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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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Overview

Replacement Information

Key Specifications Table

CAS #Empirical Formula
1256348-67-0C₁₂H₁₃FN₂O

Products

Catalog NumberPackaging Qty/Pack
5.04908.0001 Glass bottle 10 mg
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
Catalog Number GTIN
5.04908.0001 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.