835876-32-9
Chemical Structure
Platensimycin
- CAS No.: 835876-32-9
- Formula:C24H27NO7
- Molecular Weight:441.47
IUPAC Name: 3-(3-((4S,4aR,5S,7S,8S,9aS)-4,8-dimethyl-3-oxo-3,4,4a,5,6,7,8,9-octahydro-5,8-epoxy-7,9a-methanobenzo[7]annulen-4-yl)propanamido)-2,4-dihydroxybenzoic acid
InChIKey: CSOMAHTTWTVBFL-OFBLZTNGSA-N
SMILES: O=C(O)C1=CC=C(O)C(NC(CC[C@]([C@@]2([H])[C@]34C[C@]5([H])[C@@](C4)(C)O[C@@]2([H])C5)(C)C(C=C3)=O)=O)=C1O
Biological Activity: APOL1-IN-1 is a natural product antibiotic and selective FabF inhibitor discovered in Streptomyces platensis. Platensimycin exhibits IC50 values of 48 nM and 160 nM against Staphylococcus aureus and Escherichia coli FabF, respectively. Platensimycin preferentially recognizes the acyl-enzyme conformation of FabF, occupies the malonyl-binding subsite, and competes with malonyl-ACP, thereby inhibiting bacterial fatty acid elongation. Platensimycin is useful for research on bacterial fatty acid biosynthesis and Gram-positive bacterial infections[1][2][3][4][5][6].
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Platensimycin | APOL1-IN-1 is a natural product antibiotic and selective FabF inhibitor discovered in Streptomyces platensis. Platensimycin exhibits IC50 values of 48 nM and 160 nM against Staphylococcus aureus and Escherichia coli FabF, respectively. Platensimycin preferentially recognizes the acyl-enzyme conformation of FabF, occupies the malonyl-binding subsite, and competes with malonyl-ACP, thereby inhibiting bacterial fatty acid elongation. Platensimycin is useful for research on bacterial fatty acid biosynthesis and Gram-positive bacterial infections. | |||||||||||||||||||||
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References
- [1]. Wang J, et al. Platensimycin is a selective FabF inhibitor with potent antibiotic properties. Nature. 2006 May 18;441(7091):358-61.
- [2]. Cao D, Yang J, Deng Y, Su M, Wang Y, Feng X, Xiong Y, Bai E, Duan Y, Huang Y. Discovery of a mammalian FASN inhibitor against xenografts of non-small cell lung cancer and melanoma. Signal transduction and targeted therapy. 2022 Aug 24;7(1):273.
- [3]. Deng Y, et al. Late-Stage Functionalization of Platensimycin Leading to Multiple Analogues with Improved Antibacterial Activity in Vitro and in Vivo. Journal of medicinal chemistry. 2019 Jul 25;62(14):6682-6693.
- [4]. Wang Z, Liu X, Peng Y, Su M, Zhu S, Pan J, Shen B, Duan Y, Huang Y. Platensimycin-encapsulated liposomes or micelles as biosafe nanoantibiotics exhibited strong antibacterial activities against methicillin-resistant Staphylococcus aureus infection in mice. Molecular Pharmaceutics. 2020 Jun 10;17(7):2451-62.
- [5]. Liu X, et al. Platensimycin-Encapsulated Poly(lactic--glycolic acid) and Poly(amidoamine) Dendrimers Nanoparticles with Enhanced Anti-Staphylococcal Activity . Bioconjugate chemistry. 2020 May 20;31(5):1425-1437.
- [6]. Singh SB, Jayasuriya H, Ondeyka JG, Herath KB, Zhang C, Zink DL, Tsou NN, Ball RG, Basilio A, Genilloud O, Diez MT. Isolation, structure, and absolute stereochemistry of platensimycin, a broad spectrum antibiotic discovered using an antisense differential sensitivity strategy. Journal of the American Chemical Society. 2006 Sep 13;128(36):11916-20.
