| Identification | Back Directory | [Name]
Platencin | [CAS]
869898-86-2 | [Synonyms]
Platencin
Benzoic acid, 3-[[3-[(2S,4aS,8S,8aR)-1,3,4,7,8,8a-hexahydro-8-methyl-3-methylene-7-oxo-2H-2,4a-ethanonaphthalen-8-yl]-1-oxopropyl]amino]-2,4-dihydroxy- | [Molecular Formula]
C24H27NO6 | [MDL Number]
MFCD14635439 | [MOL File]
869898-86-2.mol | [Molecular Weight]
425.474 |
| Chemical Properties | Back Directory | [Boiling point ]
670.1±55.0 °C(Predicted) | [density ]
1.38±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble | [form ]
A solid | [pka]
2.14±0.13(Predicted) |
| Hazard Information | Back Directory | [Description]
Platencin is a natural, broad spectrum Gram-positive antibiotic isolated from S. platensis, which is also the source of platensimycin . Platencin inhibits two key enzymes in bacterial fatty acid synthesis, β-ketoacyl-ACP synthases II and III (FabF and FabH, respectively), unlike platensimycin which only targets FabF. The IC50 values for platencin against FabF and FabH are 1.95 and 3.91 μg/ml, respectively. It does not exhibit cross-resistance to antibiotic resistant bacterial strains, including methicillin-resistant S. aureus, vancomycin-intermediate S. aureus, and vancomycin-resistant Enterococci. For these reasons, platencin has potential applications in fighting antibiotic resistant bacteria. | [Uses]
Platencin is a novel, broad spectrum, Gram-positive antibiotic produced by strains of Streptomyces platensis. Platencin is more potent than its analogue, platensimycin. Platencin shows potent in vivo efficacy without any observed toxicity. Platencin targets two essential proteins, b-ketoacyl-acyl carrier protein (ACP) synthase II (FabF) and III (FabH) whereas platensimycin targets only FabF. | [Uses]
Platencin is a potent antibiotic that targets FabF and FabH proteins. | [Definition]
ChEBI: Platencin is a monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the polycyclic cage component. It is an antibiotic isolated from Streptomyces platensis and exhibits inhibitory activity against fatty acid synthase. It has a role as an antibacterial agent, an antimicrobial agent, an EC 2.3.1.85 (fatty acid synthase) inhibitor and a bacterial metabolite. It is a cyclic ketone, a polycyclic cage, a dihydroxybenzoic acid, a monocarboxylic acid amide and an aromatic amide. It is a conjugate acid of a platencin(1-). | [Enzyme inhibitor]
This antibiotic (FW = 425.2 g/mol; CAS 869898-86-2; Soluble in ethanol, methanol, DMF or DMSO) inhibits both Staphylococcus aureus b-ketoacyl- [acyl-carrier-protein] synthases II and III, with IC50 values of 1.95 and 3.91 μg/mL, respectively. Platencin exhibits strong, broad-spectrum, Grampositive antibacterial activity to key antibiotic resistant strains, including methicillin-resistant Staphylococcus aureus, vancomycin-intermediate S. aureus, and vancomycin-resistant Enterococcus faecium, without evidence of toxicity in humans. | [References]
[1] JUN WANG. Discovery of platencin, a dual FabF and FabH inhibitor with in vivo antibiotic properties.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2007, 104 18: 7612-7616. DOI: 10.1073/pnas.0700746104
[2] EVAN MARTENS Arnold L D. Platensimycin and platencin: promising antibiotics for future application in human medicine[J]. Journal of Antibiotics, 2011, 64 11: 705-710. DOI: 10.1038/ja.2011.80
[3] ADIL M ALLAHVERDIYEV. The use of platensimycin and platencin to fight antibiotic resistance.[J]. Infection and Drug Resistance, 2013, 6: 99-114. DOI: 10.2147/idr.s25076 |
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