Natural products play an increasingly inferior role as they are considered structurally too complex, limited in quantity, and difficult to synthesize, manipulate, and derivatize. Thus it was a sensation when a Merck research group reported that classical screening of metabolites from Streptomyces platensis has unearthed a low-molecular-weight organic compound with remarkable antibiotic properties.
Platensimycin and platencin: Inspirations for chemistry, biology, enzymology, and medicine
Biochem Pharmacol 2017 Jun 1;133:139-151.PMID:27865713DOI:10.1016/j.bcp.2016.11.013.
Natural products have served as the main source of drugs and drug leads, and natural products produced by microorganisms are one of the most prevalent sources of clinical antibiotics. Their unparalleled structural and chemical diversities provide a basis to investigate fundamental biological processes while providing access to a tremendous amount of chemical space. There is a pressing need for novel antibiotics with new mode of actions to combat the growing challenge of multidrug resistant pathogens. This review begins with the pioneering discovery and biological activities of Platensimycin (PTM) and platencin (PTN), two antibacterial natural products isolated from Streptomyces platensis. The elucidation of their unique biochemical mode of action, structure-activity relationships, and pharmacokinetics is presented to highlight key aspects of their biological activities. It then presents an overview of how microbial genomics has impacted the field of PTM and PTN and revealed paradigm-shifting discoveries in terpenoid biosynthesis, fatty acid metabolism, and antibiotic and antidiabetic therapies. It concludes with a discussion covering the future perspectives of PTM and PTN in regard to natural products discovery, bacterial diterpenoid biosynthesis, and the pharmaceutical promise of PTM and PTN as antibiotics and for the treatment of metabolic disorders. PTM and PTN have inspired new discoveries in chemistry, biology, enzymology, and medicine and will undoubtedly continue to do so.
Review of Platensimycin and Platencin: Inhibitors of β-Ketoacyl-acyl Carrier Protein (ACP) Synthase III (FabH)
Molecules 2015 Sep 3;20(9):16127-41.PMID:26404223DOI:10.3390/molecules200916127.
Platensimycin and platencin were successively discovered from the strain Streptomyces platensis through systematic screening. These natural products have been defined as promising agents for fighting multidrug resistance in bacteria by targeting type II fatty acid synthesis with slightly different mechanisms. Bioactivity studies have shown that Platensimycin and platencin offer great potential to inhibit many resistant bacteria with no cross-resistance or toxicity observed in vivo. This review summarizes the general information on Platensimycin and platencin, including antibacterial and self-resistant mechanisms. Furthermore, the total synthesis pathways of Platensimycin and platencin and their analogues from recent studies are presented.