Platencin
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| Category | Antibiotics |
| Catalog number | BBF-03961 |
| CAS | 869898-86-2 |
| Molecular Weight | 425.47 |
| Molecular Formula | C24H27NO6 |
| Purity | >99% by HPLC |
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Description
Platencin is a broad-spectrum Gram-positive antibiotic produced by Streptomyces. Platencin is an effective antibiotic against FabF and FabH proteins. No toxicity was observed.
Specification
| Storage | Store at -20°C |
| IUPAC Name | 2,4-dihydroxy-3-[3-[(1S,5S,6R,8S)-5-methyl-9-methylidene-4-oxo-5-tricyclo[6.2.2.01,6]dodec-2-enyl]propanoylamino]benzoic acid |
| Canonical SMILES | CC1(C2CC3CCC2(CC3=C)C=CC1=O)CCC(=O)NC4=C(C=CC(=C4O)C(=O)O)O |
| InChI | InChI=1S/C24H27NO6/c1-13-12-24-9-5-14(13)11-17(24)23(2,18(27)6-10-24)8-7-19(28)25-20-16(26)4-3-15(21(20)29)22(30)31/h3-4,6,10,14,17,26,29H,1,5,7-9,11-12H2,2H3,(H,25,28)(H,30,31)/t14-,17-,23-,24+/m0/s1 |
| InChI Key | DWUHGPPFFABTIY-RLWZQHMASA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Light Tan Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 670.1±55.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. The use of platensimycin and platencin to fight antibiotic resistance
Gokce Unal, Adil M Allahverdiyev, Sezen Canim Ates, Serhat Elcicek, Emrah Sefik Abamor, Melahat Bagirova, Rabia Cakir Koc, Serkan Yaman, Meral Miraloglu Infect Drug Resist . 2013 Sep 18;6:99-114. doi: 10.2147/IDR.S25076.
Infectious diseases are known as one of the most life-threatening disabilities worldwide. Approximately 13 million deaths related to infectious diseases are reported each year. The only way to combat infectious diseases is by chemotherapy using antimicrobial agents and antibiotics. However, due to uncontrolled and unnecessary use of antibiotics in particular, surviving bacteria have evolved resistance against several antibiotics. Emergence of multidrug resistance in bacteria over the past several decades has resulted in one of the most important clinical health problems in modern medicine. For instance, approximately 440,000 new cases of multidrug-resistant tuberculosis are reported every year leading to the deaths of 150,000 people worldwide. Management of multidrug resistance requires understanding its molecular basis and the evolution and dissemination of resistance; development of new antibiotic compounds in place of traditional antibiotics; and innovative strategies for extending the life of antibiotic molecules. Researchers have begun to develop new antimicrobials for overcoming this important problem. Recently, platensimycin - isolated from extracts of Streptomyces platensis - and its analog platencin have been defined as promising agents for fighting multidrug resistance. In vitro and in vivo studies have shown that these new antimicrobials have great potential to inhibit methicillin-resistant Staphylococcus aureus, vancomycin-resistant enterococci, and penicillin-resistant Streptococcus pneumoniae by targeting type II fatty acid synthesis in bacteria. Showing strong efficacy without any observed in vivo toxicity increases the significance of these antimicrobial agents for their use in humans. However, at the present time, clinical trials are insufficient and require more research. The strong antibacterial efficacies of platensimycin and platencin may be established in clinical trials and their use in humans for coping with multidrug resistance may be allowed in the foreseeable future.
2. Platensimycin and platencin: promising antibiotics for future application in human medicine
Arnold L Demain, Evan Martens J Antibiot (Tokyo) . 2011 Nov;64(11):705-10. doi: 10.1038/ja.2011.80.
Platensimycin and platencin are novel antibiotics produced by Streptomyces platensis. They are potent and non-toxic natural products active against Gram-positive pathogens, including antibiotic-resistant strains and Mycobacterium tuberculosis. They were isolated using an intriguing target-based whole-cell antisense differential sensitivity assay as inhibitors of fatty acid biosynthesis of type II. This type of biosynthesis is not present in humans. Platensimycin inhibits the elongation-condensing enzyme FabF, whereas platencin inhibits both FabF and FabH. For these antibiotics to become successful drugs, their pharmacokinetics must be improved. They have too high a rate of clearance in the body, yielding a low degree of systematic exposure. They work well when administered by continuous infusion, but this is not a useful method of delivery to patients. The two antibiotics and many analogs have been prepared by chemical synthesis. Natural congeners have also been obtained from the producing actinomycete. However, none of these molecules are as active as platensimycin and platencin. Using tools of rational metabolic engineering, superior strains have been produced making hundreds of times more antibiotic than the natural strains.
3. Formal synthesis of platencin
Pingfan Li, Hisashi Yamamoto Chem Commun (Camb) . 2010 Sep 14;46(34):6294-5. doi: 10.1039/c0cc01619e.
Formal synthesis of platencin was achieved by assembling its tricyclic core structure through a Robinson annulation reaction, whose precursor was made from a bicyclo[3.2.2] ring structure, product of a tropone Diels-Alder reaction.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
