531147 Lassomycin - Calbiochem

Lassomycin - Calbiochem MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: Mycobacterium Bactericide II, Lassomycin, {cyclic(GLRRLFAD)}-QLVGRRNI-CO₂CH₃, ClpC1P1P2 Proteolytic Complex Inhibitor, ClpP1P2 Proteolytic Activity Inhibitor

531147
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical Formula
      C₈₃H₁₄₂N₃₀O₂₀

      Pricing & Availability

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      5.31147.0001
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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.

          Brochure

          Title
          NPI Flyer- Epigenetics and Nuclear Function Feature (EMD)
          New Products - Antibodies, Small Molecule, Inhibitors

          Technical Info

          Title
          White Paper: Further considerations of antibody validation and usage. (EMD)
          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.