504908 | Myeloperoxidase Inhibitor-II - Calbiochem

504908
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical Formula
      C₁₂H₁₃FN₂O

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      5.04908.0001
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          Glass bottle 10 mg
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          Description
          OverviewA 5-fluorotryptamine derivative that inhibits myeloperoxidase/MPO activity (IC50 = 18 nM) via direct affinity interaction with enzyme active site heme pyrrole ring D, while exhibiting much reduced affinity toward serotonin reuptake transporter/SERT (Ki = 631 nM). Kinetic studies reveal that the inhibitor acts as a good one-electron donor for the intermediate Compound I "Fe(IV)=O...Por•+", facilitating the formation of Compound II (Fe(IV)-OH...Por) and thereby preventing the reduction of Compound I directly to the resting state "Fe(IV)...Por" via the "halogenation cycle", while, on the other hand, behaves as a poor electron donor for Compound II, thereby preventing the completion of the "peroxidase cycle" by stalling the further reduction of Compound II to the resting state.

          Please note that the molecular weight for this compound is batch-specific due to variable water content.
          Catalogue Number504908
          Brand Family Calbiochem®
          Synonyms4-(5-Fluoro-1H-indol-3-yl)butanamide, MPO Inhibitor II
          References
          ReferencesSoubhye, J., et al. 2013. J. Med. Chem. 56, 3943.
          Soubhye, J., et al. 2010. J. Med. Chem. 53, 8747.
          Product Information
          FormLight beige powder
          Hill FormulaC₁₂H₁₃FN₂O
          Chemical formulaC₁₂H₁₃FN₂O
          ReversibleY
          Structure formula ImageStructure formula Image
          Applications
          Biological Information
          Primary Targetmyeloperoxidase
          Purity≥95% by HPLC
          Physicochemical Information
          Cell permeableY
          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
          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

          SDS

          Title

          Safety Data Sheet (SDS) 

          References

          Reference overview
          Soubhye, J., et al. 2013. J. Med. Chem. 56, 3943.
          Soubhye, J., et al. 2010. J. Med. Chem. 53, 8747.

          Brochure

          Title
          Pathways and Biomarkers of Oxidative Stress (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.

          Revision16-August-2013 JSW
          Synonyms4-(5-Fluoro-1H-indol-3-yl)butanamide, MPO Inhibitor II
          DescriptionA 5-fluorotryptamine derivative that inhibitis the MPO-catalyzed Cl-/chloride-to-OCl-/hypochlorite oxidation in the presence of H2O2 (IC50 = 18 nM by taurine/2-aminoethan-sulfonic acid chlorination assay) as well as MPO-mediated LDL ApoB-100 (ApoB100; apolipoprotein B-100) oxidation (IC50 = 18 nM by ELISA) via direct affinity binding at the myeloperoxidase active site through ϖ-ϖ interaction between its indole and the the enzyme's heme pyrrole ring D, while exhibiting much reduced affinity toward serotonin reuptake transporter/SERT (Ki = 631 nM). Kinetic studies reveal that the inhibitor acts as a good one-electron donor for the intermediate Compound I "Fe(IV)=O...Por•+", facilitating the formation (k3 = 1,6 x 107 M-1 s-1) of Compound II (Fe(IV)-OH...Por) and thereby preventing the reduction of Compound I directly to the resting state "Fe(IV)...Por" via the "halogenation cycle", while, on the other hand, behaves as a poor electron donor for Compound II, thereby preventing the completion of the "peroxidase cycle" by stalling the further reduction of Compound II to the resting state (k4 = 92 M-1 s-1). Toxicology study using Wistar Han male rats reports no signs of adverse effects post single 10 mg/kg i.p. dosage, while signs of adverse effects are observed within the 24 h, but not after, post a higher i.p. dosage at 100 mg/kg.
          FormLight beige powder
          Intert gas (Yes/No) Packaged under inert gas
          Chemical formulaC₁₂H₁₃FN₂O
          Structure formulaStructure formula
          Purity≥95% by HPLC
          SolubilityDMSO (100 mg/ml). Use only fresh DMSO for reconstitution.
          Storage +2°C to +8°C
          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
          ReferencesSoubhye, J., et al. 2013. J. Med. Chem. 56, 3943.
          Soubhye, J., et al. 2010. J. Med. Chem. 53, 8747.