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528244 Platensimycin, Streptomyces sp. - CAS 835876-32-9 - Calbiochem

A cell-permeable Streptomyces-derived antibiotic that exhibits broad-spectrum Gram-positive antibacterial activity by selectively targeting the elongation condensing enzyme FabF.

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      Overview

      Replacement Information

      Key Spec Table

      CAS #Empirical Formula
      835876-32-9C₂₄H₂₇NO₇
      Description
      OverviewA cell-permeable Streptomyces-derived antibiotic that exhibits broad-spectrum Gram-positive antibacterial activity by selectively targeting the elongation condensing enzyme FabF (IC50 = 48 and 160 nM against S. aureus and E. coli FabF, respectively), but not the initiation condensing enzyme FabH (IC50 = 67 µM), involved in type II fatty acid synthesis (FASII). Binding studies indicate that acyl-FabF intermediate complex formation induces a FabF conformation change that is necessary for Platensimycin interaction. Platensimycin effectively kills numerous Staphylococcus aureus, Enterococcus faecium, and Streptococcus pneumoniae strains, including the ones that are resistant to methicillin and vancomycin (Cat. No. 627850). Platensimycin does not exhibit antifungal activity towards Candida albicans (no effect at 64 µg/ml) or toxicity toward mammalian HeLa culture (no effect at 1000 µg/ml) and is efficacious in treating S. aureus infection in mice in vivo (~105-fold bacteria titre reduction via a 24 h i.v. at 150 µg h-1). Although Platensimycin is ineffective toward wild-type E. coli due to the presence of functional multidrug efflux pump (no effect at 64 µg/ml), Platensimycin does inhibit the growth of efflux-negative E. coli strains. Platensimycin has been shown to potently and selectively inhibit hepatocyte FAS and fatty acid oxidation (FAO), without affecting sterol synthesis. Platensimycin is also known as Fatty Acid Synthase Inhibitor III.
      Catalogue Number528244
      Brand Family Calbiochem®
      References
      ReferencesWu, M., et al. 2011. Proc. Natl. Acad. Sci. USA in press.
      Wang, J., et al. 2007. Proc. Natl. Acad. Sci. USA 104, 7612.
      Singh, S.B., et al. 2006. J. Am. Chem. Soc. 128, 11916.
      Wang, J., et al. 2006. Nature 441, 358.
      Product Information
      CAS number835876-32-9
      FormTan solid
      Hill FormulaC₂₄H₂₇NO₇
      Chemical formulaC₂₄H₂₇NO₇
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Purity≥93% by HPLC
      Physicochemical Information
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      R PhraseR: 20/21/22

      Harmful by inhalation, in contact with skin and if swallowed.
      S PhraseS: 22-36/37/39-45

      Do not breathe dust.
      Wear suitable protective clothing, gloves and eye/face protection.
      In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Shipped with Blue Ice or with Dry Ice
      Toxicity Harmful
      Storage -20°C
      Protect from Light Protect from light
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.
      Packaging Information
      Transport Information
      Supplemental Information
      Specifications
      Global Trade Item Number
      Catalogue Number GTIN
      528244 0

      Documentation

      Platensimycin, Streptomyces sp. - CAS 835876-32-9 - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      Platensimycin, Streptomyces sp. - CAS 835876-32-9 - Calbiochem Certificates of Analysis

      TitleLot Number
      528244

      References

      Reference overview
      Wu, M., et al. 2011. Proc. Natl. Acad. Sci. USA in press.
      Wang, J., et al. 2007. Proc. Natl. Acad. Sci. USA 104, 7612.
      Singh, S.B., et al. 2006. J. Am. Chem. Soc. 128, 11916.
      Wang, J., et al. 2006. Nature 441, 358.
      Data Sheet

      Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

      Revision17-December-2018 JSW
      DescriptionA cell-permeable Streptomyces-derived antibiotic that exhibits broad-spectrum Gram-positive antibacterial activity by selectively targeting the elongation condensing enzyme FabF (IC50 = 48 and 160 nM against S. aureus and E. coli FabF, respectively), but not the initiation condensing enzyme FabH (IC50 = 67 µM), involved in type II fatty acid synthesis (FASII). Binding studies indicate that acyl-FabF intermediate complex formation induces a FabF conformation change that is necessary for Platensimycin interaction. Platensimycin effectively kills numerous Staphylococcus aureus, Enterococcus faecium, and Streptococcus pneumoniae strains, including the ones that are resistant to methicillin and vancomycin (Cat. No. 627850). Platensimycin does not exhibit antifungal activity towards Candida albicans (no effect at 64 µg/ml) or toxicity toward mammalian HeLa culture (no effect at 1000 µg/ml) and is efficacious in treating S. aureus infection in mice in vivo (~105-fold bacteria titre reduction via a 24 h i.v. at 150 µg h-1). Although Platensimycin is ineffective toward wild-type E. coli due to the presence of functional multidrug efflux pump (no effect at 64 µg/ml), Platensimycin does inhibit the growth of efflux-negative E. coli strains.
      FormTan solid
      CAS number835876-32-9
      Chemical formulaC₂₄H₂₇NO₇
      Structure formulaStructure formula
      Purity≥93% by HPLC
      SolubilityDMSO (20 mg/ml) or Ethanol (20 mg/ml)
      Storage Protect from light
      -20°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.
      Toxicity Harmful
      ReferencesWu, M., et al. 2011. Proc. Natl. Acad. Sci. USA in press.
      Wang, J., et al. 2007. Proc. Natl. Acad. Sci. USA 104, 7612.
      Singh, S.B., et al. 2006. J. Am. Chem. Soc. 128, 11916.
      Wang, J., et al. 2006. Nature 441, 358.