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504908 Myeloperoxidase Inhibitor-II - CAS 1256348-67-0 - Calbiochem

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

Synonyms: 4-(5-Fluoro-1H-indol-3-yl)butanamide, MPO Inhibitor II

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504908
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
1256348-67-0C₁₂H₁₃FN₂O

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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
      CAS number1256348-67-0
      FormLight beige powder
      Hill FormulaC₁₂H₁₃FN₂O
      Chemical formulaC₁₂H₁₃FN₂O
      ReversibleY
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      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
      Global Trade Item Number
      Catalogue Number GTIN
      5.04908.0001CN 04055977263664

      Documentation

      Myeloperoxidase Inhibitor-II - CAS 1256348-67-0 - Calbiochem 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
      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
      CAS number1256348-67-0
      Chemical formulaC₁₂H₁₃FN₂O
      Structure formulaStructure formula
      Purity≥95% by HPLC
      SolubilityDMSO (100 mg/ml). Use only fresh DMSO for reconstitution.
      Storage Protect from light
      +2°C to +8°C
      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.