531147 Lassomycin - Calbiochem

531147
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Overview

Replacement Information

Key Specifications Table

Empirical Formula
C₈₃H₁₄₂N₃₀O₂₀

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      Glass bottle 5 mg
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      Description
      OverviewA highly basic synthetic 16-aminoacid cyclic peptide that displays bactericidal activity against multiple species of growing and dormant mycobacteria, including drug-resistant Mycobacterium tuberculosis (MBC = 1- 4 µg/ml) in a time-dependent manner. Displays only a trivial activity against other bacteria (MIC > 50 µg/ml) and mammalian cells (IC50 = 350 µg/ml in NIH 3T3 and HepG2 cells). Acts by reversibly binding to a highly acidic N-terminal region of the ClpC1 ATPase complex (Kd = 410 nM) and stimulates its ATPase activity, but uncouples it from ClpP1P2-dependent proteolysis, a step that is essential for mycobacterium viability. Does not affect other related hexameric AAA ATPases. Displays greater bactericidal potency against M. tuberculosis than rifampicin (Cat. No. 557303).

      Please note that the molecular weight for this compound is batch-specific due to variable water content.
      Catalogue Number531147
      Brand Family Calbiochem®
      SynonymsMycobacterium Bactericide II, Lassomycin, {cyclic(GLRRLFAD)}-QLVGRRNI-CO₂CH₃, ClpC1P1P2 Proteolytic Complex Inhibitor, ClpP1P2 Proteolytic Activity Inhibitor
      References
      ReferencesGavrish, E., et al. 2014. Chem. Biol. 21, 509.
      Product Information
      FormWhite powder
      FormulationSupplied as a trifluoroacetate salt.
      Hill FormulaC₈₃H₁₄₂N₃₀O₂₀
      Chemical formulaC₈₃H₁₄₂N₃₀O₂₀
      Hygroscopic Hygroscopic
      ReversibleY
      Quality LevelMQ200
      Applications
      Biological Information
      Primary TargetClpC1 ATPase complex
      Purity≥95% by HPLC
      Physicochemical Information
      Cell permeableY
      Peptide Sequence{cyclic(Gly-Leu-Arg-Arg-Leu-Phe-Ala-Asp)}-Gln-Leu-Val-Gly-Arg-Arg-Asn-Ile-CO₂CH₃
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Ambient Temperature Only
      Toxicity Standard Handling
      Storage +2°C to +8°C
      Protect from Light Protect from light
      Hygroscopic Hygroscopic
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications

      Documentation

      Lassomycin - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      References

      Reference overview
      Gavrish, E., et al. 2014. Chem. Biol. 21, 509.
      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.

      Revision19-December-2014 JSW
      SynonymsMycobacterium Bactericide II, Lassomycin, {cyclic(GLRRLFAD)}-QLVGRRNI-CO₂CH₃, ClpC1P1P2 Proteolytic Complex Inhibitor, ClpP1P2 Proteolytic Activity Inhibitor
      DescriptionA synthetic 16-aa lasso peptide with an N-terminal cyclized 8-aa loop followed by an 8-aa spoke with a C-terminus methyl-ester modification, originally identified in actinomycete Lentzea kentuckyensis sp. and reported to exhibit mycobacterium-selective antibiotic activity against M. avium subsp. paratuberculosis, M. smegmatis, and M. tuberculosis (minimum inhibitory concentration/MIC from 0.78 to 3.1 µg/mL; 0.41 to 1.65 µM), including Mtb strains resistant to isoniazid, rifampicin (Cat. No. 557303), streptomycin (Cat. No. 5711), ethambutol, pyrazinamide, and flouroquinolones, while exhibiting much reduced or little potency toward a panel of 16 actinobacteria (MIC from 12.5 to 50 µg/mL against P. acnes & B. longum; MIC >50 µg/mL against the rest) or cytotoxicity in NIH 3T3 & HepG2 cultures (IC50 = 350 µg/mL). Lassomycin is shown to selectively activate the ATPase activity of Mtb ClpC1 (Kd = 0.41 µM) without affecting other AAA family ATPases, including Mtb ClpX, archaea PAN, murine 26S proteasome, and E coli. ClpA, ClpB, and GroEL, resulting in an inhibition instead of activation of ClpC1 ATPase activity-dependent ClpP1P2 proteolytic activity (by 100% at 10 µM against casein degradation; 100 nM P1P2 + 100 nM C1 + 2 mM ATP), most likely by inducing a ClpC1 conformational change via cooperative binding (Hill coefficient = 2.1) that does not prevent ClpC1 & protein substrate binding, but uncouples ClpC1 from ClpP1P2-mediated protein degradation. Unlike Rifampicin, Lassomycin is effective against not just exponentially growing, but also stationary phase, Mtb cultures.
      FormWhite powder
      FormulationSupplied as a trifluoroacetate salt.
      Intert gas (Yes/No) Packaged under inert gas
      Chemical formulaC₈₃H₁₄₂N₃₀O₂₀
      Peptide Sequence{cyclic(Gly-Leu-Arg-Arg-Leu-Phe-Ala-Asp)}-Gln-Leu-Val-Gly-Arg-Arg-Asn-Ile-CO₂CH₃
      Purity≥95% by HPLC
      SolubilityH₂O (100 mg/ml)
      Storage +2°C to +8°C
      Hygroscopic
      Protect from light
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
      Toxicity Standard Handling
      ReferencesGavrish, E., et al. 2014. Chem. Biol. 21, 509.